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N5-methyl--tetrahydropteroyl tri-L-glutamate (M2MDB006361)

Record Information
Version2.0
Creation Date2015-09-08 17:50:22 -0600
Update Date2015-09-14 16:46:44 -0600
Secondary Accession Numbers
  • ECMDB24244
Identification
Name:N5-methyl--tetrahydropteroyl tri-L-glutamate
DescriptionN5-methyl--tetrahydropteroyl tri-L-glutamate is an intermediate in L-methionine biosynthesis I and S-adenosyl-L-methionine cycle I in E.coli. In both pathways, it is a substrate for the enzyme cobalamin-dependent methionine synthase which catalyzes the reaction L-homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate → L-methionine + tetrahydropteroyl tri-L-glutamate (BioCyc compound: CPD-1302).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • N5-Methyl--tetrahydropteroyl tri-L-glutamic acid
Chemical Formula:C30H35N9O12
Weight:Average: 713.663
Monoisotopic: 713.242711923
InChI Key:HVRNKDVLFAVCJF-UHFFFAOYSA-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
CAS number:Not Available
IUPAC Name:2-(4-{4-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxylatobutanamido}-4-carboxylatobutanamido)pentanedioate
Traditional IUPAC Name:2-(4-{4-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxylatobutanamido}-4-carboxylatobutanamido)pentanedioate
SMILES:CN1C(CNC2=CC=C(C=C2)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC([O-])=O)C([O-])=O)C([O-])=O)C([O-])=O)CNC2=C1C(=O)NC(N)=N2
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Aminopyrimidine
  • Pyrimidine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Vinylogous amide
  • Azole
  • Imidazole
  • Oxolane
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.95 g/LALOGPS
logP0.11ALOGPS
logP-3.5ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)2.68ChemAxon
pKa (Strongest Basic)3.14ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area342.6 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity226.41 m³·mol⁻¹ChemAxon
Polarizability69.3 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate + Homocysteine > tetrahydropteroyltri-L-glutamate + L-Methionine
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, Positivesplash10-03di-0000000900-12c56169fecdd9f1abdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000004900-74d9c3f43e245acb61d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9220003200-ae49c32b2aa0b39c52fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-8aa96c83c5c265ff009aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-2000002900-364f6ba4e7a9e5066a1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100001000-5b24b298a89419aedc5dView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Methionine synthase
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.