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Record Information
Version	2.0
Creation Date	2012-05-31 13:52:03 -0600
Update Date	2015-06-03 15:54:05 -0600
Secondary Accession Numbers	ECMDB01412
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa20bbe5c> Close
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.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Pteridines and derivatives
Sub Class	Pterins and derivatives
Direct Parent	Pterins and derivatives
Alternative Parents	Aminobenzoic acids Benzoic acids Aniline and substituted anilines Phenylalkylamines Benzoyl derivatives Secondary alkylarylamines Hydroxypyrimidines Heteroaromatic compounds Ketimines Amino acids Carboxylic acids Azacyclic compounds Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organooxygen compounds Organopnictogen compounds Organic oxides
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	pteroic acids (CHEBI:4581 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.14 g/L ALOGPS logP -0.21 ALOGPS logP -0.26 ChemAxon logS -3.4 ALOGPS pKa (Strongest Acidic) 4.72 ChemAxon pKa (Strongest Basic) 1.76 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 141.2 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 93.1 m³·mol⁻¹ ChemAxon Polarizability 31.6 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 biosynthesis PW000908
KEGG Pathways:	Folate biosynthesis ec00790 Metabolic pathways eco01100
EcoCyc Pathways:	formylTHF biosynthesis I 1CMET2-PWY tetrahydrofolate biosynthesis PWY-6614
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0fe0-0790000000-51d5d3b08e34c7becd27 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-0v4l-2409000000-f79f449589d2247daeca View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-016s-0595000000-4ed77e34023ff886c2a5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-0940000000-de25deb5daf6b50a16a3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-01ti-0900000000-958eaaf4ee915da489c4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-0169000000-2f49a3d279aabb04affa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-02tl-2392000000-9a4efdf541287a8562e5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9420000000-e5fb759142be19739bd5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-0019000000-0ca8b4ed5ec637c71d37 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0006-9231000000-4adcc7bed47beb3f3fb9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9460000000-8c4fef4ee51806b3dc9e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-0209000000-907bcfac745eb62d4d42 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-016r-0958000000-1babfb4ccb2f4798f7d1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-06vr-0920000000-ccfcce4cf4171ef887fa View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 4581 HMDB ID HMDB01412 Pubchem Compound ID 170 Kegg ID C00921 ChemSpider ID 165 Wikipedia Dihydropteroate BioCyc ID 7-8-DIHYDROPTEROATE EcoCyc ID 7-8-DIHYDROPTEROATE Ligand Expo 78H

Enzymes