prop-2-en-1-yl (3S,5S,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylate

• ChemBase ID: 179289
• Molecular Formular: C17H28O8
• Molecular Mass: 360.39942
• Monoisotopic Mass: 360.17841786
• SMILES: O1[C@H]([C@H](O)C([C@@H](C1C(=O)OCC=C)O)O)OC(=O)C(CCC)CCC
• Canonical SMILES: C=CCOC(=O)C1O[C@@H](OC(=O)C(CCC)CCC)[C@@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C17H28O8/c1-4-7-10(8-5-2)15(21)25-17-13(20)11(18)12(19)14(24-17)16(22)23-9-6-3/h6,10-14,17-20H,3-5,7-9H2,1-2H3/t11?,12-,13-,14?,17-/m0/s1
• InChIKey: UEAJQCGOZOSZBC-SGJWWCBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl (3S,5S,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylate
• IUPAC Traditional name: prop-2-en-1-yl (3S,5S,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylate
• Synonyms: Valproic Acid β-D-Glucuronide Allyl Ester

Database IDs

• PubChem SID: 164235199
• PubChem CID: 71752851

CALCULATED PROPERTIES

• Acid pKa: 12.161994
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.7278013
• LogD (pH = 7.4): 1.7277939
• Log P: 1.7278014
• Molar Refractivity: 86.4795 cm^3
• Polarizability: 35.301834 Å^3
• Polar Surface Area: 122.52 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DCM; DMSO; Methanol,
• Apperance: Yellow Oil

DETAILS

Toronto Research Chemicals - V094780

A derivative of Valproic acid β-D-glucuronide.

REFERENCES

• Wong, H., et al.: Drug Metab. Dispos., 35, 1380 (2007)