Showing metabocard for Tetrahydrofolyl-[Glu](2) (BMDB0006825)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:28 UTC
Update Date2020-05-21 16:28:32 UTC
BMDB IDBMDB0006825
Secondary Accession Numbers
  • BMDB06825
Metabolite Identification
Common NameTetrahydrofolyl-[Glu](2)
DescriptionTetrahydrofolyl-[glu](2), also known as tetrahydrofolyl-[glu](2) 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 possibly soluble (in water) and a strong basic compound (based on its pKa). Tetrahydrofolyl-[glu](2) exists in all living organisms, ranging from bacteria to humans. Tetrahydrofolyl-[glu](2) participates in a number of enzymatic reactions, within cattle. 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 cattle, tetrahydrofolyl-[glu](2) is involved in the metabolic pathway called the folate metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
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-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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity149.67 m³·mol⁻¹ChemAxon
Polarizability57.11 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, Positivesplash10-004i-0431390000-059fa6b746299ba6e305View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fdk-6293218000-7e3064684464aa734ccbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Tetrahydrofolyl-[Glu](2),1TMS,#1" TMS) - 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_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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0150190000-a135ccbc7d7c4f480879View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-1944400000-344cf6e23a4c6bde7d83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1912000000-c58894420073d0bb7673View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0100090000-b93be3036b3a76b6c4f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zi9-1823390000-091486d46712ad051a2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufu-2901110000-1d7f03af25399d3dd6d0View 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 IDHMDB0006825
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
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
Tetrahydrofolic acid + L-Glutamic acid + Adenosine triphosphate → Tetrahydrofolyl-[Glu](2) + ADP + Hydrogen phosphatedetails
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