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Record Information
Version4.0
Creation Date2013-07-09 16:11:15 UTC
Update Date2017-09-27 08:43:58 UTC
HMDB IDHMDB0060989
Secondary Accession Numbers
  • HMDB60989
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.81 m³·mol⁻¹ChemAxon
Polarizability30.79 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0759-9610000000-a9018aef243706ee9894View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0g4i-9253300000-e397bbaa4c4dbe33005bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1190000000-6d6d2f69c29c5e9841beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-8490000000-21dbe2d2312cf3ec034bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gi-9300000000-d9a8363f652f70d55a9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1690000000-ff5bb68f749a06ea9fcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-795ea8788211bcca170eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-e2b9d74bb51e694a4856View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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
      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