Record Information
Version2.0
Creation Date2012-05-31 13:52:03 -0600
Update Date2015-06-03 15:54:05 -0600
Secondary Accession Numbers
  • ECMDB01412
Identification
Name:7,8-Dihydropteroic acid
Description7,8-dihydropteroate is an intermediate product in dihydrofolate synthesis. It occurs via the enzymic catalysis of the reaction of 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine pyrophosphate with p-aminobenzoate. The enzymes 6-hydroxymethylpterin pyrophosphokinase (EC 2.7.6.3, HPPK) and dihydropteroate synthase (EC 2.5.1.15, DHPS) catalyze sequential steps in folate biosynthesis.
Structure
Thumb
Synonyms:
  • 4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-Benzoate
  • 4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-Benzoic acid
  • 4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-Benzoate
  • 4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-Benzoic acid
  • 7,8-Dihydropteroate
  • 7,8-Dihydropteroic acid
  • DHPA
  • Dihydropterate
  • Dihydropteric acid
  • Dihydropteroate
  • Dihydropteroic acid
  • H2Pte
  • P-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-Benzoate
  • P-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-Benzoic acid
Chemical Formula:C14H14N6O3
Weight:Average: 314.2994
Monoisotopic: 314.112738344
InChI Key:WBFYVDCHGVNRBH-UHFFFAOYSA-N
InChI:InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)
CAS number:2134-76-1
IUPAC Name:4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid
Traditional IUPAC Name:7,8-dihydropteroic acid
SMILES:NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(O)=O)CN2)C(=O)N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPterins and derivatives
Alternative Parents
Substituents
  • Pterin
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Pyrimidine
  • Benzenoid
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Ketimine
  • Azacycle
  • Secondary amine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Imine
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP-0.21ALOGPS
logP-0.26ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.72ChemAxon
pKa (Strongest Basic)1.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.2 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.1 m³·mol⁻¹ChemAxon
Polarizability31.6 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + 7,8-Dihydropteroic acid + L-Glutamate <> ADP + Dihydrofolic acid + Hydrogen ion + Phosphate
p-Aminobenzoic acid + 6-Hydroxymethyl-dihydropterin pyrophosphate > 7,8-Dihydropteroic acid + Pyrophosphate
Adenosine triphosphate + 7,8-Dihydropteroic acid + L-Glutamate <> ADP + Phosphate + Dihydrofolic acid
6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <> 7,8-Dihydropteroic acid + Water
2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + p-Aminobenzoic acid + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate <> Pyrophosphate + 7,8-Dihydropteroic acid
L-Glutamate + 7,8-Dihydropteroic acid + Adenosine triphosphate > Hydrogen ion + Dihydrofolic acid + Phosphate + ADP
2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + p-Aminobenzoic acid > Pyrophosphate + 7,8-Dihydropteroic acid
Adenosine triphosphate + 7,8-Dihydropteroic acid + L-Glutamate > ADP + Inorganic phosphate + Dihydrofolic acid
6-Hydroxymethyl-dihydropterin pyrophosphate + p-Aminobenzoic acid > Pyrophosphate + 7,8-Dihydropteroic acid
7,8-Dihydropteroic acid + Adenosine triphosphate + L-Glutamic acid + L-Glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + 7,8-dihydrofolate monoglutamate + ADP + Dihydrofolic acid
Adenosine triphosphate + 7 7,8-Dihydropteroic acid + L-Glutamate <> ADP + Dihydrofolic acid + Hydrogen ion + Phosphate
6 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <>7 7,8-Dihydropteroic acid + Water
6 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <>7 7,8-Dihydropteroic acid + Water
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fe0-0790000000-51d5d3b08e34c7becd27View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0v4l-2409000000-f79f449589d2247daecaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016s-0595000000-4ed77e34023ff886c2a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0940000000-de25deb5daf6b50a16a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-0900000000-958eaaf4ee915da489c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0169000000-2f49a3d279aabb04affaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02tl-2392000000-9a4efdf541287a8562e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9420000000-e5fb759142be19739bd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-0ca8b4ed5ec637c71d37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9231000000-4adcc7bed47beb3f3fb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9460000000-8c4fef4ee51806b3dc9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0209000000-907bcfac745eb62d4d42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0958000000-1babfb4ccb2f4798f7d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vr-0920000000-ccfcce4cf4171ef887faView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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
  • 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:Bartels, Rainer; Bock, Lothar. Determination of pteroic acid by high-performance thin-layer chromatography. Contribution to the investigation of 7,8-dihydropteroate synthase. Journal of Chromatography (1994), 659(1), 185-9.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID4581
HMDB IDHMDB01412
Pubchem Compound ID170
Kegg IDC00921
ChemSpider ID165
WikipediaDihydropteroate
BioCyc ID7-8-DIHYDROPTEROATE
EcoCyc ID7-8-DIHYDROPTEROATE
Ligand Expo78H

Enzymes

General function:
Involved in tetrahydrofolylpolyglutamate synthase activity
Specific function:
Conversion of folates to polyglutamate derivatives
Gene Name:
folC
Uniprot ID:
P08192
Molecular weight:
45405
Reactions
ATP + tetrahydropteroyl-(gamma-Glu)(n) + L-glutamate = ADP + phosphate + tetrahydropteroyl-(gamma-Glu)(n+1).
ATP + 7,8-dihydropteroate + L-glutamate = ADP + phosphate + 7,8-dihydropteroylglutamate.
General function:
Involved in dihydropteroate synthase activity
Specific function:
DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide
Gene Name:
folP
Uniprot ID:
P0AC13
Molecular weight:
30615
Reactions
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate = diphosphate + dihydropteroate.