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Record Information
Version3.6
Creation Date2013-07-09 16:11:15 UTC
Update Date2017-03-02 22:05:37 UTC
HMDB IDHMDB60989
Secondary Accession NumbersNone
Metabolite Identification
Common Name4'-hydroxypropanolol
Description4'-hydroxypropanolol is a metabolite of propranolol. Propranolol is a sympatholytic non-selective beta blocker. Sympatholytics are used to treat hypertension, anxiety and panic. It was the first successful beta blocker developed. Propranolol is available in generic form as propranolol hydrochloride, as well as an AstraZeneca and Wyeth product under the brand names Inderal, Inderal LA, Avlocardyl, Deralin, Dociton, Inderalici, InnoPran XL, Sumial, Anaprilinum, Bedranol SR. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
4-Hydroxy propranololChEMBL
4-HYDROXYPROPRANOLOL sulfuric acidGenerator
4-HYDROXYPROPRANOLOL sulphateGenerator
4-HYDROXYPROPRANOLOL sulphuric acidGenerator
1-(4-Hydroxynaphth-1-yloxy)-3-isopropylamino-2- propanolMeSH
4-Hydroxypropranolol, (R)-isomerMeSH
4-Hydroxypropranolol, (S)-isomerMeSH
4-Hydroxypropranolol hydrochlorideMeSH
4-Hydroxypropranolol hydrochloride, (+-)-isomerMeSH
4-Hydroxypropranolol, (+-)-isomerMeSH
Chemical FormulaC16H21NO3
Average Molecular Weight275.3428
Monoisotopic Molecular Weight275.152143543
IUPAC Name4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}naphthalen-1-ol
Traditional Name4-[2-hydroxy-3-(isopropylamino)propoxy]naphthalen-1-ol
CAS Registry NumberNot Available
SMILES
CC(C)NCC(O)COC1=CC=C(O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C16H21NO3/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16/h3-8,11-12,17-19H,9-10H2,1-2H3
InChI KeyCWEPACWBWIOYID-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassNaphthalenes
Direct ParentNaphthols and derivatives
Alternative Parents
Substituents
  • 1-naphthol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 mg/mLALOGPS
logP1.63ALOGPS
logP1.57ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.3ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.81 m3·mol-1ChemAxon
Polarizability30.79 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00310
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60989
Metagene LinkHMDB60989
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available