(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid

• ChemBase ID: 179287
• Molecular Formular: C14H24O8
• Molecular Mass: 320.33556
• Monoisotopic Mass: 320.14711773
• SMILES: O1[C@@H]([C@H](O)[C@@H]([C@H]([C@H]1C(=O)O)O)O)OC(=O)C(CCC)CCC
• Canonical SMILES: CCCC(C(=O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)CCC
• InChI: InChI=1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19)/t8-,9-,10+,11-,14-/m1/s1
• InChIKey: XXKSYIHWRBBHIC-YNXVLUOKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid
• Synonyms: Valproic Acid Glucuronide; Valproic Acid β-D-Glucuronide; 1-(2-Propylpentanoate) β-D-Glucopyranuronic Acid; 1-O-Valproyl-β-D-glucopyranuronic Acid; Dipropylacetate Glucuronide; VPA-G; Valproate Glucuronide

Database IDs

• CAS Number: 60113-83-9
• PubChem SID: 164235197
• PubChem CID: 71752849

CALCULATED PROPERTIES

• Acid pKa: 3.4090018
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.2283062
• LogD (pH = 7.4): -2.549972
• Log P: 0.8506575
• Molar Refractivity: 72.5477 cm^3
• Polarizability: 29.858889 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 118-120°C

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer

DETAILS

Toronto Research Chemicals - V094760

A metabolite of Valproic acid.

REFERENCES

• Rudy, A., et al.: J. Pharmacol. Exp. Ther., 259, 1133 (1991)
• Nagai, K., et al.: J. Antimicrob. Chemother., 39, 295 (1991)
• Yamamura, N., et al.: Drug Metab. Dispos., 27, 724 (1999)