2.02012-05-31 13:44:45 -06002015-06-03 15:53:42 -0600ECMDB01079M2MDB0002455-Methyltetrahydropteroyltri-L-glutamic acid5-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-glutamate5-Methyltetrahydropteroyltri-L-glutamic acid5MTHTGluC25H36N8O12640.5997640.245268656(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)=OInChI=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/s1SRBIKUAVFZRKSG-SUWBZHBXSA-NCytoplasmPeriplasmlogp-3.52logs-3.67solubility1.36e-01 g/llogp-9.9pka_strongest_acidic2.33pka_strongest_basic8.48iupac(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 acidaverage_mass640.5997mono_mass640.245268656smiles[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)=OformulaC25H36N8O12inchiInChI=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/s1inchikeySRBIKUAVFZRKSG-SUWBZHBXSA-Npolar_surface_area332.37refractivity168.91polarizability61.43rotatable_bond_count20acceptor_count17donor_count9physiological_charge1formal_charge0Cysteine and methionine metabolismec00270Selenoamino acid metabolismec00450Metabolic pathwayseco01100<i>S</i>-adenosyl-L-methionine cycle IPWY-6151methionine biosynthesis IHOMOSER-METSYN-PWYSpecdb::CMs1083447Specdb::EiMs3176Specdb::NmrOneD288115Specdb::NmrOneD288116Specdb::NmrOneD288117Specdb::NmrOneD288118Specdb::NmrOneD288119Specdb::NmrOneD288120Specdb::NmrOneD288121Specdb::NmrOneD288122Specdb::NmrOneD288123Specdb::NmrOneD288124Specdb::NmrOneD288125Specdb::NmrOneD288126Specdb::NmrOneD288127Specdb::NmrOneD288128Specdb::NmrOneD288129Specdb::NmrOneD288130Specdb::NmrOneD288131Specdb::NmrOneD288132Specdb::NmrOneD288133Specdb::NmrOneD288134Specdb::MsMs23039Specdb::MsMs23040Specdb::MsMs23041Specdb::MsMs29837Specdb::MsMs29838Specdb::MsMs2983916722111389321C0448917614CPD-1302Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Methionine synthaseP13009METH_ECOLImetHhttp://ecmdb.ca/proteins/P13009.xml5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferaseP25665METE_ECOLImetEhttp://ecmdb.ca/proteins/P25665.xml5-Methyltetrahydropteroyltri-L-glutamic acid + L-Homocysteine <> Tetrahydropteroyltri-L-glutamic acid + L-MethionineR04405Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid <> Selenomethionine + Tetrahydropteroyltri-L-glutamic acidR09365L-Homocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid > L-Methionine + tetrahydropteroyl tri-L-glutamateHOMOCYSMET-RXN