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Record Information
Version4.0
Creation Date2008-08-12 15:17:10 UTC
Update Date2017-09-21 21:39:16 UTC
HMDB IDHMDB0006826
Secondary Accession Numbers
  • HMDB06826
Metabolite Identification
Common NameTetrahydrofolyl-[Glu](n)
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]. Sample structure image shows the case when n=3.
Structure
Thumb
Synonyms
ValueSource
Tetrahydrofolyl-[glu](n+1)HMDB
Tetrahydropteroyl-[gamma-glu]NHMDB
Tetrahydropteroyl-[gamma-glu]n+1HMDB
THF-L-Glutamic acidHMDB
THF-PolyglutamateHMDB
Chemical FormulaC29H37N9O12
Average Molecular Weight703.6572
Monoisotopic Molecular Weight703.256167693
IUPAC Name2-(4-{4-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid
Traditional Name2-(4-{4-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid
CAS Registry NumberNot Available
SMILES
NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N1
InChI Identifier
InChI=1S/C29H37N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,15-18,31,33H,5-12H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H4,30,32,37,38,44)
InChI KeyRXWVHRYZTWZATH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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) .
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct ParentTetrahydrofolic acids and derivatives
Alternative Parents
Substituents
  • Tetrahydrofolic acid or derivatives
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamic acid or derivatives
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Hippuric acid
  • Hippuric acid or derivatives
  • Tetracarboxylic acid or derivatives
  • Aminobenzamide
  • Alpha-amino acid or derivatives
  • Aminobenzoic acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Benzoyl
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Fatty amide
  • Pyrimidine
  • Primary aromatic amine
  • Benzenoid
  • Fatty acyl
  • Heteroaromatic compound
  • Vinylogous amide
  • 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 Descriptors
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 Solubility0.36 mg/mLALOGPS
logP-1.6ALOGPS
logP-6.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area340.07 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity177.56 m3·mol-1ChemAxon
Polarizability67.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Folate MetabolismPw000024Pw000024 greyscalePw000024 simpleMap00670
Folate malabsorption, hereditaryPw000701Pw000701 greyscalePw000701 simpleNot Available
Methotrexate PathwayPw000268Pw000268 greyscalePw000268 simpleNot Available
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)Pw000519Pw000519 greyscalePw000519 simpleNot Available
Pterine BiosynthesisPw000140Pw000140 greyscalePw000140 simpleMap00790
Displaying all 5 entries
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 IDFDB024106
KNApSAcK IDNot Available
Chemspider ID21231977
KEGG Compound IDC03541
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0006826
METLIN IDNot Available
PubChem Compound45479706
PDB IDNot Available
ChEBI ID27650
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
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