5-Methyltetrahydropteroyltri-L-glutamic acid (PAMDB000245)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000245
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
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 5-Methyltetrahydropteroyltri-L-glutamate
  • 5-Methyltetrahydropteroyltri-L-glutamic acid
  • 5MTHTGlu
Chemical Formula: C25H36N8O12
Average Molecular Weight: 640.5997
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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 ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassHexacarboxylic acids and derivatives
Direct Parent Hexacarboxylic acids and derivatives
Alternative Parents
Substituents
  • Hexacarboxylic acid or derivatives
  • Biopterin
  • Alpha-amino acid ester
  • Pterin
  • Pteridine
  • Alpha-amino acid or derivatives
  • Fatty acid ester
  • Amino fatty acid
  • Fatty acyl
  • Pyrimidine
  • Heteroaromatic compound
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • 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:
PropertyValueSource
LogP:-2.264PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.136 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity168.91 m3·mol-1ChemAxon
Polarizability61.43 Å3ChemAxon
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
L-Homocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid > L-Methionine + tetrahydropteroyl tri-L-glutamate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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