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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:31 UTC
Update Date2021-09-14 15:44:56 UTC
HMDB IDHMDB0012177
Secondary Accession Numbers
  • HMDB12177
Metabolite Identification
Common Name5-Methyltetrahydropteroyltri-L-glutamic acid
Description5-Methyltetrahydropteroyltri-L-glutamic acid (CAS: 13061-55-7) is formed during the reaction between the carbonyl group of 5-methyltetrahydropteroate and the amine group on one end of three replicates of glutamate. It is involved in several pathways as a product of enzymatic reduction such as in tetrahydrofolate biosynthesis II and methionine biosynthesis I, II, and III. It is also involved in several pathways as a product of enzymatic oxidation such as in the pathways folate polyglutamylation I and carbon tetrachloride degradation II. In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine.
Structure
Data?1583423822
Synonyms
ValueSource
5-Methyltetrahydropteroyltri-L-glutamateChEBI
5-Methyltetrahydropteroyltri-L-glutamic acidHMDB, Generator
5-Methyl-5,6,7,8-tetrahydropteroyl tri-gamma-L-glutamateHMDB
5-Methyl-5,6,7,8-tetrahydropteroyl tri-γ-L-glutamateHMDB
5-Methyltetrahydrofolate triglutamateHMDB
5-Methyltetrahydropteroyl-gamma-glutamyl-gamma-glutamylglutamic acidHMDB
5-Methyltetrahydropteroyl-γ-glutamyl-γ-glutamylglutamic acidHMDB
Chemical FormulaC30H39N9O12
Average Molecular Weight717.6838
Monoisotopic Molecular Weight717.271817757
IUPAC Name(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-5-methyl-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-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid
CAS Registry Number133321-34-3
SMILES
CN1[C@@H](CNC2=CC=C(C=C2)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)CNC2=C1C(=O)N=C(N)N2
InChI Identifier
InChI=1S/C30H39N9O12/c1-39-16(13-33-24-23(39)26(45)38-30(31)37-24)12-32-15-4-2-14(3-5-15)25(44)36-19(29(50)51)7-10-21(41)34-17(27(46)47)6-9-20(40)35-18(28(48)49)8-11-22(42)43/h2-5,16-19,32H,6-13H2,1H3,(H,34,41)(H,35,40)(H,36,44)(H,42,43)(H,46,47)(H,48,49)(H,50,51)(H4,31,33,37,38,45)/t16-,17-,18-,19-/m0/s1
InChI KeyHVRNKDVLFAVCJF-VJANTYMQSA-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
  • N-acyl-l-alpha-amino acid
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Aminobenzamide
  • Alpha-amino acid or derivatives
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Tertiary aliphatic/aromatic amine
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Monocyclic benzene moiety
  • Benzenoid
  • N-acyl-amine
  • Fatty acyl
  • Fatty amide
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Secondary amine
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot 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 Solubility0.35 g/LALOGPS
logP-1.4ALOGPS
logP-3.9ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.69ChemAxon
pKa (Strongest Basic)3.14ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area331.28 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity182.86 m³·mol⁻¹ChemAxon
Polarizability70.68 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]+241.00630932474
DeepCCS[M-H]-239.15830932474
DeepCCS[M-2H]-272.75430932474
DeepCCS[M+Na]+246.61230932474
AllCCS[M+H]+245.532859911
AllCCS[M+H-H2O]+245.432859911
AllCCS[M+NH4]+245.532859911
AllCCS[M+Na]+245.532859911
AllCCS[M-H]-242.132859911
AllCCS[M+Na-2H]-245.532859911
AllCCS[M+HCOO]-249.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Methyltetrahydropteroyltri-L-glutamic acidCN1[C@@H](CNC2=CC=C(C=C2)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)CNC2=C1C(=O)N=C(N)N26594.6Standard polar33892256
5-Methyltetrahydropteroyltri-L-glutamic acidCN1[C@@H](CNC2=CC=C(C=C2)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)CNC2=C1C(=O)N=C(N)N25400.6Standard non polar33892256
5-Methyltetrahydropteroyltri-L-glutamic acidCN1[C@@H](CNC2=CC=C(C=C2)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)CNC2=C1C(=O)N=C(N)N27157.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 10V, Positive-QTOFsplash10-0udi-0732118900-53d55fe9c0863d97f51f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 20V, Positive-QTOFsplash10-0006-0932104100-d16b89e4058f4ac3aa4c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 40V, Positive-QTOFsplash10-0006-1921101000-70b11d23c3858386d9c92015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 10V, Negative-QTOFsplash10-00r2-0000009200-85df402e63838ca104ff2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 20V, Negative-QTOFsplash10-0fi1-0110019000-44613760172916ef7e662015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 40V, Negative-QTOFsplash10-004m-5931213000-75cc50202a2eca9054cb2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 10V, Positive-QTOFsplash10-0ikc-0429311800-370ce9231396acda8d922021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 20V, Positive-QTOFsplash10-01u3-1625490000-4b2f69d8a822fdbfcca92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 40V, Positive-QTOFsplash10-02cu-1905000000-a42458750a4d98ede3302021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 10V, Negative-QTOFsplash10-0udi-0010009100-0dc6b367fdbdca7547fc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 20V, Negative-QTOFsplash10-0zir-0330119000-1542d290911c87efd0512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyltetrahydropteroyltri-L-glutamic acid 40V, Negative-QTOFsplash10-0ufr-1913110000-8e9ec4663cc7affb68952021-09-25Wishart 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 IDFDB028831
KNApSAcK IDNot Available
Chemspider ID17625689
KEGG Compound IDC04489
BioCyc IDCPD-1302
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16722111
PDB IDNot Available
ChEBI ID17614
Food Biomarker OntologyNot Available
VMH IDM01114
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