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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-12 15:17:10 UTC
Update Date2020-02-26 21:26:48 UTC
HMDB IDHMDB0006826
Secondary Accession Numbers
  • HMDB06826
Metabolite Identification
Common NameTetrahydrofolyl-[Glu](n)
DescriptionTetrahydrofolyl-[Glu](n), also known as THF-L-glutamic acid or THF-polyglutamate, 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](n) is a strong basic compound (based on its pKa). Within humans, tetrahydrofolyl-[glu](N) participates in a number of enzymatic reactions. In particular, tetrahydrofolyl-[glu](N) can be biosynthesized from tetrahydrofolyl-[glu](2) and L-glutamic acid through its interaction with the enzyme folylpolyglutamate synthase. In addition, tetrahydrofolyl-[glu](N) can be converted into tetrahydrofolyl-[glu](2) and L-glutamic acid through the action of the enzyme Gamma-glutamyl hydrolase. In humans, tetrahydrofolyl-[glu](N) is involved in folate malabsorption, hereditary. Sample structure image shows the case when n=3.
Structure
Data?1582752408
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
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-oligopeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamic acid or derivatives
  • Glutamine or derivatives
  • Tetracarboxylic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Alpha-amino 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 Descriptors
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity177.56 m³·mol⁻¹ChemAxon
Polarizability67.81 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0330229000-26f7358d09d8be8dd6bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053i-0330009000-2343f1529d5558b72f37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0960106000-948a11df3216bc17a492Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-0930102000-c63ca5bc90715eab8c7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kal-0000009200-7ef523ed0c34682f53c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rx-0110119000-94abb8fbe6ce9db951aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054p-6941203000-2220ce26cc38dbfa7133Spectrum
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 IDFDB024106
KNApSAcK IDNot Available
Chemspider ID21231977
KEGG Compound IDC03541
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45479706
PDB IDNot Available
ChEBI ID27650
Food Biomarker OntologyNot Available
VMH 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
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