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Identification
YMDB IDYMDB00293
Name7,8-Dihydropteroic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description7,8-Dihydropteroic acid, also known as dihydropteroinsaeure or H2PTE, 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. 7,8-Dihydropteroic acid is a strong basic compound (based on its pKa). 7,8-Dihydropteroic acid exists in all living species, ranging from bacteria to humans. Within yeast, 7,8-dihydropteroic acid participates in a number of enzymatic reactions. In particular, 7,8-dihydropteroic acid can be biosynthesized from 6-hydroxymethyl-7,8-dihydropterin diphosphate and p-aminobenzoic acid through the action of the enzyme folic acid synthesis. In addition, 7,8-dihydropteroic acid and L-glutamic acid can be converted into 7,8-dihydrofolate monoglutamate; which is mediated by the enzyme folic acid synthesis 3. In yeast, 7,8-dihydropteroic acid is involved in the metabolic pathway called tetrahydrofolate biosynthesis pathway.
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
  • dihydropterate
  • 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
  • 4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoic acid
  • Dihydropteroinsaeure
  • 4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoate
CAS number2134-76-1
WeightAverage: 314.2994
Monoisotopic: 314.112738344
InChI KeyWBFYVDCHGVNRBH-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid
Traditional IUPAC Name7,8-dihydropteroic acid
Chemical FormulaC14H14N6O3
SMILES[H]OC(=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]
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
tetrahydrofolate biosynthesisPW002417 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Folate biosynthesisec00790 Map00790
SMPDB Reactions
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-Aminobenzoic acidPyrophosphate + 7,8-Dihydropteroic acid
7,8-Dihydropteroic acid + Adenosine triphosphate + L-Glutamic acidADP + phosphate + hydron + 7,8-dihydrofolate monoglutamate
KEGG Reactions
Adenosine triphosphate + L-Glutamic acid + 7,8-Dihydropteroic acidphosphate + hydron + ADP + Dihydrofolic acid
2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol + 4-Aminobenzoic acidwater + 7,8-Dihydropteroic acid
(2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphate + 4-Aminobenzoic acidPyrophosphate + 7,8-Dihydropteroic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fe0-0790000000-51d5d3b08e34c7becd27JSpectraViewer
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
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: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.
External Links:
ResourceLink
CHEBI ID4581
HMDB IDHMDB01412
Pubchem Compound ID170
Kegg IDC00921
ChemSpider ID165
FOODB IDFDB030621
WikipediaDihydropteroate
BioCyc ID7-8-DIHYDROPTEROATE

Enzymes

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).
General function:
Involved in dihydropteroate synthase activity
Specific function:
Catalyzes three sequential steps of tetrahydrofolate biosynthesis
Gene Name:
FOL1
Uniprot ID:
P53848
Molecular weight:
93119.10156
Reactions
2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine → 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine + glycolaldehyde.
ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine → AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate → diphosphate + dihydropteroate.