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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:41 UTC
HMDB IDHMDB0001195
Secondary Accession Numbers
  • HMDB01195
Metabolite Identification
Common NameDyspropterin
DescriptionDyspropterin, an intermediate formed from dihydroneopterin triphosphate in the biosynthetic pathway of tetrahydrobiopterin.
Structure
Data?1547234141
Synonyms
ValueSource
6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterinChEBI
6-Pyruvoyl-5,6,7,8-tetrahydropterinChEBI
6-PyruvoyltetrahydropterinChEBI
6-Pyruvoyl-tetrahydropterinHMDB
6-Pyruvoyl tetrahydropteridineHMDB
Pyruvoyl-H4-pterinHMDB
Chemical FormulaC9H11N5O3
Average Molecular Weight237.2153
Monoisotopic Molecular Weight237.086189243
IUPAC Name1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione
Traditional Name1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione
CAS Registry Number89687-39-8
SMILES
CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2
InChI Identifier
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)
InChI KeyWBJZXBUVECZHCE-UHFFFAOYSA-N
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
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-2900000000-ea0a10643b223873638eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0090000000-e366b52537ab82676ed2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-1960000000-67fc5a413844945d775cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1091-5920000000-f119b9c54a82b7839351JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-be2ef388ef865810e924JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-1920000000-eb2749d8b0464ac6c26eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9300000000-27dfb045e7865625ad19JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Nucleus
Biospecimen LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022481
KNApSAcK IDNot Available
Chemspider ID114280
KEGG Compound IDC03684
BioCyc ID6-PYRUVOYL-5678-TETRAHYDROPTERIN
BiGG ID42328
Wikipedia LinkDyspropterin
METLIN ID6071
PubChem Compound128973
PDB IDNot Available
ChEBI ID17804
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. [PubMed:3326735 ]
  3. Dhondt JL, Hayte JM: [Screening of tetrahydrobiopterin deficiency among hyperphenylalaninemic patients]. Ann Biol Clin (Paris). 2002 Mar-Apr;60(2):165-71. [PubMed:11937441 ]
  4. 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 ]

Enzymes

General function:
Involved in 6-pyruvoyltetrahydropterin synthase activity
Specific function:
Involved in the biosynthesis of tetrahydrobiopterin, an essential cofactor of aromatic amino acid hydroxylases. Catalyzes the transformation of 7,8-dihydroneopterin triphosphate into 6-pyruvoyl tetrahydropterin.
Gene Name:
PTS
Uniprot ID:
Q03393
Molecular weight:
16385.63
Reactions
Dihydroneopterin triphosphate → Dyspropterin + Triphosphatedetails
Dihydroneopterin triphosphate → Dyspropterin + PPPidetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
Gene Name:
SPR
Uniprot ID:
P35270
Molecular weight:
28048.13
Reactions
L-erythro-tetrahydrobiopterin + NADP → Dyspropterin + NADPHdetails
6-Lactoyltetrahydropterin + NADP → Dyspropterin + NADPH + Hydrogen Iondetails