epam / epam/Indigo

Bingo NoSQL similarity errors

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#634 1 comment 0 reactions 1 assignee Claimed by @mkviatkovskii View on GitHub
Indigo API ReCheck
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C++
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Description

I'm seeing a number of errors emitted by the following code. It seems odd that molecules inserted into the db would later produce errors when comparing against an input.

```
indigo.setOption('similarity-type', 'sim')
b = bingo.Bingo.loadDatabaseFile(indigo, ...)
m = load_molecule(MOL)
matcher = b.searchSim(m, 0.7, 1.0, 'sim')
while True:
try:
if not matcher.next():
break
...
except BingoException as e:
# error occurs
...
```

The failures that are thrown are as follows. The smiles/inchi corresponding to the reported bingo ID of molecules inserted into the database are given (the mol objects were created using the SMILES string for insertion into the db in this case).

```
Input: O=C(Nc1nccs1)c1cc(-c2cccnc2)nc2ccc(Br)cc12
Reported bingo ID (SMILES): [H][C@]([H]C(=O)[C@H](C)NC)(C1CCC(CC1)C(=O)NCCCCNC(=O)N2CCC(CC2)[C@@H](C(=O)N3CCC[C@H]3C(=O)NC4=C(N=C(S4)NC(=O)CCC)C5=CC=CC=C5)NC(=O)[C@H](C)NC)C(=O)N6CCC[C@H]6C(=O)NC7=C(N=C(S7)NC(=O)CCC)C8=CC=CC=C8
Reported bingo ID (inchi): InChI=1S/C65H91N14O10S2/c1-7-19-48(80)70-63-73-50(41-21-11-9-12-22-41)58(90-63)75-56(84)46-25-17-35-78(46)60(86)52(72-54(82)39(3)66-5)43-31-37-77(38-32-43)65(89)69-34-16-15-33-68-55(83)45-29-27-44(28-30-45)53(92-62(88)40(4)67-6)61(87)79-36-18-26-47(79)57(85)76-59-51(42-23-13-10-14-24-42)74-64(91-59)71-49(81)20-8-2/h9-14,21-24,39-40,43-47,52-53,66-67H,7-8,15-20,25-38H2,1-6H3,(H,68,83)(H,69,89)(H,72,82)(H,75,84)(H,76,85)(H,70,73,80)(H,71,74,81)/t39-,40-,44?,45?,46-,47-,52-,53-/m0/s1
Reported error: stereocenters: restorePyramid(): extra hydrogen on id=XXX

Input: Cc1ccccc1N1CCN(c2ccc(C(=O)NC3CC3)cn2)CC1
Reported bingo ID (SMILES): CCc1nn(-c2ccc(OC)cc2)c2c1CCN(c1ccc(/N=[N+](\[O-])c3ccc(N4CCc5c(C)nn(-c6ccc(C)cc6)c5C4=O)cc3)cc1)C2=O
Reported bingo ID (inchi): InChI=1S/C41H38N8O4/c1-5-37-36-23-25-46(41(51)39(36)48(44-37)32-18-20-34(53-4)21-19-32)29-12-8-28(9-13-29)43-49(52)33-16-14-30(15-17-33)45-24-22-35-27(3)42-47(38(35)40(45)50)31-10-6-26(2)7-11-31/h6-21H,5,22-25H2,1-4H3/b49-43-
Reported error: cis-trans: restoreSubstituents(): not a cis-trans bond on id=XXX
```

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