Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000213
Identification
Name: N10-Formyl-THF
Description:N10-Formyl-THF is a substrate for Trifunctional purine biosynthetic protein adenosine-3, Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, 10-formyltetrahydrofolate dehydrogenase, Folylpolyglutamate synthase, Bifunctional purine biosynthesis protein PURH and C-1-tetrahydrofolate synthase (cytoplasmic).
Structure
Thumb
Synonyms:
  • 10-Formyl-(6RS)-tetrahydrofolate
  • 10-Formyl-(6RS)-tetrahydrofolic acid
  • 10-Formyl-H4PteGlu1
  • 10-formyl-H4PteGlu1
  • 10-Formyl-tetrahydrofolate
  • 10-Formyl-tetrahydrofolic acid
  • 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-tetrahydrofolate
  • N10-formyl-tetrahydrofolic acid
  • N10-formyl-THF
  • N10-Formyltetrahydrofolate
  • N10-Formyltetrahydrofolic acid
  • N10-Formyltetrahydropteroylglutamate
  • N10-Formyltetrahydropteroylglutamic acid
  • N10-formyl-H4F
  • N10-formyl-tetrahydrofolate
  • N10-formyl-THF
Chemical Formula: C20H23N7O7
Average Molecular Weight: 473.4393
Monoisotopic Molecular Weight: 473.165896125
InChI Key: AUFGTPPARQZWDO-YUZLPWPTSA-N
InChI:InChI=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
CAS number: 2800-34-2
IUPAC Name:(2S)-2-{[4-(N-{[(6R)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid
Traditional IUPAC Name: 10-formyltetrahydrofolic acid
SMILES:NC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassBenzamides
Direct Parent Hippuric acids
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Pterin
  • Pteridine
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Benzoic acid or derivatives
  • Aminobenzamide
  • Benzoyl
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Amino fatty acid
  • Fatty acyl
  • Pyrimidine
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.349 mg/mLALOGPS
logP-1.8ALOGPS
logP-3.4ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
pKa (Strongest Basic)4.47ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.55 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.88 m3·mol-1ChemAxon
Polarizability46.63 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Water + 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion
N10-Formyl-THF + Water <> Formic acid + Hydrogen ion + Tetrahydrofolic acid
N10-Formyl-THF + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose <> Hydrogen ion + Tetrahydrofolic acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose
N10-Formyl-THF + Glycineamideribotide <> 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid
N10-Formyl-THF + L-Methionyl-tRNA (Met) > N-Formylmethionyl-tRNA + Hydrogen ion + Tetrahydrofolic acid
N10-Formyl-THF + Phosphoribosyl formamidocarboxamide <> Phosphoribosyl formamidocarboxamide + Tetrahydrofolic acid
N10-Formyl-THF + Water <> Formic acid + Tetrahydrofolic acid
L-Methionyl-tRNA + N10-Formyl-THF <> Tetrahydrofolic acid + N-Formylmethionyl-tRNA
N10-Formyl-THF + Glycineamideribotide <> Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide
N10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide
N10-Formyl-THF + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose <> Tetrahydrofolic acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose
Adenosine triphosphate + Formic acid + Tetrahydrofolic acid > ADP + Phosphate + N10-Formyl-THF
N10-Formyl-THF + 4-Amino-4-deoxy-L-arabinose > Tetrahydrofolic acid + UDP-4-Deoxy-4-formamido-beta-L-arabinose
N10-Formyl-THF + L-methionyl-tRNA(fMet) > Tetrahydrofolic acid + N-formylmethionyl-tRNA(fMet)
5,10-Methenyltetrahydrofolate + Water > N10-Formyl-THF
Tetrahydrofolic acid + FAICAR + Tetrahydrofolic acid > 10-Formyltetrahydrofolate + AICAR + N10-Formyl-THF

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-0301900000-731bc9348489f24f80ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-0936800000-ade646bc1baf4b8851afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0910000000-a7975e3a08f3a92a4ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-53fa6981f67bce467289View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uml-1122900000-95a426dd0ca2a0207dbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9741000000-dbaf84d2dcb0c0d71757View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15637
HMDB IDHMDB00972
Pubchem Compound ID10
Kegg IDC00234
ChemSpider ID109092
Wikipedia10-formyl-tetrahydrofolate
BioCyc ID10-FORMYL-THF
EcoCyc ID10-FORMYL-THF