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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:25 UTC
Update Date2021-09-14 14:57:37 UTC
HMDB IDHMDB0012290
Secondary Accession Numbers
  • HMDB12290
Metabolite Identification
Common NameTetrahydropteroyltri-L-glutamic acid
DescriptionTetrahydropteroyltri-L-glutamic acid (CAS: 4227-85-4), also known as (6S)-H4pteglu3, 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). Tetrahydropteroyltri-L-glutamic acid is a strong basic compound (based on its pKa). In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine. Tetrahydropteroyltri-L-glutamica cid exists in all living species, ranging from bacteria to humans. Tetrahydropteroyltri-L-glutamic acid is an intermediate in the synthesis of methionine by bacteria. It is a substrate for the enzyme 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase which catalyzes the reaction 5-methyltetrahydropteroyltri-L-glutamic acid + L-homocysteine = tetrahydropteroyltri-L-glutamic acid + L-methionine.
Structure
Data?1594313457
Synonyms
ValueSource
Tetrahydropteroyltri-L-glutamateChEBI
(6S)-H4PteGlu3Kegg
Tetrahydropteroyltri-L-glutamic acidGenerator
Tetrahydropteroyltri-gamma-glutamic acidHMDB
Tetrahydropteroyltri-γ-glutamic acidHMDB
Tetrahydropteroyl tri-L-glutamateHMDB
Tetrahydropteroyl tri-L-glutamic acidHMDB
Chemical FormulaC29H37N9O12
Average Molecular Weight703.6572
Monoisotopic Molecular Weight703.256167693
IUPAC Name(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid
Traditional Name(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-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 Number88903-89-3
SMILES
NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](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)/t15-,16-,17-,18-/m0/s1
InChI KeyRXWVHRYZTWZATH-XSLAGTTESA-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-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Aminobenzamide
  • Alpha-amino acid or derivatives
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Phenylalkylamine
  • Benzoyl
  • Aniline or substituted anilines
  • 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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP-1.6ALOGPS
logP-4.3ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.59ChemAxon
pKa (Strongest Basic)3.12ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area340.07 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity177.56 m³·mol⁻¹ChemAxon
Polarizability69.1 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+241.81230932474
DeepCCS[M-H]-239.98730932474
DeepCCS[M-2H]-273.88330932474
DeepCCS[M+Na]+247.70330932474
AllCCS[M+H]+240.732859911
AllCCS[M+H-H2O]+240.632859911
AllCCS[M+NH4]+240.832859911
AllCCS[M+Na]+240.832859911
AllCCS[M-H]-238.632859911
AllCCS[M+Na-2H]-241.832859911
AllCCS[M+HCOO]-245.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tetrahydropteroyltri-L-glutamic acidNC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N17167.2Standard polar33892256
Tetrahydropteroyltri-L-glutamic acidNC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N15532.8Standard non polar33892256
Tetrahydropteroyltri-L-glutamic acidNC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N17385.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0330229000-26f7358d09d8be8dd6bc2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 10V, Positive-QTOFsplash10-053i-0430109000-eac2681831f71dca6e8b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 20V, Positive-QTOFsplash10-001i-0950105000-4fcd371853d69be99f612015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 40V, Positive-QTOFsplash10-001i-0930101000-93bebce6dc25dfe950c32015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 10V, Negative-QTOFsplash10-0kal-0000009200-1222553f516303fcc67b2015-09-16Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 20V, Negative-QTOFsplash10-01po-0110119000-86fae98cd0220bb8d84f2015-09-16Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 40V, Negative-QTOFsplash10-054p-6941212000-00e3dffa2369077ff1f02015-09-16Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 10V, Positive-QTOFsplash10-0f72-0190125500-66fcaf7dd19aada1c2a52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 20V, Positive-QTOFsplash10-055e-0890461000-4f80e46b7c8bdfa769472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 40V, Positive-QTOFsplash10-01q9-1960030000-fb370cb9f66800f069e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 10V, Negative-QTOFsplash10-0udi-0001009700-73c689fed96633d0e3c42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 20V, Negative-QTOFsplash10-0ufr-0921105100-6c0b5caba5aa9d72304b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydropteroyltri-L-glutamic acid 40V, Negative-QTOFsplash10-0ufr-1910000000-3587158aa91827b1a1f22021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 IDFDB028919
KNApSAcK IDNot Available
Chemspider ID17625690
KEGG Compound IDC04144
BioCyc IDCPD-1301
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16722112
PDB ID39S
ChEBI ID17420
Food Biomarker OntologyNot Available
VMH IDM02979
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91
Reactions
Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid → Selenomethionine + Tetrahydropteroyltri-L-glutamic aciddetails