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
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0pds-9221000000-c4a088ea62b38f27162d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000b-9303000000-67e0df0cd8df88898589
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1609000000-5eb06e033b05af8292bc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052n-9300000000-8867a3342b6d304f30a0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004m-2910000000-1be50364d2605ce643a2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-9310000000-ee65b4bf889abf4759a7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6t-9710000000-a01ff99ad96618e9b87b
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-190.4547259
predicted
DarkChem Lite v0.1.0
[M-H]-179.64125
predicted
DeepCCS 1.0 (2019)
[M+H]+192.1759259
predicted
DarkChem Lite v0.1.0
[M+H]+182.03682
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.9016259
predicted
DarkChem Lite v0.1.0
[M+Na]+187.97716
predicted
DeepCCS 1.0 (2019)
Human Metabolome Database
HMDB0000901
ChemSpider
79488
ChEBI
168243
ChEMBL
CHEMBL3526941
ZINC
ZINC000005509740
Predicted Properties
PropertyValueSource
Water Solubility22.2 mg/mLALOGPS
logP0.2ALOGPS
logP0.85Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.41Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area133.52 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity72.55 m3·mol-1Chemaxon
Polarizability32.52 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon