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Identification
YMDB IDYMDB00773
Name5,6,7,8-tetrahydrofolyl-L-glutamic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5,6,7,8-tetrahydrofolyl-L-glutamic acid, also known as tetrahydrofolyl-[glu](2) or THF-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) . 5,6,7,8-tetrahydrofolyl-L-glutamic acid is a strong basic compound (based on its pKa). 5,6,7,8-tetrahydrofolyl-L-glutamic acid may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • Tetrahydrofolyl-[Glu](2)
  • Tetrahydrofolyl-[Glu](n+1)
  • Tetrahydropteroyl-[gamma-Glu]n
  • Tetrahydropteroyl-[gamma-Glu]n+1
  • THF-L-glutamate
  • THF-L-glutamic acid
  • THF-polyglutamate
  • 5,6,7,8-Tetrahydrofolyl-L-glutamate
CAS numberNot Available
WeightAverage: 574.5432
Monoisotopic: 574.213574598
InChI KeyZAOGJXDWOQXFBW-FGRDXJNISA-N
InChIInChI=1S/C24H30N8O9/c25-24-31-19-18(21(37)32-24)28-13(10-27-19)9-26-12-3-1-11(2-4-12)20(36)30-15(23(40)41)5-7-16(33)29-14(22(38)39)6-8-17(34)35/h1-4,13-15,26,28H,5-10H2,(H,29,33)(H,30,36)(H,34,35)(H,38,39)(H,40,41)(H4,25,27,31,32,37)/t13?,14-,15-/m0/s1
IUPAC Name(2S)-2-[(4S)-4-[(4-{[(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido]pentanedioic acid
Traditional IUPAC Name(2S)-2-[(4S)-4-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido]pentanedioic acid
Chemical FormulaC24H30N8O9
SMILESNC1=NC2=C(NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)CN2)C(=O)N1
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-dipeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamic acid or derivatives
  • Glutamine 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
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Benzoyl
  • 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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP-2ALOGPS
logP-4.3ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)4.66ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area273.67 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity149.67 m³·mol⁻¹ChemAxon
Polarizability57.44 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 PathwaysNot Available
KEGG Pathways
Folate biosynthesisec00790 Map00790
SMPDB ReactionsNot Available
KEGG Reactions
Adenosine triphosphate + 5,6,7,8-Tetrahydrofolic acid + L-Glutamic acidphosphate + 5,6,7,8-tetrahydrofolyl-L-glutamic acid + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057j-0710090000-3a35aca787d6f8c13308JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8a-0920120000-d528bbeaaf6eca707783JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-1900000000-2c920e973fa570e49c99JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0000190000-a8cc679033cf52b0b32eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0213290000-bebf00ed7964426b173cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9643020000-3dd0179e9030230b65d4JSpectraViewer
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
  • Cherest, H., Thomas, D., Surdin-Kerjan, Y. (2000). "Polyglutamylation of folate coenzymes is necessary for methionine biosynthesis and maintenance of intact mitochondrial genome in Saccharomyces cerevisiae." J Biol Chem 275:14056-14063.10799479
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27650
HMDB IDHMDB06825
Pubchem Compound ID442163
Kegg IDC09332
ChemSpider ID21864891
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Coenzyme transport and metabolism
Specific function:
Conversion of folates to polyglutamate derivatives
Gene Name:
MET7
Uniprot ID:
Q08645
Molecular weight:
62150.89844
Reactions
ATP + tetrahydropteroyl-(gamma-Glu)(n) + L-glutamate → ADP + phosphate + tetrahydropteroyl-(gamma-Glu)(n+1).