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Record Information
Version3.6
Creation Date2009-04-06 16:20:31 UTC
Update Date2016-02-11 01:23:46 UTC
HMDB IDHMDB12177
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Methyltetrahydropteroyltri-L-glutamate
Description5-Methyltetrahydropteroyltri-L-glutamate is formed under reaction between carbonyl group of 5-Methyltetrahydropteroate and amine group on one end of three replicates of glutamate. It is involved in several pathways such as tetrahydrofolate biosynthesis II, methionine biosynthesis I,II,III as a product of enzymatic reduction; while in pathways folate polyglutamylation I and carbon tetrachloride degradation II as a product of enzymatic oxidation. In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine.
Structure
Thumb
Synonyms
ValueSource
5-Methyltetrahydropteroyltri-L-glutamic 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 NumberNot Available
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 KeyInChIKey=HVRNKDVLFAVCJF-VJANTYMQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzamides
Direct ParentHippuric acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • Tetracarboxylic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Pterin
  • Pteridine
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Benzoic acid or derivatives
  • Aminobenzamide
  • Phenylalkylamine
  • Substituted aniline
  • Dialkylarylamine
  • Benzoyl
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Aniline
  • Amino fatty acid
  • Fatty acyl
  • Pyrimidine
  • Heteroaromatic compound
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility0.35 mg/mLALOGPS
logP-1.4ALOGPS
logP-5.7ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)-3.2ChemAxon
pKa (Strongest Basic)3.54ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area331.28 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity182.86 m3·mol-1ChemAxon
Polarizability70.76 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0732118900-53d55fe9c0863d97f51fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0932104100-d16b89e4058f4ac3aa4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1921101000-70b11d23c3858386d9c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00r2-0000009200-85df402e63838ca104ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi1-0110019000-44613760172916ef7e66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004m-5931213000-75cc50202a2eca9054cbView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028831
KNApSAcK IDNot Available
Chemspider ID17625689
KEGG Compound IDC04489
BioCyc IDCPD-1302
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12177
Metagene LinkHMDB12177
METLIN IDNot Available
PubChem Compound16722111
PDB IDNot Available
ChEBI ID17614
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