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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:49:12 UTC
Update Date2021-09-14 15:46:31 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
Data?1563866148
Synonyms
ValueSource
4-Hydroxyalprenolol, (+-)-isomerHMDB
4-Hydroxyalprenolol hydrochlorideHMDB
4-HydroxyalprenololMeSH
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
Description Belongs to the class of organic compounds known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class4-alkoxyphenols
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.51531661259
DarkChem[M-H]-160.57331661259
DeepCCS[M+H]+162.32430932474
DeepCCS[M-H]-159.96630932474
DeepCCS[M-2H]-193.31330932474
DeepCCS[M+Na]+168.47930932474
AllCCS[M+H]+165.632859911
AllCCS[M+H-H2O]+162.232859911
AllCCS[M+NH4]+168.732859911
AllCCS[M+Na]+169.632859911
AllCCS[M-H]-166.632859911
AllCCS[M+Na-2H]-167.132859911
AllCCS[M+HCOO]-167.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-alprenololCC(C)NCC(O)COC1=CC=C(O)C=C1CC=C3255.1Standard polar33892256
4-Hydroxy-alprenololCC(C)NCC(O)COC1=CC=C(O)C=C1CC=C2191.2Standard non polar33892256
4-Hydroxy-alprenololCC(C)NCC(O)COC1=CC=C(O)C=C1CC=C2163.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-alprenolol,1TMS,isomer #1C=CCC1=CC(O)=CC=C1OCC(CNC(C)C)O[Si](C)(C)C2160.8Semi standard non polar33892256
4-Hydroxy-alprenolol,1TMS,isomer #2C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(O)CNC(C)C2109.7Semi standard non polar33892256
4-Hydroxy-alprenolol,1TMS,isomer #3C=CCC1=CC(O)=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C2310.5Semi standard non polar33892256
4-Hydroxy-alprenolol,2TMS,isomer #1C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(CNC(C)C)O[Si](C)(C)C2093.9Semi standard non polar33892256
4-Hydroxy-alprenolol,2TMS,isomer #2C=CCC1=CC(O)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C2334.5Semi standard non polar33892256
4-Hydroxy-alprenolol,2TMS,isomer #3C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C2296.8Semi standard non polar33892256
4-Hydroxy-alprenolol,3TMS,isomer #1C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C2335.2Semi standard non polar33892256
4-Hydroxy-alprenolol,3TMS,isomer #1C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C2315.1Standard non polar33892256
4-Hydroxy-alprenolol,3TMS,isomer #1C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C2451.4Standard polar33892256
4-Hydroxy-alprenolol,1TBDMS,isomer #1C=CCC1=CC(O)=CC=C1OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C2395.2Semi standard non polar33892256
4-Hydroxy-alprenolol,1TBDMS,isomer #2C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(O)CNC(C)C2346.0Semi standard non polar33892256
4-Hydroxy-alprenolol,1TBDMS,isomer #3C=CCC1=CC(O)=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C2560.0Semi standard non polar33892256
4-Hydroxy-alprenolol,2TBDMS,isomer #1C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C2533.3Semi standard non polar33892256
4-Hydroxy-alprenolol,2TBDMS,isomer #2C=CCC1=CC(O)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2805.0Semi standard non polar33892256
4-Hydroxy-alprenolol,2TBDMS,isomer #3C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C2756.1Semi standard non polar33892256
4-Hydroxy-alprenolol,3TBDMS,isomer #1C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2980.1Semi standard non polar33892256
4-Hydroxy-alprenolol,3TBDMS,isomer #1C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2892.5Standard non polar33892256
4-Hydroxy-alprenolol,3TBDMS,isomer #1C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2723.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-alprenolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-9620000000-d14d23d1e5df360da99e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-alprenolol GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-8229000000-acf1b0eaeec0730d0ae12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-alprenolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-alprenolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 10V, Positive-QTOFsplash10-014i-1290000000-5fa6264542e41cb1f6132017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 20V, Positive-QTOFsplash10-00di-9570000000-faf719c7ad297ea8732b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 40V, Positive-QTOFsplash10-05gl-9200000000-f95fffa79d89f3644dcf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 10V, Negative-QTOFsplash10-03dj-1590000000-48c9d70677c024e397c02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 20V, Negative-QTOFsplash10-0002-0900000000-a8c2fec677337aab90ee2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 40V, Negative-QTOFsplash10-0a4j-2900000000-0474bc91645edb1610ba2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 10V, Negative-QTOFsplash10-03di-0920000000-70eee85ef7926c991fce2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 20V, Negative-QTOFsplash10-0002-1900000000-056bea127ffd10c18fd72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 40V, Negative-QTOFsplash10-0a4j-9500000000-47c5e74c113807ed37a52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 10V, Positive-QTOFsplash10-014i-0090000000-4e146c2147293d54f35a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 20V, Positive-QTOFsplash10-00xs-9640000000-9892af4087b99ffabe592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 40V, Positive-QTOFsplash10-05fr-9300000000-131bf0104097437c3a7e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound171322
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available