(6R)-Tetrahydrobiopterin dihydrochloride (CHEM017560)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:27:51 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017560
Identification
Common Name(6R)-Tetrahydrobiopterin dihydrochloride
ClassSmall Molecule
DescriptionThe dihydrochloride salt of sapropterin. It is used for the diagnosis and treatment of variant forms of phenylketonuria (hyperphenylalaninaemia) associated with tetrahydrobiopterin deficiency. Natural cofactor for phenylalanine hydroxylase, tyrosine hydroxylase, tryptophan hydroxylase, and nitric oxide synthetase.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6R)-Tetrahydrobiopterin dihydrochlorideChEBI
(6R)-Tetrahydrobiopterin hydrochlorideChEBI
Sapropterin 2HCLChEBI
Sapropterin hydrochlorideChEBI
BioptenKegg
KuvanKegg
5,6,7,8-TetrahydrobiopterinMeSH
tetrahydro-6-BiopterinMeSH
Sapropterin dihydrochlorideMeSH
TetrahydrobiopterinMeSH
5,6,7,8-tetrahydro-L-ErythrobiopterinMeSH
5,6,7,8-erythro-TetrahydrobiopterinMeSH
5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomerMeSH
5,6,7,8-TetrahydrodictyopterinMeSH
BPH4MeSH
D-threo-TetrahydrobiopterinMeSH
6R-L-erythro-5,6,7,8-TetrahydrobiopterinMeSH
THBPMeSH
6R-BH4MeSH
Phenylalanine hydroxylase cofactorMeSH
SapropterinMeSH
Chemical FormulaC9H17Cl2N5O3
Average Molecular Mass314.170 g/mol
Monoisotopic Mass313.071 g/mol
CAS Registry Number69056-38-8
IUPAC Name(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3,4,5,6,7,8-hexahydropteridin-4-one dihydrochloride
Traditional Name6R-5,6,7,8-tetrahydrobiopterin dihydrochloride
SMILESCl.Cl.[H][C@@]1(CNC2=C(N1)C(=O)NC(N)=N2)[C@@H](O)[C@H](C)O
InChI IdentifierInChI=1S/C9H15N5O3.2ClH/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7;;/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17);2*1H/t3-,4+,6-;;/m0../s1
InChI KeyRKSUYBCOVNCALL-NTVURLEBSA-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
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • 1,3-aminoalcohol
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-aminoalcohol
  • 1,2-diol
  • Secondary alcohol
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Hydrochloride
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility2.03 g/LALOGPS
logP-1.8ALOGPS
logP-2.3ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)1.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area132 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.63 m³·mol⁻¹ChemAxon
Polarizability23.59 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-1f734a32f72840dcbe52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-1f734a32f72840dcbe52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009000000-1f734a32f72840dcbe52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-94e05be52826768dc03aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-94e05be52826768dc03aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0009000000-94e05be52826768dc03aSpectrum
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 IDDBSALT001133
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTetrahydrobiopterin
Chemspider IDNot Available
ChEBI ID32120
PubChem Compound ID636369
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20179079
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20206791
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20418136
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20556789
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20667834
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20714359
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20830319
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21077779
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21645517
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21646032
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21967857
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22112818
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22310224