(2S,3S,4S,5R,6R)-6-{[(1R,3S,5S)-3-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-5-hydroxy-2-methylidenecyclopentyl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168014
• Molecular Formular: C18H23N5O9
• Molecular Mass: 453.40332
• Monoisotopic Mass: 453.14957734
• SMILES: [nH]1c(nc2c(c1=O)ncn2[C@H]1C[C@@H]([C@H](C1=C)CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)O)N
• Canonical SMILES: O[C@H]1C[C@@H](C(=C)[C@@H]1CO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C18H23N5O9/c1-5-6(3-31-17-12(27)10(25)11(26)13(32-17)16(29)30)8(24)2-7(5)23-4-20-9-14(23)21-18(19)22-15(9)28/h4,6-8,10-13,17,24-27H,1-3H2,(H,29,30)(H3,19,21,22,28)/t6-,7-,8-,10-,11-,12+,13-,17+/m0/s1
• InChIKey: MCUVCQZONGVYQH-XLVBJRJESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1R,3S,5S)-3-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-5-hydroxy-2-methylidenecyclopentyl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(1R,3S,5S)-3-(2-amino-6-oxo-1H-purin-9-yl)-5-hydroxy-2-methylidenecyclopentyl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one 3’’-O-β-D-Glucuronide; Entecavir 3''-O-β-D-Glucuronide

Database IDs

• PubChem SID: 162262146
• PubChem CID: 71316337

CALCULATED PROPERTIES

• Acid pKa: 3.1865494
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -5.718627
• LogD (pH = 7.4): -6.864051
• Log P: -3.654098
• Molar Refractivity: 103.7149 cm^3
• Polarizability: 40.029655 Å^3
• Polar Surface Area: 221.98 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E558910

A metabolite of Entecavir (E558900).

REFERENCES

• Sweeney, M.J., et al.: Cancer Res., 31, 477 (1971)
• Conners, T.A., et al.: J. Biochem. Pharmacol., 22, 1971 (1971)