2.0 2012-07-30 14:55:07 -0600 2015-06-03 17:21:00 -0600 ECMDB21252 M2MDB001660 N-Methyltryptophan N-methyltryptophan is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group. N-Methyltryptophan is catabolized by MTOX. N-Methyltryptophan oxidase (MTOX) is a flavoenzyme that catalyzes the oxidative demethylation of N-methyl-L-tryptophan and other N-methyl amino acids, including sarcosine, which is a poor substrate. (PMID 11170472) MTOX is converted to a 2-electron reduced form upon anaerobic reaction with N-methyl-L-tryptophan, sarcosine, or the carbinolamine formed with L-tryptophan and formaldehyde. (PMID 11170473) (2S)-3-(1H-indol-3-yl)-2-(methylamino)propanoate (2S)-3-(1H-indol-3-yl)-2-(methylamino)propanoic acid Abrine L-2-Methyltryptophan L-Abrine N-Methyl-L-tryptophan N-Methyl-L-tryptophane C12H14N2O2 218.2518 218.105527702 3-(1H-indol-3-yl)-2-(methylamino)propanoic acid 3-(1H-indol-3-yl)-2-(methylamino)propanoic acid 526-31-8 CNC(CC1=CNC2=CC=CC=C12)C(O)=O InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16) CZCIKBSVHDNIDH-UHFFFAOYSA-N Cytosol logp 0.41 ALOGPS logs -2.48 ALOGPS solubility 7.18e-01 g/l ALOGPS logp -0.86 ChemAxon pka_strongest_acidic 2.16 ChemAxon pka_strongest_basic 10.64 ChemAxon iupac 3-(1H-indol-3-yl)-2-(methylamino)propanoic acid ChemAxon average_mass 218.2518 ChemAxon mono_mass 218.105527702 ChemAxon smiles CNC(CC1=CNC2=CC=CC=C12)C(O)=O ChemAxon formula C12H14N2O2 ChemAxon inchi InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16) ChemAxon inchikey CZCIKBSVHDNIDH-UHFFFAOYSA-N ChemAxon polar_surface_area 65.12 ChemAxon refractivity 60.98 ChemAxon polarizability 23.16 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 25175 Specdb::MsMs 25176 Specdb::MsMs 25177 Specdb::MsMs 31733 Specdb::MsMs 31734 Specdb::MsMs 31735 914 890 C02983 15334 N-METHYLTRYPTOPHAN van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 N-methyl-L-tryptophan oxidase P40874 MTOX_ECOLI solA http://ecmdb.ca/proteins/P40874.xml N-Methyltryptophan + Water + Oxygen > Formaldehyde + Hydrogen peroxide + L-Tryptophan RXN0-301