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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:40 UTC
HMDB IDHMDB01441
Secondary Accession NumbersNone
Metabolite Identification
Common NameDihydropteridine
DescriptionDihydropteridine is a generic compound; the product of the reduction of 5,6,7,8-Tetrahydropteridine, which is catalyzed by 6,7-dihydropteridine reductase (EC 1.5.1.34). (KEGG) This compound is recognised as a cause of tetrahydrobiopterin (BH(4)) deficiency, leading to hyperphenylalaninemia (HPA) and impaired biogenic amine deficiency. (PMID: 14705166 ).
Structure
Thumb
Synonyms
ValueSource
DihydropteridineChEBI
Chemical FormulaC6H6N4
Average Molecular Weight134.1386
Monoisotopic Molecular Weight134.059246212
IUPAC Name6,7-dihydropteridine
Traditional Namedihydropteridine
CAS Registry NumberNot Available
SMILES
C1CN=C2N=CN=CC2=N1
InChI Identifier
InChI=1S/C6H6N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4H,1-2H2
InChI KeyInChIKey=KVDQMARGGBLIJM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassNot Available
Direct ParentPteridines and derivatives
Alternative Parents
Substituents
  • Pteridine
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • 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
  • Cytoplasm (predicted from logP)
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 Solubility0.44 mg/mLALOGPS
logP-0.08ALOGPS
logP-0.37ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)2.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.44 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.9 m3·mol-1ChemAxon
Polarizability12.75 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, Positivesplash10-000i-0900000000-49823c54408ec671a5d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-996f0a38abb69b99422dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc3-9200000000-6ff1cc9fd050a1f6dab5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-902c30cb0987a50b982eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-08ce8b47ca4815053a05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-9200000000-4984023b11676528aeb3View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot 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 IDFDB022624
KNApSAcK IDNot Available
Chemspider ID162
KEGG Compound IDC05649
BioCyc ID67-DIHYDROPTERIDINE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01441
Metagene LinkHMDB01441
METLIN ID6249
PubChem Compound167
PDB IDNot Available
ChEBI ID30156
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Koslow SH, Butler IJ: Biogenic amine synthesis defect in dihydropteridine reductase deficiency. Science. 1977 Nov 4;198(4316):522-3. [20665 ]
  2. Ponzone A, Spada M, Ferraris S, Dianzani I, de Sanctis L: Dihydropteridine reductase deficiency in man: from biology to treatment. Med Res Rev. 2004 Mar;24(2):127-50. [14705166 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
The product of this enzyme, tetrahydrobiopterin (BH-4), is an essential cofactor for phenylalanine, tyrosine, and tryptophan hydroxylases.
Gene Name:
QDPR
Uniprot ID:
P09417
Molecular weight:
25789.295
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295