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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 11:29:59 UTC
Update Date2020-02-26 21:26:26 UTC
HMDB IDHMDB0006485
Secondary Accession Numbers
  • HMDB06485
Metabolite Identification
Common Name10-Formyldihydrofolate
Description10-formyldihydrofolate is a folate compound that has not been found as a component of intracellular folates in normal tissues but has been identified in the cytosol of methotrexate (MTX)-treated MCF-7 breast cancer cells and normal human myeloid precursor cells. The origin of 10-formyldihydrofolate remains an enigma. Its appearance only in the extracts from MTX-treated cells is not consistent with a simple oxidation of lO-formyl-H4folate during the extraction procedure. This, however, does not exclude the occurrence of spontaneous oxidation of 10-formyl-H4folate within the intact cells prior to the folate extraction. (PMID: 3366769 ).
Structure
Data?1582752386
Synonyms
ValueSource
10-Formyl-7,8-dihydrofolateChEBI
N-(10-Formyl-7,8-dihydropteroyl)-L-glutamateChEBI
10-Formyl-7,8-dihydrofolic acidGenerator
N-(10-Formyl-7,8-dihydropteroyl)-L-glutamic acidGenerator
10-Formyldihydrofolic acidGenerator
10-FormyldihydropteroylglutamateHMDB
10-FormyldihydrofolateChEBI
Chemical FormulaC20H21N7O7
Average Molecular Weight471.4234
Monoisotopic Molecular Weight471.150246061
IUPAC Name(2S)-2-[(4-{N-[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
Traditional Name10-formyldihydrofolic acid
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(N=C(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1
InChI Identifier
InChI=1S/C20H21N7O7/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/h1-4,9,13H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t13-/m0/s1
InChI KeyUXFQDXABPXWSTK-ZDUSSCGKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sphingosylphosphorylcholines. These are sphingolipids containing a sphingosine attached to the phosphate group of a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentSphingosylphosphorylcholines
Alternative Parents
Substituents
  • Sphingosylphosphorylcholine
  • Phosphocholine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Alcohol
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP-1.3ALOGPS
logP-2.4ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)3.51ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area215.88 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.49 m³·mol⁻¹ChemAxon
Polarizability44.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-2677900000-d63b78529e7720c7d76bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-7219863000-81e4d17f4e1531c8674cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0300900000-ee4c7216428a12cfd298Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0646900000-d899d6171b33c5c8cf4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-0920000000-76564757defeef5f3508Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-f04c0efc195b89e2311cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0015900000-7cbcd449fe6a5c204951Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9651100000-2958845f39ef795999bbSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Lysosome
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023935
KNApSAcK IDNot Available
Chemspider ID147665
KEGG Compound IDC03204
BioCyc IDNot Available
BiGG ID2304175
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound168809
PDB IDNot Available
ChEBI ID15634
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Baram J, Chabner BA, Drake JC, Fitzhugh AL, Sholar PW, Allegra CJ: Identification and biochemical properties of 10-formyldihydrofolate, a novel folate found in methotrexate-treated cells. J Biol Chem. 1988 May 25;263(15):7105-11. [PubMed:3366769 ]