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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:59 UTC
HMDB IDHMDB01195
Secondary Accession NumbersNone
Metabolite Identification
Common NameDyspropterin
DescriptionDyspropterin, an intermediate formed from dihydroneopterin triphosphate in the biosynthetic pathway of tetrahydrobiopterin.
Structure
Thumb
Synonyms
  1. 6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterin
  2. 6-Pyruvoyl-5,6,7,8-tetrahydropterin
  3. 6-Pyruvoyl-tetrahydropterin
  4. 6-Pyruvoyltetrahydropterin
  5. Dyspropterin
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 KeyInChIKey=WBJZXBUVECZHCE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Gamma-aminoketone
  • Beta-aminoketone
  • Alpha-diketone
  • Heteroaromatic compound
  • Vinylogous amide
  • Alpha-aminoketone
  • Lactam
  • Ketone
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Folate biosynthesis
ApplicationNot Available
Cellular locations
  • Nucleus
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 mg/mLALOGPS
logP-1ALOGPS
logP-1.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)11.12ChemAxon
pKa (Strongest Basic)4.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.02 m3·mol-1ChemAxon
Polarizability21.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02z0000000-e366b52537ab82676ed2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-4zo0000000-67fc5a413844945d775cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-jz90000000-f119b9c54a82b7839351View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-39z0000000-be2ef388ef865810e924View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-6za0000000-eb2749d8b0464ac6c26eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-zc00000000-27dfb045e7865625ad19View in MoNA
Biological Properties
Cellular Locations
  • Nucleus
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
  • Placenta
Pathways
NameSMPDB LinkKEGG Link
Dopa-responsive dystoniaSMP00486Not Available
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiencySMP00487Not Available
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)SMP00488Not Available
Hyperphenylalaninemia due to dhpr-deficiencySMP00489Not Available
Pterine BiosynthesisSMP00005map00790
Segawa syndromeSMP00490Not Available
Sepiapterin reductase deficiencySMP00491Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022481
KNApSAcK IDNot Available
Chemspider ID114280
KEGG Compound IDC03684
BioCyc ID6-PYRUVOYL-5678-TETRAHYDROPTERIN
BiGG ID42328
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01195
Metagene LinkHMDB01195
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. [11238300 ]
  2. Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. [3326735 ]
  3. Dhondt JL, Hayte JM: [Screening of tetrahydrobiopterin deficiency among hyperphenylalaninemic patients] Ann Biol Clin (Paris). 2002 Mar-Apr;60(2):165-71. [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. [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