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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:19 UTC
HMDB IDHMDB0001410
Secondary Accession Numbers
  • HMDB01410
Metabolite Identification
Common Name2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine
Description2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine 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. 2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine is a moderately basic compound (based on its pKa). This compound It is a byproduct of 6-pyruvoyltetrahydropterin synthase (EC4.2.3.12), and associated with 6-Pyruvoyltetrahydropterin synthase deficiency (an autosomal recessive disorder that causes malignant hyperphenylalaninemia due to tetrahydrobiopterin deficiency).
Structure
Data?1582752199
SynonymsNot Available
Chemical FormulaC9H9N5O5
Average Molecular Weight267.1983
Monoisotopic Molecular Weight267.060368423
IUPAC Name1-(2-amino-7,8-dihydroxy-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)propane-1,2-dione
Traditional Name1-(2-amino-7,8-dihydroxy-4-oxo-3,7-dihydropteridin-6-yl)propane-1,2-dione
CAS Registry NumberNot Available
SMILES
CC(=O)C(=O)C1=NC2=C(N=C(N)NC2=O)N(O)C1O
InChI Identifier
InChI=1S/C9H9N5O5/c1-2(15)5(16)3-8(18)14(19)6-4(11-3)7(17)13-9(10)12-6/h8,18-19H,1H3,(H3,10,12,13,17)
InChI KeyQBHQZPRDJMYEDG-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
  • Aminopyrimidine
  • Pyrimidone
  • Alpha-diketone
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketimine
  • Ketone
  • Alkanolamine
  • Azacycle
  • N-organohydroxylamine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Imine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

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 Solubility0.52 g/LALOGPS
logP-0.83ALOGPS
logP-1.2ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)10.77ChemAxon
pKa (Strongest Basic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area157.68 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.81 m³·mol⁻¹ChemAxon
Polarizability23.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-7690000000-ac11927f620bfa5bf2d9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9163000000-81e44c10368b189ecf7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0090000000-cd9967bc8703cb1b9409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-0890000000-15c22983d0ad048835deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2970000000-bcf2f8767f8d71d3004eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-e76aaed34040fb812349Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i1-2960000000-a220189d0a8094d22fc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9410000000-8188f2e124d9fd4a5f20Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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
FooDB IDFDB022605
KNApSAcK IDNot Available
Chemspider ID389496
KEGG Compound IDC05255
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135532281
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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