(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-ene-1-carboxylic acid

• ChemBase ID: 158806
• Molecular Formular: C14H16N6O2
• Molecular Mass: 300.31584
• Monoisotopic Mass: 300.13347378
• SMILES: n1c(nc2c(c1NC1CC1)ncn2[C@H]1C=C[C@H](C1)C(=O)O)N
• Canonical SMILES: OC(=O)[C@@H]1C=C[C@@H](C1)n1cnc2c1nc(N)nc2NC1CC1
• InChI: InChI=1S/C14H16N6O2/c15-14-18-11(17-8-2-3-8)10-12(19-14)20(6-16-10)9-4-1-7(5-9)13(21)22/h1,4,6-9H,2-3,5H2,(H,21,22)(H3,15,17,18,19)/t7-,9+/m1/s1
• InChIKey: OCSMNHMMTKMVCP-APPZFPTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-ene-1-carboxylic acid
• IUPAC Traditional name: abacavir carboxylate
• Synonyms: (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-carboxylic Acid; 2269W; Abacavir Carboxylate

Database IDs

• CAS Number: 384380-52-3
• PubChem SID: 162252941
• PubChem CID: 56927907

CALCULATED PROPERTIES

• Acid pKa: 3.785553
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.0452863
• LogD (pH = 7.4): -2.5924559
• Log P: 0.5580281
• Molar Refractivity: 82.4627 cm^3
• Polarizability: 29.915344 Å^3
• Polar Surface Area: 118.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 208-210°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A105005

A major metabolite of Abacavir (A105000) in human urine and cerebrospinal fluid.

REFERENCES

• Hoetelmans, R., et al.: Pharm. World Sci., 19, 159 (1997)
• Beach, J., et al.: Clin. Ther., 20, 2 (1997)
• McDowell, J., et al.: Antimicrob. Agents Chemother., 43, 2855 (1997)