Record Information
Version2.0
Creation Date2015-09-08 17:50:02 -0600
Update Date2015-09-14 16:46:32 -0600
Secondary Accession Numbers
  • ECMDB24199
Identification
Name: N5-methyl--tetrahydropteroyl tri-L-glutamate
DescriptionN5-methyl--tetrahydropteroyl tri-L-glutamate is an intermediate in pathways L-methionine biosynthesis I and S-adenosyl-L-methionine cycle I in E.coli. It is a substrate for enzyme cobalamin-independent homocysteine transmethylase in both pathways and a substrate for enzyme cobalamin-dependent methionine synthase in pathway L-methionine biosynthesis I (BioCyc compound: CPD-1302).
Structure
Thumb
Synonyms:
  • N5-Methyl--tetrahydropteroyl tri-L-glutamic acid
Chemical Formula:C30H35N9O12
Weight:Average: 713.663
Monoisotopic: 713.242711923
InChI Key:HVRNKDVLFAVCJF-VJANTYMQSA-J
InChI: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)/p-4/t16-,17-,18-,19-/m0/s1
CAS number:Not Available
IUPAC Name:(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[4-({[(6S)-2-imino-5-methyl-4-oxido-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-1-oxidobutylidene]amino}-1-oxidobutylidene]amino}butanoate
Traditional IUPAC Name:(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[4-({[(6S)-2-imino-5-methyl-4-oxido-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}-1-oxidobutylidene]amino}-1-oxidobutylidene]amino}butanoate
SMILES:[H][C@@](CCC([O-])=N[C@@]([H])(CCC([O-])=N[C@@]([H])(CCC([O-])=O)C(O)=O)C(O)=O)(NC(=O)C1=CC=C(NC[C@@]2([H])CNC3=C(N2C)C([O-])=NC(=N)N3)C=C1)C(O)=O
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
  • Alpha-amino acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Monocyclic benzene moiety
  • Benzenoid
  • N-acyl-amine
  • Fatty acyl
  • Fatty amide
  • Vinylogous amide
  • Heteroaromatic compound
  • Tertiary amine
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary amine
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP0.17ALOGPS
logP-2.7ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.33ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area350.57 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity237.4 m³·mol⁻¹ChemAxon
Polarizability69.36 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
methionine biosynthesisPW000814 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0000000900-622abdc32cc315dd322cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-0000006900-3ddf859d7290a4a4d352View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1110016900-06be6f05afb65b6aac2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-49d9a35d9762d5451de9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2000001900-3cde656cf075950f0b36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000001100-f03d9d7c285194175ee5View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID58207
HMDB IDNot Available
Pubchem Compound ID49852302
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in methionine synthase activity
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
Gene Name:
metH
Uniprot ID:
P13009
Molecular weight:
135996
Reactions
5-methyltetrahydrofolate + L-homocysteine = tetrahydrofolate + L-methionine.
General function:
Involved in 5-methyltetrahydropteroyltriglutamate-homocysteine S-methyltransferase activity
Specific function:
Catalyzes the transfer of a methyl group from 5- methyltetrahydrofolate to homocysteine resulting in methionine formation
Gene Name:
metE
Uniprot ID:
P25665
Molecular weight:
84673
Reactions
5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine.