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Dihydrofolic acid (YMDB00079)

Identification
YMDB IDYMDB00079
NameDihydrofolic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDihydrofolic acid, also known as 7,8-dihydrofolate or H2PTEGLU, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Dihydrofolic acid is a moderately basic compound (based on its pKa). Dihydrofolic acid exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 7,8-Dihydro-L-folic acid
  • 7,8-dihydrofolate
  • 7,8-Dihydrofolic acid
  • 7,8-Dihydropteroylglutamate
  • dihydrofolate
  • H2PteGlu
  • H2PteGlu1
  • 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-Glutamic acid
  • N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
  • N-(7,8-dihydropteroyl)-L-glutamic acid
  • 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-Glutamic acid
  • 7,8-Dihydropteroylglutamic acid
  • N-(7,8-Dihydropteroyl)-L-glutamate
  • Vitamin b9
  • Dihydrofolate, (D)-isomer
CAS number4033-27-6
WeightAverage: 443.4133
Monoisotopic: 443.155331439
InChI KeyOZRNSSUDZOLUSN-LBPRGKRZSA-N
InChIInChI=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
IUPAC Name(2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional IUPAC Namedihydrofolic acid
Chemical FormulaC19H21N7O6
SMILES[H]OC(=O)C([H])([H])C([H])([H])[C@]([H])(N([H])C(=O)C1=C([H])C([H])=C(N([H])C([H])([H])C2=NC3=C(N=C(N([H])[H])N([H])C3=O)N([H])C2([H])[H])C([H])=C1[H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Pterin
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Pteridine
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Amino acid
  • Secondary carboxylic acid amide
  • Ketimine
  • Carboxamide group
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic oxygen compound
  • Imine
  • Hydrocarbon derivative
  • Carbonyl group
  • Amine
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP-0.93ALOGPS
logP-1.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)2.09ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area207.6 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity120.99 m³·mol⁻¹ChemAxon
Polarizability44.31 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
One Carbon Pool by Folate IPW002468 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Folate biosynthesisec00790 Map00790
One carbon pool by folateec00670 Map00670
Pyrimidine metabolismec00240 Map00240
SMPDB Reactions
Dihydrofolic acid + NADP → Folic acid + NADPH + hydron
Dihydrofolic acid + NADPH + hydron → Tetrahydrofolic acid + NADP
Dihydrofolic acid + 5-Thymidylic acid → 5,10-Methylene-THF + dUMP
dUMP + 5,10-methenyltetrahydrofolate mono-L-glutamate → Dihydrofolic acid + 5-Thymidylic acid
KEGG Reactions
NADPH + hydron + Dihydrofolic acid → NADP + 5,6,7,8-Tetrahydrofolic acid
Adenosine triphosphate + L-Glutamic acid + 7,8-Dihydropteroic acid → phosphate + hydron + ADP + Dihydrofolic acid
dUMP + 5,10-Methylene-THF → 5-Thymidylic acid + Dihydrofolic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2469100000-dfb9d32424c0c60215dcJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-3320390000-c5791f4954b5cefa68e1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-1920000000-6de8a6f7059365047fe2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0322900000-3bd8be8b6fc531102b49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0952200000-3a44b5c375b9b981244fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1930000000-71775fd6210c3e719dc1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0113900000-62b9c33c60c2e2fd46c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xv-1349500000-3d3bae7b4497b96fc55dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9441000000-c0339a106358ca6d7221JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-0070900000-6a1481e87925b9b385e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2591100000-9c973398e9038b5cdb47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00wa-1971000000-080ecbf4dd42ca5adb42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-0119700000-93e6d0f8c27c8bbe21a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08n9-2918500000-f3937a7ae1b8e159f6cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-3921000000-fea748c5be0567e97935JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Bayly, A. M., Berglez, J. M., Patel, O., Castelli, L. A., Hankins, E. G., Coloe, P., Hopkins Sibley, C., Macreadie, I. G. (2001). "Folic acid utilisation related to sulfa drug resistance in Saccharomyces cerevisiae." FEMS Microbiol Lett 204:387-390.11731153
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.
External Links:
ResourceLink
CHEBI ID15633
HMDB IDHMDB01056
Pubchem Compound ID98792
Kegg IDC00415
ChemSpider ID89228
FOODB IDFDB022395
WikipediaDihydrofolic acid
BioCyc IDDIHYDROFOLATE

Enzymes

Protein Details
1. Dihydrofolate reductase
General function:
Involved in dihydrofolate reductase activity
Specific function:
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis
Gene Name:
DFR1
Uniprot ID:
P07807
Molecular weight:
24260.80078
Reactions
5,6,7,8-tetrahydrofolate + NADP(+) → 7,8-dihydrofolate + NADPH.
Protein Details
2. Folylpolyglutamate synthase 1
General function:
Involved in tetrahydrofolylpolyglutamate synthase activity
Specific function:
Conversion of folates to polyglutamate derivatives
Gene Name:
FOL3
Uniprot ID:
Q12676
Molecular weight:
47850.80078
Reactions
ATP + tetrahydropteroyl-(gamma-Glu)(n) + L-glutamate → ADP + phosphate + tetrahydropteroyl-(gamma-Glu)(n+1).
Protein Details
3. Thymidylate synthase
General function:
Involved in thymidylate synthase activity
Specific function:
Required for both nuclear and mitochondrial DNA synthesis
Gene Name:
TMP1
Uniprot ID:
P06785
Molecular weight:
35046.89844
Reactions
5,10-methylenetetrahydrofolate + dUMP → dihydrofolate + dTMP.