1.0 2016-09-30 22:30:59 UTC 2020-06-04 19:37:14 UTC BMDB0000452 BMDB00452 L-Alpha-aminobutyric acid 2-Aminobutyrate, also known as L-butyrine or L-homoalanine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 2-Aminobutyrate exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Aminobutyrate exists in all eukaryotes, ranging from yeast to humans. (-)-2-Aminobutyric acid (2S)-2-Aminobutyric acid (S)-2-Aminobutanoate (S)-2-Aminobutanoic acid (S)-2-Aminobutyric acid L-(+)-2-Aminobutyric acid L-2-Aminobuttersaeure L-2-Aminobutyric acid L-alpha-Amino-N-butyric acid L-Butyrine S-Butyrine (-)-2-Aminobutyrate (2S)-2-Aminobutyrate (S)-2-Aminobutyrate L-(+)-2-Aminobutyrate L-2-Aminobutyrate L-a-Amino-N-butyrate L-a-Amino-N-butyric acid L-alpha-Amino-N-butyrate L-Α-amino-N-butyrate L-Α-amino-N-butyric acid L-a-Aminobutyrate L-a-Aminobutyric acid L-alpha-Aminobutyrate L-Α-aminobutyrate L-Α-aminobutyric acid (+)-2-Aminobutanoate (+)-2-Aminobutanoic acid (+)-2-Aminobutyric acid (+)-alpha-Aminobutyric acid (2S)-2-Aminobutanoate (2S)-2-Aminobutanoic acid (S)-(+)-alpha-Aminobutyric acid (S)-2-amino-Butanoate (S)-2-amino-Butanoic acid 2-Aminobutanoate 2-Aminobutanoic acid 2-Aminobutyrate 2S-amino-Butanoate 2S-amino-Butanoic acid alpha-Aminobutyric acid L-2-amino-N-Butyric acid L-Ethylglycine Butyrine, (R)-isomer 2-Aminobutyric acid alpha-Aminobutyric acid, (+-)-isomer Butyrine Butyrine, (S)-isomer L-Homoalanine alpha-Aminobutyric acid, (S)-isomer Homoalanine alpha-Aminobutyric acid, (R)-isomer Butyrine, (+-)-isomer L-2-Aminobutanoate C4H9NO2 103.1198 103.063328537 (2S)-2-aminobutanoic acid (-)-2-aminobutyric acid 1492-24-6 CC[C@H](N)C(O)=O InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1 QWCKQJZIFLGMSD-VKHMYHEASA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues L-alpha-amino acids Amino acids Carbonyl compounds Carboxylic acids Fatty acids and conjugates Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Amine Amino acid Carbonyl group Carboxylic acid Fatty acid Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Aliphatic acyclic compounds Amino fatty acids Amino fatty acids alpha-aminobutyric acid non-proteinogenic L-alpha-amino acid Solid melting_point 291 °C logp -3.17 HANSCH,C ET AL. (1995) logp -2.55 ALOGPS logs 0.54 ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 2.62 ChemAxon pka_strongest_basic 9.53 ChemAxon iupac (2S)-2-aminobutanoic acid ChemAxon average_mass 103.1198 ChemAxon mono_mass 103.063328537 ChemAxon smiles CC[C@H](N)C(O)=O ChemAxon formula C4H9NO2 ChemAxon inchi InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1 ChemAxon inchikey QWCKQJZIFLGMSD-VKHMYHEASA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 25.02 ChemAxon polarizability 10.34 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 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 Specdb::NmrTwoD 1320 Specdb::MsIr 532 Specdb::MsIr 533 Specdb::MsIr 534 Specdb::NmrOneD 1376 Specdb::NmrOneD 143970 Specdb::NmrOneD 143971 Specdb::NmrOneD 143972 Specdb::NmrOneD 143973 Specdb::NmrOneD 143974 Specdb::NmrOneD 143975 Specdb::NmrOneD 143976 Specdb::NmrOneD 143977 Specdb::NmrOneD 143978 Specdb::NmrOneD 143979 Specdb::NmrOneD 143980 Specdb::NmrOneD 143981 Specdb::NmrOneD 143982 Specdb::NmrOneD 143983 Specdb::NmrOneD 143984 Specdb::NmrOneD 143985 Specdb::NmrOneD 143986 Specdb::NmrOneD 143987 Specdb::NmrOneD 143988 Specdb::NmrOneD 143989 Specdb::MsMs 659 Specdb::MsMs 660 Specdb::MsMs 661 Specdb::MsMs 4065 Specdb::MsMs 4066 Specdb::MsMs 4067 Specdb::MsMs 4068 Specdb::MsMs 4069 Specdb::MsMs 4070 Specdb::MsMs 4071 Specdb::MsMs 4072 Specdb::MsMs 4073 Specdb::MsMs 4075 Specdb::MsMs 4076 Specdb::MsMs 179358 Specdb::MsMs 179359 Specdb::MsMs 179360 Specdb::MsMs 181686 Specdb::MsMs 181687 Specdb::MsMs 181688 Specdb::MsMs 437324 Specdb::MsMs 437325 Specdb::MsMs 437326 Specdb::MsMs 437327 Specdb::MsMs 439231 Specdb::CMs 551 Specdb::CMs 945 Specdb::CMs 1119 Specdb::CMs 3038 Specdb::CMs 30588 Specdb::CMs 31147 Specdb::CMs 31148 Specdb::CMs 37546 Specdb::CMs 167727 Specdb::CMs 1062959 Specdb::CMs 1062961 Specdb::CMs 1062963 Blood Detected by NMR De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014. 25372282 Kidney 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 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Milk 1 - 10 uM Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. 20338431 Milk Milk from Friesuan Holstein cows (n=1035) 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 Semen Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was identified by probable match parameters of the NIST Mass Spectral Search Program Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018. 29634739 FDB012537 72524 80283 C02356 35619 CPD0-1942 Alpha-Aminobutyric acid 12 Fotheringham, I. G.; Grinter, N.; Pantaleone, D. P.; Senkpeil, R. F.; Taylor, P. P. Engineering of a novel biochemical pathway for the biosynthesis of l-2-aminobutyric acid in Escherichia coli K12. Bioorganic & Medicinal Chemistry (1999), 7(10), 2209-2213. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. 20338431 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 Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809