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Identification
YMDB IDYMDB00080
NameN10-Formyl-THF
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description10-Formyltetrahydrofolate is an intermediate in the tetrahydrofolate salvage pathway. 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. [Biocyc PWY-6613]
Structure
Thumb
Synonyms
  • 10-Formyl-(6RS)-tetrahydrofolic acid
  • 10-formyl-H4PteGlu1
  • 10-formyl-tetrahydrofolate
  • 10-formyl-THF
  • 10-formyltetrahydrofolate
  • 10-formyltetrahydrofolic acid
  • 10-formyltetrahydropteroylglutamate
  • 10-formyltetrahydropteroylglutamic acid
  • 10-fthf
  • N-[p-[N-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-Glutamate
  • N-[p-[N-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-Glutamic acid
  • N-[p-[N-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-Glutamate
  • N-[p-[N-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-Glutamic acid
  • N10-Formyl-5,6,7,8-tetrahydrofolate
  • N10-Formyl-5,6,7,8-tetrahydrofolic acid
  • N10-formyl-H4F
  • N10-formyl-THF
  • N10-Formyltetrahydrofolate
  • N10-Formyltetrahydrofolic acid
  • N10-Formyltetrahydropteroylglutamate
CAS number2800-34-2
WeightAverage: 473.4393
Monoisotopic: 473.165896125
InChI KeyAUFGTPPARQZWDO-YUZLPWPTSA-N
InChIInChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1
IUPAC Name(2S)-2-[(4-{N-[(4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
Traditional IUPAC Name(2S)-2-[(4-{N-[(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}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(C([H])=C1[H])N(C([H])=O)C([H])([H])C1([H])N([H])C2=C(N([H])C(=NC2=O)N([H])[H])N([H])C1([H])[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
  • Acylaminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • Anilide
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Pyrimidone
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP-1.5ALOGPS
logP-4ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)5.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area216.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity135.7 m³·mol⁻¹ChemAxon
Polarizability46.38 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
glycine metabolismPW002398 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
serine metabolismPW002402 ThumbThumb?image type=greyscaleThumb?image type=simple
tetrahydrofolate biosynthesisPW002417 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
One carbon pool by folateec00670 Map00670
SMPDB Reactions
5,10-Methenyltetrahydrofolic acid + waterN10-Formyl-THF + hydron
N10-Formyl-THF + ADP + phosphateAdenosine triphosphate + Formic acid + Tetrahydrofolic acid
N10-Formyl-THF + 5'-Phosphoribosyl-N-formylglycinamideTetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide
Tetrahydrofolic acid + FAICARN10-Formyl-THF + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamideN10-Formyl-THF + Glycineamideribotide
KEGG Reactions
Adenosine triphosphate + N5-Formyl-THF + waterN10-Formyl-THF + phosphate + hydron + ADP
Adenosine triphosphate + 5,6,7,8-Tetrahydrofolic acid + Formic acidN10-Formyl-THF + phosphate + ADP
L-Tyrosine + N10-Formyl-THFN-Formyl-L-tyrosine + 5,6,7,8-Tetrahydrofolic acid + hydron
(6R)-5,10-Methenyltetrahydrofolic acid + waterN10-Formyl-THF + hydron
N10-Formyl-THF + Met-tRNA(Met) → 5,6,7,8-Tetrahydrofolic acid + fMet-tRNA(fMet) + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-2733900000-d416b73a1673d1220b87JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0v4i-2913374000-7b894dbf7f83fe5cd9d7JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05cr-0401900000-21104c38dc03ca4e7a0eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-0935700000-2f12524764eca10dcf15JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0910000000-03f41886e7967d0201ebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-1244cea99701ed75f41cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bc-1123900000-cdcadc51a3f47cb93886JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9842000000-62efadef6701421ce2c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0002900000-e6e9d4109ecb3ef0bbeeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1729400000-02f5fdbf97e3ce7a3a95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-0932000000-68bdb6e09b80b22288c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-19d839ffa3d1b1988450JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0200900000-93ad732aff1ff91aa085JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v03-4920300000-17e6f1c09b0e093800efJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Denis V; Daignan-Fornier B Synthesis of glutamine, glycine and 10-formyl tetrahydrofolate is coregulated with purine biosynthesis in Saccharomyces cerevisiae. Molecular & general genetics : MGG (1998), 259(3), 246-55.
External Links:
ResourceLink
CHEBI ID15637
HMDB IDHMDB00972
Pubchem Compound ID10
Kegg IDC00234
ChemSpider ID109092
FOODB IDFDB030256
Wikipedia10-formyl-tetrahydrofolate
BioCyc ID10-FORMYL-THF

Enzymes

General function:
Involved in hydroxymethyl-, formyl- and related transferase activity
Specific function:
10-formyltetrahydrofolate + N(1)-(5-phospho-D- ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5- phospho-D-ribosyl)glycinamide
Gene Name:
ADE8
Uniprot ID:
P04161
Molecular weight:
23540.0
Reactions
10-formyltetrahydrofolate + N(1)-(5-phospho-D-ribosyl)glycinamide → tetrahydrofolate + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide.
General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxylate = 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2)
Gene Name:
ADE2
Uniprot ID:
P21264
Molecular weight:
62338.69922
Reactions
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate → 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2).
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH
Gene Name:
MIS1
Uniprot ID:
P09440
Molecular weight:
106216.0
Reactions
5,10-methylenetetrahydrofolate + NADP(+) → 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O → 10-formyltetrahydrofolate.
ATP + formate + tetrahydrofolate → ADP + phosphate + 10-formyltetrahydrofolate.
General function:
Involved in IMP cyclohydrolase activity
Specific function:
10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Gene Name:
ADE17
Uniprot ID:
P38009
Molecular weight:
65262.60156
Reactions
10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide → tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
IMP + H(2)O → 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
General function:
Involved in IMP cyclohydrolase activity
Specific function:
10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Gene Name:
ADE16
Uniprot ID:
P54113
Molecular weight:
65281.80078
Reactions
10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide → tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
IMP + H(2)O → 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
General function:
Involved in methionyl-tRNA formyltransferase activity
Specific function:
Formylates methionyl-tRNA in mitochondria
Gene Name:
FMT1
Uniprot ID:
P32785
Molecular weight:
44616.19922
Reactions
10-formyltetrahydrofolate + L-methionyl-tRNA(fMet) + H(2)O → tetrahydrofolate + N-formylmethionyl-tRNA(fMet).
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH
Gene Name:
ADE3
Uniprot ID:
P07245
Molecular weight:
102204.0
Reactions
5,10-methylenetetrahydrofolate + NADP(+) → 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O → 10-formyltetrahydrofolate.
ATP + formate + tetrahydrofolate → ADP + phosphate + 10-formyltetrahydrofolate.