10-formyl-tetrahydrofolate (PAMDB120503)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120503
Identification
Name: 10-formyl-tetrahydrofolate
Description:Dianion of 10-formyltetrahydrofolic acid arising from deprotonation of both carboxylic acid functions.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 10-formyltetrahydrofolate
  • 10-formyltetrahydrofolate dianion
Chemical Formula: C20H21N7O7
Average Molecular Weight: 471.429
Monoisotopic Molecular Weight: 473.1659
InChI Key: AUFGTPPARQZWDO-YUZLPWPTSA-L
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)/p-2/t11?,13-/m0/s1
CAS number: 2800-34-2
IUPAC Name:N-[4-(N-{[(6S)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)benzoyl]-L-glutamate
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
SMILES:C2(C(CN(C=O)C1(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=1))NC3(C(=O)NC(N)=NC(N2)=3))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct Parent Tetrahydrofolic acids
Alternative Parents
Substituents
  • Tetrahydrofolic acid
  • Glutamic acid or derivatives
  • Acylaminobenzoic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Anilide
  • Benzoyl
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Primary aromatic amine
  • Pyrimidine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Secondary amine
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary amine
  • Carbonyl group
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 mg/mLALOGPS
logP-1.5ALOGPS
logP-4.4ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.73ChemAxon
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.55 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.68 m3·mol-1ChemAxon
Polarizability46.21 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
L-Phenylalanine + 10-formyl-tetrahydrofolate + Oxygen → CPD-14931 + L-Tyrosine
N5-hydroxy-L-ornithine + 10-formyl-tetrahydrofolate → N5-formyl-N5-hydroxy-L-ornithine + tetrahydrofolate
Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + 10-formyl-tetrahydrofolate → Hydrogen ion + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + tetrahydrofolate
10-formyl-tetrahydrofolate + N1-(5-phospho-β-D-ribosyl)glycinamide → Hydrogen ion + tetrahydrofolate + N2-formyl-N1-(5-phospho-β-D-ribosyl)glycinamide
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • Xu L, Li C, Olson AJ, Wilson IA: Crystal structure of avian aminoimidazole-4-carboxamide ribonucleotide transformylase in complex with a novel non-folate inhibitor identified by virtual ligand screening. J Biol Chem. 2004 Nov 26;279(48):50555-65. Epub 2004 Sep 7. [15355974 ]
  • Baggott JE, Tamura T: Bioactivity of orally administered unnatural isomers, [6R]-5-formyltetrahydrofolate and [6S]-5,10-methenyltetrahydrofolate, in humans. Biochim Biophys Acta. 1999 Oct 18;1472(1-2):323-32. [10572954 ]
  • Johlin FC, Swain E, Smith C, Tephly TR: Studies on the mechanism of methanol poisoning: purification and comparison of rat and human liver 10-formyltetrahydrofolate dehydrogenase. Mol Pharmacol. 1989 Jun;35(6):745-50. [2733692 ]
  • Kirksey TJ, Appling DR: Site-directed mutagenesis of a highly conserved aspartate in the putative 10-formyl-tetrahydrofolate binding site of yeast C1-tetrahydrofolate synthase. Arch Biochem Biophys. 1996 Sep 1;333(1):251-9. [8806778 ]
  • Baggott JE, Robinson CB, Johnston KE: Bioactivity of [6R]-5-formyltetrahydrofolate, an unusual isomer, in humans and Enterococcus hirae, and cytochrome c oxidation of 10-formytetrahydrofolate to 10-formyldihydrofolate. Biochem J. 2001 Feb 15;354(Pt 1):115-22. [11171086 ]
  • Boger DL, Labroli MA, Marsilje TH, Jin Q, Hedrick MP, Baker SJ, Shim JH, Benkovic SJ: Conformationally restricted analogues designed for selective inhibition of GAR Tfase versus thymidylate synthase or dihydrofolate reductase. Bioorg Med Chem. 2000 May;8(5):1075-86. [10882019 ]
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
METABOLIGHTSMTBLC57454
HMDBHMDB00972
BIGG34337
CHEBI57454
PUBCHEM46878370
LIGAND-CPDC00234
CAS2800-34-2