Incorrect InChI Annotations

User ab23579928

27-08-2015 15:08:51

For the molecule "Triciribine" the provided InChI = 


1/C13H16N6O4/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(22)8(21)6(3-20)23-13/h2,4,6,8-9,13,20-22H,3H2,1H3,(H2,14,17)


 


However, when I search this InChI I receive a different molecule.


 


The SMILES code for this molecule spits out the correct structure:


CN1N=C(N)C2=CN(C3OC(CO)C(O)C3O)C3=NC=NC1=C23


 


Please advise on whether this is an issue of the InChI code, or how Chemicalize is reading this code. I have many stored InChI values for molecules, just want to be sure I can use ChemAxon to go through the list!


 


Thanks,


Justin

ChemAxon e7b9408ca1

28-08-2015 09:09:47

Where do you search for this InChI, and what do you find?


A google search of this InChI finds several pages, most of which list Triciribine as one of its names.


That said, it does happen that various sources interpret the same common name with some (usually small) differences. But I do think the InChI and the SMILES you included do represent exactly the same structure.

User ab23579928

28-08-2015 11:35:45

Sorry, I searched for Triciribine on Chemicalize, then took the InChI provided there and plugged it back in to the chemicalize search bar and it spit out a new structure. Chemicalize is using ChemAxon so I guess they direct their technical inquiries here?

ChemAxon e7b9408ca1

31-08-2015 11:30:19

There seems to be indeed two structures named as Triciribine by various sources:


CN1N=C(N)C2=CN(C3OC(CO)C(O)C3O)C3=NC=NC1=C23


CN1NC(=N)C2=CN(C3OC(CO)C(O)C3O)C3=NC=NC1=C23


They are tautomers. InChI by default represents both in exactly the same way, only non-standard InChI can assign different representations to tautomers. See http://www.inchi-trust.org/technical-faq/#6.1


I think this means that if you want to distinguish tautomers, you should not use standard InChI, but for instance SMILES.