(2S,3S,4S,5R,6R)-6-{[4-cyano-4-(3,4-dimethoxyphenyl)-4-(propan-2-yl)butyl][2-(3,4-dimethoxyphenyl)ethyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 175736
• Molecular Formular: C32H44N2O10
• Molecular Mass: 616.69916
• Monoisotopic Mass: 616.29959562
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1C(=O)O)O)O)N(CCCC(c1ccc(c(c1)OC)OC)(C(C)C)C#N)CCc1ccc(c(c1)OC)OC
• Canonical SMILES: COc1ccc(cc1OC)CCN([C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CCCC(c1ccc(c(c1)OC)OC)(C(C)C)C#N
• InChI: InChI=1S/C32H44N2O10/c1-19(2)32(18-33,21-9-11-23(41-4)25(17-21)43-6)13-7-14-34(15-12-20-8-10-22(40-3)24(16-20)42-5)30-28(37)26(35)27(36)29(44-30)31(38)39/h8-11,16-17,19,26-30,35-37H,7,12-15H2,1-6H3,(H,38,39)/t26-,27-,28+,29-,30+,32?/m0/s1
• InChIKey: PMBMAYXZKGXGNE-OOIBDUHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[4-cyano-4-(3,4-dimethoxyphenyl)-4-(propan-2-yl)butyl][2-(3,4-dimethoxyphenyl)ethyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutyl][2-(3,4-dimethoxyphenyl)ethyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[[4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl][2-(3,4-dimethoxyphenyl)ethyl]amino]-1-deoxy-β-D-glucopyranuronic Acid; Nor Verapamil N-β-D-Glucuronide

Database IDs

• CAS Number: 126883-99-6
• PubChem SID: 164231646
• PubChem CID: 71751261

CALCULATED PROPERTIES

• H Donor: 4
• LogD (pH = 5.5): 0.22841397
• LogD (pH = 7.4): -0.18112144
• Log P: 0.23483948
• Molar Refractivity: 160.1774 cm^3
• Polarizability: 63.176777 Å^3
• Polar Surface Area: 171.17 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false
• Acid pKa: 2.920484
• H Acceptors: 12

DETAILS

Toronto Research Chemicals - N877510

A metabolite of Verapamil.

REFERENCES

• Mutlib, A., et al.: J. Pharm. Exp. Ther., 252, 539 (1990)
• Walles, M., et al.: Drug Metab. Dispos., 29, 761 (1990)
• Borlak, J., et al.: Xenobiotica, 33, 655 (1990)