Showing metabocard for Tetrahydrofolyl-[Glu](n) (BMDB0006826)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:29 UTC
Update Date2020-05-21 16:28:32 UTC
BMDB IDBMDB0006826
Secondary Accession Numbers
  • BMDB06826
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 possibly soluble (in water) and a strong basic compound (based on its pKa). Tetrahydrofolyl-[glu](N) participates in a number of enzymatic reactions, within cattle. In particular, Tetrahydrofolyl-[glu](N) can be biosynthesized from tetrahydrofolyl-[glu](2) and L-glutamic acid; which is catalyzed by the enzyme folylpolyglutamate synthase. In addition, Tetrahydrofolyl-[glu](N) can be converted into tetrahydrofolyl-[glu](2) and L-glutamic acid; which is catalyzed by the enzyme Gamma-glutamyl hydrolase. In cattle, tetrahydrofolyl-[glu](N) is involved in the metabolic pathway called the folate metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0330229000-26f7358d09d8be8dd6bcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053i-0330009000-2343f1529d5558b72f37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0960106000-948a11df3216bc17a492View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-0930102000-c63ca5bc90715eab8c7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kal-0000009200-7ef523ed0c34682f53c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rx-0110119000-94abb8fbe6ce9db951aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054p-6941203000-2220ce26cc38dbfa7133View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001009700-73c689fed96633d0e3c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0921105100-6c0b5caba5aa9d72304bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-1910000000-3587158aa91827b1a1f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f72-0190125500-66fcaf7dd19aada1c2a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-055e-0890461000-4f80e46b7c8bdfa76947View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-1960030000-fb370cb9f66800f069e9View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006826
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Folylpolyglutamate synthase, mitochondrial
General function:
Coenzyme transport and metabolism
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.
Gene Name:
FPGS
Uniprot ID:
A6H751
Molecular weight:
64900.0
Reactions
Tetrahydrofolyl-[Glu](2) + Adenosine triphosphate + L-Glutamic acid → Tetrahydrofolyl-[Glu](n) + ADP + Hydrogen phosphatedetails
Enzyme Details
2. Gamma-glutamyl hydrolase
General function:
Not Available
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. Exhibits either endo- or exopeptidase activity depending upon the tissue of origin. When secreted, it acts primarily as an endopeptidase (By similarity).
Gene Name:
GGH
Uniprot ID:
A7YWG4
Molecular weight:
35683.0
Reactions
Tetrahydrofolyl-[Glu](n) + Water → Tetrahydrofolyl-[Glu](2) + L-Glutamic aciddetails