1.0 2016-09-30 22:07:18 UTC 2020-05-11 22:52:21 UTC BMDB0000008 BMDB00008 2-Hydroxybutyric acid 2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate or 2-hydroxybutanoate, 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. 2-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxybutyric acid is a potentially toxic compound. (S)-2-Hydroxybutanoic acid 2-Hydroxybutyrate 2-Hydroxybutyric acid L-2-Hydroxybutanoic acid L-2-Hydroxybutyric acid L-alpha-Hydroxybutanoic acid L-alpha-Hydroxybutyric acid (S)-2-Hydroxybutanoate L-2-Hydroxybutanoate L-2-Hydroxybutyrate L-a-Hydroxybutanoate L-a-Hydroxybutanoic acid L-alpha-Hydroxybutanoate L-Α-hydroxybutanoate L-Α-hydroxybutanoic acid L-a-Hydroxybutyrate L-a-Hydroxybutyric acid L-alpha-Hydroxybutyrate L-Α-hydroxybutyrate L-Α-hydroxybutyric acid (S)-2-Hydroxybutyrate 2-Hydroxybutanoate (+)-2-Hydroxy-n-butyric acid (+)-2-Hydroxybutanoic acid (+)-2-Hydroxybutyric acid (+)-alpha-Hydroxybutyric acid (+)-α-Hydroxybutyric acid (2S)-2-Hydroxybutanoic acid (S)-(+)-2-Hydroxybutanoic acid (S)-2-Hydroxybutyric acid 2-Hydroxybutanoic acid alpha-Hydroxy-n-butyric acid alpha-Hydroxybutanoic acid alpha-Hydroxybutyric acid α-Hydroxy-n-butyric acid α-Hydroxybutanoic acid α-Hydroxybutyric acid C4H8O3 104.105 104.047344118 (2S)-2-hydroxybutanoic acid (S)-2-hydroxybutyric acid CC[C@H](O)C(O)=O InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1 AFENDNXGAFYKQO-VKHMYHEASA-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. Organic compounds Organic acids and derivatives Hydroxy acids and derivatives Alpha hydroxy acids and derivatives Alpha hydroxy acids and derivatives 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 Aliphatic acyclic compounds 2-hydroxybutyric acid Hydroxy fatty acids Hydroxy fatty acids Solid melting_point 44.2 °C logp -0.16 ALOGPS logs 0.67 ALOGPS logp 0.051 ChemAxon pka_strongest_acidic 3.99 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac (2S)-2-hydroxybutanoic acid ChemAxon average_mass 104.105 ChemAxon mono_mass 104.047344118 ChemAxon smiles CC[C@H](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)/t3-/m0/s1 ChemAxon inchikey AFENDNXGAFYKQO-VKHMYHEASA-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 number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Propanoate Metabolism SMP0087248 Specdb::NmrTwoD 2063 Specdb::CMs 102797 Specdb::CMs 102798 Specdb::CMs 102799 Specdb::CMs 102800 Specdb::CMs 102801 Specdb::CMs 102802 Specdb::CMs 102803 Specdb::CMs 159343 Specdb::CMs 1046865 Specdb::CMs 1046867 Specdb::CMs 1046868 Specdb::CMs 1046870 Specdb::CMs 1046872 Specdb::CMs 1046873 Specdb::MsMs 1250182 Specdb::MsMs 1250183 Specdb::MsMs 1250184 Specdb::MsMs 1365478 Specdb::MsMs 1365479 Specdb::MsMs 1365480 Specdb::MsMs 1448541 Specdb::MsMs 1448542 Specdb::MsMs 1448543 Specdb::MsMs 1448544 Specdb::MsMs 1448545 Specdb::MsMs 1448546 Specdb::MsMs 2253310 Specdb::MsMs 2257260 Specdb::MsMs 2257338 Specdb::MsMs 2259269 Specdb::MsMs 2259286 Specdb::MsMs 2734025 Specdb::MsMs 2734026 Specdb::MsMs 2734027 Specdb::MsMs 2971863 Specdb::MsMs 2971864 Specdb::MsMs 2971865 Specdb::MsIr 88 Specdb::MsIr 89 Specdb::MsIr 90 Specdb::NmrOneD 5245 Specdb::NmrOneD 5246 Specdb::NmrOneD 5312 Specdb::NmrOneD 5313 Specdb::NmrOneD 5314 Specdb::NmrOneD 5315 Specdb::NmrOneD 5316 Specdb::NmrOneD 5317 Specdb::NmrOneD 5318 Specdb::NmrOneD 5319 Specdb::NmrOneD 5320 Specdb::NmrOneD 5321 Specdb::NmrOneD 5322 Specdb::NmrOneD 5323 Specdb::NmrOneD 5324 Specdb::NmrOneD 5325 Specdb::NmrOneD 5326 Specdb::NmrOneD 5327 Specdb::NmrOneD 5328 Specdb::NmrOneD 5329 Specdb::NmrOneD 5330 Specdb::NmrOneD 5331 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Raw milk, by GC-TOF/MS Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. 29197344 Milk Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Muscle Detected by NMR in beef muscle (longissimus dorsi). S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404 doi: 10.1007/s11306-010-0206-y Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB021867 C05984 389701 50613 440864 CPD-3564 2-Hydroxybutyric_acid Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. 29197344