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Identification
YMDB IDYMDB00080
NameN10-Formyl-THF
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description10-Formyltetrahydrofolate, also known as 10-formyl-THF or 10-formyl-H4pteglu1, 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. 10-Formyltetrahydrofolate is a strong basic compound (based on its pKa). 10-Formyltetrahydrofolate exists in all eukaryotes, ranging from yeast to humans. Within yeast, 10-formyltetrahydrofolate participates in a number of enzymatic reactions. In particular, 10-formyltetrahydrofolate and 1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxamide can be biosynthesized from tetrahydrofolic acid and FAICAR; which is catalyzed by the enzyme phosphoribosylaminoimidazolecarboxamide formyltransferase. In addition, 10-formyltetrahydrofolate and glycineamideribotide can be biosynthesized from tetrahydrofolic acid and 5'-phosphoribosyl-N-formylglycinamide; which is catalyzed by the enzyme phosphoribosylglycinamide formyltransferase 2. In yeast, 10-formyltetrahydrofolate is involved in the metabolic pathway called the one carbon pool by folate I pathway.
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-[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
Traditional IUPAC Name(2S)-2-[(4-{N-[(2-amino-4-oxo-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-4.4ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)2.73ChemAxon
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.55 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.68 m³·mol⁻¹ChemAxon
Polarizability46.21 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 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
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 IDFDB022345
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.