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

• ChemBase ID: 153280
• Molecular Formular: C14H20N6O5S
• Molecular Mass: 384.4108
• Monoisotopic Mass: 384.12158877
• SMILES: c1nc2c(nc(nc2n1[C@@H]1C[C@@H](C=C1)CO)N)NC1CC1.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.OC[C@@H]1C=C[C@@H](C1)n1cnc2c1nc(N)nc2NC1CC1
• InChI: InChI=1S/C14H18N6O.H2O4S/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;1-5(2,3)4/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19);(H2,1,2,3,4)/t8-,10+;/m1./s1
• InChIKey: MBFKCGGQTYQTLR-SCYNACPDSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 188062-50-2
• MDL Number: MFCD04112763
• PubChem SID: 162247419
• PubChem CID: 9843042

CALCULATED PROPERTIES

• Acid pKa: 15.406518
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.3435351
• LogD (pH = 7.4): 0.38620126
• 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

PROPERTIES

Physical Property

• Solubility: H2O: ≥17 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H18N6O · 0.5 H2SO4

DETAILS

Sigma Aldrich - SML0089

Biochem/physiol Actions
Abacavir sulfate is a Nucleoside analog reverse transcriptase inhibitor (NRTI); guanosine analog used to treat HIV and AIDS.