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Record Information
Version	2.0
Creation Date	2012-05-31 13:44:45 -0600
Update Date	2015-06-03 15:53:42 -0600
Secondary Accession Numbers	ECMDB01079
Identification
Name:	5-Methyltetrahydropteroyltri-L-glutamic acid
Description	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)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa0ecdaec> Close
Synonyms:	5-Methyltetrahydropteroyltri-L-glutamate 5-Methyltetrahydropteroyltri-L-glutamic acid 5MTHTGlu
Chemical Formula:	C25H36N8O12
Weight:	Average: 640.5997 Monoisotopic: 640.245268656
InChI Key:	SRBIKUAVFZRKSG-SUWBZHBXSA-N
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
CAS number:	Not Available
IUPAC Name:	(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
Traditional IUPAC Name:	(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
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
Chemical Taxonomy
Description	belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Hexacarboxylic acids and derivatives
Direct Parent	Hexacarboxylic acids and derivatives
Alternative Parents	Biopterins and derivatives Glutamic acid and derivatives Alpha amino acid esters Tertiary alkylarylamines Secondary alkylarylamines Amino fatty acids Aminopyrimidines and derivatives Fatty acid esters Imidolactams Heteroaromatic compounds Amino acids Carboxylic acid esters Enamines Carboxylic acids Azacyclic compounds Organic oxides Carbonyl compounds Organopnictogen compounds Hydrocarbon derivatives Monoalkylamines
Substituents	Hexacarboxylic acid or derivatives Biopterin Glutamic acid or derivatives Alpha-amino acid ester Pterin Alpha-amino acid or derivatives Pteridine Tertiary aliphatic/aromatic amine Amino fatty acid Aminopyrimidine Fatty acid ester Secondary aliphatic/aromatic amine Fatty acyl Pyrimidine Imidolactam Heteroaromatic compound Tertiary amine Amino acid or derivatives Amino acid Carboxylic acid ester Organoheterocyclic compound Secondary amine Azacycle Carboxylic acid Enamine Organic oxygen compound Hydrocarbon derivative Primary aliphatic amine Organonitrogen compound Carbonyl group Organooxygen compound Organic oxide Organopnictogen compound Primary amine Organic nitrogen compound Amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	1
Melting point:	Not Available
Experimental Properties:	Property Value Source LogP: -2.264 PhysProp
Predicted Properties	Property Value Source Water Solubility 0.14 g/L ALOGPS logP -3.5 ALOGPS logP -9.9 ChemAxon logS -3.7 ALOGPS pKa (Strongest Acidic) 2.33 ChemAxon pKa (Strongest Basic) 8.48 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 332.37 Ų ChemAxon Rotatable Bond Count 20 ChemAxon Refractivity 168.91 m³·mol⁻¹ ChemAxon Polarizability 61.43 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	5-Methyltetrahydropteroyltri-L-glutamic acid + L-Homocysteine <> Tetrahydropteroyltri-L-glutamic acid + L-Methionine Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid <> Selenomethionine + Tetrahydropteroyltri-L-glutamic acid L-Homocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid > L-Methionine + tetrahydropteroyl tri-L-glutamate
SMPDB Pathways:	Not Available
KEGG Pathways:	Cysteine and methionine metabolism ec00270 Metabolic pathways eco01100 Selenoamino acid metabolism ec00450
EcoCyc Pathways:	S-adenosyl-L-methionine cycle I PWY-6151 methionine biosynthesis I HOMOSER-METSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_19) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-05fr-0000419000-4aece9ee9aeb687f3a1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0zgl-5603933000-11aa5a14e6cacf5eb9b8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0pk9-6613920000-ea8b525c3404c241f810 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-024u-0600779000-a67e6d858a1b2e40dd23 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0204-0902844000-86ab2a5c4ea00fb1ec1d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000j-2709100000-5fa0d5508195227cc0f9 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 22080510 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. Pubmed: 21097882 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. Pubmed: 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. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17614 HMDB ID Not Available Pubchem Compound ID 16722111 Kegg ID C04489 ChemSpider ID 389321 Wikipedia ID Not Available BioCyc ID CPD-1302 EcoCyc ID CPD-1302

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