[(1R,4S)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol

• ChemBase ID: 158808
• Molecular Formular: C14H18N6O
• Molecular Mass: 286.33232
• Monoisotopic Mass: 286.15420923
• SMILES: n1c(nc2c(c1NC1CC1)ncn2[C@@H]1C=C[C@@H](C1)CO)N
• Canonical SMILES: OC[C@H]1C=C[C@H](C1)n1cnc2c1nc(N)nc2NC1CC1
• InChI: InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m0/s1
• InChIKey: MCGSCOLBFJQGHM-WCBMZHEXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R,4S)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol
• IUPAC Traditional name: ABC
• Synonyms: (1R,4S)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol; (1R-cis)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol; (1R,4S)-Abacavir; ent-Abacavir

Database IDs

• CAS Number: 136470-79-6
• PubChem SID: 162252943
• PubChem CID: 469584

CALCULATED PROPERTIES

• Acid pKa: 15.406518
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.38658103
• LogD (pH = 7.4): 0.38677147
• Log P: 0.3867739
• Molar Refractivity: 82.6231 cm^3
• Polarizability: 29.981058 Å^3
• Polar Surface Area: 101.88 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A105015

The enatiomer of the nucleoside reverse transcriptase inhibitor (NRTI) Abacavir (A105000) with similar antiviral properties.

REFERENCES

• Hanumegowda, U., et al.: Chem. Res. Toxicol., 23, 749 (2010)
• Prasse, C., et al.: Environ. Sci. Technol., 44, 1728 (2010)