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Showing metabocard for 10-Formyldihydrofolate (HMDB0006485)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 11:29:59 UTC
Update Date2019-07-23 05:47:22 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?1563860842
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
10-Formyl-7,8-dihydrofolateChEBI
N-(10-Formyl-7,8-dihydropteroyl)-L-glutamateChEBI
10-Formyl-7,8-dihydrofolic acidGenerator
10-Formyldihydrofolic acidGenerator
N-(10-Formyl-7,8-dihydropteroyl)-L-glutamic acidGenerator
10-FormyldihydropteroylglutamateHMDB
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
DescriptionThis compound belongs to the class of organic compounds known as dihydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6-dihydropteroic acid/7,8-dihydropteroic acid skeleton conjugated with one or more L-glutamic acid units (or derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentDihydrofolic acids and derivatives
Alternative Parents
Substituents
  • Dihydrofolic acid or derivatives
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • Acylaminobenzoic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Hippuric acid
  • Hippuric acid or derivatives
  • Alpha-amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Anilide
  • Benzoyl
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Pyrimidine
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Vinylogous amide
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Amino acid
  • Ketimine
  • Secondary carboxylic acid amide
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-2677900000-d63b78529e7720c7d76bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-7219863000-81e4d17f4e1531c8674cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0300900000-ee4c7216428a12cfd298JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0646900000-d899d6171b33c5c8cf4eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-0920000000-76564757defeef5f3508JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-f04c0efc195b89e2311cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0015900000-7cbcd449fe6a5c204951JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9651100000-2958845f39ef795999bbJSpectraViewer | MoNA
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
FoodDB 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
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 ]