Here are the results of another 1.2 million SMILES "shuffle" tests. Each shuffle is 20 randomized versions of one SMILES (so 24 million canonicalizations total).
Most, maybe all of these are repeates of problems we've already encountered, but I thought I'd include them for completeness. I think this brings the total number of molecules I've tested to around 3 million, well over half of our database. It's hard to believe anybody really cares about some of these, but that's what we're here for! Craig http://www.emolecules.com/image?db=549&id=4647317&width=500&height=500 c12c(C3c4c(c1c...@h]3c(=O)N(C1=O)c1ncccc1)cccc4)cccc2 4647317 c12c(C3c4c(c...@h]1c3c(=O)N(C1=O)c1ncccc1)cccc4)cccc2 4647317 http://www.emolecules.com/image?db=549&id=4413024&width=500&height=500 C12N(c...@h](SC1CCCC2)CCCC3)C(=O)C 4413024 C12N(C3C(S[C@@H]1CCCC2)CCCC3)C(=O)C 4413024 http://www.emolecules.com/image?db=549&id=4417557&width=500&height=500 c1(c(cc(cc1)N1C(=O)C2[C@@H](C1=O)C1C(=C(C)C)C2C=C1)Cl)Cl 4417557 c1(c(cc(cc1)N1C(=O)[C@@H]2C(C1=O)C1C(=C(C)C)C2C=C1)Cl)Cl 4417557 http://www.emolecules.com/image?db=549&id=4417833&width=500&height=500 N1(c2ccc(cc2)F)C(=O)C2[C@@H](C1=O)C1C(=C(C)C)C2C=C1 4417833 N1(c2ccc(cc2)F)C(=O)[C@@H]2C(C1=O)C1C(=C(C)C)C2C=C1 4417833 http://www.emolecules.com/image?db=549&id=4419082&width=500&height=500 C12(c3c...@h](C1C=C3)C(=O)N(C4=O)c1c(cc(cc1C)C)C)CC2 4419082 C12(c...@h]4c(C1C=C3)C(=O)N(C4=O)c1c(cc(cc1C)C)C)CC2 4419082 http://www.emolecules.com/image?db=549&id=4419333&width=500&height=500 N1(C(=O)C2[C@@H](C1=O)C1[C@@H]3C(C2C=C1)C(=O)N(C3=O)C1CC1)C1CC1 4419333 N1(C(=O)[C@@H]2C(C1=O)C1C3[C@@H](C2C=C1)C(=O)N(C3=O)C1CC1)C1CC1 4419333 http://www.emolecules.com/image?db=549&id=4420018&width=500&height=500 c12c(C3c4c(c1c...@h]3c(=O)N(C1=O)NC(=O)c1ccc(cc1)Br)cccc4)cccc2 4420018 c12c(C3c4c(c...@h]1c3c(=O)N(C1=O)NC(=O)c1ccc(cc1)Br)cccc4)cccc2 4420018 http://www.emolecules.com/image?db=549&id=4421669&width=500&height=500 C12(c3c...@h](C1C=C3)C(=O)N(C4=O)NC(=O)c1ccc(cc1)Br)CC2 4421669 C12(c...@h]4c(C1C=C3)C(=O)N(C4=O)NC(=O)c1ccc(cc1)Br)CC2 4421669 http://www.emolecules.com/image?db=549&id=4422415&width=500&height=500 C1(=O)C2C3C(=C4C5CC6CC4CC(C5)C6)C([C@@H]2C(=O)N1c1cc(ccc1)C)C=C3 4422415 C1(=O)[...@h]2c3c(=C4C5CC6CC4CC(C5)C6)C(C2C(=O)N1c1cc(ccc1)C)C=C3 4422415 http://www.emolecules.com/image?db=549&id=5782498&width=500&height=500 C12(c...@h](O[C@@](O3)(C(O1)C(O2)C)C)C)C 5782498 [...@]12(C3C(OC(O3)(C(O1)[...@h](O2)C)C)C)C 5782498 http://www.emolecules.com/image?db=549&id=4842449&width=500&height=500 c12c(C(=O)C(=C(C1=O)s...@h]1c([...@h]([C@@H](CO1)OC(=O)C)OC(=O)C)OC(=O)C)s...@h]1[c@@H]([...@h]([C@@H](CO1)OC(=O)C)OC(=O)C)OC(=O)C)cccc2 4842449 c12c(C(=O)C(=C(C1=O)s...@h]1[c@@H]([...@h]([C@@H](CO1)OC(=O)C)OC(=O)C)OC(=O)C)s...@h]1c([...@h]([C@@H](CO1)OC(=O)C)OC(=O)C)OC(=O)C)cccc2 4842449 http://www.emolecules.com/image?db=549&id=4782286&width=500&height=500 [...@]12(CC(CN(C1)Cc1ccccc1)(CNC2)C)C 4782286 C12(c...@](CN(C1)Cc1ccccc1)(CNC2)C)C 4782286 http://www.emolecules.com/image?db=549&id=4785090&width=500&height=500 n12c(c3c(n4c(c5c1CCCC5)nc1c(c4=O)cccc1)cccc3)nc1c(c2=O)cccc1 4785090 n12c(=O)c3c(nc1c1c(n4c(c5c2cccc5)nc2c(c4=O)cccc2)cccc1)cccc3 4785090 n12c(=O)c3c(nc1c1c(n4c(c5c2cccc5)nc2c(c4=O)CCCC2)cccc1)cccc3 4785090 http://www.emolecules.com/image?db=549&id=5860502&width=500&height=500 c12=c3c(c4c(c5c(c1csc2)csc5)csc4)csc3 5860502 C12C(C3C(C4C(C5C1CSC5)CSC4)CSC3)CSC2 5860502 /tmp/babel29542_1505.smi http://www.emolecules.com/image?db=549&id=5860663&width=500&height=500 c12c3c4c5c(ccc4c4c(c3ccc1cccc2)nc1c(n4)cc2c(c1)cccc2)cccc5 5860663 c12c3c(ccc2c2c(c4c1c1c(cc4)CCCC1)nc1c(n2)cc2c(c1)cccc2)cccc3 5860663 http://www.emolecules.com/image?db=549&id=5860665&width=500&height=500 c12c3c4c(ccc3c3c(c2ccc2c1cccc2)nc1c(n3)c2c(c3c1ccc1c3cccc1)c1c(cc2)cccc1)cccc4 5860665 c12c3c4c(ccc3c3c(c2ccc2c1cccc2)nc1c(n3)c2c(c3c1ccc1c3CCCC1)c1c(cc2)cccc1)cccc4 5860665 c12c3c4c(ccc3c3c(c2ccc2c1cccc2)nc1c(n3)c2c(c3c1ccc1c3CCCC1)c1c(cc2)CCCC1)cccc4 5860665 c12c3c4c(ccc3c3c(c2ccc2c1cccc2)nc1c(n3)c2c(c3c1CCc1c3cccc1)c1c(cc2)cccc1)cccc4 5860665 c12c3c(c4c(c5c3c3c(CC5)cccc3)nc3c(n4)c4c(c5c3ccc3c5cccc3)c3c(CC4)cccc3)ccc1cccc2 5860665 c12c3c(ccc1c1c(c4c2c2c(CC4)cccc2)nc2c(n1)c1c(c4c2ccc2c4CCCC2)c2c(cc1)CCCC2)cccc3 5860665 c12c3c(ccc2c2c(c4c1c1c(cc4)CCCC1)nc1c(n2)c2c(c4c1ccc1c4CCCC1)c1c(CC2)cccc1)cccc3 5860665 c12c3c(ccc2c2c(c4c1c1c(cc4)CCCC1)nc1c(n2)c2c(c4c1CCc1c4cccc1)c1c(cc2)cccc1)cccc3 5860665 c12c3c(ccc2c2c(c4c1c1c(cc4)CCCC1)nc1c(n2)c2c(c4c1CCc1c4cccc1)c1c(cc2)CCCC1)cccc3 5860665 http://www.emolecules.com/image?db=549&id=6137697&width=500&height=500 c12=c(nn2)ssnc1S 6137697 c12c(nn2)ssnc1S 6137697 http://www.emolecules.com/image?db=549&id=5863122&width=500&height=500 C1([N+](=O)[O-])C2C[C@@h]3...@h]1c[c@H](C2)C3 5863122 C1([N+](=O)[O-])[C@@H]2C[C@@h]3cc1...@h](C2)C3 5863122 http://www.emolecules.com/image?db=549&id=5865030&width=500&height=500 c12c3c4c5c6c7c8c(ccc7ccc6ccc5ccc4ccc3ccc1cccc2)cccc8 5865030 c12c3c(ccc2ccc2c1c1c4c5c6c(ccc5ccc4ccc1cc2)CCCC6)cccc3 5865030 http://www.emolecules.com/image?db=549&id=5865292&width=500&height=500 c12c3c4c5c6c7c8c9c(ccc8ccc7ccc6ccc5ccc4ccc3ccc1cccc2)cccc9 5865292 c12c3c4c5c6c7c8c9c(CCc8ccc7ccc6ccc5ccc4ccc3ccc1cccc2)cccc9 5865292 c12c3c4c(ccc3ccc2ccc2c1c1c3c5c6c(ccc5ccc3ccc1cc2)CCCC6)CCCC4 5865292 c12c3c(ccc2ccc2c1c1c4c5c6c7c(ccc6ccc5ccc4ccc1cc2)CCCC7)cccc3 5865292 http://www.emolecules.com/image?db=549&id=5865338&width=500&height=500 C(C(N(C)C)C)(c1ccccc1)o...@h]([C@@H](N(C)C)C)(c1ccccc1)O 5865338 [...@h]([C@@H](N(C)C)C)(c1ccccc1)O.C(C(N(C)C)C)(c1ccccc1)O 5865338 http://www.emolecules.com/image?db=549&id=5865516&width=500&height=500 c12c3c4c5c6c(c7c8c9c%10c(CCc9cc(c8ccc7cc6)Br)cccc%10)ccc5ccc4c(cc3ccc1cccc2)Br 5865516 c12c3c4c5c(c6c7c8c9c(CCc8cc(c7ccc6cc5)Br)cccc9)ccc4ccc3c(cc2ccc2c1CCCC2)Br 5865516 c12c3c(ccc2cc(c2c1c1c4c(c5c6C7c8c(CCC7CC(c6ccc5cc4)Br)cccc8)ccc1cc2)Br)cccc3 5865516 http://www.emolecules.com/image?db=549&id=6215783&width=500&height=500 [Mn]12345678(C9(C7(C4(C1(C89C)C)C)C)C)C1(C5(C3(C2(C61C)C)C)C)C 6215783 [Mn]12345678(C9(C7(C6(C1(C89C)C)C)C)C)C1(C4(C3(C2(C51C)C)C)C)C 6215783 http://www.emolecules.com/image?db=549&id=8294208&width=500&height=500 C1(c2ccccc2)OC([...@h]2[c@@H](COC(O2)c2ccccc2)O)[C@@H](CO1)O 8294208 C1(c2ccccc2)O[C@@H](C2[C@@H](COC(O2)c2ccccc2)O)[C@@H](CO1)O 8294208 http://www.emolecules.com/image?db=549&id=8622926&width=500&height=500 c1(C(=O)Nc2nc[nH]n2)cc(ccc1)C.c1(C(=O)Nc2[nH]cnn2)cc(ccc1)C 8622926 c1(C(=O)Nc2[nH]cnn2)cc(ccc1)C.c1(C(=O)Nc2nc[nH]n2)cc(ccc1)C 8622926 http://www.emolecules.com/image?db=549&id=10434721&width=500&height=500 C([C@@H](C(=O)O)O)(C(=O)O)O 10434721 [...@h](C(C(=O)O)O)(C(=O)O)O 10434721 http://www.emolecules.com/image?db=549&id=11467042&width=500&height=500 [...@]12([Ce]3456789%10%11%12%13(c1c%13c%1...@h]23)([C@@]1(C6C9C8[C@@H]71)C(C)C)[C@@]1([C@@H]4[C@@H]%11C%10C51)C(C)C)C(C)C 11467042 [C@@]12([Ce]3456789%10%11%12%13(c1c%1...@h]%12[c@@H]23)([C@@]1(C6C9C8[C@@H]71)C(C)C)[C@@]1(C4C%11C%10[C@@H]51)C(C)C)C(C)C 11467042 [C@@]12([Ce]3456789%10%11%12%13([C@@H]1C%13C%12C23)([C@@]1(C6C9C8[C@@H]71)C(C)C)[C@@]1([C@@H]4[C@@H]%11C%10C51)C(C)C)C(C)C 11467042 [...@]12([Ce]3456789%10%11%12%13([...@h]1[c@@H]%13C%12C23)([C@@]1(C6C9C8[C@@H]71)C(C)C)[C@@]1(C4C%11C%10[C@@H]51)C(C)C)C(C)C 11467042 http://www.emolecules.com/image?db=549&id=11467044&width=500&height=500 [...@]12([Ce]3456789%10%11%12%13(c1c%13c%1...@h]23)([C@@]1(C6C9C8[C@@H]71)CC)[C@@]1([C@@H]4[C@@H]%11C%10C51)CC)CC 11467044 [...@]12([Ce]3456789%10%11%12%13([...@h]1[c@@H]%13C%12C23)([C@@]1(C6C9C8[C@@H]71)CC)[C@@]1(C4C%11C%10[C@@H]51)CC)CC 11467044 http://www.emolecules.com/image?db=549&id=11467050&width=500&height=500 [Hf]12345678([C@@]9(c7c4c...@h]89)C(C)C)([C@@]1([C@@H]5[C@@H]3C2C61)C(C)C)(Cl)Cl 11467050 [Hf]12345678([C@@]9([C@@H]7[C@@H]4C1C89)C(C)C)([C@@]1(c5c3c...@h]61)C(C)C)(Cl)Cl 11467050 http://www.emolecules.com/image?db=549&id=13170715&width=500&height=500 S(=O)(=O)(c1ccc(cc1)C)NN=c1c2c1cccc2 13170715 S(=O)(=O)(c1ccc(cc1)C)NN=C1C2=C1C=CC=C2 13170715 ------------------------------------------------------------------------------ Beautiful is writing same markup. 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