2.0 2012-07-30 14:55:21 -0600 2015-06-03 17:21:11 -0600 ECMDB21338 M2MDB001738 gamma-Hydroxybutyrate 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) &gamma;-hydroxybutyrate &gamma;-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 C4H8O3 104.1045 104.047344122 4-hydroxybutanoic acid gamma hydroxybutyric acid 591-81-1 OCCCC(O)=O InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7) SJZRECIVHVDYJC-UHFFFAOYSA-N Solid Cytosol logp -0.63 ALOGPS logs 0.68 ALOGPS solubility 4.94e+02 g/l ALOGPS logp -0.51 ChemAxon pka_strongest_acidic 4.44 ChemAxon pka_strongest_basic -2.4 ChemAxon iupac 4-hydroxybutanoic acid ChemAxon average_mass 104.1045 ChemAxon mono_mass 104.047344122 ChemAxon smiles OCCCC(O)=O ChemAxon formula C4H8O3 ChemAxon inchi InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7) ChemAxon inchikey SJZRECIVHVDYJC-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 23.8 ChemAxon polarizability 10.17 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 986 Specdb::CMs 14061 Specdb::CMs 31203 Specdb::CMs 32047 Specdb::CMs 37710 Specdb::CMs 135411 Specdb::CMs 143145 Specdb::CMs 1072680 Specdb::CMs 1072682 Specdb::CMs 1072684 Specdb::CMs 1072685 Specdb::CMs 1072687 Specdb::EiMs 314 Specdb::NmrOneD 256408 Specdb::NmrOneD 256409 Specdb::NmrOneD 256410 Specdb::NmrOneD 256411 Specdb::NmrOneD 256412 Specdb::NmrOneD 256413 Specdb::NmrOneD 256414 Specdb::NmrOneD 256415 Specdb::NmrOneD 256416 Specdb::NmrOneD 256417 Specdb::NmrOneD 256418 Specdb::NmrOneD 256419 Specdb::NmrOneD 256420 Specdb::NmrOneD 256421 Specdb::NmrOneD 256422 Specdb::NmrOneD 256423 Specdb::NmrOneD 256424 Specdb::NmrOneD 256425 Specdb::NmrOneD 256426 Specdb::NmrOneD 256427 Specdb::MsMs 26384 Specdb::MsMs 26385 Specdb::MsMs 26386 Specdb::MsMs 32942 Specdb::MsMs 32943 Specdb::MsMs 32944 Specdb::MsMs 1470825 Specdb::MsMs 1472610 Specdb::MsMs 1472611 Specdb::MsMs 1472612 Specdb::MsMs 1472613 Specdb::MsMs 1472614 Specdb::MsMs 1472615 Specdb::MsMs 1472616 Specdb::MsMs 1472617 Specdb::MsMs 1472618 Specdb::MsMs 1472619 Specdb::MsMs 1472620 Specdb::MsMs 1472621 Specdb::MsMs 1472622 Specdb::MsMs 1472623 Specdb::MsMs 1472624 Specdb::MsMs 1472625 Specdb::MsMs 1472626 Specdb::MsMs 1477816 HMDB00710 10413 9984 C01991 30830 4-HYDROXY-BUTYRATE Gamma-hydroxybutyrate 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. 19372223 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. 15939164 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. 3126356 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. 7707697 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. 2407302 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. 12127325 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. 14595661 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. 16620539 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. 17658710 Uncharacterized oxidoreductase yihU P0A9V8 YIHU_ECOLI yihU http://ecmdb.ca/proteins/P0A9V8.xml Hydrogen ion + NADH + Succinic acid semialdehyde <> gamma-Hydroxybutyrate + NAD 4-HYDROXYBUTYRATE-DEHYDROGENASE-RXN NAD + gamma-Hydroxybutyrate <> Hydrogen ion + NADH + Succinic acid semialdehyde 4-HYDROXYBUTYRATE-DEHYDROGENASE-RXN