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

• ChemBase ID: 163688
• Molecular Formular: C17H31N6O11P3
• Molecular Mass: 589.37557784
• Monoisotopic Mass: 589.12972057
• SMILES: N(CC)(CC)CC.n1c([nH]c2c(c1=O)n[13cH]n2[C@H]1C=C[C@H](C1)COP(=O)(OP(=O)(OP(=O)(O)O)O)O)N
• Canonical SMILES: Nc1nc(=O)c2c([nH]1)n([13cH]n2)[C@H]1C=C[C@H](C1)COP(=O)(OP(=O)(OP(=O)(O)O)O)O.CCN(CC)CC
• InChI: InChI=1S/C11H16N5O11P3.C6H15N/c12-11-14-9-8(10(17)15-11)13-5-16(9)7-2-1-6(3-7)4-25-29(21,22)27-30(23,24)26-28(18,19)20;1-4-7(5-2)6-3/h1-2,5-7H,3-4H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,12,14,15,17);4-6H2,1-3H3/t6-,7+;/m1./s1/i5+1
• InChIKey: VOPCLDVIXTWVHC-VJCZYWNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(1S,4R)-4-[2-amino-6-oxo-6,9-dihydro(8-^1^3C)-3H-purin-9-yl]cyclopent-2-en-1-yl](^2H₂)methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid; triethylamine
• IUPAC Traditional name: ({[(1S,4R)-4-[2-amino-6-oxo(8-^1^3C)-3H-purin-9-yl]cyclopent-2-en-1-yl](^2H₂)methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid; triethylamine
• Synonyms: rel-P-[[(1R,4S)-4-(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl] Ester-13C,d2 Triphosphoric Acid Triethylamine Salt; cis-(±)-P-[[4-(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl] Ester-13C,d2 Triphosphoric Acid Triethylamine Salt; (±)-Carbovir-13C,d2 Triphosphate Triethylamine Salt; Carbovir-13C,d2 Triphosphate Triethylamine Salt

Database IDs

• PubChem SID: 162257823
• PubChem CID: 71314520

CALCULATED PROPERTIES

• Acid pKa: 0.893373
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -7.9673886
• LogD (pH = 7.4): -8.796755
• Log P: -3.0765061
• Molar Refractivity: 98.8829 cm^3
• Polarizability: 37.945206 Å^3
• Polar Surface Area: 245.12 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C177757

A labelled active metabolite of Abacavir (A104990) used to study the molecular mechanism of inhibition and drug resistance for HIV-1 reverse transcriptase.

REFERENCES

• Ray, A.S. et al.: Biochem., 41, 5150 (2002)
• Goicochea, M. et al.: J. Clin. Pharmacol., 50, 968 (2002)
• Hawkins, T. et al.: JAIDS, J. Acq. Imm. Defic. Synd., 39, 406 (2002)