1.0 2011-09-21 00:04:15 UTC 2024-11-29 22:28:02 UTC FDB021869 (R)-3-Hydroxybutyric acid (R)-3-Hydroxybutyric acid is a butyric acid substituted with a hydroxyl group in the beta or 3 position. It is involved in the synthesis and degradation of ketone bodies. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in the blood and urine in ketosis. Beta-hydroxybutyrate is a typical partial-degradation product of branched-chain amino acids (primarily valine) released from muscle for hepatic and renal gluconeogenesis This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of D-3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circulating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. It can also be used for the synthesis of biodegradable plastics . [HMDB] (R)-(-)-b-Hydroxybutyrate (R)-(-)-b-Hydroxybutyric acid (R)-(-)-beta-Hydroxybutyrate (R)-(-)-beta-Hydroxybutyric acid (R)-(-)-β-hydroxybutyrate (R)-(-)-β-hydroxybutyric acid (R)-3-Hydroxybutanoate (R)-3-Hydroxybutanoic acid (R)-3-Hydroxybutyrate 3-D-hydroxybutyrate 3-D-hydroxybutyric acid 3-delta-hydroxybutyrate 3-delta-hydroxybutyric acid BHIB D-(-)-3-hydroxybutyrate D-3-hydroxybutyrate D-3-hydroxybutyric acid D-beta-hydroxybutyrate delta-(-)-3-hydroxybutyrate delta-3-hydroxybutyrate delta-3-hydroxybutyric acid delta-beta-hydroxybutyrate C4H8O3 104.1045 104.047344122 (3R)-3-hydroxybutanoic acid (-)-3-hydroxybutyric acid 625-72-9 C[C@@H](O)CC(O)=O InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1 WHBMMWSBFZVSSR-GSVOUGTGSA-N belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Beta hydroxy acids and derivatives Organic compounds Organic acids and derivatives Hydroxy acids and derivatives Beta 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 Short-chain hydroxy acids and derivatives Alcohol Aliphatic acyclic compound Beta-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 Short-chain hydroxy acid 3-hydroxybutyric acid Hydroxy fatty acids ketone body Solid logp -0.50 ALOGPS logs 0.71 ALOGPS solubility 5.39e+02 g/l ALOGPS logp -0.39 ChemAxon pka_strongest_acidic 4.41 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac (3R)-3-hydroxybutanoic acid ChemAxon average_mass 104.1045 ChemAxon mono_mass 104.047344122 ChemAxon smiles C[C@@H](O)CC(O)=O ChemAxon formula C4H8O3 ChemAxon inchi InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1 ChemAxon inchikey WHBMMWSBFZVSSR-GSVOUGTGSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 23.46 ChemAxon polarizability 9.96 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Ketone Body Metabolism SMP00071 map00072 Metabolism and Physiological Effects of β-Hydroxybutyric acid SMP0126987 Specdb::EiMs 2010 Specdb::MsIr 91 Specdb::MsIr 92 Specdb::MsIr 93 Specdb::NmrTwoD 920 Specdb::NmrOneD 1027 Specdb::NmrOneD 5332 Specdb::NmrOneD 5333 Specdb::NmrOneD 5334 Specdb::NmrOneD 5335 Specdb::NmrOneD 5336 Specdb::NmrOneD 5337 Specdb::NmrOneD 5338 Specdb::NmrOneD 5339 Specdb::NmrOneD 5340 Specdb::NmrOneD 5341 Specdb::NmrOneD 5342 Specdb::NmrOneD 5343 Specdb::NmrOneD 5344 Specdb::NmrOneD 5345 Specdb::NmrOneD 5346 Specdb::NmrOneD 5347 Specdb::NmrOneD 5348 Specdb::NmrOneD 5349 Specdb::NmrOneD 5350 Specdb::NmrOneD 5351 Specdb::MsMs 16 Specdb::MsMs 17 Specdb::MsMs 18 Specdb::MsMs 2526 Specdb::MsMs 2527 Specdb::MsMs 2528 Specdb::MsMs 2529 Specdb::MsMs 2530 Specdb::MsMs 324085 Specdb::MsMs 324086 Specdb::MsMs 324087 Specdb::MsMs 372409 Specdb::MsMs 372410 Specdb::MsMs 372411 Specdb::MsMs 437816 Specdb::MsMs 437817 Specdb::MsMs 437818 Specdb::MsMs 437819 Specdb::MsMs 437820 Specdb::MsMs 440114 Specdb::MsMs 2233646 Specdb::MsMs 2252490 Specdb::MsMs 2253978 Specdb::MsMs 2254601 Specdb::MsMs 2255993 Specdb::CMs 26212 Specdb::CMs 30136 Specdb::CMs 37241 Specdb::CMs 99520 Specdb::CMs 133294 Specdb::CMs 141028 Specdb::CMs 1046881 Specdb::CMs 1046882 Specdb::CMs 1046884 Specdb::CMs 1046886 Specdb::CMs 1046888 HMDB00011 17066 3HR #<Reference:0x000055ce31f2b598> #<Reference:0x000055ce31f2b340> #<Reference:0x000055ce31f2b188> #<Reference:0x000055ce31f2af80> #<Reference:0x000055ce31f2ad28> #<Reference:0x000055ce31f2ab70> #<Reference:0x000055ce31f2a940> #<Reference:0x000055ce31f2a738> #<Reference:0x000055ce31f2a558> #<Reference:0x000055ce31f2a350> #<Reference:0x000055ce31f2a120> #<Reference:0x000055ce31f29f68> #<Reference:0x000055ce31f29d60> #<Reference:0x000055ce31f29b58> #<Reference:0x000055ce31f299a0> #<Reference:0x000055ce31f29798> #<Reference:0x000055ce31f29590> #<Reference:0x000055ce31f293d8> #<Reference:0x000055ce31f291d0> #<Reference:0x000055ce31f28fc8> 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 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 Novel protein similar to 3-hydroxymethyl-3-methylglutaryl-Coenzyme A lyase (Hydroxymethylglutaricaciduria) Q9NT06 DKFZp434G1411