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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:21 -0600
Update Date	2015-06-03 17:21:11 -0600
Secondary Accession Numbers	ECMDB21338
Identification
Name:	gamma-Hydroxybutyrate
Description	Gamma-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9b5b7598> Close
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Hydroxy fatty acids
Alternative Parents	Short-chain hydroxy acids and derivatives Straight chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	4-hydroxy monocarboxylic acid (CHEBI:30830 ) hydroxybutyric acid (CHEBI:30830 ) Hydroxy fatty acids (LMFA01050006 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 494 g/L ALOGPS logP -0.63 ALOGPS logP -0.51 ChemAxon logS 0.68 ALOGPS pKa (Strongest Acidic) 4.44 ChemAxon pKa (Strongest Basic) -2.4 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 57.53 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 23.8 m³·mol⁻¹ ChemAxon Polarizability 10.17 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Hydrogen ion + NADH + Succinic acid semialdehyde <> gamma-Hydroxybutyrate + NAD NAD + gamma-Hydroxybutyrate <> Hydrogen ion + NADH + Succinic acid semialdehyde
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (2 TMS) splash10-0159-2920000000-131f94186a93d0aa315d View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0159-2920000000-131f94186a93d0aa315d View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-0910000000-7240955b6b16291cf793 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0a5c-9000000000-915d32c0dbd6e6d19a55 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00di-9610000000-52e5254f6eba257ad184 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - QqQ 10V, positive splash10-14ii-9400000000-77378d9d837f1823ed37 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 0V, negative splash10-0udi-0900000000-ca02549abb7c7402b481 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 1V, negative splash10-0udi-0900000000-942af3cd327a2dd39887 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 1V, negative splash10-0udi-1900000000-671c45f3bda2eabba3c1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 1V, negative splash10-0udi-1900000000-36fabc35679210a4621a View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 1V, negative splash10-0udi-2900000000-146b4ca6698f6c40d476 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 2V, negative splash10-0udi-4900000000-32e86ae76401d830a8a1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 2V, negative splash10-0udi-8900000000-07fc17585cf5e8d2ba9b View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 3V, negative splash10-0pbi-9400000000-70777a3c6521e72b59b4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 7V, negative splash10-0a4i-9000000000-cad0cc415c906a783cfc View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 3V, negative splash10-0zg0-9500000000-9dfcd62aeff3ff1e731d View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 3V, negative splash10-0pb9-9300000000-0e1b3056ef85c0fbe59d View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 3V, negative splash10-0a4i-9200000000-144d4f05dfc0b2dbd827 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 4V, negative splash10-0a4i-9100000000-5a807248d180fcc738ee View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 5V, negative splash10-0a4i-9000000000-aeb70e18a8467ef1b4b1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 5V, negative splash10-0a4i-9000000000-50691ede3dffed6a4afb View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 6V, negative splash10-0a4i-9000000000-13adfaf490932a7c0fb9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 7V, negative splash10-000i-9000000000-3051dc4fe82b4abf5478 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 0V, positive splash10-0002-0900000000-8f691ae372d6f1d18226 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-9100000000-80636ab7e3cb47d4d58f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-05n4-9000000000-71899633e269029ab7f9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-910235f5bc92bcca7469 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-8900000000-5890f0a527dd16d9ac75 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0k9i-9200000000-241210fedf9304168090 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9000000000-21d09118dfcfcb093f8d View in MoNA MS Mass Spectrum (Electron Ionization) splash10-0006-9000000000-d55d971a361b41564681 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 30830 HMDB ID HMDB00710 Pubchem Compound ID 10413 Kegg ID C01991 ChemSpider ID 9984 Wikipedia Gamma-hydroxybutyrate BioCyc ID 4-HYDROXY-BUTYRATE EcoCyc ID 4-HYDROXY-BUTYRATE

Enzymes