dmcg_analysis.ipynb

{
 "cells": [
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "Verify that our `dmcg.py` script gets the same results on the drug_processed set as reported in the DMCG paper.\n",
    "\n",
    " * `drugs_processed/drugs.dmcg.sdf` - the test set smiles turned into sdf by dmcg.py\n",
    " * `drugs_processed/drugs.dmcg2.sdf` - same, generated with different random seed\n",
    "\n",
    " * `drugs_processed/drugs.ref.sdf.gz` - the reference sdfs"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 103,
   "metadata": {},
   "outputs": [],
   "source": [
    "from rdkit import Chem\n",
    "import gzip\n",
    "import numpy as np\n",
    "from tqdm import tqdm\n",
    "from rdkit.Chem import rdMolAlign as MA\n",
    "from rdkit.Chem import rdFMCS\n",
    "\n",
    "from rdkit.Chem.rdmolops import RemoveHs\n",
    "from rdkit import DataStructs\n",
    "import multiprocessing\n",
    "import copy"
   ]
  },
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "Adapting code from DMCG/evaluate.py"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 180,
   "metadata": {},
   "outputs": [],
   "source": [
    "def get_best_rmsd(gen_mol, ref_mol):\n",
    "    gen_mol = RemoveHs(gen_mol)\n",
    "    ref_mol = RemoveHs(ref_mol)\n",
    "    try:\n",
    "        rmsd = MA.GetBestRMS(gen_mol, ref_mol)\n",
    "    except:\n",
    "        #lack perfect match\n",
    "        mcs = rdFMCS.FindMCS([gen_mol,ref_mol],atomCompare=rdFMCS.AtomCompare.CompareAny,bondCompare=rdFMCS.BondCompare.CompareAny)\n",
    "        submol = mcs.queryMol\n",
    "        if mcs.numAtoms != gen_mol.GetNumAtoms():\n",
    "            raise\n",
    "        rms = []\n",
    "        for a in gen_mol.GetSubstructMatches(submol):\n",
    "            for b in ref_mol.GetSubstructMatches(submol):\n",
    "                rms.append(MA.GetBestRMS(gen_mol,ref_mol,map = [list(zip(a,b))]))\n",
    "        rmsd = np.min(rms)\n",
    "        \n",
    "    return rmsd\n",
    "\n",
    "def get_rmsd_min(inputargs):\n",
    "    mols, threshold = inputargs\n",
    "    gen_mols, ref_mols = mols\n",
    "    rmsd_mat = np.zeros([len(ref_mols), len(gen_mols)], dtype=np.float32)\n",
    "    for i, gen_mol in enumerate(gen_mols):\n",
    "        gen_mol_c = copy.deepcopy(gen_mol)\n",
    "        for j, ref_mol in enumerate(ref_mols):\n",
    "            ref_mol_c = copy.deepcopy(ref_mol)\n",
    "            rmsd_mat[j, i] = get_best_rmsd(gen_mol_c, ref_mol_c)\n",
    "    rmsd_mat_min = rmsd_mat.min(-1)\n",
    "    return (rmsd_mat_min <= threshold).mean(), rmsd_mat_min.mean()\n"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 181,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "array([2.511996 , 2.431173 , 2.1458929, 2.3037882, 1.9481905, 2.4850197,\n",
       "       2.4518783, 2.6659184, 2.3970592, 2.379571 , 2.4020786, 2.181613 ,\n",
       "       1.7855121, 2.13329  , 1.6502929, 2.252782 , 2.257792 , 2.2047238,\n",
       "       2.3032427, 2.2843485, 2.3084002, 1.8175057, 2.2844248, 1.9012657,\n",
       "       2.320043 , 2.23418  , 2.657883 , 2.544342 , 2.5010183, 1.5962297,\n",
       "       2.2741652, 2.1443455, 1.947057 , 2.4633627, 2.4573176, 2.6218529,\n",
       "       1.8700916, 2.7246943, 1.7355028, 2.866373 , 2.948463 , 2.3839364,\n",
       "       2.4039772, 1.7200216, 2.9209046, 1.2063236, 2.9300506, 2.9308527,\n",
       "       1.9859898, 2.167662 , 2.9277284, 2.9930522, 2.2112591, 2.9588475,\n",
       "       2.9564836, 3.0046372, 2.8061185, 2.9914172, 3.0071952, 2.9680064,\n",
       "       3.0026522, 2.7887785, 2.560516 , 3.0236948, 2.9993813, 2.0033731,\n",
       "       1.0226122, 2.3163717, 2.4694157, 1.5905163, 1.5856162, 2.5042882,\n",
       "       2.2772048, 1.8546922, 1.761928 , 2.6115227, 2.6476068, 2.9476752,\n",
       "       2.223573 , 2.614943 ], dtype=float32)"
      ]
     },
     "execution_count": 181,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "rmsd_mat.min(-1)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  },
  {
   "cell_type": "code",
   "execution_count": 182,
   "metadata": {},
   "outputs": [],
   "source": [
    "supp = Chem.ForwardSDMolSupplier(open('drugs_processed/drugs.dmcg.sdf','rb'))\n",
    "mol_preds = [mol for mol in supp]"
   ]
  },
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "DMCG evaluate.py generates two conformers for each individual input, which seems suspect, but that's what they do (it adds a few percent of coverage)."
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 183,
   "metadata": {},
   "outputs": [],
   "source": [
    "supp = Chem.ForwardSDMolSupplier(open('drugs_processed/drugs.dmcg2.sdf','rb'))\n",
    "mol_preds2 = [mol for mol in supp]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 184,
   "metadata": {},
   "outputs": [],
   "source": [
    "supp = Chem.ForwardSDMolSupplier(gzip.open('drugs_processed/drugs.ref.sdf.gz','rb'))\n",
    "mol_labels = [mol for mol in supp]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 185,
   "metadata": {},
   "outputs": [],
   "source": [
    "smis = []\n",
    "smimols = []\n",
    "smifingers = []\n",
    "for line in open('drugs_processed/drugs.smi'):\n",
    "    m = Chem.MolFromSmiles(line.strip())\n",
    "    smimols.append(m)\n",
    "    smis.append(Chem.MolToSmiles(m,isomericSmiles=False))\n",
    "    smifingers.append(Chem.RDKFingerprint(smimols[-1]))"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 186,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "'C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1'"
      ]
     },
     "execution_count": 186,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "smis[1363]"
   ]
  },
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "DMCG evaluate gets to replace coordinates on the same rdmol, so there's no issues matching up smiles, but when you go through sdf output and don't have explicit hydrogens this doesn't always work, so need to make sure our indices are lined up (they are)."
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 187,
   "metadata": {
    "scrolled": true
   },
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "1363 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1364 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1365 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1366 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1367 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1368 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1369 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1370 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1371 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1372 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1373 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1374 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1375 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1376 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1377 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1378 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1379 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1380 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1381 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1382 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1383 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1384 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1385 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1386 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1387 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1388 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1389 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1390 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1391 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1392 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1393 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1394 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1395 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1396 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1397 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1398 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1399 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1400 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1401 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1402 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1403 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1404 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1405 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1406 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1407 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1408 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1409 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1410 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1411 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1412 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "2926 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2927 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2928 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2929 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2930 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2931 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2932 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2933 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2934 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2935 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2936 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2937 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2938 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2939 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2940 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2941 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2942 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2943 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2944 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2945 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2946 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2947 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2948 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2949 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2950 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2951 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2952 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2953 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2954 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2955 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2956 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2957 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2958 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2959 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2960 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2961 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2962 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2963 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2964 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2965 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2966 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2967 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2968 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2969 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2970 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2971 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2972 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2973 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2974 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2975 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2976 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "4034 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4035 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4036 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4037 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4038 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4039 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4040 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4041 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4042 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4043 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4044 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4045 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4046 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4047 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4048 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4049 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4050 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "4051 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4052 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4053 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4054 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4055 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4056 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4057 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4058 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4059 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4060 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4061 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4062 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4063 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4064 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4065 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4066 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4067 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4068 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4069 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4070 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4071 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4072 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4073 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4074 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4075 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4076 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4077 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4078 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4079 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4080 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4081 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4082 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4083 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4084 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4085 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4086 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4087 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4088 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4089 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4090 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4091 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4092 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4093 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4094 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "7956 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7957 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7958 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7959 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7960 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7961 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7962 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7963 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7964 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7965 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7966 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7967 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7968 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7969 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7970 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7971 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7972 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7973 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7974 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7975 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7976 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7977 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7978 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7979 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7980 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7981 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7982 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7983 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7984 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7985 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7986 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7987 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7988 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7989 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7990 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7991 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7992 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7993 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7994 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7995 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7996 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7997 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7998 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7999 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8000 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8001 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8002 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8003 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8004 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8005 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8006 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8007 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8008 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8009 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8010 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8011 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8012 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8013 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8014 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8015 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8016 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8017 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8018 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8019 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8020 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8021 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8022 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8023 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8024 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8025 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8026 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8027 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8028 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8029 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8030 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8031 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8032 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8033 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8034 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8035 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8036 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8037 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8038 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8039 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8040 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "10007 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10008 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10009 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10010 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10011 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10012 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10013 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10014 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10015 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10016 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10017 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10018 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10019 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10020 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10021 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10022 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10023 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10024 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10025 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10026 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10027 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10028 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10029 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10030 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10031 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10032 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10033 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10034 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10035 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10036 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10037 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10038 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10039 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10040 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10041 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10042 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10043 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10044 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10045 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10046 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10047 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10048 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10049 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10050 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10051 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10052 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10053 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10054 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10055 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10056 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10057 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10058 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10059 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10060 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10061 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10062 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10063 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10064 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10065 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10066 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10067 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10596 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10597 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10598 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10600 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10640 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10653 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n"
     ]
    }
   ],
   "source": [
    "smiles2pairs = dict()\n",
    "for i,gen_mol in enumerate(mol_preds):\n",
    "    smiles = Chem.MolToSmiles(gen_mol,isomericSmiles=False)\n",
    "    if smiles != smis[i]:\n",
    "        fp = Chem.RDKFingerprint(gen_mol)\n",
    "        sim = DataStructs.FingerprintSimilarity(fp,smifingers[i])\n",
    "        if sim != 1.0:\n",
    "            print(i,sim,smiles,smis[i])\n",
    "    smiles = smis[i]\n",
    "    if smiles not in smiles2pairs:\n",
    "        smiles2pairs[smiles] = [[gen_mol]]\n",
    "    else:\n",
    "        smiles2pairs[smiles][0].append(gen_mol)\n",
    "    smiles2pairs[smiles][0].append(mol_preds2[i])\n",
    "        \n",
    "for i,ref_mol in enumerate(mol_labels):\n",
    "    smiles = Chem.MolToSmiles(ref_mol,isomericSmiles=False)\n",
    "    if smiles != smis[i]:\n",
    "        fp = Chem.RDKFingerprint(gen_mol)\n",
    "        sim = DataStructs.FingerprintSimilarity(fp,smifingers[i])\n",
    "        if sim != 1.0:\n",
    "            print(i,sim,smiles,smis[i])\n",
    "    smiles = smis[i]\n",
    "    \n",
    "    if len(smiles2pairs[smiles]) == 1:\n",
    "        smiles2pairs[smiles].append([ref_mol])\n",
    "    else:\n",
    "        smiles2pairs[smiles][1].append(ref_mol)\n"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 188,
   "metadata": {},
   "outputs": [],
   "source": [
    "del_smiles = []\n",
    "for smiles in smiles2pairs.keys():\n",
    "    if len(smiles2pairs[smiles][1]) < 50 or len(smiles2pairs[smiles][1]) > 500:\n",
    "        del_smiles.append(smiles)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 189,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "0"
      ]
     },
     "execution_count": 189,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "len(del_smiles)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 190,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(0.975, 0.78643715)"
      ]
     },
     "execution_count": 190,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "get_rmsd_min((smiles2pairs[smis[0]],1.25))"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  },
  {
   "cell_type": "code",
   "execution_count": 191,
   "metadata": {},
   "outputs": [
    {
     "name": "stderr",
     "output_type": "stream",
     "text": [
      "100%|██████████| 200/200 [02:06<00:00,  1.58it/s] "
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "cov mean 0.9753586931752829 med 1.0\n",
      "mat mean 0.6954147219657898 med 0.6825993657112122\n"
     ]
    },
    {
     "name": "stderr",
     "output_type": "stream",
     "text": [
      "\n"
     ]
    }
   ],
   "source": [
    "\n",
    "cov_list = []\n",
    "mat_list = []\n",
    "pool = multiprocessing.Pool()\n",
    "\n",
    "def input_args():\n",
    "    for smiles in smiles2pairs.keys():\n",
    "        yield smiles2pairs[smiles], 1.25\n",
    "\n",
    "for res in tqdm(pool.imap(get_rmsd_min, input_args(), chunksize=10), total=len(smiles2pairs)):\n",
    "    cov_list.append(res[0])\n",
    "    mat_list.append(res[1])\n",
    "print(f\"cov mean {np.mean(cov_list)} med {np.median(cov_list)}\")\n",
    "print(f\"mat mean {np.mean(mat_list)} med {np.median(mat_list)}\")\n"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  },
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "Let's evaluate rdkit.."
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 192,
   "metadata": {},
   "outputs": [],
   "source": [
    "supp = Chem.ForwardSDMolSupplier(open('drugs_processed/drugs.rdkitm.sdf','rb'))\n",
    "mol_preds = [mol for mol in supp]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 196,
   "metadata": {},
   "outputs": [],
   "source": [
    "supp = Chem.ForwardSDMolSupplier(open('drugs_processed/drugs.rdkit2.sdf','rb'))\n",
    "mol_preds2 = [mol for mol in supp]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 197,
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "1363 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1364 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1365 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1366 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1367 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1368 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1369 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1370 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1371 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1372 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1373 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1374 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1375 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1376 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1377 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1378 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1379 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1380 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1381 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1382 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1383 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1384 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1385 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1386 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1387 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1388 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1389 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1390 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1391 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1392 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1393 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1394 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1395 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1396 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1397 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1398 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1399 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1400 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1401 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1402 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1403 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1404 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1405 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1406 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1407 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1408 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1409 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1410 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1411 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "1412 0.23545210384959714 C=CCNC1=[S+]C(=[S+]c2ncccc2N([O-])[O-])N=N1 C=CCNc1nnc(Sc2ncccc2[N+](=O)[O-])s1\n",
      "2926 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2927 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2928 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2929 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2930 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2931 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2932 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2933 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2934 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2935 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2936 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2937 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2938 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2939 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2940 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2941 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2942 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2943 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2944 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2945 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2946 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2947 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2948 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2949 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2950 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2951 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2952 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2953 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2954 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2955 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2956 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2957 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2958 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2959 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2960 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2961 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2962 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2963 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2964 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2965 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2966 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2967 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2968 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2969 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2970 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2971 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2972 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2973 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2974 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2975 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "2976 0.2766761095372993 CCOc1ccc(C(=O)[NH+]=C2N=CC=[S+]2)cc1N([O-])[O-] CCOc1ccc(C(=O)Nc2nccs2)cc1[N+](=O)[O-]\n",
      "4034 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4035 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4036 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4037 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4038 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4039 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4040 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4041 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4042 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4043 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4044 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4045 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4046 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4047 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4048 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4049 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "4050 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4051 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4052 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4053 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4054 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4055 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4056 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4057 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4058 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4059 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4060 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4061 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4062 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4063 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4064 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4065 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4066 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4067 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4068 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4069 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4070 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4071 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4072 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4073 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4074 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4075 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4076 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4077 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4078 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4079 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4080 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4081 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4082 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4083 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4084 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4085 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4086 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4087 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4088 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4089 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4090 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4091 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4092 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4093 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "4094 0.24167378309137488 Cc1cc(C)n2cc(C[S+]=C3N=CC=CC3=C([O-])O)nc2n1 Cc1cc(C)n2cc(CSc3ncccc3C(=O)O)nc2n1\n",
      "7956 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7957 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7958 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7959 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7960 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7961 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7962 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7963 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7964 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7965 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7966 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7967 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7968 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7969 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7970 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7971 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7972 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7973 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7974 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7975 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7976 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7977 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7978 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7979 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7980 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7981 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7982 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7983 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7984 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7985 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7986 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7987 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7988 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7989 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7990 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7991 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7992 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7993 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7994 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7995 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7996 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7997 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7998 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "7999 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8000 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8001 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8002 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8003 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8004 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8005 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8006 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8007 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8008 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8009 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8010 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8011 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8012 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8013 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8014 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8015 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8016 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8017 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8018 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8019 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8020 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8021 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8022 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8023 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8024 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8025 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8026 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8027 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8028 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8029 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8030 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8031 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8032 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8033 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8034 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8035 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8036 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8037 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8038 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8039 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n",
      "8040 0.2704447632711621 CC(=O)N1CCN(C(=O)CCc2nc3[s+]c4c(c-3c([O-])[nH]2)CCCC4)CC1 CC(=O)N1CCN(C(=O)CCc2nc3sc4c(c3c(=O)[nH]2)CCCC4)CC1\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "10007 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10008 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10009 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10010 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10011 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10012 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10013 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10014 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10015 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10016 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10017 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10018 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10019 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10020 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10021 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10022 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10023 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10024 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10025 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10026 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10027 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10028 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10029 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10030 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10031 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10032 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10033 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10034 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10035 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10036 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10037 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10038 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10039 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10040 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10041 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10042 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10043 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10044 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10045 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10046 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10047 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10048 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10049 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10050 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10051 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10052 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10053 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10054 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10055 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10056 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10057 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10058 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10059 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10060 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10061 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10062 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10063 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10064 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10065 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10066 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10067 0.21643109540636044 CC1=CC(=C([O-])NCCCn2ccnc2)[S+]=C1c1ccccc1 Cc1cc(C(=O)NCCCn2ccnc2)sc1-c1ccccc1\n",
      "10596 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10597 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10598 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10600 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10640 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n",
      "10653 0.27925340990667624 O=S1(=O)CC2C(C1)[S+]1OC(C3CCCCC3)=NC1=[N+]2c1ccc(F)cc1 O=C(N=C1SC2CS(=O)(=O)CC2N1c1ccc(F)cc1)C1CCCCC1\n"
     ]
    }
   ],
   "source": [
    "smiles2pairsrd = dict()\n",
    "for i,gen_mol in enumerate(mol_preds):\n",
    "    smiles = Chem.MolToSmiles(gen_mol,isomericSmiles=False)\n",
    "    if smiles != smis[i]:\n",
    "        fp = Chem.RDKFingerprint(gen_mol)\n",
    "        sim = DataStructs.FingerprintSimilarity(fp,smifingers[i])\n",
    "        if sim != 1.0:\n",
    "            print(i,sim,smiles,smis[i])\n",
    "    smiles = smis[i]\n",
    "    if smiles not in smiles2pairsrd:\n",
    "        smiles2pairsrd[smiles] = [[gen_mol]]\n",
    "    else:\n",
    "        smiles2pairsrd[smiles][0].append(gen_mol)\n",
    "    smiles2pairsrd[smiles][0].append(mol_preds2[i])\n",
    "        \n",
    "for i,ref_mol in enumerate(mol_labels):\n",
    "    smiles = Chem.MolToSmiles(ref_mol,isomericSmiles=False)\n",
    "    if smiles != smis[i]:\n",
    "        fp = Chem.RDKFingerprint(gen_mol)\n",
    "        sim = DataStructs.FingerprintSimilarity(fp,smifingers[i])\n",
    "        if sim != 1.0:\n",
    "            print(i,sim,smiles,smis[i])\n",
    "    smiles = smis[i]\n",
    "    \n",
    "    if len(smiles2pairsrd[smiles]) == 1:\n",
    "        smiles2pairsrd[smiles].append([ref_mol])\n",
    "    else:\n",
    "        smiles2pairsrd[smiles][1].append(ref_mol)\n"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 198,
   "metadata": {},
   "outputs": [
    {
     "name": "stderr",
     "output_type": "stream",
     "text": [
      "100%|██████████| 200/200 [02:04<00:00,  1.61it/s] "
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "cov mean 0.6759354439155887 med 0.740281030444965\n",
      "mat mean 1.107517123222351 med 0.9973100423812866\n"
     ]
    },
    {
     "name": "stderr",
     "output_type": "stream",
     "text": [
      "\n"
     ]
    }
   ],
   "source": [
    "\n",
    "cov_list = []\n",
    "mat_list = []\n",
    "pool = multiprocessing.Pool()\n",
    "\n",
    "def input_args():\n",
    "    for smiles in smiles2pairsrd.keys():\n",
    "        yield smiles2pairsrd[smiles], 1.25\n",
    "\n",
    "for res in tqdm(pool.imap(get_rmsd_min, input_args(), chunksize=10), total=len(smiles2pairs)):\n",
    "    cov_list.append(res[0])\n",
    "    mat_list.append(res[1])\n",
    "print(f\"cov mean {np.mean(cov_list)} med {np.median(cov_list)}\")\n",
    "print(f\"mat mean {np.mean(mat_list)} med {np.median(mat_list)}\")"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  }
 ],
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    "name": "ipython",
    "version": 3
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   "file_extension": ".py",
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