4a-Hydroxytetrahydrobiopterin (CHEM035399)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:43:53 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035399
Identification
Common Name4a-Hydroxytetrahydrobiopterin
ClassSmall Molecule
DescriptionA tetrahydropterin that is 5,6,7,8-tetrahydrobiopterin carrying an additional hydroxy substituent at the 4a-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4a-Hydroxy-5,6,4,8-tetrahydrobiopterinChEBI
(6R)-6-(L-erythro-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterinChEBI, HMDB
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-5,6,7,8-tetrahydrobiopterinHMDB
4alpha-HydroxytetrahydrobiopterinHMDB
4a-HTHBMeSH, HMDB
Chemical FormulaC9H14N4O3
Average Molecular Mass226.233 g/mol
Monoisotopic Mass226.107 g/mol
CAS Registry Number70110-58-6
IUPAC Name2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one
Traditional Name4a-hydroxytetrahydrobiopterin
SMILESC[C@H](O)C(O)[C@@H]1CNC2=C(N1)C(=O)N=CN2
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
Chemical Taxonomy
Description belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Hydropyrimidine
  • 1,2,5,6-tetrahydropyrimidine
  • Imidolactam
  • 1,2-diol
  • Secondary alcohol
  • Alkanolamine
  • Amidine
  • Carboxylic acid amidine
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.81 g/LALOGPS
logP-2.3ALOGPS
logP-3.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9.81ChemAxon
pKa (Strongest Basic)3.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area152.56 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.6 m³·mol⁻¹ChemAxon
Polarizability24.2 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-4930000000-89d1b72adfc56cf4e3fdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0zfr-5293600000-e1bc928bae70ea520f93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0090000000-364ec2c50acd77d83ef0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00gl-0690000000-f15f00b5ba6b8f2959b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9720000000-7a2198134bfe87159831Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-2290000000-43723819afb4c98b5cebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9210000000-fa8eb33fdfed731f1c82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c550affb7745a16d59b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-2e38d752208e421512bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0390000000-8910ee8de849000f68e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-5900000000-b0f630ab5b90aa052132Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-195221ba76407cd71968Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-1690000000-492a38357ab54f3370a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0296-9820000000-44ae87e7d45d04a8c51aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0304198
FooDB IDFDB030533
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-5881
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID114908
ChEBI ID15374
PubChem Compound ID129803
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available