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

• ChemBase ID: 166161
• Molecular Formular: C11H14N6O
• Molecular Mass: 246.26846
• Monoisotopic Mass: 246.1229091
• SMILES: n1c(nc2c(c1N)ncn2[C@H]1C=C[C@H](C1)CO)N
• Canonical SMILES: OC[C@@H]1C=C[C@@H](C1)n1cnc2c1nc(N)nc2N
• InChI: InChI=1S/C11H14N6O/c12-9-8-10(16-11(13)15-9)17(5-14-8)7-2-1-6(3-7)4-18/h1-2,5-7,18H,3-4H2,(H4,12,13,15,16)/t6-,7+/m1/s1
• InChIKey: ZKJUXHDSLJYKED-RQJHMYQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,4R)-4-(2,6-diamino-9H-purin-9-yl)cyclopent-2-en-1-yl]methanol
• IUPAC Traditional name: [(1S,4R)-4-(2,6-diaminopurin-9-yl)cyclopent-2-en-1-yl]methanol
• Synonyms: (1S,4R)-4-(2,6-Diamino-9H-purin-9-yl)-2-cyclopentene-1-methanol; Descyclopropyl Abacavir

Database IDs

• CAS Number: 124752-25-6
• PubChem SID: 162260294
• PubChem CID: 130245

CALCULATED PROPERTIES

• Acid pKa: 15.41305
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.38073215
• LogD (pH = 7.4): -0.38049772
• Log P: -0.3804947
• Molar Refractivity: 69.9185 cm^3
• Polarizability: 25.195038 Å^3
• Polar Surface Area: 115.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 180-182°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D288865

Abacavir Intermediate.

REFERENCES

• Zimmerman, C., et al.: Pharm. Res., 13, 1417 (1996)
• Ando, T., et al.: Bioorg. Med. Chem., 6, 3809 (1996)