2-amino-9-[(1R,3R)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 168017
• Molecular Formular: C12H15N5O3
• Molecular Mass: 277.2792
• Monoisotopic Mass: 277.11748937
• SMILES: C1C([C@H](C(=C)[C@@H]1n1c2c(c(=O)[nH]c(n2)N)nc1)CO)O
• Canonical SMILES: OC[C@@H]1C(O)C[C@H](C1=C)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7+,8?/m0/s1
• InChIKey: QDGZDCVAUDNJFG-KJFJCRTCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(1R,3R)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(1R,3R)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
• Synonyms: 2-Amino-1,9-dihydro-9-[(1R,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one; Entecavir Isomer Impurity 3; (1’R,3’R,4’S)-Entecavir Isomer; 1'-epi-Entecavir

Database IDs

• PubChem SID: 162262149
• PubChem CID: 71316340

CALCULATED PROPERTIES

• Acid pKa: 10.16698
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.9623985
• LogD (pH = 7.4): -1.9629238
• Log P: -1.96227
• Molar Refractivity: 71.4342 cm^3
• Polarizability: 26.239368 Å^3
• Polar Surface Area: 125.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E558920

An epimeric impurity of the antiviral drug Entecavir (E558900).