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Record Information
Version2.0
Creation Date2012-07-30 14:55:21 -0600
Update Date2015-06-03 17:21:11 -0600
Secondary Accession Numbers
  • ECMDB21338
Identification
Name:gamma-Hydroxybutyrate
DescriptionGamma-hydroxybutyrate (GHB) is also known as 4-hydroxybutanoic acid. It is a carboxylic acid with an attached alcohol (hydroxyl) group. GHB can be produced as a result of fermentation, and so is found in small quantities in some beers and wines. (Wikipedia, PMID 15939164) In E. coli, 4-hydroxybutanoate can be produced from the reduction of succinate semialdehyde by the enzyme 4-hydroxybutanoate dehydrogenase. (EcoCyc, PMID: 19372223)
Structure
Thumb
Synonyms:
  • γ-hydroxybutyrate
  • γ-hydroxybutyric acid
  • 3-Carboxypropoxy acid
  • 4-Hydroxy-Butanoate
  • 4-Hydroxy-Butanoic acid
  • 4-Hydroxy-butyrate
  • 4-Hydroxy-butyric acid
  • 4-Hydroxybutanoate
  • 4-Hydroxybutanoic acid
  • 4-Hydroxybutyrate
  • 4-Hydroxybutyrate monosodium salt
  • 4-Hydroxybutyrate sodium
  • 4-Hydroxybutyric acid
  • 4-Hydroxybutyric acid monosodium salt
  • 4-Hydroxybutyric acid sodium
  • 4-OH-but
  • g Hydroxybutyrate
  • g Hydroxybutyric acid
  • g-Hydroxy butyrate
  • g-Hydroxy butyric acid
  • g-Hydroxy sodium butyrate
  • g-Hydroxy sodium butyric acid
  • G-Hydroxybutyrate
  • g-Hydroxybutyrate sodium
  • G-Hydroxybutyric acid
  • g-Hydroxybutyric acid sodium
  • Gamma Hydroxybutyrate
  • Gamma Hydroxybutyric Acid
  • Gamma-Hydroxy butyrate
  • Gamma-Hydroxy butyric acid
  • Gamma-Hydroxy sodium butyrate
  • Gamma-Hydroxy sodium butyric acid
  • Gamma-Hydroxybutyrate
  • Gamma-Hydroxybutyrate sodium
  • Gamma-Hydroxybutyric acid
  • Gamma-Hydroxybutyric acid sodium
  • GHB
  • Hydroxybutyrate
  • Hydroxybutyric acid
  • Juice
  • Liquid Ecstasy
  • Monosodium salt
  • Oxy-N-butyrate
  • Oxy-N-butyric acid
  • Oxybate sodium
  • Oxybic acid sodium
  • Sodium g-hydroxybutyrate
  • Sodium g-hydroxybutyric acid
  • Sodium g-oxybutyrate
  • Sodium g-oxybutyric acid
  • Sodium gamma-hydroxybutyrate
  • Sodium gamma-hydroxybutyric acid
  • Sodium gamma-oxybutyrate
  • Sodium gamma-oxybutyric acid
  • Sodium oxybate
  • Sodium oxybic acid
  • Sodium γ-hydroxybutyrate
  • Sodium γ-hydroxybutyric acid
  • Sodium γ-oxybutyrate
  • Sodium γ-oxybutyric acid
  • Xyrem
  • γ Hydroxybutyrate
  • γ Hydroxybutyric acid
  • γ-Hydroxy butyrate
  • γ-Hydroxy butyric acid
  • γ-Hydroxy sodium butyrate
  • γ-Hydroxy sodium butyric acid
  • γ-Hydroxybutyrate
  • γ-Hydroxybutyrate sodium
  • γ-Hydroxybutyric acid
  • γ-Hydroxybutyric acid sodium
Chemical Formula:C4H8O3
Weight:Average: 104.1045
Monoisotopic: 104.047344122
InChI Key:SJZRECIVHVDYJC-UHFFFAOYSA-N
InChI:InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
CAS number:591-81-1
IUPAC Name:4-hydroxybutanoic acid
Traditional IUPAC Name:gamma hydroxybutyric acid
SMILES:OCCCC(O)=O
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
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility494 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0159-2920000000-131f94186a93d0aa315dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2920000000-131f94186a93d0aa315dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-7240955b6b16291cf793View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5c-9000000000-915d32c0dbd6e6d19a55View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9610000000-52e5254f6eba257ad184View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-14ii-9400000000-77378d9d837f1823ed37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0udi-0900000000-ca02549abb7c7402b481View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0udi-0900000000-942af3cd327a2dd39887View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0udi-1900000000-671c45f3bda2eabba3c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0udi-1900000000-36fabc35679210a4621aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0udi-2900000000-146b4ca6698f6c40d476View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0udi-4900000000-32e86ae76401d830a8a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0udi-8900000000-07fc17585cf5e8d2ba9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0pbi-9400000000-70777a3c6521e72b59b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0a4i-9000000000-cad0cc415c906a783cfcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0zg0-9500000000-9dfcd62aeff3ff1e731dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0pb9-9300000000-0e1b3056ef85c0fbe59dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0a4i-9200000000-144d4f05dfc0b2dbd827View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a4i-9100000000-5a807248d180fcc738eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9000000000-aeb70e18a8467ef1b4b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9000000000-50691ede3dffed6a4afbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9000000000-13adfaf490932a7c0fb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-000i-9000000000-3051dc4fe82b4abf5478View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0002-0900000000-8f691ae372d6f1d18226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-80636ab7e3cb47d4d58fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n4-9000000000-71899633e269029ab7f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-910235f5bc92bcca7469View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-8900000000-5890f0a527dd16d9ac75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9i-9200000000-241210fedf9304168090View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-21d09118dfcfcb093f8dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-d55d971a361b41564681View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Brown GK, Cromby CH, Manning NJ, Pollitt RJ: Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation. J Inherit Metab Dis. 1987;10(4):367-75. Pubmed: 3126356
  • Elliott, S., Burgess, V. (2005). "The presence of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic and non-alcoholic beverages." Forensic Sci Int 151:289-292. Pubmed: 15939164
  • Ergezinger K, Jeschke R, Frauendienst-Egger G, Korall H, Gibson KM, Schuster VH: Monitoring of 4-hydroxybutyric acid levels in body fluids during vigabatrin treatment in succinic semialdehyde dehydrogenase deficiency. Ann Neurol. 2003 Nov;54(5):686-9. Pubmed: 14595661
  • Gibson KM, Aramaki S, Sweetman L, Nyhan WL, DeVivo DC, Hodson AK, Jakobs C: Stable isotope dilution analysis of 4-hydroxybutyric acid: an accurate method for quantification in physiological fluids and the prenatal diagnosis of 4-hydroxybutyric aciduria. Biomed Environ Mass Spectrom. 1990 Feb;19(2):89-93. Pubmed: 2407302
  • Gibson KM, Baumann C, Ogier H, Rossier E, Vollmer B, Jakobs C: Pre- and postnatal diagnosis of succinic semialdehyde dehydrogenase deficiency using enzyme and metabolite assays. J Inherit Metab Dis. 1994;17(6):732-7. Pubmed: 7707697
  • Kankaanpaa A, Liukkonen R, Ariniemi K: Determination of gamma-hydroxybutyrate (GHB) and its precursors in blood and urine samples: a salting-out approach. Forensic Sci Int. 2007 Aug 6;170(2-3):133-8. Epub 2007 Jul 20. Pubmed: 17658710
  • LeBeau MA, Montgomery MA, Morris-Kukoski C, Schaff JE, Deakin A, Levine B: A comprehensive study on the variations in urinary concentrations of endogenous gamma-hydroxybutyrate (GHB). J Anal Toxicol. 2006 Mar;30(2):98-105. Pubmed: 16620539
  • Saito, N., Robert, M., Kochi, H., Matsuo, G., Kakazu, Y., Soga, T., Tomita, M. (2009). "Metabolite profiling reveals YihU as a novel hydroxybutyrate dehydrogenase for alternative succinic semialdehyde metabolism in Escherichia coli." J Biol Chem 284:16442-16451. Pubmed: 19372223
  • Shinka T, Inoue Y, Ohse M, Ito A, Ohfu M, Hirose S, Kuhara T: Rapid and sensitive detection of urinary 4-hydroxybutyric acid and its related compounds by gas chromatography-mass spectrometry in a patient with succinic semialdehyde dehydrogenase deficiency. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Aug 25;776(1):57-63. Pubmed: 12127325
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID30830
HMDB IDHMDB00710
Pubchem Compound ID10413
Kegg IDC01991
ChemSpider ID9984
WikipediaGamma-hydroxybutyrate
BioCyc ID4-HYDROXY-BUTYRATE
EcoCyc ID4-HYDROXY-BUTYRATE

Enzymes

General function:
Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:
Specific function unknown
Gene Name:
yihU
Uniprot ID:
P0A9V8
Molecular weight:
31158