[(1S,4R)-4-(2-amino-6-{[(2,2,3,3-2H4)cyclopropyl]amino}-9H-purin-9-yl)cyclopent-2-en-1-yl]methanol

• ChemBase ID: 158805
• 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+/m1/s1
• InChIKey: MCGSCOLBFJQGHM-SCZZXKLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,4R)-4-(2-amino-6-{[(2,2,3,3-^2H₄)cyclopropyl]amino}-9H-purin-9-yl)cyclopent-2-en-1-yl]methanol
• IUPAC Traditional name: [(1S,4R)-4-{2-amino-6-[(2,2,3,3-^2H₄)cyclopropylamino]purin-9-yl}cyclopent-2-en-1-yl]methanol
• Synonyms: (1S,4R)-4-[2-Amino-6-(cyclopropylamino-d4)-9H-purin-9-yl]-2-cyclopentene-1-methanol; (1S-cis)-4-[2-Amino-6-(cyclopropylamino-d4)-9H-purin-9-yl]-2-cyclopentene-1-methanol; 1592U89-d4; ABC-d4; Abacavir-d4

Database IDs

• PubChem SID: 162252940
• PubChem CID: 46779835

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: 29.981073 Å^3
• Polar Surface Area: 101.88 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 84-89°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A105002

A labelled nucleoside reverse transcriptase inhibitor (NRTI).

REFERENCES

• Daluge, S.M., et al.: Antimicrob. Ag. Chemother., 41, 1082 (1997)
• Foster, R.H., et al.: Drugs, 55, 729 (1997)
• Staszewski, S., et al.: J. Am. Med. Assoc., 285, 1155 (1997)