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6,7-Dihydropteridine (M2MDB000390)

Record Information
Version2.0
Creation Date2012-05-31 13:52:51 -0600
Update Date2015-06-03 15:54:07 -0600
Secondary Accession Numbers
  • ECMDB01441
Identification
Name:6,7-Dihydropteridine
Description6,7-Dihydropteridine is 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)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 6,7-Dihydropteridine
  • Dihydropteridine
Chemical Formula:C6H6N4
Weight:Average: 134.1386
Monoisotopic: 134.059246212
InChI Key:KVDQMARGGBLIJM-UHFFFAOYSA-N
InChI:InChI=1S/C6H6N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4H,1-2H2
CAS number:Not Available
IUPAC Name:6,7-dihydropteridine
Traditional IUPAC Name:dihydropteridine
SMILES:C1CN=C2N=CN=CC2=N1
Chemical Taxonomy
Description 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
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-1.586PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.9 m³·mol⁻¹ChemAxon
Polarizability12.75 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
6,7-Dihydropteridine + 3 Hydrogen ion + NADH <> NAD + Tetrahydropteridine
6,7-Dihydropteridine + 3 Hydrogen ion + NADPH <> NADP + Tetrahydropteridine
NAD(P)<sup>+</sup> + Tetrahydropteridine <> NAD(P)H + 6,7-Dihydropteridine + Hydrogen ion
Tetrahydropteridine + NAD > 6,7-Dihydropteridine + NADH
Tetrahydropteridine + NADP > 6,7-Dihydropteridine + NADPH
Tetrahydropteridine + NAD + NADP <> 6,7-Dihydropteridine + NADH + NADPH + Hydrogen ion
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, Positivesplash10-0a59-2900000000-1af9a14b7fe86259c10cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-a57814c94b02f689b01aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4900000000-31022f7fd1a28ebea679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9500000000-4a5ee8ca0c19b685ff11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-e10d63974416ce234c6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-7a7332ad3447b0989e69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fur-9700000000-7f5be35b6305fd2ba8b6View 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:
  • 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
  • Koslow SH, Butler IJ: Biogenic amine synthesis defect in dihydropteridine reductase deficiency. Science. 1977 Nov 4;198(4316):522-3. Pubmed: 20665
  • 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. Pubmed: 14705166
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID30156
HMDB IDHMDB01441
Pubchem Compound ID167
Kegg IDC05649
ChemSpider ID162
Wikipedia IDNot Available
BioCyc ID67-DIHYDROPTERIDINE
EcoCyc ID67-DIHYDROPTERIDINE

Enzymes

Protein Details
1. Flavohemoprotein
General function:
Involved in oxidoreductase activity
Specific function:
Various electron acceptors are also reduced by HMP in vitro, including dihydropterine, ferrisiderophores, ferric citrate, cytochrome c, nitrite, S-nitrosoglutathione, and alkylhydroperoxides. However, it is unknown if these reactions are of any biological significance in vivo
Gene Name:
hmp
Uniprot ID:
P24232
Molecular weight:
43867
Reactions
2 NO + 2 O(2) + NAD(P)H = 2 NO(3)(-) + NAD(P)(+).
Protein Details
2. Oxygen-insensitive NAD(P)H nitroreductase
General function:
Involved in oxidoreductase activity
Specific function:
Reduction of a variety of nitroaromatic compounds using NADH (and to lesser extent NADPH) as source of reducing equivalents; two electrons are transferred. Capable of reducing nitrofurazone, quinones and the anti-tumor agent CB1954 (5- (aziridin-1-yl)-2,4-dinitrobenzamide). The reduction of CB1954 results in the generation of cytotoxic species
Gene Name:
nfnB
Uniprot ID:
P38489
Molecular weight:
23905
Reactions
A 5,6,7,8-tetrahydropteridine + NAD(P)(+) = a 6,7-dihydropteridine + NAD(P)H.