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Identification
YMDB IDYMDB00516
Name5-Formyltetrahydrofolic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Formyltetrahydrofolate (N5-Formyl-THF) is a folate coenzyme. Tetrahydrofolate (vitamin B9) and its derivatives, commonly termed folates, are essential cofactors that facilitate the transfer of one-carbon units from donor molecules into important biosynthetic pathways leading to methionine, purine, and pyrimidine biosynthesis. Folates also mediate the interconversion of serine and glycine, and play a role in histidine catabolism. Although 5-Formyl-tetrahydrofolate is the most stable derivative of the reduced folates, it is the only folate derivative that does not serve as a cofactor in C1-metabolism. [Biocyc PWY-2201] [PMID: 11923304]
Structure
Thumb
Synonyms
  • (6R,S)-5-Formyltetrahydrofolate
  • (6S)-5-formyltetrahydrofolate
  • (6S)-5-HCO-H4folate
  • [(6S)-5-formyl-5,6,7,8-tetrahydropteroyl]glutamate
  • 10-Formyl-7,8-dihydrofolate
  • 10-Formyl-7,8-dihydrofolic acid
  • 5-Formyl-5,6,7,8-tetrahydrofolate
  • 5-Formyl-5,6,7,8-tetrahydrofolic acid
  • 5-Formyltetrahydrofolate
  • 5-formyltetrahydrofolic acid
  • 5-Formyltetrahydropteroylglutamate
  • 5-Formyltetrahydropteroylglutamic acid
  • folinate
  • folinic acid
  • Folinic acid-SF
  • l-Leucovorin
  • l(-)-5-formyl-5,6,7,8-tetrahydrofolic acid
  • Leucal
  • Leucovorin
  • Levoleucovorin
  • N-(5-formyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid
  • N5-Formyl-5,6,7,8-tetrahydrofolate
  • N5-Formyl-5,6,7,8-tetrahydrofolic acid
  • N5-Formyltetrahydrofolate
  • N5-Formyltetrahydrofolic acid
  • Welcovorin
  • (6S)-5-Formyl-5,6,7,8-tetrahydrofolic acid
  • (6S)-Folinic acid
  • (6S)-Leucovorin
  • (S)-Leucovorin
  • Citrovorum factor
  • L-Folinic acid
  • Levofolene
  • Levofolinic acid
  • N-[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
  • (6S)-5-Formyl-5,6,7,8-tetrahydrofolate
  • (6S)-Folinate
  • L-Folinate
  • Levofolinate
  • N-[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamate
  • Pteroyl-D-glutamate
  • 5 Formyltetrahydropteroylglutamate
  • Calcium folinate
  • Leucovorin, (S)-isomer
  • Leucovorin, monosodium salt
  • Leucovorin, (R)-isomer
  • Leucovorin, calcium
  • Leucovorin, calcium (1:1) salt, (DL)-isomer
  • Leucovorin, calcium (1:1) salt, (S)-isomer
  • Leukovorin
  • Leukovorum
  • Monosodium salt leucovorin
  • Wellcovorin
  • Levo leucovorin
  • 6 S Leucovorin
  • Acid, folinic
  • Factor, citrovorum
  • Folinic acid SF
  • Fusilev
  • Leucovorin, calcium (1:1) salt, pentahydrate
  • Leucovorin, monopotassium salt, (S)-isomer
  • N(5)-Formyltetrahydrofolate
  • S-Leucovorin
  • 5 Formyltetrahydrofolate
  • 6-S-Leucovorin
  • 6S Leucovorin
  • 6S-Leucovorin
  • Calcium leucovorin
  • Folinate, calcium
  • Leucovorin, (D)-isomer
  • Leucovorin, (DL)-isomer
  • Leucovorin, calcium (1:1) salt
  • Leucovorin, monosodium salt, (S)-isomer
  • S Leucovorin
  • Levo-leucovorin
  • 5-Formyl-(6S)-tetrahydrofolic acid
  • CF
  • Kunyrin
  • Leucoverin
  • N5-Formyl-THF
  • (6S)-5-Formyltetrahydrofolic acid
CAS number58-05-9
WeightAverage: 473.4393
Monoisotopic: 473.165896125
InChI KeyVVIAGPKUTFNRDU-STQMWFEESA-N
InChIInChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12-,13-/m0/s1
IUPAC Name(2S)-2-{[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
Traditional IUPAC Name(2S)-2-{[4-({[(6S)-2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
Chemical FormulaC20H23N7O7
SMILES[H]C(=O)N1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(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. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentTetrahydrofolic acids
Alternative Parents
Substituents
  • Tetrahydrofolic acid
  • Glutamic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Alpha-amino acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point245 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP-1.1ALOGPS
logP-2.7ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)2.81ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.55 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.46 m³·mol⁻¹ChemAxon
Polarizability46.34 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
One carbon pool by folateec00670 Map00670
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0adi-0031900000-15cbae867ecd4a003ef0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0393400000-73f11f6c59198eafb45fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-0591000000-ea5c6303d77ffa4af0cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-a3ae54a4d9b2cae45b72JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bc-1243900000-4ea7b3b1902e6a1204e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-7973000000-df3edd5bd8661611dd06JSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15640
HMDB IDHMDB01562
Pubchem Compound ID54575
Kegg IDC03479
ChemSpider ID131714
FOODB IDFDB022689
WikipediaFolinate
BioCyc ID5-FORMYL-THF

Enzymes

General function:
Involved in ATP binding
Specific function:
Utilizes 5-formyltetrahydrofolate (folinic acid) as substrate in an alternative way of folate biosynthesis
Gene Name:
FAU1
Uniprot ID:
P40099
Molecular weight:
24058.5
Reactions
ATP + 5-formyltetrahydrofolate → ADP + phosphate + 5,10-methenyltetrahydrofolate.
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2)
Gene Name:
PDA1
Uniprot ID:
P16387
Molecular weight:
46342.69922
Reactions
Pyruvate + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine → [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + CO(2).