Tetrahydrofolyl-[Glu](2) (ECMDB21661) (M2MDB002051)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (407)
Record Information
Version2.0
Creation Date2012-08-15 08:51:36 -0600
Update Date2015-06-03 17:22:02 -0600
Secondary Accession Numbers
  • ECMDB21661
Identification
Name:Tetrahydrofolyl-[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
MOLSDFPDBSMILESInChI
Synonyms:
  • N-[(4-{[(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-g-glutamyl-L-glutamate
  • N-[(4-{[(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-g-glutamyl-L-glutamic acid
  • N-[(4-{[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-gamma-glutamyl-L-glutamate
  • N-[(4-{[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-gamma-glutamyl-L-glutamic acid
  • N-[(4-{[(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-γ-glutamyl-L-glutamate
  • N-[(4-{[(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-γ-glutamyl-L-glutamic acid
  • Tetrahydrofolyl-[Glu](2)
  • Tetrahydrofolyl-[Glu](N+1)
  • Tetrahydropteroyl-[g-glu]N
  • Tetrahydropteroyl-[g-glu]n+1
  • Tetrahydropteroyl-[gamma-Glu]N
  • Tetrahydropteroyl-[gamma-Glu]N+1
  • Tetrahydropteroyl-[γ-glu]N
  • Tetrahydropteroyl-[γ-glu]n+1
  • THF-L-glutamate
  • THF-L-glutamic acid
  • THF-polyglutamate
  • THF-polyglutamic acid
Chemical Formula:C24H30N8O9
Weight:Average: 574.5432
Monoisotopic: 574.213574598
InChI Key:ZAOGJXDWOQXFBW-UHFFFAOYSA-N
InChI: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)
CAS number:Not Available
IUPAC Name:2-{4-[(4-{[(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}pentanedioic acid
Traditional IUPAC Name:2-{4-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}pentanedioic acid
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
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
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Tetrahydrofolic acid + L-Glutamate <> ADP + Phosphate + Tetrahydrofolyl-[Glu](2)
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
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 SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27650
HMDB IDHMDB06825
Pubchem Compound ID442163
Kegg IDC09332
ChemSpider ID390680
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Bifunctional protein folC
General function:
Involved in tetrahydrofolylpolyglutamate synthase activity
Specific function:
Conversion of folates to polyglutamate derivatives
Gene Name:
folC
Uniprot ID:
P08192
Molecular weight:
45405
Reactions
ATP + tetrahydropteroyl-(gamma-Glu)(n) + L-glutamate = ADP + phosphate + tetrahydropteroyl-(gamma-Glu)(n+1).
ATP + 7,8-dihydropteroate + L-glutamate = ADP + phosphate + 7,8-dihydropteroylglutamate.