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Human Metabolome Database Version 3.5

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Showing metabocard for 10-formyldihydrofolate (HMDB06485)

Record Information
Version 3.5
Creation Date 2007-05-23 05:29:59 -0600
Update Date 2013-02-08 17:14:52 -0700
HMDB ID HMDB06485
Secondary Accession Numbers None
Metabolite Identification
Common Name 10-formyldihydrofolate
Description 10-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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 10-Formyl-7,8-dihydrofolate
  2. 10-Formyldihydrofolic acid
  3. 10-Formyldihydropteroylglutamate
  4. N-(10-Formyl-7,8-dihydropteroyl)-L-glutamate
Chemical Formula C20H21N7O7
Average Molecular Weight 471.4234
Monoisotopic Molecular Weight 471.150246061
IUPAC Name (2S)-2-[(4-{N-[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
Traditional IUPAC Name (2S)-2-[(4-{N-[(2-amino-4-oxo-7,8-dihydro-3H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
CAS Registry Number Not 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 Key UXFQDXABPXWSTK-ZDUSSCGKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pteridines and Derivatives
Sub Class Pterins and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • dihydrofolate(ChEBI)
Substituents
  • Alpha Amino Acid Or Derivative
  • Aminobenzamide
  • Aminopyrimidine
  • Benzamide
  • Benzoyl
  • Carboxamide Group
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Hippurate
  • Imine
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Pteroic Acid Derivative
  • Pyrimidine
  • Pyrimidone
  • Secondary Carboxylic Acid Amide
  • Tertiary Carboxylic Acid Amide
Direct Parent Folic Acid Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Lysosome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.1 g/L ALOGPS
LogP -1.26 ALOGPS
LogP -2.4 ChemAxon
LogS -3.66 ALOGPS
pKa (strongest acidic) 2.96 ChemAxon
pKa (strongest basic) 3.51 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 215.88 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 124.49 ChemAxon
Polarizability 44.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Lysosome
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023935
KNApSAcK ID Not Available
Chemspider ID 147665 Link_out
KEGG Compound ID C03204 Link_out
BioCyc ID Not Available
BiGG ID 2304175 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06485 Link_out
Metagene Link HMDB06485 Link_out
METLIN ID Not Available
PubChem Compound 168809 Link_out
PDB ID Not Available
ChEBI ID 15634 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available