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7,8-Dihydropteroic acid (YMDB00293)

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
MOLSDFPDBSMILESInChI
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 acid → Pyrophosphate + 7,8-Dihydropteroic acid
7,8-Dihydropteroic acid + Adenosine triphosphate + L-Glutamic acid → ADP + phosphate + hydron + 7,8-dihydrofolate monoglutamate
KEGG Reactions
Adenosine triphosphate + L-Glutamic acid + 7,8-Dihydropteroic acid → phosphate + hydron + ADP + Dihydrofolic acid
2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol + 4-Aminobenzoic acid → water + 7,8-Dihydropteroic acid
(2-Amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl trihydrogen diphosphate + 4-Aminobenzoic acid → Pyrophosphate + 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-0ca8b4ed5ec637c71d37JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9231000000-4adcc7bed47beb3f3fb9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9460000000-8c4fef4ee51806b3dc9eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0209000000-907bcfac745eb62d4d42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0958000000-1babfb4ccb2f4798f7d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vr-0920000000-ccfcce4cf4171ef887faJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. Folylpolyglutamate synthase 1
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).
Protein Details
2. Folic acid synthesis protein FOL1
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.