ChEMBL Structure Pipeline example.ipynb

{
 "cells": [
  {
   "cell_type": "code",
   "execution_count": 24,
   "id": "8c00690f",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "2021.03.1\n",
      "1.0.0\n"
     ]
    }
   ],
   "source": [
    "from rdkit import Chem\n",
    "from rdkit.Chem import Draw\n",
    "from rdkit.Chem.Draw import IPythonConsole\n",
    "import chembl_structure_pipeline\n",
    "import rdkit\n",
    "print(rdkit.__version__)\n",
    "print(chembl_structure_pipeline.__version__)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 25,
   "id": "599d9597",
   "metadata": {},
   "outputs": [],
   "source": [
    "import gzip\n",
    "with gzip.open('/home/glandrum/T5/Data/Pubchem/Substance_000000001_000500000.sdf.gz') as inf:\n",
    "    records = []\n",
    "    record = []\n",
    "    for line in inf:\n",
    "        record.append(line)\n",
    "        if line == b'$$$$\\n':\n",
    "            records.append(b''.join(record).decode())\n",
    "            record = []\n",
    "        if len(records)>=1000:\n",
    "            break"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 27,
   "id": "872ddd6f",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "1\n",
      "  -OEChem-02062013022D\n",
      "\n",
      " 19 20  0     0  0  0  0  0  0999 V2000\n",
      "    2.6268    3.2326    0.0000 F  -1  0  0  0  0  0  0  0  0  0  0  0\n",
      "    3.6373    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    7.3937    6.0326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    0.0000    0.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    1.2124    2.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    4.8497    2.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    4.8497    4.3652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    7.3937    1.8326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    8.6061    3.9326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    9.8185    1.8326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    6.1812    2.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    6.1812    3.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    4.0268    3.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    7.3937    4.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    8.6061    2.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    4.8497    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    2.4249    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    1.2124    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "    2.4249    2.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0\n",
      "  1 13  1  0  0  0  0\n",
      "  2 16  1  0  0  0  0\n",
      "  2 17  1  0  0  0  0\n",
      "  3 14  2  0  0  0  0\n",
      "  4 18  1  0  0  0  0\n",
      "  5 19  1  0  0  0  0\n",
      "  6 11  1  0  0  0  0\n",
      "  6 13  1  0  0  0  0\n",
      "  6 16  1  0  0  0  0\n",
      "  7 12  1  0  0  0  0\n",
      "  7 13  2  0  0  0  0\n",
      "  8 11  1  0  0  0  0\n",
      "  8 15  2  0  0  0  0\n",
      "  9 14  1  0  0  0  0\n",
      "  9 15  1  0  0  0  0\n",
      " 10 15  1  0  0  0  0\n",
      " 11 12  2  0  0  0  0\n",
      " 12 14  1  0  0  0  0\n",
      " 17 18  1  0  0  0  0\n",
      " 17 19  1  0  0  0  0\n",
      "M  ISO  1   1  18\n",
      "M  END\n",
      "> <PUBCHEM_COMPOUND_ID_TYPE>\n",
      "0\n",
      "\n",
      "> <PUBCHEM_TOTAL_CHARGE>\n",
      "0\n",
      "\n",
      "> <PUBCHEM_SUBSTANCE_ID>\n",
      "1\n",
      "\n",
      "> <PUBCHEM_SUBSTANCE_VERSION>\n",
      "1\n",
      "\n",
      "> <PUBCHEM_EXT_DATASOURCE_NAME>\n",
      "MOLI\n",
      "\n",
      "> <PUBCHEM_EXT_DATASOURCE_REGID>\n",
      "MOLI000002\n",
      "\n",
      "> <PUBCHEM_SUBSTANCE_COMMENT>\n",
      "MOLI - NCI Molecular Imaging Agents\n",
      "FGCV\n",
      "\n",
      "> <PUBCHEM_SUBSTANCE_SYNONYM>\n",
      "MOLI000002\n",
      "\n",
      "> <PUBCHEM_XREF_EXT_ID>\n",
      "MOLI000002\n",
      "\n",
      "> <PUBCHEM_CID_ASSOCIATIONS>\n",
      "135398523  1\n",
      "\n",
      "> <PUBCHEM_COORDINATE_TYPE>\n",
      "1\n",
      "3\n",
      "\n",
      "$$$$\n",
      "\n"
     ]
    }
   ],
   "source": [
    "print(records[0])"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 4,
   "id": "78f2c27a",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "()"
      ]
     },
     "execution_count": 4,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "chembl_structure_pipeline.check_molblock(records[0])"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 18,
   "id": "bb7c5663",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "1 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "4 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has an atom with multiple stereo bonds'))\n",
      "5 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "7 ((7, 'InChI: Unknown element(s)'),)\n",
      "8 ((7, 'InChI: Unknown element(s)'),)\n",
      "10 ((7, 'InChI: Unknown element(s)'),)\n",
      "16 ((5, 'Mol/Inchi/RDKit stereo mismatch'),)\n",
      "17 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "18 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "19 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "20 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "21 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "22 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "23 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "24 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "30 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "31 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "34 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "36 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "37 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "38 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "39 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "40 ((7, 'InChI: Unknown element(s)'),)\n",
      "41 ((7, 'InChI: Unknown element(s)'),)\n",
      "42 ((7, 'InChI: Unknown element(s)'),)\n",
      "43 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "44 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "45 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "46 ((7, 'InChI: Unknown element(s)'),)\n",
      "47 ((7, 'InChI: Unknown element(s)'),)\n",
      "50 ((7, 'InChI: Unknown element(s)'),)\n",
      "51 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "52 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "53 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "54 ((7, 'InChI: Unknown element(s)'),)\n",
      "55 ((7, 'InChI: Unknown element(s)'),)\n",
      "57 ((6, 'InChI: Accepted unusual valence(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "58 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "62 ((2, 'InChI: Not chiral'),)\n",
      "63 ((2, 'InChI: Not chiral'),)\n",
      "67 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "69 ((7, 'InChI: Unknown element(s)'),)\n",
      "70 ((7, 'InChI: Unknown element(s)'),)\n",
      "71 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "74 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "75 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "78 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "82 ((7, 'InChI: Unknown element(s)'),)\n",
      "83 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "85 ((2, 'molecule has a stereo bond in a ring'),)\n",
      "86 ((2, 'molecule has a stereo bond in a ring'),)\n",
      "87 ((6, 'InChI: Accepted unusual valence(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has an atom with multiple stereo bonds'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "88 ((6, 'InChI: Accepted unusual valence(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has an atom with multiple stereo bonds'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "91 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "92 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "93 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "94 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "95 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "96 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "97 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "98 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "99 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "100 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "101 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "102 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "103 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "104 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "105 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "106 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "108 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "109 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "110 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "111 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "112 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "113 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "115 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "116 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "118 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "119 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "120 ((2, 'InChI: Not chiral'),)\n",
      "121 ((2, 'molecule has a stereo bond in a ring'),)\n",
      "122 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "123 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "124 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "130 ((7, 'InChI: Unknown element(s)'),)\n",
      "131 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "132 ((2, 'InChI: Not chiral'),)\n",
      "133 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "134 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "135 ((2, 'InChI: Not chiral'),)\n",
      "139 ((2, 'InChI: Not chiral'),)\n",
      "140 ((7, 'InChI: Unknown element(s)'),)\n",
      "142 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "143 ((7, 'InChI: Unknown element(s)'),)\n",
      "144 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "145 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "146 ((7, 'InChI: Unknown element(s)'),)\n",
      "147 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "148 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "150 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "151 ((7, 'InChI: Unknown element(s)'),)\n",
      "152 ((2, 'InChI: Not chiral'),)\n",
      "153 ((7, 'InChI: Unknown element(s)'),)\n",
      "154 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "155 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "156 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "157 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "167 ((2, 'InChI: Charges were rearranged'),)\n",
      "168 ((2, 'InChI: Charges were rearranged'),)\n",
      "170 ((2, 'InChI: Charges were rearranged'),)\n",
      "171 ((2, 'InChI: Charges were rearranged'),)\n",
      "183 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "184 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "185 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "187 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "188 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "189 ((2, 'InChI: Not chiral'),)\n",
      "190 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "191 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'molecule has an atom with multiple stereo bonds'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "208 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "209 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "211 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "213 ((2, 'molecule has a stereo bond in a ring'), (2, 'InChI: Not chiral'))\n",
      "215 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "216 ((2, 'InChI: Not chiral'),)\n",
      "217 ((2, 'InChI: Not chiral'),)\n",
      "219 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "222 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "223 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "224 ((2, 'InChI: Not chiral'),)\n",
      "225 ((2, 'InChI: Not chiral'),)\n",
      "226 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has an stereo bond to a stereocenter'))\n",
      "227 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has an stereo bond to a stereocenter'))\n",
      "228 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "237 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "238 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "239 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "240 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "241 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "242 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "243 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "244 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "245 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "246 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "247 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "248 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "249 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "257 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "259 ((2, 'InChI: Not chiral'),)\n",
      "261 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "262 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "265 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "266 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "267 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "268 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "271 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "272 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "273 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "278 ((6, 'InChI: Accepted unusual valence(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "279 ((6, 'InChI: Accepted unusual valence(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "280 ((7, 'InChI: Unknown element(s)'),)\n",
      "281 ((7, 'InChI: Unknown element(s)'),)\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "290 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "291 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "292 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "293 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "294 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "295 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "296 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "297 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "298 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "299 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "300 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "301 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "302 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "303 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "304 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "305 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "306 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "307 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "308 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "309 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "310 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "311 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "312 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "313 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "314 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "315 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "316 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "317 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "318 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "319 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "320 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "321 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "322 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "323 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "324 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "325 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "326 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "327 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "328 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "329 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "330 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "331 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "332 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "335 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Metal was disconnected'))\n",
      "336 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "337 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "338 ((7, 'InChI: Unknown element(s)'),)\n",
      "339 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "341 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "342 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "345 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'molecule has a stereo bond in a ring'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "346 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'molecule has a stereo bond in a ring'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "347 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'molecule has a stereo bond in a ring'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "351 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "352 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "354 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "355 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "356 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "357 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "358 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "360 ((2, 'InChI: Charges were rearranged'),)\n",
      "361 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "362 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'), (2, 'InChI: Charges were rearranged'))\n",
      "364 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "365 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "366 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "367 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "368 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "369 ((7, 'InChI: Unknown element(s)'),)\n",
      "370 ((7, 'InChI: Unknown element(s)'),)\n",
      "371 ((7, 'InChI: Unknown element(s)'),)\n",
      "372 ((7, 'InChI: Unknown element(s)'),)\n",
      "373 ((7, 'InChI: Unknown element(s)'),)\n",
      "376 ((7, 'InChI: Unknown element(s)'),)\n",
      "377 ((7, 'InChI: Unknown element(s)'),)\n",
      "378 ((7, 'InChI: Unknown element(s)'),)\n",
      "379 ((7, 'InChI: Unknown element(s)'),)\n",
      "380 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "381 ((7, 'InChI: Unknown element(s)'),)\n",
      "382 ((7, 'InChI: Unknown element(s)'),)\n",
      "383 ((7, 'InChI: Unknown element(s)'),)\n",
      "384 ((7, 'InChI: Unknown element(s)'), (5, 'Mol/Inchi/RDKit stereo mismatch'))\n",
      "385 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "386 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "387 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'), (2, 'InChI: Charges were rearranged'))\n",
      "388 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "389 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "390 ((7, 'InChI: Unknown element(s)'),)\n",
      "391 ((7, 'InChI: Unknown element(s)'),)\n",
      "392 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "393 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "394 ((7, 'InChI: Unknown element(s)'),)\n",
      "395 ((7, 'InChI: Unknown element(s)'),)\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "396 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "398 ((7, 'InChI: Unknown element(s)'),)\n",
      "399 ((7, 'InChI: Unknown element(s)'),)\n",
      "400 ((7, 'InChI: Unknown element(s)'),)\n",
      "401 ((7, 'InChI: Unknown element(s)'),)\n",
      "402 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'))\n",
      "403 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "404 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "405 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "406 ((7, 'InChI: Unknown element(s)'),)\n",
      "407 ((7, 'InChI: Unknown element(s)'),)\n",
      "408 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "409 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "410 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "411 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "412 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "413 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has a stereo bond in a ring'))\n",
      "416 ((7, 'InChI: Unknown element(s)'),)\n",
      "417 ((7, 'InChI: Unknown element(s)'),)\n",
      "418 ((7, 'InChI: Unknown element(s)'),)\n",
      "419 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'))\n",
      "420 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "421 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "422 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "423 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "424 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "425 ((7, 'InChI: Unknown element(s)'),)\n",
      "426 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "427 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "428 ((7, 'InChI: Unknown element(s)'),)\n",
      "429 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "430 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "431 ((7, 'InChI: Unknown element(s)'),)\n",
      "432 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "434 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "435 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "436 ((2, 'InChI: Not chiral'),)\n",
      "438 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "439 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "440 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "441 ((7, 'InChI: Unknown element(s)'),)\n",
      "442 ((7, 'InChI: Unknown element(s)'),)\n",
      "443 ((7, 'InChI: Unknown element(s)'),)\n",
      "447 ((6, 'molecule has a radical that is not found in the known list'),)\n",
      "449 ((2, 'InChI: Not chiral'),)\n",
      "452 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "455 ((2, 'InChI: Not chiral'),)\n",
      "456 ((2, 'InChI: Not chiral'),)\n",
      "457 ((2, 'InChI: Not chiral'),)\n",
      "458 ((2, 'InChI: Not chiral'),)\n",
      "459 ((2, 'InChI: Not chiral'),)\n",
      "460 ((2, 'InChI: Not chiral'),)\n",
      "461 ((2, 'InChI: Not chiral'),)\n",
      "462 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "463 ((2, 'InChI: Not chiral'),)\n",
      "464 ((2, 'InChI: Not chiral'),)\n",
      "465 ((2, 'InChI: Not chiral'),)\n",
      "466 ((2, 'InChI: Not chiral'),)\n",
      "467 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "468 ((2, 'InChI: Not chiral'),)\n",
      "469 ((2, 'InChI: Not chiral'),)\n",
      "470 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "471 ((7, 'InChI: Unknown element(s)'),)\n",
      "472 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "476 ((2, 'InChI: Charges were rearranged'),)\n",
      "477 ((7, 'InChI: Unknown element(s)'),)\n",
      "478 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "479 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "481 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "482 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "483 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "484 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "485 ((7, 'InChI: Unknown element(s)'),)\n",
      "487 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "488 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "489 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "490 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "491 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "492 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "495 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "496 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "497 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "498 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "499 ((7, 'InChI: Unknown element(s)'),)\n",
      "500 ((7, 'InChI: Unknown element(s)'),)\n",
      "501 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "502 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "503 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "504 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "505 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "506 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "507 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "508 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "509 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "510 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "511 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "512 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "513 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "514 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "515 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "516 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "517 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "518 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "519 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "520 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "521 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "523 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "524 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "526 ((2, 'InChI: Not chiral'),)\n",
      "527 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "528 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "534 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "535 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "536 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "543 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "544 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "545 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "546 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "547 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Charges were rearranged'))\n",
      "551 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "552 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "553 ((6, 'molecule has a radical that is not found in the known list'), (2, 'InChI: Proton(s) added/removed'))\n",
      "554 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "555 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "556 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "557 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "558 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "559 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "560 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "561 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "562 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "563 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "564 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "566 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "567 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "568 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "569 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "570 ((2, 'InChI: Not chiral'),)\n",
      "580 ((2, 'molecule has an stereo bond to a stereocenter'),)\n",
      "584 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "588 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "589 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "590 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "591 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'))\n",
      "592 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'))\n",
      "602 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "603 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "607 ((7, 'InChI: Unknown element(s)'),)\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "610 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "611 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "612 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "614 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "615 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "619 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "622 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "623 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "624 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "625 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "626 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "627 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "628 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "629 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'molecule has a stereo bond in a ring'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "630 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "631 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "632 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "633 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "634 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "635 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "638 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "639 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "640 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "641 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "642 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "643 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "644 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "645 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "646 ((7, 'InChI: Unknown element(s)'),)\n",
      "647 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "648 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "649 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "650 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "651 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "652 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "653 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "654 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "655 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "656 ((7, 'InChI: Unknown element(s)'),)\n",
      "657 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "658 ((7, 'InChI: Unknown element(s)'),)\n",
      "659 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "660 ((7, 'InChI: Unknown element(s)'),)\n",
      "661 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'), (2, 'InChI: Charges were rearranged'))\n",
      "662 ((7, 'InChI: Unknown element(s)'),)\n",
      "663 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "664 ((7, 'InChI: Unknown element(s)'),)\n",
      "665 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "666 ((7, 'InChI: Unknown element(s)'),)\n",
      "667 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "668 ((7, 'InChI: Unknown element(s)'),)\n",
      "669 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "670 ((7, 'InChI: Unknown element(s)'),)\n",
      "671 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "672 ((7, 'InChI: Unknown element(s)'),)\n",
      "673 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "674 ((7, 'InChI: Unknown element(s)'),)\n",
      "680 ((7, 'InChI: Unknown element(s)'),)\n",
      "681 ((7, 'InChI: Unknown element(s)'),)\n",
      "682 ((7, 'InChI: Unknown element(s)'),)\n",
      "683 ((7, 'InChI: Unknown element(s)'),)\n",
      "684 ((7, 'InChI: Unknown element(s)'),)\n",
      "685 ((7, 'InChI: Unknown element(s)'),)\n",
      "686 ((7, 'InChI: Unknown element(s)'),)\n",
      "687 ((7, 'InChI: Unknown element(s)'),)\n",
      "688 ((7, 'InChI: Unknown element(s)'),)\n",
      "689 ((7, 'InChI: Unknown element(s)'),)\n",
      "690 ((7, 'InChI: Unknown element(s)'),)\n",
      "691 ((7, 'InChI: Unknown element(s)'),)\n",
      "692 ((7, 'InChI: Unknown element(s)'),)\n",
      "693 ((7, 'InChI: Unknown element(s)'),)\n",
      "694 ((7, 'InChI: Unknown element(s)'),)\n",
      "695 ((7, 'InChI: Unknown element(s)'),)\n",
      "696 ((7, 'InChI: Unknown element(s)'),)\n",
      "697 ((7, 'InChI: Unknown element(s)'),)\n",
      "698 ((7, 'InChI: Unknown element(s)'),)\n",
      "699 ((7, 'InChI: Unknown element(s)'),)\n",
      "700 ((7, 'InChI: Unknown element(s)'),)\n",
      "701 ((7, 'InChI: Unknown element(s)'),)\n",
      "702 ((7, 'InChI: Unknown element(s)'),)\n",
      "703 ((7, 'InChI: Unknown element(s)'),)\n",
      "704 ((7, 'InChI: Unknown element(s)'),)\n",
      "709 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "710 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "711 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "712 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "713 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "714 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "715 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "716 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "717 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "718 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "719 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "720 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "721 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'), (2, 'InChI: Charges were rearranged'))\n",
      "722 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'), (2, 'InChI: Charges were rearranged'))\n",
      "727 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "728 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "729 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "730 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "731 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "732 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "733 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "734 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "735 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "736 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "737 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "738 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "739 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "740 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "741 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "742 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "743 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "745 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "746 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "749 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "750 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "751 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "752 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "753 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "754 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "755 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "756 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "757 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "758 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "760 ((7, 'InChI: Unknown element(s)'), (6, 'molecule has six (or more) atoms with exactly the same coordinates'))\n",
      "761 ((7, 'InChI: Unknown element(s)'), (6, 'molecule has six (or more) atoms with exactly the same coordinates'))\n",
      "762 ((7, 'InChI: Unknown element(s)'), (6, 'molecule has six (or more) atoms with exactly the same coordinates'))\n",
      "763 ((7, 'InChI: Unknown element(s)'),)\n",
      "764 ((7, 'InChI: Unknown element(s)'),)\n",
      "765 ((7, 'InChI: Unknown element(s)'), (5, 'molecule has two (or more) atoms with exactly the same coordinates'))\n",
      "771 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "772 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "773 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "774 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "775 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "776 ((6, 'InChI: Accepted unusual valence(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has a stereo bond in a ring'), (2, 'InChI: Metal was disconnected'))\n",
      "777 ((6, 'molecule has a radical that is not found in the known list'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "778 ((6, 'molecule has a radical that is not found in the known list'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "779 ((6, 'molecule has a radical that is not found in the known list'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "780 ((6, 'molecule has a radical that is not found in the known list'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "781 ((6, 'molecule has a radical that is not found in the known list'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "782 ((6, 'molecule has a radical that is not found in the known list'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "783 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "785 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "786 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "787 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "788 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "789 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "790 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "791 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "792 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "793 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "794 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "795 ((2, 'InChI: Not chiral'),)\n",
      "796 ((2, 'InChI: Not chiral'),)\n",
      "797 ((2, 'InChI: Not chiral'),)\n",
      "798 ((2, 'InChI: Not chiral'),)\n",
      "799 ((2, 'InChI: Not chiral'),)\n",
      "800 ((2, 'InChI: Not chiral'),)\n",
      "801 ((2, 'InChI: Not chiral'),)\n",
      "802 ((2, 'InChI: Not chiral'),)\n",
      "803 ((2, 'InChI: Not chiral'),)\n",
      "804 ((7, 'InChI: Unknown element(s)'),)\n",
      "805 ((7, 'InChI: Unknown element(s)'),)\n",
      "806 ((7, 'InChI: Unknown element(s)'),)\n",
      "807 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "809 ((6, 'molecule has a radical that is not found in the known list'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "810 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "811 ((7, 'InChI: Unknown element(s)'),)\n",
      "812 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "813 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "815 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "818 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "821 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "823 ((2, 'InChI: Not chiral'),)\n",
      "824 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "826 ((7, 'InChI: Unknown element(s)'),)\n",
      "827 ((7, 'InChI: Unknown element(s)'),)\n",
      "829 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "831 ((2, 'InChI: Omitted undefined stereo'),)\n",
      "832 ((7, 'InChI: Unknown element(s)'),)\n",
      "836 ((7, 'InChI: Unknown element(s)'),)\n",
      "837 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "840 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "841 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "842 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "844 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "845 ((7, 'InChI: Unknown element(s)'),)\n",
      "852 ((7, 'InChI: Unknown element(s)'),)\n",
      "854 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "855 ((7, 'InChI: Unknown element(s)'),)\n",
      "856 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "858 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "860 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "867 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "868 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "869 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "870 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "871 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "872 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "873 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "874 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "881 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "882 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "883 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "884 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "885 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "886 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "887 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "888 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "889 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'), (2, 'InChI: Charges were rearranged'))\n",
      "890 ((7, 'InChI: Unknown element(s)'),)\n",
      "891 ((7, 'InChI: Unknown element(s)'),)\n",
      "892 ((7, 'InChI: Unknown element(s)'),)\n",
      "893 ((7, 'InChI: Unknown element(s)'),)\n",
      "894 ((7, 'InChI: Unknown element(s)'),)\n",
      "895 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "896 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "897 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "898 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "899 ((2, 'InChI: Not chiral'),)\n",
      "900 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "901 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "904 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "905 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n"
     ]
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "906 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "907 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "908 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has an atom with multiple stereo bonds'))\n",
      "912 ((7, 'InChI: Unknown element(s)'),)\n",
      "913 ((2, 'molecule has a stereo bond in a ring'),)\n",
      "914 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "915 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "916 ((7, 'InChI: Unknown element(s)'),)\n",
      "917 ((7, 'InChI: Unknown element(s)'),)\n",
      "918 ((7, 'InChI: Unknown element(s)'),)\n",
      "919 ((7, 'InChI: Unknown element(s)'),)\n",
      "922 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Metal was disconnected'))\n",
      "923 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "924 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "926 ((2, 'InChI: Not chiral'),)\n",
      "927 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "928 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'))\n",
      "929 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'))\n",
      "930 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "931 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "932 ((2, 'InChI: Charges were rearranged'),)\n",
      "933 ((2, 'InChI: Charges were rearranged'),)\n",
      "934 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "935 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "936 ((7, 'InChI: Unknown element(s)'),)\n",
      "937 ((7, 'InChI: Unknown element(s)'),)\n",
      "946 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "949 ((2, 'molecule has an stereo bond to a stereocenter'),)\n",
      "950 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "951 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "952 ((2, 'molecule has a stereo bond in a ring'), (2, 'InChI: Proton(s) added/removed'))\n",
      "954 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "955 ((2, 'molecule has a stereo bond in a ring'), (2, 'InChI: Omitted undefined stereo'))\n",
      "956 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "957 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "962 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Metal was disconnected'))\n",
      "963 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "964 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'), (2, 'InChI: Metal was disconnected'), (2, 'InChI: Ambiguous stereo'))\n",
      "966 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "968 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "972 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "975 ((2, 'InChI: Proton(s) added/removed'),)\n",
      "977 ((6, 'InChI: Accepted unusual valence(s)'), (2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Metal was disconnected'))\n",
      "980 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "981 ((2, 'molecule has an atom with multiple stereo bonds'),)\n",
      "982 ((2, 'InChI: Omitted undefined stereo'),)\n",
      "983 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "984 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'))\n",
      "985 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "986 ((2, 'InChI: Proton(s) added/removed'), (2, 'InChI: Not chiral'))\n",
      "987 ((7, 'InChI: Unknown element(s)'), (5, 'RDKit_Mol/InChI stereo mismatch'), (2, 'molecule has an atom with multiple stereo bonds'))\n",
      "988 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "991 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "995 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n",
      "998 ((2, 'InChI: Omitted undefined stereo'), (2, 'InChI: Not chiral'))\n"
     ]
    }
   ],
   "source": [
    "for i,record in enumerate(records):\n",
    "    res = chembl_structure_pipeline.check_molblock(record)\n",
    "    if res:\n",
    "        print(i,res)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 28,
   "id": "5b282eac",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "application/vnd.jupyter.widget-view+json": {
       "model_id": "9211e544e8ef4aaf86e5a7a6e9e2c481",
       "version_major": 2,
       "version_minor": 0
      },
      "text/plain": [
       "interactive(children=(Dropdown(description='idx', options=(0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 1…"
      ]
     },
     "metadata": {},
     "output_type": "display_data"
    }
   ],
   "source": [
    "from ipywidgets import interact,fixed\n",
    "from rdkit.Chem.Draw import rdMolDraw2D\n",
    "from IPython.display import SVG\n",
    "\n",
    "@interact(idx=range(0,len(records)),records=fixed(records))\n",
    "def show_mol(idx,records):\n",
    "    record = records[idx]\n",
    "    print(chembl_structure_pipeline.check_molblock(record))\n",
    "    m = Chem.MolFromMolBlock(record,sanitize=False)\n",
    "    m.UpdatePropertyCache()\n",
    "    Chem.GetSymmSSSR(m)\n",
    "    print(Chem.MolToSmiles(m))\n",
    "    d2d = rdMolDraw2D.MolDraw2DSVG(450,400)\n",
    "    d2d.drawOptions().prepareMolsBeforeDrawing=False\n",
    "    d2d.DrawMolecule(m)\n",
    "    d2d.FinishDrawing()\n",
    "    return SVG(d2d.GetDrawingText())"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 22,
   "id": "5a8d554e",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "application/vnd.jupyter.widget-view+json": {
       "model_id": "30cf7fad332b442bbc7ddea09db2a776",
       "version_major": 2,
       "version_minor": 0
      },
      "text/plain": [
       "interactive(children=(Dropdown(description='idx', options=(0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 1…"
      ]
     },
     "metadata": {},
     "output_type": "display_data"
    }
   ],
   "source": [
    "from ipywidgets import interact,fixed\n",
    "from rdkit.Chem.Draw import rdMolDraw2D\n",
    "from IPython.display import SVG\n",
    "from rdkit import RDLogger\n",
    "RDLogger.DisableLog('rdApp.info')\n",
    "@interact(idx=range(0,len(records)),records=fixed(records))\n",
    "def show_standardized_mol(idx,records):\n",
    "    record = records[idx]\n",
    "    checks = chembl_structure_pipeline.check_molblock(record)\n",
    "    if checks and checks[0][0]>6:\n",
    "        print(f\"Failed validation: {checks}\")\n",
    "        return None\n",
    "\n",
    "    standard_record = chembl_structure_pipeline.standardize_molblock(record)\n",
    "    standard_parent,exclude = chembl_structure_pipeline.get_parent_molblock(standard_record)\n",
    "    m1 = Chem.MolFromMolBlock(record,sanitize=False)\n",
    "    m1.UpdatePropertyCache(strict=False)\n",
    "    Chem.GetSymmSSSR(m1)\n",
    "    if exclude:\n",
    "        print(f'Excluded: {Chem.MolToSmiles(m1)}')\n",
    "        return m1\n",
    "    m2 = Chem.MolFromMolBlock(standard_record,sanitize=False)\n",
    "    m2.UpdatePropertyCache(strict=False)\n",
    "    Chem.GetSymmSSSR(m2)\n",
    "    m3 = Chem.MolFromMolBlock(standard_parent,sanitize=False)\n",
    "    m3.UpdatePropertyCache(strict=False)\n",
    "    Chem.GetSymmSSSR(m3)\n",
    "    print(Chem.MolToSmiles(m1))\n",
    "    print(Chem.MolToSmiles(m2))\n",
    "    print(Chem.MolToSmiles(m3))\n",
    "    d2d = rdMolDraw2D.MolDraw2DSVG(700,300,350,300)\n",
    "    #d2d.drawOptions().prepareMolsBeforeDrawing=False\n",
    "    d2d.DrawMolecules((m2,m3))\n",
    "    d2d.FinishDrawing()\n",
    "    return SVG(d2d.GetDrawingText())"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "id": "3351d6e6",
   "metadata": {},
   "outputs": [],
   "source": []
  }
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