({4-[2-amino-6-oxo-6,9-dihydro(8-13C)-3H-purin-9-yl]cyclopent-2-en-1-yl}(2H2)methoxy)phosphonic acid

• ChemBase ID: 163685
• Molecular Formular: C11H14N5O5P
• Molecular Mass: 328.22577584
• Monoisotopic Mass: 328.07661004
• SMILES: n1c([nH]c2c(c1=O)n[13cH]n2C1C=CC(C1)COP(=O)(O)O)N
• Canonical SMILES: Nc1nc(=O)c2c([nH]1)n([13cH]n2)C1C=CC(C1)COP(=O)(O)O
• InChI: InChI=1S/C11H14N5O5P/c12-11-14-9-8(10(17)15-11)13-5-16(9)7-2-1-6(3-7)4-21-22(18,19)20/h1-2,5-7H,3-4H2,(H2,18,19,20)(H3,12,14,15,17)/i5+1
• InChIKey: OJDRNVIJFVCXOM-HOSYLAQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({4-[2-amino-6-oxo-6,9-dihydro(8-^1^3C)-3H-purin-9-yl]cyclopent-2-en-1-yl}(^2H₂)methoxy)phosphonic acid
• IUPAC Traditional name: {4-[2-amino-6-oxo(8-^1^3C)-3H-purin-9-yl]cyclopent-2-en-1-yl}(^2H₂)methoxyphosphonic acid
• Synonyms: rel-2-Amino-1,9-dihydro-9-[(1R,4S)-4-[(phosphonooxy)methyl]-2-cyclopenten-1-yl]-6H-purin-6-one-13C,d2; cis-(±)-2-Amino-1,9-dihydro-9-[4-[(phosphonooxy)methyl]-2-cyclopenten-1-yl]-6H-purin-6-one-13C,d2; Carbovir-13C,d2 5’-Phosphate; Carbovir-13C,d2 Monophosphate

Database IDs

• PubChem SID: 162257820
• PubChem CID: 71314518

CALCULATED PROPERTIES

• Acid pKa: 1.7174903
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.8330824
• LogD (pH = 7.4): -3.6245866
• Log P: -1.532114
• Molar Refractivity: 77.1371 cm^3
• Polarizability: 28.427666 Å^3
• Polar Surface Area: 152.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C177747

A labelled phosphorilated metabolite of the human immunodeficiency virus inhibitor Carbovir (C177740). It is converted from Abacavir 5’-phosphate by the enzyme N6-Methyl-AMP aminohydrolase.

REFERENCES

• Vince, R.: Nucl. Acids Symp. Ser., 25, 193 (1991)
• Schinkmanova, M. et al.: Biochem. Pharmacol., 71, 1370 (1991)