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Record Information
Version3.6
Creation Date2008-08-12 15:13:45 UTC
Update Date2016-02-11 01:07:59 UTC
HMDB IDHMDB06825
Secondary Accession NumbersNone
Metabolite Identification
Common NameTetrahydrofolyl-[Glu](2)
DescriptionTetrahydrofolyl-[Glu](n) is involved in the folate biosynthesis pathway. Tetrahydrofolyl-[Glu](n) can be reversibly converted into Tetrahydrofolyl-[Glu](2) by folylpolyglutamate synthase [EC:6.3.2.17]. Tetrahydrofolyl-[Glu](n) can be irreversibly converted into tetrahydrofolate by gamma-glutamyl hydrolase [EC:3.4.19.9].
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 KeyInChIKey=ZAOGJXDWOQXFBW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Gamma-glutamyl alpha-amino acid
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Aminobenzamide
  • Phenylalkylamine
  • Substituted aniline
  • Benzoyl
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Aniline
  • Amino fatty acid
  • Fatty acyl
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • Primary aromatic amine
  • N-acyl-amine
  • Fatty amide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.33 mg/mLALOGPS
logP-2ALOGPS
logP-4.3ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)4.66ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area273.67 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity149.67 m3·mol-1ChemAxon
Polarizability57.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-0410190000-7e18aec9e8f122cf92f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0921130000-025c9f73d4425eb4ee45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1910000000-951a2810a73575ecd649View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05i0-0000090000-ab2a9f7e2194ab306ab6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vi-0212290000-f6a40031e0e2a9d446a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002g-6942010000-9cf36a2897355a7adb91View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Folate malabsorption, hereditarySMP00724Not Available
Folate MetabolismSMP00053map00670
Methotrexate PathwaySMP00432Not Available
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)SMP00543Not Available
Pterine BiosynthesisSMP00005map00790
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024105
KNApSAcK IDNot Available
Chemspider ID390680
KEGG Compound IDC03541
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06825
Metagene LinkHMDB06825
METLIN IDNot Available
PubChem Compound442163
PDB IDNot Available
ChEBI ID28624
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 + L-Glutamic acid → ADP + Phosphoric acid + 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