Metabolite Valproic acid β-O-glucuronide
- Name
- Valproic acid β-O-glucuronide
- Description
- Valproic acid glucuronide is the glucuronidation product of valproic acid. Valproic acid, or 2-Propylpentanoic acid, is a chemical compound that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy and bipolar disorder, but also used to treat migraine headaches and schizophrenia. In epileptics, valproic acid is used to control absence seizures, tonic-clonic seizures (grand mal), complex partial seizures, and the seizures associated with Lennox-Gastaut syndrome. Glucuronidation is a vital phase 2 metabolic (conjugative) process by which a wide range of drugs and other xenobiotics may be rendered water-soluble, detoxified and excreted. Acyl (ester) glucuronides (AGs) of carboxylic acids are potentially reactive metabolites. In particular, AGs are important phase 2 metabolites for a wide range of carboxylic acid-containing drugs. (PMID: 18201150 , 17496767 , 17496206 ).
- Structure
- Synonyms
- Not Available
- UNII
- SB05J7266C
- CAS number
- 60113-83-9
- Weight
- Average: 320.3356
Monoisotopic: 320.147117744 - Chemical Formula
- C14H24O8
- InChI Key
- XXKSYIHWRBBHIC-JVWRJRKNSA-N
- 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-/m0/s1
- IUPAC Name
- (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid
- SMILES
- CCCC(CCC)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
- Reactions
- Valproic acid Valproic acid β-O-glucuronide
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 190.4547259 predictedDarkChem Lite v0.1.0 [M-H]- 179.64125 predictedDeepCCS 1.0 (2019) [M+H]+ 192.1759259 predictedDarkChem Lite v0.1.0 [M+H]+ 182.03682 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.9016259 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.97716 predictedDeepCCS 1.0 (2019) - External Links
- Human Metabolome Database
- HMDB0000901
- ChemSpider
- 79488
- ChEBI
- 168243
- ChEMBL
- CHEMBL3526941
- ZINC
- ZINC000005509740
- Predicted Properties
Property Value Source Water Solubility 22.2 mg/mL ALOGPS logP 0.2 ALOGPS logP 0.85 Chemaxon logS -1.2 ALOGPS pKa (Strongest Acidic) 3.41 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 133.52 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 72.55 m3·mol-1 Chemaxon Polarizability 32.52 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon