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Dyspropterin (M2MDB000292)

Record Information
Version2.0
Creation Date2012-05-31 13:47:20 -0600
Update Date2015-06-03 15:53:50 -0600
Secondary Accession Numbers
  • ECMDB01195
Identification
Name:Dyspropterin
DescriptionDyspropterin, an intermediate formed from dihydroneopterin triphosphate in the biosynthetic pathway of tetrahydrobiopterin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterin
  • 6-Pyruvoyl-5,6,7,8-tetrahydropterin
  • 6-Pyruvoyl-tetrahydropterin
  • 6-Pyruvoyltetrahydropterin
  • Dyspropterin
  • PPH4
  • Pyruvoyl-H4-pterin
  • Pyruvoyl-H4-pterin
Chemical Formula:C9H11N5O3
Weight:Average: 237.2153
Monoisotopic: 237.086189243
InChI Key:WBJZXBUVECZHCE-UHFFFAOYSA-N
InChI:InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)
CAS number:89687-39-8
IUPAC Name:1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione
Traditional IUPAC Name:1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione
SMILES:CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2
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
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Alpha-diketone
  • Beta-aminoketone
  • Gamma-aminoketone
  • Pyrimidine
  • Alpha-aminoketone
  • Heteroaromatic compound
  • Ketone
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.65 g/LALOGPS
logP-1ALOGPS
logP-1.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
pKa (Strongest Basic)1.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.02 m³·mol⁻¹ChemAxon
Polarizability21.98 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate
Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate
Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-2900000000-ea0a10643b223873638eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0090000000-e366b52537ab82676ed2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-1960000000-67fc5a413844945d775cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1091-5920000000-f119b9c54a82b7839351View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-be2ef388ef865810e924View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-1920000000-eb2749d8b0464ac6c26eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9300000000-27dfb045e7865625ad19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-0920000000-0aa60cfee054c5a9fa2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-0900000000-52e64f000baee84b7972View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-742331329c354591f810View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0290000000-3af6dea1e92f19bfed1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0940000000-86b33ca35b9f411d94eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9600000000-a447ecf4063026f52e7bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bonafe L, Thony B, Leimbacher W, Kierat L, Blau N: Diagnosis of dopa-responsive dystonia and other tetrahydrobiopterin disorders by the study of biopterin metabolism in fibroblasts. Clin Chem. 2001 Mar;47(3):477-85. Pubmed: 11238300
  • Dhondt JL, Hayte JM: [Screening of tetrahydrobiopterin deficiency among hyperphenylalaninemic patients] Ann Biol Clin (Paris). 2002 Mar-Apr;60(2):165-71. Pubmed: 11937441
  • Iwanaga N, Yamamasu S, Tachibana D, Nishio J, Nakai Y, Shintaku H, Ishiko O: Activity of synthetic enzymes of tetrahydrobiopterin in the human placenta. Int J Mol Med. 2004 Jan;13(1):117-20. Pubmed: 14654981
  • 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
  • Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. Pubmed: 3326735
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17804
HMDB IDHMDB01195
Pubchem Compound ID128973
Kegg IDC03684
ChemSpider ID114280
Wikipedia IDDyspropterin
BioCyc ID6-PYRUVOYL-5678-TETRAHYDROPTERIN
EcoCyc ID6-PYRUVOYL-5678-TETRAHYDROPTERIN

Enzymes

Protein Details
1. 6-carboxy-5,6,7,8-tetrahydropterin synthase
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the conversion of 7,8-dihydroneopterin triphosphate (H2NTP) to 6-carboxy-5,6,7,8-tetrahydropterin (CPH4) and acetaldehyde. Can also convert 6-pyruvoyltetrahydropterin (PPH4) and sepiapterin to CPH4; these 2 compounds are probably intermediates in the reaction from H2NTP
Gene Name:
queD
Uniprot ID:
P65870
Molecular weight:
13773
Reactions
7,8-dihydroneopterin 3'-triphosphate + H(2)O = 6-carboxy-5,6,7,8-tetrahydropterin + acetaldehyde + triphosphate.