1.0 2011-09-21 00:04:13 UTC 2019-11-26 03:21:00 UTC FDB021867 2-Hydroxybutyric acid 2-Hydroxybutyric acid is an organic acid that is involved in propanoate metabolism. It is produced in mammalian tissues (principaly hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyrate is released as a by-product when cystathionine is cleaved to cysteine that is incorporated into glutathione. 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g., birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early stage type II diabetes (PMID: 19166731). It was concluded from studies done in the mid 1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydorxybutyric acid (PMID: 168632) [HMDB] (RS)-2-Hydroxybutyrate (RS)-2-Hydroxybutyric acid 2-hydroxy-Butanoate 2-hydroxy-Butanoic acid 2-hydroxy-DL-Butyrate 2-hydroxy-DL-Butyric acid 2-Hydroxy-n-butyrate 2-Hydroxy-n-butyric acid 2-Hydroxybutanoate 2-Hydroxybutanoic acid 2-Hydroxybutyrate a-Hydroxy-n-butyrate a-Hydroxy-n-butyric acid a-Hydroxybutanoate a-Hydroxybutanoic acid a-Hydroxybutyrate a-Hydroxybutyric acid alpha-hydroxy-n-butyrate alpha-hydroxy-n-butyric acid alpha-Hydroxybutanoate alpha-Hydroxybutanoic acid alpha-Hydroxybutyrate alpha-Hydroxybutyric acid DL-2-Hydroxybutanoate DL-2-Hydroxybutanoic acid DL-a-Hydroxybutyrate DL-a-Hydroxybutyric acid DL-alpha-Hydroxybutyrate DL-alpha-Hydroxybutyric acid α-hydroxybutanoate α-hydroxybutanoic acid α-hydroxybutyrate α-hydroxybutyric acid C4H8O3 104.1045 104.047344122 2-hydroxybutanoic acid α-hydroxybutyric acid 600-15-7 CCC(O)C(O)=O InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) AFENDNXGAFYKQO-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. Alpha hydroxy acids and derivatives Organic compounds Organic acids and derivatives Hydroxy acids and derivatives Alpha hydroxy acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Fatty acids and conjugates Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol 2-hydroxy monocarboxylic acid Hydroxy fatty acids hydroxybutyric acid Solid logp -0.16 ALOGPS logs 0.67 ALOGPS solubility 4.84e+02 g/l ALOGPS logp 0.051 ChemAxon pka_strongest_acidic 3.99 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 2-hydroxybutanoic acid ChemAxon average_mass 104.1045 ChemAxon mono_mass 104.047344122 ChemAxon smiles CCC(O)C(O)=O ChemAxon formula C4H8O3 ChemAxon inchi InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) ChemAxon inchikey AFENDNXGAFYKQO-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 23.36 ChemAxon polarizability 9.98 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 918 Specdb::MsMs 10 Specdb::MsMs 11 Specdb::MsMs 12 Specdb::MsMs 2523 Specdb::MsMs 180072 Specdb::MsMs 180073 Specdb::MsMs 180074 Specdb::MsMs 182406 Specdb::MsMs 182407 Specdb::MsMs 182408 Specdb::MsMs 438648 Specdb::MsMs 440124 Specdb::NmrOneD 1025 Specdb::NmrOneD 3229 Specdb::CMs 278 Specdb::CMs 279 Specdb::CMs 919 Specdb::CMs 3385 Specdb::CMs 26964 Specdb::CMs 30572 Specdb::CMs 30898 Specdb::CMs 30946 Specdb::CMs 37239 HMDB00008 #<Reference:0x000055ce33195f30> #<Reference:0x000055ce33195d78> #<Reference:0x000055ce33195bc0> #<Reference:0x000055ce33195a08> #<Reference:0x000055ce33195850> #<Reference:0x000055ce33195698> #<Reference:0x000055ce331954e0> #<Reference:0x000055ce33195328> #<Reference:0x000055ce33195170> #<Reference:0x000055ce33194fb8> #<Reference:0x000055ce33194e00> #<Reference:0x000055ce33194c48> #<Reference:0x000055ce33194a90> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823