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Record Information
Version4.0
Creation Date2012-09-06 15:00:23 UTC
Update Date2017-09-27 08:27:27 UTC
HMDB IDHMDB0013898
Secondary Accession Numbers
  • HMDB13898
Metabolite Identification
Common Name5-Hydroxyvalproic acid
Description5-Hydroxyvalproic acid is only found in individuals that have used or taken Valproic Acid. 5-Hydroxyvalproic acid is a metabolite of Valproic Acid. 5-hydroxyvalproic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.
Structure
Thumb
Synonyms
ValueSource
2-N-Propyl-5-hydroxypentanoic acidKegg
5-OH-VPAKegg
2-N-Propyl-5-hydroxypentanoateGenerator
5-HydroxyvalproateGenerator
5-Hydroxy-valproateMeSH
Chemical FormulaC8H16O3
Average Molecular Weight160.2108
Monoisotopic Molecular Weight160.109944378
IUPAC Name5-hydroxy-2-propylpentanoic acid
Traditional Name5-OH-vpa
CAS Registry Number53660-23-4
SMILES
CCCC(CCCO)C(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-2-4-7(8(10)11)5-3-6-9/h7,9H,2-6H2,1H3,(H,10,11)
InChI KeyZIWBCJXKYKOLJK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Hydroxy fatty acid
  • Branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

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 Solubility20.7 g/LALOGPS
logP1.37ALOGPS
logP1.36ChemAxon
logS-0.89ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.18 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1900000000-ff181ae7ba65e96f29d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9700000000-b2742310d658da1dbeddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-32cfdcc6e80672ec47c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-ce6b2d6e25fc5f04cda2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066s-5900000000-589dde3bee79266f372aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9200000000-04154608ae46d4fd3508View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Valproic Acid Metabolism PathwayPw000611Pw000611 greyscalePw000611 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00061
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID119147
KEGG Compound IDC16650
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135244
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]