2-amino-9-{4-[hydroxy(2H2)methyl]cyclopent-2-en-1-yl}-6,9-dihydro(8-13C)-3H-purin-6-one

• ChemBase ID: 163683
• Molecular Formular: C11H13N5O2
• Molecular Mass: 248.24587484
• Monoisotopic Mass: 248.11027952
• SMILES: C1=CC(CC1CO)n1c2c(n[13cH]1)c(=O)nc([nH]2)N
• Canonical SMILES: Nc1nc(=O)c2c([nH]1)n(C1CC(C=C1)CO)[13cH]n2
• InChI: InChI=1S/C11H13N5O2/c12-11-14-9-8(10(18)15-11)13-5-16(9)7-2-1-6(3-7)4-17/h1-2,5-7,17H,3-4H2,(H3,12,14,15,18)/i5+1
• InChIKey: XSSYCIGJYCVRRK-HOSYLAQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-{4-[hydroxy(^2H₂)methyl]cyclopent-2-en-1-yl}-6,9-dihydro(8-^1^3C)-3H-purin-6-one
• IUPAC Traditional name: 2-amino-9-{4-[hydroxy(^2H₂)methyl]cyclopent-2-en-1-yl}(8-^1^3C)-3H-purin-6-one
• Synonyms: rel-2-Amino-1,9-dihydro-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-6H-purin-6-one-13C,d2; (+/-)-Carbovir-13C,d2; cis-Carbovir-13C,d2; GR 90352X-13C,d2; NSC 614846-13C,d2; Carbovir-13C,d2

Database IDs

• CAS Number: 1246816-59-0
• PubChem SID: 162257818
• PubChem CID: 71314517

CALCULATED PROPERTIES

• Acid pKa: 8.003562
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.33027697
• LogD (pH = 7.4): -0.41949734
• Log P: -0.3279983
• Molar Refractivity: 66.2642 cm^3
• Polarizability: 23.93189 Å^3
• Polar Surface Area: 105.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 266-268°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C177742

Labelled Carbovir (C177740). A nucleoside/nucleotide reverse transcriptase inhibitor (NRTI) caused mitochondrial toxicity in human hepatoma carcinoma cell.

REFERENCES

• Suo, Z., et al.: J. Biol. Chem., 273, 27250 (1998)
• Ray, A., et al.: Antimicrob. Agents Chemother., 48, 1089 (1998)
• Lynx, M., et al.: Biochem. Pharmacol., 71, 1342 (1998)