Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


Tetrahydropteridine (M2MDB000302)

Record Information
Version2.0
Creation Date2012-05-31 13:47:53 -0600
Update Date2015-06-03 15:53:51 -0600
Secondary Accession Numbers
  • ECMDB01216
Identification
Name:Tetrahydropteridine
DescriptionTetrahydropteridine is a member of the chemical class 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. In a reversible reaction catalyzed by a nitroreductase / dihydropteridine reductase (EC 1.5.1.34), tetrahydropteridine can be converted to dihydropteridine while reducing NAD(P)+ to NAD(P)H. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 5,6,7,8-Tetrahydro-Pteridine
  • 5,6,7,8-Tetrahydropteridine
  • H4-biopterin
  • Tetrahydropteridine
  • THP
Chemical Formula:C6H8N4
Weight:Average: 136.1545
Monoisotopic: 136.074896276
InChI Key:IDAICLIJTRXNER-UHFFFAOYSA-N
InChI:InChI=1S/C6H8N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4,8H,1-2H2,(H,7,9,10)
CAS number:10593-78-9
IUPAC Name:5,6,7,8-tetrahydropteridine
Traditional IUPAC Name:5,6,7,8-tetrahydropteridine
SMILES:C1CNC2=C(N1)C=NC=N2
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
  • Secondary aliphatic/aromatic amine
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-0.512PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.43 g/LALOGPS
logP0.29ALOGPS
logP-0.58ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)19.35ChemAxon
pKa (Strongest Basic)5.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.84 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.45 m³·mol⁻¹ChemAxon
Polarizability13.53 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, Positivesplash10-0a4i-2900000000-f10ca50f06250e5030d3View 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-0900000000-9a1ed9296c96ac152018View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-63f9acde2a431bff2488View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-9100000000-9987b7952a5c983f7c8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-93507d1f946deac8a074View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-36867a49c6c36342b032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9800000000-c2d528a7546845512953View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-278b0289a2d1c7916e5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-7f4a76469d170f8d43f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-7900000000-e829877fe8774c9c13f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-06cd9080747456c7643dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c5f7233447b8e475f5c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-a22ac8b5a57e8c2437f7View 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:
  • Hoffman DR, Hoffman LH, Snyder F: Cytotoxicity and metabolism of alkyl phospholipid analogues in neoplastic cells. Cancer Res. 1986 Nov;46(11):5803-9. Pubmed: 3756924
  • 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
  • Rao GN, Cotlier E: The enzymatic activities of GTP cyclohydrolase, sepiapterin reductase, dihydropteridine reductase and dihydrofolate reductase; and tetrahydrobiopterin content in mammalian ocular tissues and in human senile cataracts. Comp Biochem Physiol B. 1985;80(1):61-6. Pubmed: 3881214
  • Thoeni G, Werner ER, Werner-Felmayer G: Tetrahydropteridines suppress gene expression and induce apoptosis of activated RAW264.7 cells via formation of hydrogen peroxide. Free Radic Biol Med. 2004 Aug 1;37(3):375-85. Pubmed: 15223071
  • 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
  • Werner ER, Hermetter A, Prast H, Golderer G, Werner-Felmayer G: Widespread occurrence of glyceryl ether monooxygenase activity in rat tissues detected by a novel assay. J Lipid Res. 2007 Jun;48(6):1422-7. Epub 2007 Feb 15. Pubmed: 17303893
  • 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 ID28889
HMDB IDHMDB01216
Pubchem Compound ID156
Kegg IDC05650
ChemSpider ID151
Wikipedia IDNot Available
BioCyc ID5678-TETRAHYDROPTERIDINE
EcoCyc ID5678-TETRAHYDROPTERIDINE

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.