2.0 2012-08-03 14:57:55 -0600 2015-09-13 12:56:16 -0600 ECMDB21403 M2MDB001798 2-Aminoisobutyric acid 2-Aminoisobutyric acid (or AIB) is a nonprotein amino acid that is found in certain antibiotics. It can be used as a nitrogen source by certain soil bacteria. AIB may also be produced as an end-product of pyrimidine metabolism. This compound has been identified in metabolomic experiments on E. coli. 2-Amino-2-methylpropanoate 2-Amino-2-methylpropanoic acid 2-Aminoisobutyrate 2-Methylalanine A-Aminoisobutanoate A-Aminoisobutanoic acid A-Aminoisobutyrate A-Aminoisobutyric acid A-Methylalanine AIB Alpha-Aminoisobutanoate Alpha-Aminoisobutanoic acid Alpha-Aminoisobutyrate Alpha-Aminoisobutyric acid Alpha-Methylalanine α-Aminoisobutanoate α-Aminoisobutanoic acid α-Aminoisobutyrate α-Aminoisobutyric acid α-Methylalanine C4H9NO2 103.1198 103.063328537 2-amino-2-methylpropanoic acid α-aminoisobutyric acid 62-57-7 CC(C)(N)C(O)=O InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7) FUOOLUPWFVMBKG-UHFFFAOYSA-N Solid Cytoplasm logp -2.45 ALOGPS logs 0.51 ALOGPS solubility 3.37e+02 g/l ALOGPS melting_point 335 oC logp -2.4 ChemAxon pka_strongest_acidic 2.58 ChemAxon pka_strongest_basic 9.72 ChemAxon iupac 2-amino-2-methylpropanoic acid ChemAxon average_mass 103.1198 ChemAxon mono_mass 103.063328537 ChemAxon smiles CC(C)(N)C(O)=O ChemAxon formula C4H9NO2 ChemAxon inchi InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7) ChemAxon inchikey FUOOLUPWFVMBKG-UHFFFAOYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 25.21 ChemAxon polarizability 10.33 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 792 Specdb::CMs 952 Specdb::CMs 6982 Specdb::CMs 30420 Specdb::CMs 31374 Specdb::CMs 38181 Specdb::CMs 135483 Specdb::CMs 143217 Specdb::NmrOneD 1305 Specdb::NmrOneD 1794 Specdb::NmrOneD 9922 Specdb::NmrOneD 9923 Specdb::NmrOneD 9924 Specdb::NmrOneD 9925 Specdb::NmrOneD 9926 Specdb::NmrOneD 9927 Specdb::NmrOneD 9928 Specdb::NmrOneD 9929 Specdb::NmrOneD 9930 Specdb::NmrOneD 9931 Specdb::NmrOneD 9932 Specdb::NmrOneD 9933 Specdb::NmrOneD 9934 Specdb::NmrOneD 9935 Specdb::NmrOneD 9936 Specdb::NmrOneD 9937 Specdb::NmrOneD 9938 Specdb::NmrOneD 9939 Specdb::NmrOneD 9940 Specdb::NmrOneD 9941 Specdb::NmrOneD 166454 Specdb::MsMs 1825 Specdb::MsMs 1826 Specdb::MsMs 1827 Specdb::MsMs 5597 Specdb::MsMs 5598 Specdb::MsMs 5599 Specdb::MsMs 5600 Specdb::MsMs 5601 Specdb::MsMs 5602 Specdb::MsMs 5603 Specdb::MsMs 5605 Specdb::MsMs 5606 Specdb::MsMs 251034 Specdb::MsMs 251035 Specdb::MsMs 251036 Specdb::MsMs 270975 Specdb::MsMs 270976 Specdb::MsMs 270977 Specdb::MsMs 437156 Specdb::MsMs 437157 Specdb::MsMs 439123 Specdb::MsMs 440108 Specdb::MsMs 445581 Specdb::MsMs 445582 Specdb::MsMs 445583 Specdb::NmrTwoD 1734 HMDB01906 6119 5891 C03665 AIB 2-Aminoisobutyric acid Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Lucarelli C, Betto P, Ricciarello G, Grossi G: High-performance liquid chromatographic determination of L-3-(3,4-dihydroxyphenyl)-2-methylalanine (alpha-methyldopa) in human urine and plasma. J Chromatogr. 1991 Mar 22;541(1-2):285-96. 2037651 HARRIS H: Family studies on the urinary excretion of beta-aminoisobutyric acid. Ann Eugen. 1953 Jun;18(1):43-9. 13058271 CRUMPLER HR, DENT CE, HARRIS H, WESTALL RG: beta-Aminoisobutyric acid (alpha-methyl-beta-alanine); a new amino-acid obtained from human urine. Nature. 1951 Feb 24;167(4243):307-8. 14806475 http://hmdb.ca/system/metabolites/msds/000/001/497/original/HMDB01906.pdf?1358462489 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 10.8 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 43200 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776