Dear Chris,
Fingerprints being lossy encodings of molecules:
it is possible that different molecules end-up
with the same fingerprint.
If you use an unfolded-counted fingerprint (instead of folded-uncounted,
usually),
this "funny" event should occur less frequently.
Another possibility might be to use a fingerprints with more bits.
Which fingerprint are you using by the way?
Regards,
F.
On 06/12/2021 01:37, Wolcott, Chris (NIH/NCI) [C] via OpenBabel-discuss
wrote:
Is it expected or is there any easy explanation why three different
smiles create the same fingerprint? Are compounds come from the same
synthetic library.
1st Compound
Canonical Smile:
O=C1N[C@H]2C[C@H](N(C2)Cc2ccncc2)C(=O)N2CCO[C@@H](C2)CN(C[C@H]2O[C@@H](C1)[C@H](O)[C@@H]2O)C(=O)C1CC1
InchiKey: FQBFZRAABMTECZ-BLZXGSKESA-N
Formula: C27H37N5O7
Mol Weight: 543.612
2nd Compound
Canonical Smile:
O=C1N[C@@H]2CN([C@@H](C2)C(=O)N2CCO[C@@H](C2)CN(C[C@H]2O[C@@H](C1)[C@H](O)[C@@H]2O)C(=O)CC(C)(C)C)Cc1ccncc1
InchiKey: MGQQDDGDXATMAK-QEHADNFDSA-N
Formula: C29H43N5O7
Mol Weight: 573.681
3rd Compound
Canonical Smile:
O=C1N[C@H]2C[C@H](N(C2)Cc2ccncc2)C(=O)N2CCO[C@@H](C2)CN(C[C@H]2O[C@@H](C1)[C@H](O)[C@@H]2O)C(=O)C
InchiKey: VCBCUIGRWFWUDB-KDTKDTIDSA-N
Formula: C25H35N5O7
Mol Weight: 517.575
The Fingerprint generated for all three compounds is the same:
8399392, 537051136, 393233, 134218496, 2415919137, 8388608,
1073741824, 805323777,
168820760, 931135619, 941393456, 1073741856, 513, 31465472,
33554432, 270532616,
1016076, 2151158792, 25698305, 2516617274, 1073983488, 2097156,
16843232, 2097152,
536875016, 0, 2097168, 1835200, 2214659584, 1065216, 16808960,
491586
Using OpenBabel 3.1.1 via the PHP extension
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