Dihydrofolic acid (PAMDB000235)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000235
Identification
Name: Dihydrofolic acid
Description:Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division. It can be targeted with drug analogs to prevent nucleic acid synthesis. Dihydrofolic acid is also known by the name Dihydrofolate - more commonly Vitamin B9.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 7,8-Dihydro-L-folate
  • 7,8-Dihydro-L-folic acid
  • 7,8-Dihydrofolate
  • 7,8-Dihydrofolic acid
  • 7,8-Dihydropteroyl monoglutamate
  • 7,8-Dihydropteroyl monoglutamic acid
  • 7,8-Dihydropteroylglutamate
  • 7,8-Dihydropteroylglutamic acid
  • DHF
  • DHFA
  • Dihydrofolate
  • Dihydrofolic acid
  • FH2
  • H2PteGlu
  • H2PteGlu1
  • H2PteGlu1
  • L-N-[p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-Glutamate
  • L-N-[p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid
  • N-(4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-Glutamate
  • N-(4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-Glutamic acid
  • N-(4-{[(2-Amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamate
  • N-(4-{[(2-Amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
  • N-(7,8-Dihydropteroyl)-L-glutamate
  • N-(7,8-Dihydropteroyl)-L-glutamic acid
  • N-[4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-Glutamate
  • N-[4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-Glutamic acid
  • N-[4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-Glutamate
  • N-[4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-Glutamic acid
Chemical Formula: C19H21N7O6
Average Molecular Weight: 443.4133
Monoisotopic Molecular Weight: 443.155331439
InChI Key: OZRNSSUDZOLUSN-LBPRGKRZSA-N
InChI:InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1
CAS number: 4033-27-6
IUPAC Name:(4S)-4-carboxy-4-[(4-{[(2-imino-4-oxido-1,2,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]butanoate
Traditional IUPAC Name: (4S)-4-carboxy-4-[(4-{[(2-imino-4-oxido-7,8-dihydro-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]butanoate
SMILES:NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.11 mg/mLALOGPS
logP0.1ALOGPS
logP-1ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)2.44ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area214.25 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity153.39 m3·mol-1ChemAxon
Polarizability43.53 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Dihydrofolic acid + Hydrogen ion + NADPH <> NADP + Tetrahydrofolic acid
dUMP + 5,10-Methylene-THF <> Dihydrofolic acid + 5-Thymidylic acid
Tetrahydrofolic acid + NAD <> Dihydrofolic acid + NADH + Hydrogen ion
Dihydrofolic acid + NAD <> Folic acid + NADH + Hydrogen ion
Dihydrofolic acid + NADP <> Folic acid + NADPH + Hydrogen ion
Adenosine triphosphate + 7,8-Dihydropteroic acid + L-Glutamate <> ADP + Phosphate + Dihydrofolic acid
L-Glutamate + 7,8-Dihydropteroic acid + Adenosine triphosphate > Hydrogen ion + Dihydrofolic acid + Phosphate + ADP
Tetrahydrofolic acid + NADP > Dihydrofolic acid + NADPH
Adenosine triphosphate + 7,8-Dihydropteroic acid + L-Glutamate > ADP + Inorganic phosphate + Dihydrofolic acid
Dihydrofolic acid + NADP + Dihydrofolic acid > Folic acid + NADPH + Hydrogen ion + NADPH
Dihydrofolic acid + NADPH + Hydrogen ion + Dihydrofolic acid + NADPH > Tetrahydrofolic acid + NADP + Tetrahydrofolic acid
7,8-dihydrofolate monoglutamate + Hydrogen ion + NADPH + Dihydrofolic acid + NADPH > NADP + Tetrahydrofolic acid + Tetrahydrofolic acid
Dihydrofolic acid + 5-Thymidylic acid + Dihydrofolic acid > 5,10-Methylene-THF + dUMP + 5,10-Methylene-THF
dUMP + 5,10-methenyltetrahydrofolate mono-L-glutamate + 5,10-methenyltetrahydrofolate mono-L-glutamate > Dihydrofolic acid + 5-Thymidylic acid + Dihydrofolic acid
7,8-Dihydropteroic acid + Adenosine triphosphate + L-Glutamic acid + L-Glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + 7,8-dihydrofolate monoglutamate + ADP + Dihydrofolic acid
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:
  • 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
  • Navarro-Peran E, Cabezas-Herrera J, Garcia-Canovas F, Durrant MC, Thorneley RN, Rodriguez-Lopez JN: The antifolate activity of tea catechins. Cancer Res. 2005 Mar 15;65(6):2059-64. Pubmed: 15781612
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Smith, Karin; Scrimgeour, K. G.; Huennekens, F. M. Folic acid coenzymes and one-carbon metabolism. XV. Synthesis of a new form of dihydrofolate. Biochemical and Biophysical Research Communications (1963), 11(5), 388-92.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15633
HMDB IDHMDB01056
Pubchem Compound ID98792
Kegg IDC00415
ChemSpider ID89228
WikipediaDihydrofolate
BioCyc IDDIHYDROFOLATE
EcoCyc IDDIHYDROFOLATE
Ligand ExpoDHF