(2S,3S,4S,5R,6R)-6-{[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 158807
• Molecular Formular: C20H26N6O7
• Molecular Mass: 462.45644
• Monoisotopic Mass: 462.1862972
• SMILES: n1c(nc2c(c1NC1CC1)ncn2[C@H]1C=C[C@H](C1)CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)N
• Canonical SMILES: Nc1nc(NC2CC2)c2c(n1)n(cn2)[C@H]1C=C[C@H](C1)CO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H26N6O7/c21-20-24-16(23-9-2-3-9)11-17(25-20)26(7-22-11)10-4-1-8(5-10)6-32-19-14(29)12(27)13(28)15(33-19)18(30)31/h1,4,7-10,12-15,19,27-29H,2-3,5-6H2,(H,30,31)(H3,21,23,24,25)/t8-,10+,12+,13+,14-,15+,19-/m1/s1
• InChIKey: WGTDUQBKKUUVMK-OLMRCODSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: abacavir 5'-glucuronide
• Synonyms: [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl]methyl-β-D-Glucopyranosiduronic Acid; Abacavir 5’-Glucuronide; Abacavir 5'-β-D-Glucuronide

Database IDs

• CAS Number: 384329-76-4
• PubChem SID: 162252942
• PubChem CID: 29969962

CALCULATED PROPERTIES

• Acid pKa: 3.5011148
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -3.0742803
• LogD (pH = 7.4): -4.444883
• Log P: -1.2432767
• Molar Refractivity: 114.9038 cm^3
• Polarizability: 43.664135 Å^3
• Polar Surface Area: 198.1 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >211°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A105010

A metabolite of Abacavir (A105000).

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)