7,8-Dihydropteroic acid (PAMDB000376)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000376
Identification
Name: 7,8-Dihydropteroic acid
Description:7,8-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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 314.2994
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pteridines and derivatives
Sub ClassPterins and derivatives
Direct Parent Pterins and derivatives
Alternative Parents
Substituents
  • Pterin
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Phenylalkylamine
  • Substituted aniline
  • Benzoyl
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Aniline
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • Primary aromatic amine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.137 mg/mLALOGPS
logP-0.21ALOGPS
logP-0.48ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
pKa (Strongest Basic)3.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.2 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.1 m3·mol-1ChemAxon
Polarizability31.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
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
L-Glutamate + 7,8-Dihydropteroic acid + Adenosine triphosphate > Hydrogen ion + Dihydrofolic acid + Phosphate + ADP
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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