(2S,3S,4S,5R,6S)-6-{[(10S)-10-acetamido-3,4,14-trimethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 165771
• Molecular Formular: C27H31NO12
• Molecular Mass: 561.53454
• Monoisotopic Mass: 561.18462544
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)OC)NC(=O)C)OC)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COc1c(O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C)OC
• InChI: InChI=1S/C27H31NO12/c1-11(29)28-15-7-5-12-9-18(39-27-22(33)20(31)21(32)25(40-27)26(34)35)23(37-3)24(38-4)19(12)13-6-8-17(36-2)16(30)10-14(13)15/h6,8-10,15,20-22,25,27,31-33H,5,7H2,1-4H3,(H,28,29)(H,34,35)/t15-,20-,21-,22+,25-,27+/m0/s1
• InChIKey: KQDLHFSBXJJZRS-BVLXLYFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(10S)-10-acetamido-3,4,14-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(10S)-10-acetamido-3,4,14-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (7S)-7-(Acetylamino)-5,6,7,9-tetrahydro-1,2,10-trimethoxy-9-oxobenzo[a]heptalen-3-yl β-D-Glucopyranosiduronic Acid; 3-Demethyl Colchicine 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 913079-71-7
• PubChem SID: 162259904
• PubChem CID: 71315384

CALCULATED PROPERTIES

• Acid pKa: 2.9421606
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -3.1471014
• LogD (pH = 7.4): -4.1128216
• Log P: -0.631699
• Molar Refractivity: 138.9051 cm^3
• Polarizability: 53.482544 Å^3
• Polar Surface Area: 190.31 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D230990

The glucuronide analogue of the 3-O-desmethyl metabolite of Colchicine (C640000).

REFERENCES

• Baratto, L. et al.: J. Mol. Cat. B. Enzym., 39, 3 (2006)