5-Methyltetrahydropteroyltri-L-glutamic acid (ECMDB01079) (M2MDB000245)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (749)
Record Information
Version2.0
Creation Date2012-05-31 13:44:45 -0600
Update Date2015-06-03 15:53:42 -0600
Secondary Accession Numbers
  • ECMDB01079
Identification
Name:5-Methyltetrahydropteroyltri-L-glutamic acid
Description5-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
Thumb
MOLSDFPDBSMILESInChI
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassHexacarboxylic acids and derivatives
Direct ParentHexacarboxylic acids and derivatives
Alternative Parents
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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.264PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP-3.5ALOGPS
logP-9.9ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.33ChemAxon
pKa (Strongest Basic)8.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area332.37 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity168.91 m³·mol⁻¹ChemAxon
Polarizability61.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_19) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000419000-4aece9ee9aeb687f3a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgl-5603933000-11aa5a14e6cacf5eb9b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pk9-6613920000-ea8b525c3404c241f810View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-024u-0600779000-a67e6d858a1b2e40dd23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0204-0902844000-86ab2a5c4ea00fb1ec1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000j-2709100000-5fa0d5508195227cc0f9View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID17614
HMDB IDNot Available
Pubchem Compound ID16722111
Kegg IDC04489
ChemSpider ID389321
Wikipedia IDNot Available
BioCyc IDCPD-1302
EcoCyc IDCPD-1302

Enzymes

Protein Details
1. Methionine synthase
General function:
Involved in methionine synthase activity
Specific function:
Catalyzes the transfer of a methyl group from methyl- cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate
Gene Name:
metH
Uniprot ID:
P13009
Molecular weight:
135996
Reactions
5-methyltetrahydrofolate + L-homocysteine = tetrahydrofolate + L-methionine.
Protein Details
2. 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase
General function:
Involved in 5-methyltetrahydropteroyltriglutamate-homocysteine S-methyltransferase activity
Specific function:
Catalyzes the transfer of a methyl group from 5- methyltetrahydrofolate to homocysteine resulting in methionine formation
Gene Name:
metE
Uniprot ID:
P25665
Molecular weight:
84673
Reactions
5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine.