Tetrahydropteroyltri-L-glutamic acid (ECMDB01174) (M2MDB000283)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (749)
Record Information
Version2.0
Creation Date2012-05-31 13:46:50 -0600
Update Date2015-06-03 15:53:48 -0600
Secondary Accession Numbers
  • ECMDB01174
Identification
Name:Tetrahydropteroyltri-L-glutamic acid
DescriptionTetrahydropteroyltri-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. tetrahydropteroyltri-L-glutamic acid (CHEBI:17420) is a tetrahydropteroyltri-L-glutamate (CHEBI:26920) tetrahydropteroyltri-L-glutamic acid (CHEBI:17420) is conjugate acid of tetrahydropteroyltri-L-glutamate (CHEBI:58140)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Tetrahydropteroyltri-L-glutamate
  • Tetrahydropteroyltri-L-glutamic acid
  • THPTGlu
Chemical Formula:C24H34N8O12
Weight:Average: 626.5732
Monoisotopic: 626.229618592
InChI Key:XPPZDBCBKYATPW-MQXOEPKGSA-N
InChI:InChI=1S/C24H34N8O12/c1-9(42-21(39)10(25)2-5-14(33)34)18(43-22(40)11(26)3-6-15(35)36)13-8-29-19-17(30-13)20(32-24(28)31-19)44-23(41)12(27)4-7-16(37)38/h8-12,18,30H,2-7,25-27H2,1H3,(H,33,34)(H,35,36)(H,37,38)(H3,28,29,31,32)/t9?,10-,11-,12-,18?/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-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-5,8-dihydro-1H-pteridin-6-yl)propan-2-yl)oxy]-5-oxopentanoic acid
SMILES:[H][C@](N)(CCC(O)=O)C(=O)OC1=NC(=N)NC2=C1NC(=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
  • Fatty acid ester
  • Amino fatty acid
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Imidolactam
  • Pyrimidine
  • Fatty acyl
  • Heteroaromatic compound
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary amine
  • Carboxylic acid
  • Enamine
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • 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:-2.043PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP-3.5ALOGPS
logP-10ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.44ChemAxon
pKa (Strongest Basic)8.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area341.16 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity163.61 m³·mol⁻¹ChemAxon
Polarizability59.11 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
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_25) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0btc-0000798000-a39b992c09f3cd640b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-4501941000-dc29949cddfbf159e32fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zir-5421910000-0a69615ec7aa6f337088View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0400935000-f1aa921f4b3d29deb419View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0601912000-a85d64e7980866e2fb68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xs-2709200000-f23ed20992da7d0e757fView in MoNA
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
  • 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 ID17420
HMDB IDNot Available
Pubchem Compound ID16722112
Kegg IDC04144
ChemSpider ID389223
Wikipedia IDNot Available
BioCyc IDNot Available

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.