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Record Information
Version4.0
Creation Date2013-07-22 19:49:12 UTC
Update Date2017-09-27 08:44:02 UTC
HMDB IDHMDB0061122
Secondary Accession Numbers
  • HMDB61122
Metabolite Identification
Common Name4-Hydroxy-alprenolol
Description4-Hydroxy-alprenolol is a metabolite of alprenolol. Alprenolol, or alfeprol, alpheprol, and alprenololum (Gubernal, Regletin, Yobir, Apllobal, Aptine, Aptol Duriles), is a non-selective beta blocker as well as 5-HT1A receptor antagonist, used in the treatment of angina pectoris. It is no longer marketed by AstraZeneca, but may still be available from other pharmaceutical companies or generically. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
4-Hydroxyalprenolol, (+-)-isomerMeSH
4-Hydroxyalprenolol hydrochlorideMeSH
Chemical FormulaC15H23NO3
Average Molecular Weight265.348
Monoisotopic Molecular Weight265.167793607
IUPAC Name4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-3-(prop-2-en-1-yl)phenol
Traditional Name4-[2-hydroxy-3-(isopropylamino)propoxy]-3-(prop-2-en-1-yl)phenol
CAS Registry NumberNot Available
SMILES
CC(C)NCC(O)COC1=CC=C(O)C=C1CC=C
InChI Identifier
InChI=1S/C15H23NO3/c1-4-5-12-8-13(17)6-7-15(12)19-10-14(18)9-16-11(2)3/h4,6-8,11,14,16-18H,1,5,9-10H2,2-3H3
InChI KeyHNXRWPIZRBNFDD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct Parent4-alkoxyphenols
Alternative Parents
Substituents
  • 4-alkoxyphenol
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.99 g/LALOGPS
logP1.52ALOGPS
logP1.86ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.07ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity76.64 m³·mol⁻¹ChemAxon
Polarizability30.38 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0uk9-9620000000-d14d23d1e5df360da99eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-8229000000-acf1b0eaeec0730d0ae1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1290000000-5fa6264542e41cb1f613View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9570000000-faf719c7ad297ea8732bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gl-9200000000-f95fffa79d89f3644dcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1590000000-48c9d70677c024e397c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-a8c2fec677337aab90eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-2900000000-0474bc91645edb1610baView 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 IDDBMET00740
      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