[({[4-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)cyclopent-2-en-1-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

• ChemBase ID: 163692
• Molecular Formular: C11H15N5O8P2
• Molecular Mass: 407.213022
• Monoisotopic Mass: 407.03958573
• SMILES: n1c([nH]c2c(c1=O)ncn2C1C=CC(C1)COP(=O)(OP(=O)(O)O)O)N
• Canonical SMILES: Nc1nc(=O)c2c([nH]1)n(cn2)C1C=CC(C1)COP(=O)(OP(=O)(O)O)O
• InChI: InChI=1S/C11H15N5O8P2/c12-11-14-9-8(10(17)15-11)13-5-16(9)7-2-1-6(3-7)4-23-26(21,22)24-25(18,19)20/h1-2,5-7H,3-4H2,(H,21,22)(H2,18,19,20)(H3,12,14,15,17)
• InChIKey: LBDJPXUIKREEKI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[4-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)cyclopent-2-en-1-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: {[4-(2-amino-6-oxo-3H-purin-9-yl)cyclopent-2-en-1-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: Diphosphoric Acid rel-Mono[[(1R,4S)-4-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl] Ester Triammonium Salt; Diphosphoric Acid cis-(±)-[4-(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl Ester Triammonium Salt; rac Carbovir Diphosphate Triammonium Salt

Database IDs

• PubChem SID: 162257827
• PubChem CID: 10092783

CALCULATED PROPERTIES

• Acid pKa: 1.7364585
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -5.272756
• LogD (pH = 7.4): -5.9986362
• Log P: -1.9577281
• Molar Refractivity: 88.01 cm^3
• Polarizability: 33.16752 Å^3
• Polar Surface Area: 198.59 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C177770

Carbovir Diphosphate is a phosphorylated metabolite of the antiretroviral agent Carbovir (C177740).

REFERENCES

• Vince, R.: Nucl. Acids Symp. Ser., 25, 193 (1991)