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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-12 15:13:45 UTC
Update Date2021-09-14 15:47:35 UTC
HMDB IDHMDB0006825
Secondary Accession Numbers
  • HMDB06825
Metabolite Identification
Common NameTetrahydrofolyl-[Glu](2)
DescriptionTetrahydrofolyl-[Glu](2), also known as tetrahydropteroyldiglutamate or (6S)-H4pteglu2, belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof) . Tetrahydrofolyl-[Glu](2) is a strong basic compound (based on its pKa). Tetrahydrofolyl-[Glu](2) exists in all living organisms, ranging from bacteria to humans. Within humans, tetrahydrofolyl-[glu](2) participates in a number of enzymatic reactions. In particular, tetrahydrofolyl-[glu](2) can be biosynthesized from tetrahydrofolic acid and L-glutamic acid; which is catalyzed by the enzyme folylpolyglutamate synthase. In addition, tetrahydrofolyl-[glu](2) and L-glutamic acid can be converted into tetrahydrofolyl-[glu](N); which is catalyzed by the enzyme folylpolyglutamate synthase. In humans, tetrahydrofolyl-[glu](2) is involved in the metabolic disorder called the methylenetetrahydrofolate reductase deficiency (mthfrd) pathway.
Structure
Thumb
Synonyms
ValueSource
TetrahydropteroyldiglutamateKegg
(6S)-H4PteGlu2Kegg
Tetrahydropteroyldiglutamic acidGenerator
Tetrahydrofolyl-[glu](n+1)HMDB
Tetrahydropteroyl-[gamma-glu]NHMDB
Tetrahydropteroyl-[gamma-glu]n+1HMDB
THF-L-GlutamateHMDB
THF-L-Glutamic acidHMDB
THF-PolyglutamateHMDB
Chemical FormulaC24H30N8O9
Average Molecular Weight574.5432
Monoisotopic Molecular Weight574.213574598
IUPAC Name2-{4-[(4-{[(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}pentanedioic acid
Traditional Name2-{4-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}pentanedioic acid
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)CN2)C(=O)N1
InChI Identifier
InChI=1S/C24H30N8O9/c25-24-31-19-18(21(37)32-24)28-13(10-27-19)9-26-12-3-1-11(2-4-12)20(36)30-15(23(40)41)5-7-16(33)29-14(22(38)39)6-8-17(34)35/h1-4,13-15,26,28H,5-10H2,(H,29,33)(H,30,36)(H,34,35)(H,38,39)(H,40,41)(H4,25,27,31,32,37)
InChI KeyZAOGJXDWOQXFBW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentTetrahydrofolic acids and derivatives
Alternative Parents
Substituents
  • Tetrahydrofolic acid or derivatives
  • Alpha-dipeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamic acid or derivatives
  • Glutamine or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Aminobenzoic acid or derivatives
  • Aminobenzamide
  • Tricarboxylic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Benzoyl
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • N-acyl-amine
  • Pyrimidine
  • Fatty acyl
  • Monocyclic benzene moiety
  • Fatty amide
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Secondary amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024105
KNApSAcK IDNot Available
Chemspider ID390680
KEGG Compound IDC09332
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442163
PDB IDNot Available
ChEBI ID28624
Food Biomarker OntologyNot Available
VMH IDTHFGLU
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in tetrahydrofolylpolyglutamate synthase activity
Specific function:
Catalyzes conversion of folates to polyglutamate derivatives allowing concentration of folate compounds in the cell and the intracellular retention of these cofactors, which are important substrates for most of the folate-dependent enzymes that are involved in one-carbon transfer reactions involved in purine, pyrimidine and amino acid synthesis. Unsubstitued reduced folates are the preferred substrates. Metabolizes methotrexate (MTX) to polyglutamates.
Gene Name:
FPGS
Uniprot ID:
Q05932
Molecular weight:
59173.37
Reactions
Adenosine triphosphate + Tetrahydrofolic acid + Glutamic acid → ADP + Phosphate + Tetrahydrofolyl-[Glu](2)details
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the polyglutamate sidechains of pteroylpolyglutamates. Progressively removes gamma-glutamyl residues from pteroylpoly-gamma-glutamate to yield pteroyl-alpha-glutamate (folic acid) and free glutamate. May play an important role in the bioavailability of dietary pteroylpolyglutamates and in the metabolism of pteroylpolyglutamates and antifolates.
Gene Name:
GGH
Uniprot ID:
Q92820
Molecular weight:
35964.045
Reactions
Tetrahydrofolyl-[Glu](2) + → Tetrahydrofolic acid + details