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Showing Compound Tetrahydropteridine (FDB022495)

Record Information
Version1.0
Creation date2011-09-21 00:14:54 UTC
Update date2015-07-21 06:57:14 UTC
Primary IDFDB022495
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTetrahydropteridine
DescriptionTetrahydrobiopterin serves well-characterized cofactor functions for hydroxylating aromatic amino acids and ether lipids and for formation of nitric oxide (NO) from L-arginine. Formation of NO involves two cycles of oxidation of Tetrahydrobiopterin to its radical with subsequent rehydroxylation into Tetrahydrobiopterin, one for reduction of the heme-bound arginine-Fe(II)O2 complex of NO synthase (NOS), the other for reduction of the N-hydroxy-L-arginine-Fe(II)O2 complex. Tetrahydrobiopterin-dependent glyceryl ether monooxygenase (EC 1.14.16.5) is found not only in liver and the gastrointestinal tract but also in brain and other organs (this enzyme plays an essential role in conjugation with the cleavage enzyme in the regulation of cellular levels of -alkyl moieties in glycerolipids). Tetrahydrobiopterin is essential for the enzymatic reaction of tyrosine 3-monooxygenase (EC 1.14.16.2) for the first step in the biosynthesis of catecholamines such as norepinephrine, epinephrine and dopamine. Limited Tetrahydrobiopterin availability not only decreases formation of NO but also causes NOS-derived superoxide/hydrogen peroxide production leading to formation of peroxynitrite as well as S-nitrosoglutathione. As a consequence of its oxygen-activating potential, Tetrahydrobiopterin is also subject to autoxidation in a free radical chain reaction in leading to formation of superoxide and finally to hydrogen peroxide. On the other hand, Tetrahydrobiopterin, like other H4-pterins, can scavenge reactive oxygen species and peroxynitrite. Thus, Tetrahydrobiopterin may have opposing effects in various biological systems depending on whether its cofactor roles outweigh its chemical reactivity or vice versa. Sepiapterin reductase (EC 1.1.1.153) catalyzes the reduction of tetrahydro-sepiapterin to tetrahydrobiopterin -the terminal step in this biosynthetic pathway for tetrahydrobiopterin. This reaction is N-acetyl-serotonin-sensitive and can completely inhibit tetrahydrobiopterin synthesis. (PMID: 3881214, 17303893, 3756924, 15223071) [HMDB]
CAS Number10593-78-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
5,6,7,8-TetrahydropteridineKegg
5,6,7,8-Tetrahydro-pteridineHMDB
H4-BiopterinHMDB
THPHMDB
TetrahydropteridineChEBI
5,6,7,8-tetrahydro-Pteridinehmdb
H4-biopterinhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H8N4
IUPAC name5,6,7,8-tetrahydropteridine
InChI IdentifierInChI=1S/C6H8N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4,8H,1-2H2,(H,7,9,10)
InChI KeyIDAICLIJTRXNER-UHFFFAOYSA-N
Isomeric SMILESC1CNC2=C(N1)C=NC=N2
Average Molecular Weight136.1545
Monoisotopic Molecular Weight136.074896276
Classification
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
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTetrahydropteridine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-2900000000-f10ca50f06250e5030d3Spectrum
Predicted GC-MSTetrahydropteridine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-9a1ed9296c96ac1520182015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-63f9acde2a431bff24882015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-9100000000-9987b7952a5c983f7c8e2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-93507d1f946deac8a0742015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-36867a49c6c36342b0322015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9800000000-c2d528a75468455129532015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-278b0289a2d1c7916e5b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-7f4a76469d170f8d43f92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-7900000000-e829877fe8774c9c13f92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-06cd9080747456c7643d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c5f7233447b8e475f5c62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-a22ac8b5a57e8c2437f72021-09-24View Spectrum
NMRNot Available
ChemSpider ID151
ChEMBL IDNot Available
KEGG Compound IDC05650
Pubchem Compound ID156
Pubchem Substance IDNot Available
ChEBI ID28889
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01216
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTHP
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference