2.0 2012-08-09 09:16:11 -0600 2015-09-13 12:56:16 -0600 ECMDB21418 M2MDB001813 3-Hydroxybutyric acid 3-Hydroxybutyric acid or beta-hydroxybutyrate belongs to a group of compounds known as ketone bodies. Other ketone bodies include acetoacetate and acetone. 3-hydroxybutyric acid is chiral and so it has 2 enantiomeric forms. (Wikipedia) In some strains of E. coli, such as E. coli O8 IAI1, the enzyme 3-hydroxybutyrate dehydrogenase (EC:1.1.1.30) catalyzes a reversible redox reaction that converts 3-hydroxybutyric acid to acetoacetate, which can then be converted into acetoacetyl-CoA and participate in fatty acid metabolism. (KEGG). Hydroxybutyrate can also serve as a substrate for short-chain acylCo-A ligase and become a precursor for lipid synthesis. β-hydroxybutyrate β-hydroxybutyric acid (R)-3-Hydroxybutanoate (R)-3-hydroxybutanoic acid (R)-3-Hydroxybutyrate (R)-3-hydroxybutyric acid 3-hydroxy-butanoate 3-hydroxy-butanoic acid 3-hydroxy-butyrate 3-hydroxy-butyric acid 3-Hydroxybutanoate 3-Hydroxybutanoic acid 3-Hydroxybutyrate 3-OH-Butyrate 3-OH-butyric acid B-Hydroxy-n-butyrate B-Hydroxy-n-butyric acid B-Hydroxybutanoate B-Hydroxybutanoic acid b-Hydroxybuttersaeure B-Hydroxybutyrate B-hydroxybutyric acid Beta-Hydroxy-n-butyrate Beta-Hydroxy-n-butyric acid Beta-Hydroxybutanoate Beta-Hydroxybutanoic acid Beta-Hydroxybuttersaeure Beta-Hydroxybutyrate Beta-Hydroxybutyric acid Biopol D-β-hydroxybutyrate D-β-hydroxybutyric acid D-3-hydroxybutyrate D-3-Hydroxybutyric acid DL-3-Hydroxybutyrate DL-3-Hydroxybutyric acid DL-b-Hydroxybutyrate DL-b-Hydroxybutyric acid DL-beta-Hydroxybutyrate DL-beta-Hydroxybutyric acid DL-β-Hydroxybutyrate DL-β-Hydroxybutyric acid β-Hydroxy-N-butyrate β-Hydroxy-N-butyric acid β-Hydroxybutanoate β-Hydroxybutanoic acid β-Hydroxybuttersaeure β-Hydroxybutyrate β-Hydroxybutyric acid C4H8O3 104.1045 104.047344122 3-hydroxybutanoic acid 3 hydroxybutyrate 300-85-6 CC(O)CC(O)=O InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) WHBMMWSBFZVSSR-UHFFFAOYSA-N Solid logp -0.50 ALOGPS logs 0.71 ALOGPS solubility 5.39e+02 g/l ALOGPS melting_point 46 oC logp -0.39 ChemAxon pka_strongest_acidic 4.41 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac 3-hydroxybutanoic acid ChemAxon average_mass 104.1045 ChemAxon mono_mass 104.047344122 ChemAxon smiles CC(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) ChemAxon inchikey WHBMMWSBFZVSSR-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 23.46 ChemAxon polarizability 10.01 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 543 Specdb::CMs 544 Specdb::CMs 545 Specdb::CMs 941 Specdb::CMs 2955 Specdb::CMs 30441 Specdb::CMs 30444 Specdb::CMs 30864 Specdb::CMs 31131 Specdb::CMs 32006 Specdb::CMs 37461 Specdb::EiMs 1304 Specdb::NmrOneD 1230 Specdb::NmrOneD 1344 Specdb::NmrOneD 5056 Specdb::MsMs 573 Specdb::MsMs 574 Specdb::MsMs 575 Specdb::MsMs 4034 Specdb::MsMs 179178 Specdb::MsMs 179179 Specdb::MsMs 179180 Specdb::MsMs 181503 Specdb::MsMs 181504 Specdb::MsMs 181505 Specdb::MsMs 439062 Specdb::MsMs 447333 Specdb::NmrTwoD 1020 Specdb::NmrTwoD 1286 HMDB00357 441 428 C01089 20067 CPD-335 3-Hydroxybutyric acid van der Werf, M. 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Am J Physiol. 1982 Sep;243(3):R304-11. 7051864 http://hmdb.ca/system/metabolites/msds/000/000/276/original/HMDB00357.pdf?1358462668 Short-chain-fatty-acid--CoA ligase P38135 FADK_ECOLI fadK http://ecmdb.ca/proteins/P38135.xml