2.0 2012-05-31 13:44:45 -0600 2015-06-03 15:53:42 -0600 ECMDB01079 M2MDB000245 5-Methyltetrahydropteroyltri-L-glutamic acid 5-methyltetrahydropteroyltri-L-glutamic acid is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative.5-Methyltetrahydropteroyltri-L-glutamate is formed under reaction between carbonyl group of 5-methyltetrahydropteroate and amine group on one end of three replicates of glutamate. It is involved in several pathways such as tetrahydrofolate biosynthesis and methionine biosynthesis. (YMDB00518) 5-Methyltetrahydropteroyltri-L-glutamate 5-Methyltetrahydropteroyltri-L-glutamic acid 5MTHTGlu C25H36N8O12 640.5997 640.245268656 (4S)-4-amino-5-[(1-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-1-(4-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-2-imino-5-methyl-1,2,5,8-tetrahydropteridin-6-yl)propan-2-yl)oxy]-5-oxopentanoic acid (4S)-4-amino-5-[(1-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-1-(4-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-2-imino-5-methyl-1,8-dihydropteridin-6-yl)propan-2-yl)oxy]-5-oxopentanoic acid [H][C@](N)(CCC(O)=O)C(=O)OC1=NC(=N)NC2=C1N(C)C(=CN2)C([H])(OC(=O)[C@@]([H])(N)CCC(O)=O)C([H])(C)OC(=O)[C@@]([H])(N)CCC(O)=O InChI=1S/C25H36N8O12/c1-10(43-22(40)11(26)3-6-15(34)35)19(44-23(41)12(27)4-7-16(36)37)14-9-30-20-18(33(14)2)21(32-25(29)31-20)45-24(42)13(28)5-8-17(38)39/h9-13,19H,3-8,26-28H2,1-2H3,(H,34,35)(H,36,37)(H,38,39)(H3,29,30,31,32)/t10?,11-,12-,13-,19?/m0/s1 SRBIKUAVFZRKSG-SUWBZHBXSA-N Cytoplasm Periplasm logp -3.52 ALOGPS logs -3.67 ALOGPS solubility 1.36e-01 g/l ALOGPS logp -9.9 ChemAxon pka_strongest_acidic 2.33 ChemAxon pka_strongest_basic 8.48 ChemAxon iupac (4S)-4-amino-5-[(1-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-1-(4-{[(2S)-2-amino-4-carboxybutanoyl]oxy}-2-imino-5-methyl-1,2,5,8-tetrahydropteridin-6-yl)propan-2-yl)oxy]-5-oxopentanoic acid ChemAxon average_mass 640.5997 ChemAxon mono_mass 640.245268656 ChemAxon smiles [H][C@](N)(CCC(O)=O)C(=O)OC1=NC(=N)NC2=C1N(C)C(=CN2)C([H])(OC(=O)[C@@]([H])(N)CCC(O)=O)C([H])(C)OC(=O)[C@@]([H])(N)CCC(O)=O ChemAxon formula C25H36N8O12 ChemAxon inchi InChI=1S/C25H36N8O12/c1-10(43-22(40)11(26)3-6-15(34)35)19(44-23(41)12(27)4-7-16(36)37)14-9-30-20-18(33(14)2)21(32-25(29)31-20)45-24(42)13(28)5-8-17(38)39/h9-13,19H,3-8,26-28H2,1-2H3,(H,34,35)(H,36,37)(H,38,39)(H3,29,30,31,32)/t10?,11-,12-,13-,19?/m0/s1 ChemAxon inchikey SRBIKUAVFZRKSG-SUWBZHBXSA-N ChemAxon polar_surface_area 332.37 ChemAxon refractivity 168.91 ChemAxon polarizability 61.43 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Selenoamino acid metabolism ec00450 Metabolic pathways eco01100 <i>S</i>-adenosyl-L-methionine cycle I PWY-6151 methionine biosynthesis I HOMOSER-METSYN-PWY Specdb::CMs 1083447 Specdb::EiMs 3176 Specdb::NmrOneD 288115 Specdb::NmrOneD 288116 Specdb::NmrOneD 288117 Specdb::NmrOneD 288118 Specdb::NmrOneD 288119 Specdb::NmrOneD 288120 Specdb::NmrOneD 288121 Specdb::NmrOneD 288122 Specdb::NmrOneD 288123 Specdb::NmrOneD 288124 Specdb::NmrOneD 288125 Specdb::NmrOneD 288126 Specdb::NmrOneD 288127 Specdb::NmrOneD 288128 Specdb::NmrOneD 288129 Specdb::NmrOneD 288130 Specdb::NmrOneD 288131 Specdb::NmrOneD 288132 Specdb::NmrOneD 288133 Specdb::NmrOneD 288134 Specdb::MsMs 23039 Specdb::MsMs 23040 Specdb::MsMs 23041 Specdb::MsMs 29837 Specdb::MsMs 29838 Specdb::MsMs 29839 16722111 389321 C04489 17614 CPD-1302 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 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 Methionine synthase P13009 METH_ECOLI metH http://ecmdb.ca/proteins/P13009.xml 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase P25665 METE_ECOLI metE http://ecmdb.ca/proteins/P25665.xml 5-Methyltetrahydropteroyltri-L-glutamic acid + L-Homocysteine <> Tetrahydropteroyltri-L-glutamic acid + L-Methionine R04405 Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid <> Selenomethionine + Tetrahydropteroyltri-L-glutamic acid R09365 L-Homocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid > L-Methionine + tetrahydropteroyl tri-L-glutamate HOMOCYSMET-RXN