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

• ChemBase ID: 158803
• Molecular Formular: C14H19ClN6O
• Molecular Mass: 322.79326
• Monoisotopic Mass: 322.13088694
• SMILES: Cl.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.Cl
• InChI: InChI=1S/C14H18N6O.ClH/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);1H/t8-,10-;/m0./s1
• InChIKey: QXNOPHSMRJNHHG-GNAZCLTHSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162252938
• PubChem CID: 71312693

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

DETAILS

Toronto Research Chemicals - A104997

The labelled trans-isomer of Abacavir (A104990), a nucleoside reverse transcriptase inhibitor (NRTI). Abacavir USP impurity.

REFERENCES

• Foster, R., et al.: Drugs, 55, 729 (1998)
• Hanumegowda, U., et al.: Chem. Res. Toxicol., 23, 749 (1998)
• Prasse, C., et al.: Environ. Sci. Technol., 44, 1728 (1998)