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Record Information
Version3.6
Creation Date2013-07-04 18:56:39 UTC
Update Date2016-02-11 08:12:11 UTC
HMDB IDHMDB60744
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxyvalproic acid CoA
Description3-Hydroxyvalproicd acid CoA is a metabolite of valproic acid. Valproic acid (VPA) is a chemical compound and an acid that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy, bipolar disorder, and, less commonly, major depression. It is also used to treat migraine headaches and schizophrenia. VPA is a liquid at room temperature, but it can be reacted with a base such as sodium hydroxide to form the salt sodium valproate, which is a solid. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H50N7O18P3S
Average Molecular Weight909.73
Monoisotopic Molecular Weight909.214588057
IUPAC Name(2S)-4-({[({[(2S,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-[2-({2-[(3-hydroxy-2-propylpentanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid
Traditional Name(2S)-4-[({[(2S,3R,4S,5S)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-[2-({2-[(3-hydroxy-2-propylpentanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid
CAS Registry NumberNot Available
SMILES
CCCC(C(O)CC)C(=O)SCCN=C(O)CCN=C(O)[C@@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@H]1O[C@@H]([C@@H](O)[C@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1/C29H50N7O18P3S/c1-5-7-16(17(37)6-2)28(42)58-11-10-31-19(38)8-9-32-26(41)23(40)29(3,4)13-51-57(48,49)54-56(46,47)50-12-18-22(53-55(43,44)45)21(39)27(52-18)36-15-35-20-24(30)33-14-34-25(20)36/h14-18,21-23,27,37,39-40H,5-13H2,1-4H3,(H,31,38)(H,32,41)(H,46,47)(H,48,49)(H2,30,33,34)(H2,43,44,45)/t16?,17?,18-,21-,22-,23+,27-/s2
InChI KeyInChIKey=TWESTLCGODTUDY-QREYSPMQNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-hydroxyacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.8 mg/mLALOGPS
logP0.16ALOGPS
logP-4.8ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area390.84 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity202.37 m3·mol-1ChemAxon
Polarizability85.02 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00714
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60744
Metagene LinkHMDB60744
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available