(2S,3S,4S,5R,6R)-6-{[(1R,3S,5S)-3-[6-amino-4-oxo(4,7a-13C2,3-15N)-1H,4H,5H-imidazo[4,5-c]pyridin-1-yl]-5-hydroxy-2-methylidenecyclopentyl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168015
• Molecular Formular: C19H24N4O9
• Molecular Mass: 455.39397857
• Monoisotopic Mass: 455.15807294
• SMILES: [nH]1c(c[13c]2c([13c]1=O)[15n]cn2[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)n1c[15n]c2[13c]1cc(N)[nH][13c]2=O
• InChI: InChI=1S/C19H24N4O9/c1-6-7(4-31-19-15(27)13(25)14(26)16(32-19)18(29)30)10(24)2-8(6)23-5-21-12-9(23)3-11(20)22-17(12)28/h3,5,7-8,10,13-16,19,24-27H,1-2,4H2,(H,29,30)(H3,20,22,28)/t7-,8-,10-,13-,14-,15+,16-,19+/m0/s1/i9+1,17+1,21+1
• InChIKey: GMQIDGQRNSPPBH-ZHOTVWESSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1R,3S,5S)-3-[6-amino-4-oxo(4,7a-^1^3C₂,3-^1^5N)-1H,4H,5H-imidazo[4,5-c]pyridin-1-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-[6-amino-4-oxo(4,7a-^1^3C₂,3-^1^5N)-5H-imidazo[4,5-c]pyridin-1-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-13C2,15N 3’’-O-β-D-Glucuronide; Entecavir-13C2,15N 3''-O-β-D-Glucuronide

Database IDs

• PubChem SID: 162262147
• PubChem CID: 71316338

CALCULATED PROPERTIES

• Acid pKa: 3.3194041
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -5.2834587
• LogD (pH = 7.4): -6.6395326
• Log P: -4.1297536
• Molar Refractivity: 114.5222 cm^3
• Polarizability: 40.90045 Å^3
• Polar Surface Area: 209.62 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E558912

A labelled 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)