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Identification
YMDB IDYMDB00298
NameN5-Formyl-THF
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. 5-Formyl-tetrahydrofolate is the most stable derivative of the reduced folates but 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
  • 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-N-[p-[[(2-amino-5-formyl-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid
  • Leucal
  • Levoleucovorin
  • N5-Formyl-5,6,7,8-tetrahydrofolate
  • N5-Formyl-5,6,7,8-tetrahydrofolic acid
  • N5-Formyltetrahydrofolate
  • N5-Formyltetrahydrofolic acid
  • Welcovorin
  • Leucovorin
  • Rescuvolin
  • L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acid
  • L(-)-5-Formyl-5,6,7,8-tetrahydrofolate
  • Acid, folinic
  • Folinate, calcium
  • Leucovorin, (D)-isomer
  • Leucovorin, (DL)-isomer
  • Leucovorin, calcium (1:1) salt
  • 5 Formyltetrahydrofolate
  • Citrovorum factor
  • Factor, citrovorum
  • Folinic acid SF
  • Leucovorin, calcium (1:1) salt, pentahydrate
  • Leukovorin
  • N(5)-Formyltetrahydrofolate
  • Leucovorin, (R)-isomer
  • Leucovorin, calcium (1:1) salt, (DL)-isomer
  • Leukovorum
  • Monosodium salt leucovorin
  • Wellcovorin
  • 5 Formyltetrahydropteroylglutamate
  • Calcium folinate
  • Calcium leucovorin
  • Leucovorin, calcium
  • Leucovorin, monosodium salt
CAS number58-05-9
WeightAverage: 473.4393
Monoisotopic: 473.165896125
InChI KeyVVIAGPKUTFNRDU-UHFFFAOYSA-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)
IUPAC Name2-[(4-{[(2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional IUPAC Name2-[(4-{[(2-amino-5-formyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Chemical FormulaC20H23N7O7
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])(N([H])C(=O)C1=C([H])C([H])=C(N([H])C([H])([H])C2([H])N(C([H])=O)C3=C(N=C(N([H])[H])N([H])C3=O)N([H])C2([H])[H])C([H])=C1[H])C(=O)O[H]
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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point245 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP-1.6ALOGPS
logP-2.3ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)2.81ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.55 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.66 m³·mol⁻¹ChemAxon
Polarizability46.54 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
One Carbon Pool by Folate IPW002468 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
One carbon pool by folateec00670 Map00670
SMPDB Reactions
water + 5,10-Methenyltetrahydrofolic acidN5-Formyl-THF
KEGG Reactions
Adenosine triphosphate + N5-Formyl-THF(6R)-5,10-Methenyltetrahydrofolic acid + phosphate + ADP
Adenosine triphosphate + N5-Formyl-THF + waterN10-Formyl-THF + phosphate + hydron + ADP
(6R)-5,10-Methenyltetrahydrofolic acid + waterN5-Formyl-THF + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2332900000-5c40a0014d3bb486cb20JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fk9-7225198000-aa48aa22224db36842c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0031900000-31498c227b611f3360eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0393400000-f81606ae4f4b27aadbacJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1591000000-825bc8196995ef0bc1e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-203ae236b032df3233d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0umj-1131900000-5174748fd5288f6523fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9674000000-192da85bfca095ec870eJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Zakrzewski, Sigmund F.; Sansone, Annette M. Preparation of folinic acid (N5-formyltetrahydro folic acid). Methods Enzymol. (1971), 18(Pt. B), 731-3.
External Links:
ResourceLink
CHEBI ID15640
HMDB IDHMDB01562
Pubchem Compound ID143
Kegg IDC03479
ChemSpider ID140
FOODB IDFDB022689
Wikipediafolinate
BioCyc ID5-FORMYL-THF

Enzymes

General function:
Involved in aminomethyltransferase activity
Specific function:
The glycine cleavage system (glycine decarboxylase complex) catalyzes the degradation of glycine
Gene Name:
GCV1
Uniprot ID:
P48015
Molecular weight:
44468.69922
Reactions
[Protein]-S(8)-aminomethyldihydrolipoyllysine + tetrahydrofolate → [protein]-dihydrolipoyllysine + 5,10-methylenetetrahydrofolate + NH(3).
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.