Record Information
Version1.0
Creation date2011-09-21 00:22:10 UTC
Update date2015-07-21 06:57:26 UTC
Primary IDFDB022944
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4a-Hydroxytetrahydrobiopterin
DescriptionTetrahydrobiopterin (BH4) is essential to catalyze the conversion of phenylalanine to tyrosine by phenylalanine hydroxylase. During this physiological reaction, the oxidation of BH4 creates 4a-hydroxytetrahydropterin intermediates and hydrogen peroxide is formed. The hydrogen peroxide and the hydroxytetrahydropterin can both derive from alternate routes of breakdown of a common precursor, the corresponding 4a-hydroperoxytetrahydropterin. (PMID 8323303) [HMDB]
CAS Number70110-58-6
Structure
Thumb
Synonyms
SynonymSource
HydroxypterinHMDB
(6R)-6-(L-erythro-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterinhmdb
2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-5,6,7,8-tetrahydropteridin-4(4aH)-onehmdb
2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxy-4(4aH)-Pteridinonehmdb
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4a-hydroxy-1,5,6,7-tetrahydropteridin-4-onehmdb
4a-Hydroxy-5,6,4,8-tetrahydrobiopterinChEBI
4a-Hydroxy-5,6,7,8-tetrahydrobiopterinhmdb
4a-Hydroxytetrahydrobiopterinhmdb
4alpha-Hydroxytetrahydrobiopterinhmdb
Predicted Properties
PropertyValueSource
Water Solubility8.55 g/LALOGPS
logP-0.33ALOGPS
logP-1.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)12.87ChemAxon
pKa (Strongest Basic)1.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.09 m³·mol⁻¹ChemAxon
Polarizability21.8 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H14N4O3
IUPAC name(2S)-1-[(6S)-4-hydroxy-5,6,7,8-tetrahydropteridin-6-yl]propane-1,2-diol
InChI IdentifierInChI=1S/C9H14N4O3/c1-4(14)7(15)5-2-10-8-6(13-5)9(16)12-3-11-8/h3-5,7,13-15H,2H2,1H3,(H2,10,11,12,16)/t4-,5-,7?/m0/s1
InChI KeyXHZMOKNFPZDZBZ-CNGBTNQNSA-N
Isomeric SMILESC[C@H](O)C(O)[C@@H]1CNC2=C(N1)C(=O)N=CN2
Average Molecular Weight226.2325
Monoisotopic Molecular Weight226.106590334
Classification
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
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,3-aminoalcohol
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4900000000-f3e5b3304ffe899f9d67JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4392000000-1f614c11ed4d65424d44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0190000000-e2b72214da6014ff2836JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi0-0950000000-3f1b3f8d141c4b69f3bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2900000000-bb57df49863ca49a6228JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0390000000-83b723a3557258440824JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-0930000000-f053279fdd676141402eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9500000000-4cd2209cb306991f7ad7JSpectraViewer
ChemSpider ID114908
ChEMBL IDNot Available
KEGG Compound IDC15522
Pubchem Compound ID129803
Pubchem Substance IDNot Available
ChEBI ID15642
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02281
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 IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Tyrosine 3-monooxygenaseTHP07101
Phenylalanine-4-hydroxylasePAHP00439
Tryptophan 5-hydroxylase 1TPH1P17752
Tryptophan 5-hydroxylase 2TPH2Q8IWU9
Pterin-4-alpha-carbinolamine dehydratasePCBD1P61457
Pterin-4-alpha-carbinolamine dehydratase 2PCBD2Q9H0N5
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference