Record Information
Version1.0
Creation date2011-09-21 00:16:48 UTC
Update date2020-04-21 18:02:15 UTC
Primary IDFDB022607
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7,8-Dihydropteroic acid
DescriptionIn the mammalian host, dihydrofolate biosynthesis occurs via the reduction of folic acid, whereas in plasmodia (Plasmodium berghei, a malaria parasite) the biosynthesis of 7,8-dihydropteroate, an intermediate product in dihydrofolate synthesis, occurs via the enzymic catalysis of the reaction of 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine pyrophosphate with p-aminobenzoate. Malaria parasites synthesize their folate cofactors de novo and that the antimalarial action of sulfonamides is due to their inhibiting the plasmodial dihydropteroate synthesis. 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. They are present in microorganisms but absent in mammals and therefore are especially suitable targets for antimicrobials. Sulfa drugs (sulfonamides and sulfones) currently are used as antimicrobials targeting DHPS, although resistance to these drugs is increasing. A NADPH-coupled microplate photometric assay could be used for rapid screening of chemical libraries for novel inhibitors of folate biosynthesis as the first step in developing new antimicrobial drugs targeting the folate biosynthetic pathway; in the microplate the product of the DHPS reaction, 7,8-Dihydropteroic acid, is reduced to tetrahydropteroate by excess dihydrofolate reductase (DHFR) using the cofactor NADPH. (17134675, 4354403, 3546688) [HMDB]. 7,8-Dihydropteroic acid is found in many foods, some of which are lovage, sweet potato, hazelnut, and tarragon.
CAS Number2134-76-1
Structure
Thumb
Synonyms
SynonymSource
4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoic acidChEBI
7,8-DihydropteroateChEBI
DihydropteroateChEBI
DihydropteroinsaeureChEBI
4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoateGenerator
Dihydropteroic acidGenerator
4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoateHMDB
4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acidHMDB
4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoateHMDB
4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acidHMDB
DihydropterateHMDB
H2PteHMDB
p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-benzoateHMDB
p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-benzoic acidHMDB
4-(((2-amino-1,4,7,8-Tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoateGenerator
4-(((2-amino-1,4,7,8-Tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoic acidChEBI
4-[[(2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-Benzoatehmdb
4-[[(2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-Benzoic acidhmdb
4-[[(2-amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-Benzoatehmdb
4-[[(2-amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-Benzoic acidhmdb
7,8-dihydropteroatehmdb
7,8-dihydropteroic acidhmdb
dihydropteratehmdb
p-[[(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-Benzoatehmdb
p-[[(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-Benzoic acidhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H14N6O3
IUPAC name4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid
InChI IdentifierInChI=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)
InChI KeyWBFYVDCHGVNRBH-UHFFFAOYSA-N
Isomeric SMILESNC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(O)=O)CN2)C(=O)N1
Average Molecular Weight314.2994
Monoisotopic Molecular Weight314.112738344
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fe0-0790000000-51d5d3b08e34c7becd27JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0v4l-2409000000-f79f449589d2247daecaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016s-0595000000-4ed77e34023ff886c2a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0940000000-de25deb5daf6b50a16a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-0900000000-958eaaf4ee915da489c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0169000000-2f49a3d279aabb04affaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02tl-2392000000-9a4efdf541287a8562e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9420000000-e5fb759142be19739bd5JSpectraViewer
ChemSpider ID165
ChEMBL IDCHEMBL1614805
KEGG Compound IDC00921
Pubchem Compound ID170
Pubchem Substance IDNot Available
ChEBI ID4581
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01412
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID78H
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDihydropteroate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Folylpolyglutamate synthase, mitochondrialFPGSQ05932
Pathways
NameSMPDB LinkKEGG Link
Pterine BiosynthesisSMP00005 map00790
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference