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Identification
YMDB IDYMDB00518
Name5-Methyltetrahydropteroyltri-L-glutamic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Methyltetrahydropteroyltri-L-glutamate 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) . 5-Methyltetrahydropteroyltri-L-glutamate is a strong basic compound (based on its pKa). 5-Methyltetrahydropteroyltri-L-glutamate exists in all living species, ranging from bacteria to humans. selenohomocysteine and 5-methyltetrahydropteroyltri-L-glutamate can be converted into selenomethionine and tetrahydropteroyltri-L-glutamate; which is mediated by the enzyme N5-methyltetrahydropteroyltriglutamate-homocysteine methyltransferase. In yeast, 5-methyltetrahydropteroyltri-L-glutamate is involved in the metabolic pathway called the selenocompound metabolism pathway.
Structure
Thumb
Synonyms
  • 5-Methyltetrahydropteroyltri-L-glutamate
  • 5-methyltetrahydropteroyltri-L-glutamic acid
CAS numberNot Available
WeightAverage: 717.6838
Monoisotopic: 717.271817757
InChI KeyHVRNKDVLFAVCJF-VJANTYMQSA-N
InChIInChI=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
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 IUPAC 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
Chemical FormulaC30H39N9O12
SMILESCN1[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)NC(N)=N2
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity182.86 m³·mol⁻¹ChemAxon
Polarizability70.76 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
Selenocompound metabolismPW002472 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Selenocompound metabolismec00450 Map00450
SMPDB ReactionsNot Available
KEGG Reactions
L-Homocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acidL-Methionine + Tetrahydropteroyltri-L-glutamate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0732118900-53d55fe9c0863d97f51fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0932104100-d16b89e4058f4ac3aa4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1921101000-70b11d23c3858386d9c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00r2-0000009200-85df402e63838ca104ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi1-0110019000-44613760172916ef7e66JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004m-5931213000-75cc50202a2eca9054cbJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Csaikl, U., Csaikl, F. (1986). "Molecular cloning and characterization of the MET6 gene of Saccharomyces cerevisiae." Gene 46:207-214.3542720
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17614
HMDB IDHMDB12177
Pubchem Compound ID16722111
Kegg IDC04489
ChemSpider ID17625689
FOODB IDFDB028831
Wikipedia IDNot Available
BioCyc IDCPD-1302

Enzymes

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:
MET6
Uniprot ID:
P05694
Molecular weight:
85859.20313
Reactions
5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine → tetrahydropteroyltri-L-glutamate + L-methionine.