Record Information
Version1.0
Creation date2011-09-21 00:11:53 UTC
Update date2015-07-21 06:57:08 UTC
Primary IDFDB022308
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameValproic acid glucuronide
DescriptionValproic 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) [HMDB]
CAS Number60113-83-9
Structure
Thumb
Synonyms
SynonymSource
Valproate glucuronideGenerator
1-(2-propylpentanoatehmdb
1-(2-propylpentanoate) beta-D-Glucopyranuronatehmdb
1-(2-propylpentanoate) beta-D-Glucopyranuronic acidhmdb
1-(2-propylpentanoate) beta-delta-Glucopyranuronatehmdb
1-(2-propylpentanoate) beta-delta-Glucopyranuronic acidhmdb
1-(2-propylpentanoic acidhmdb
1-O-Valproyl-b-D-glucopyranuronic acidhmdb
1-O-Valproyl-beta-delta-glucopyranuronic acidhmdb
3,4,5-trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylatehmdb
3,4,5-trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acidhmdb
Dipropylacetate glucuronidehmdb
MyproateHMDB
Myproic acidHMDB
ValproateHMDB
Valproic acidHMDB
VPA-Ghmdb
VPAGhmdb
Predicted PropertiesNot Available
Chemical FormulaC14H24O8
IUPAC name
InChI IdentifierInChI=1S/C14H24O8/c1-4-5-7(6(2)3)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h6-11,14-17H,4-5H2,1-3H3,(H,18,19)/t7?,8-,9-,10+,11-,14?/m0/s1
InChI KeyHFJIBPMXGQVSGX-HGIFLAPPSA-N
Isomeric SMILES[H][C@]1(O)C(OC(=O)C(CCC)C(C)C)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]1([H])O
Average Molecular Weight320.3356
Monoisotopic Molecular Weight320.147117744
Classification
Description Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Fatty acyl
  • Oxane
  • Pyran
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Carboxylic acid
  • Polyol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID79488
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID88111
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00901
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDValproic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Beta-glucuronidaseGUSBP08236
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference