You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:25 UTC
Update Date2019-07-23 05:57:43 UTC
HMDB IDHMDB0012290
Secondary Accession Numbers
  • HMDB12290
Metabolite Identification
Common NameTetrahydropteroyltri-L-glutamate
DescriptionTetrahydropteroyltri-L-glutamate 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-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine. In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine.
Structure
Data?1563861463
SynonymsNot Available
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 NumberNot Available
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
DescriptionThis compound 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
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
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
Polarizability69.2 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0330229000-26f7358d09d8be8dd6bcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053i-0430109000-eac2681831f71dca6e8bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0950105000-4fcd371853d69be99f61JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0930101000-93bebce6dc25dfe950c3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kal-0000009200-1222553f516303fcc67bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01po-0110119000-86fae98cd0220bb8d84fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054p-6941212000-00e3dffa2369077ff1f0JSpectraViewer | MoNA
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
FoodDB IDFDB028919
KNApSAcK IDNot Available
Chemspider ID17625690
KEGG Compound IDC04144
BioCyc IDCPD-1302
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16722112
PDB ID39S
ChEBI ID17420
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-glutamate → Selenomethionine + Tetrahydropteroyltri-L-glutamatedetails