(2S,3S,4S,5R,6S)-6-{[5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169597
• Molecular Formular: C21H30O9
• Molecular Mass: 426.4575
• Monoisotopic Mass: 426.18898254
• SMILES: c1cc(cc(c1C)OCCCC(C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)(C)C)C
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)C(CCCOc2cc(C)ccc2C)(C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H30O9/c1-11-6-7-12(2)13(10-11)28-9-5-8-21(3,4)20(27)30-19-16(24)14(22)15(23)17(29-19)18(25)26/h6-7,10,14-17,19,22-24H,5,8-9H2,1-4H3,(H,25,26)/t14-,15-,16+,17-,19-/m0/s1
• InChIKey: CJMNXSKEVNPQOK-LVEJAMMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoate] β-D-Glucopyranuroic Acid; Gemfibrozil Glucuronide; Gemfibrozil 1-O-β-Glucuronide

Database IDs

• CAS Number: 91683-38-4
• PubChem SID: 162263729
• PubChem CID: 88127

CALCULATED PROPERTIES

• Acid pKa: 3.4917974
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.442291
• LogD (pH = 7.4): -0.93597525
• Log P: 2.4418502
• Molar Refractivity: 104.1177 cm^3
• Polarizability: 41.734947 Å^3
• Polar Surface Area: 142.75 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 123-130°C

Safety Information

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

DETAILS

Toronto Research Chemicals - G305760

The major metabolite of Gemfibrozil.