Showing metabocard for 4-Hydroxybutyric acid (BMDB0000710)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:17 UTC
Update Date2020-06-04 20:23:42 UTC
BMDB IDBMDB0000710
Secondary Accession Numbers
  • BMDB00710
Metabolite Identification
Common Name4-Hydroxybutyric acid
Description4-Hydroxybutyric acid, also known as 4-hydroxybutanoate or gamma hydroxybutyrate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 4-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Hydroxybutyric acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Carboxypropoxy acidChEBI
4-Hydroxy-butyric acidChEBI
4-Hydroxyalkanoic acidChEBI
4-HydroxybutanoateChEBI
4-Hydroxybutanoic acidChEBI
4-Hydroxycarboxylic acidChEBI
Gamma Hydroxybutyric acidChEBI
gamma-Hydroxybutyric acidChEBI
GHBChEBI
Oxy-N-butyric acidChEBI
XyremChEBI
4-Hydroxy-butyrateGenerator
4-HydroxyalkanoateGenerator
4-HydroxycarboxylateGenerator
g HydroxybutyrateGenerator
g Hydroxybutyric acidGenerator
gamma HydroxybutyrateGenerator
Γ hydroxybutyrateGenerator
Γ hydroxybutyric acidGenerator
g-HydroxybutyrateGenerator
g-Hydroxybutyric acidGenerator
gamma-HydroxybutyrateGenerator
Γ-hydroxybutyrateGenerator
Γ-hydroxybutyric acidGenerator
Oxy-N-butyrateGenerator
4-HydroxybutyrateGenerator
4-Hydroxy-butanoateHMDB
4-Hydroxy-butanoic acidHMDB
4-Hydroxybutyrate sodiumHMDB
4-Hydroxybutyric acid monosodium saltHMDB
gamma-Hydroxy butyrateHMDB
gamma-Hydroxy sodium butyrateHMDB
gamma-Hydroxybutyrate sodiumHMDB
Hydroxybutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name4-hydroxybutanoic acid
Traditional Namegamma hydroxybutyric acid
CAS Registry Number591-81-1
SMILES
OCCCC(O)=O
InChI Identifier
InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
InChI KeySJZRECIVHVDYJC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Straight chain 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
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.63ALOGPS
logP-0.51ChemAxon
logS0.68ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity23.8 m³·mol⁻¹ChemAxon
Polarizability10.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000710
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022196
KNApSAcK IDNot Available
Chemspider ID9984
KEGG Compound IDC01991
BioCyc ID4-HYDROXY-BUTYRATE
BiGG IDNot Available
Wikipedia LinkOxybate
METLIN ID5678
PubChem Compound10413
PDB IDNot Available
ChEBI ID30830
References
Synthesis ReferenceTakigawa, Shinichiro; Araya, Shuzo. Process for the preparation of g-hydroxybutyric acid as a synthetic intermediate. Jpn. Kokai Tokkyo Koho (1988), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Hydroxyacid-oxoacid transhydrogenase, mitochondrial
General function:
Energy production and conversion
Specific function:
Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). L-3-hydroxybutyrate (L-3-OHB) is also a substrate for HOT when using 2-KG as hydrogen acceptor, resulting in the formation of D-2-HG (By similarity).
Gene Name:
ADHFE1
Uniprot ID:
A6QP15
Molecular weight:
50343.0