Showing metabocard for Gamma Hydroxybutyric Acid (BMDB0062044)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:46:21 UTC
Update Date2020-04-22 15:51:13 UTC
BMDB IDBMDB0062044
Secondary Accession Numbers
  • BMDB62044
Metabolite Identification
Common NameGamma Hydroxybutyric Acid
DescriptionGamma-Hydroxybutyric acid, also known as gamma-hydroxybutyrate or 4-hydroxybutyrate sodium, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Gamma-Hydroxybutyric acid is a drug which is used as a general anesthetic, to treat conditions such as insomnia, clinical depression, narcolepsy, and alcoholism, and to improve athletic performance. . Gamma-Hydroxybutyric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Gamma-Hydroxybutyric acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-HydroxybutanoateChEBI
gamma-HydroxybutyrateChEBI
GHBChEBI
4-Hydroxybutanoic acidGenerator
g-HydroxybutyrateGenerator
g-Hydroxybutyric acidGenerator
Γ-hydroxybutyrateGenerator
Γ-hydroxybutyric acidGenerator
g HydroxybutyrateGenerator
g Hydroxybutyric acidGenerator
gamma HydroxybutyrateGenerator, MeSH
γ hydroxybutyrateGenerator
γ hydroxybutyric acidGenerator
gamma-Hydroxybutyric acidGenerator
4-Hydroxy-butanoic acidHMDB
4-Hydroxybutyric acidHMDB
JuiceHMDB
Liquid ecstasyHMDB
Sodium oxybateHMDB, MeSH
4 Hydroxybutyrate sodiumMeSH
Sodium gamma hydroxybutyrateMeSH
Sodium gamma-hydroxybutyrateMeSH
Oxybutyrate, sodiumMeSH
Sodium oxybutyrateMeSH
SomsanitMeSH
4-Hydroxybutyrate sodiumMeSH
Oxybate sodiumMeSH
Oxybate, sodiumMeSH
XyremMeSH
Chemical FormulaC4H7O3
Average Molecular Weight103.0966
Monoisotopic Molecular Weight103.03951909
IUPAC Name4-hydroxybutanoate
Traditional Namegamma-hydroxybutyrate
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)/p-1
InChI KeySJZRECIVHVDYJC-UHFFFAOYSA-M
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
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.11e+02 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.6ALOGPS
logP-0.51ChemAxon
logS0.77ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.64 m³·mol⁻¹ChemAxon
Polarizability9.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-0f79-9300000000-c9f15c4e690d7ce0c483View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-60d9eb4fee2765103cc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2778628ee4808ab8a9a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-9200000000-c2c3e382f03ed27a420cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kgc-9100000000-76b2d87492ff88ac0cd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-9000000000-463520cec00f6f78dfbeView in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0015507
DrugBank IDDB01440
Phenol Explorer Compound IDNot Available
FooDB IDFDB030502
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Hydroxybutyric acid
METLIN IDNot Available
PubChem Compound3037032
PDB IDNot Available
ChEBI ID16724
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]