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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:47 UTC
Update Date2022-03-07 02:57:14 UTC
HMDB IDHMDB0041935
Secondary Accession Numbers
  • HMDB41935
Metabolite Identification
Common NameMoprolol
DescriptionMoprolol is a beta-adrenergic antagonist, or beta blocker, typically prescribed to treat hypertension, high blood pressure, angina pectoris, arrhythmias, anxiety, and glaucoma. Moprolol was prominent in both literature and clinical trials up until the 1990s. At this point, moprolol was pulled from the market. This could have been for a number of reasons, including FDA recalls and ineffective formulations. Through some clinical trials, it was seen that moprolol was not as effective for treating blood pressure as originally thought (Wikipedia).
Structure
Data?1563863716
Synonyms
ValueSource
DL-MoprololHMDB
MoprololMeSH
Chemical FormulaC13H21NO3
Average Molecular Weight239.3107
Monoisotopic Molecular Weight239.152143543
IUPAC Name1-(2-methoxyphenoxy)-3-[(propan-2-yl)amino]propan-2-ol
Traditional Name1-(isopropylamino)-3-(2-methoxyphenoxy)propan-2-ol
CAS Registry Number5741-22-0
SMILES
COC1=CC=CC=C1OCC(O)CNC(C)C
InChI Identifier
InChI=1S/C13H21NO3/c1-10(2)14-8-11(15)9-17-13-7-5-4-6-12(13)16-3/h4-7,10-11,14-15H,8-9H2,1-3H3
InChI KeyLFTFGCDECFPSQD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Anisole
  • Methoxybenzene
  • Phenoxy compound
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.10Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.7 g/LALOGPS
logP1.43ALOGPS
logP1.44ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area50.72 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity66.84 m³·mol⁻¹ChemAxon
Polarizability27.08 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]+157.20531661259
DarkChem[M-H]-156.3231661259
DeepCCS[M+H]+154.31830932474
DeepCCS[M-H]-151.9630932474
DeepCCS[M-2H]-185.86530932474
DeepCCS[M+Na]+160.75430932474
AllCCS[M+H]+158.432859911
AllCCS[M+H-H2O]+154.932859911
AllCCS[M+NH4]+161.732859911
AllCCS[M+Na]+162.632859911
AllCCS[M-H]-158.932859911
AllCCS[M+Na-2H]-159.632859911
AllCCS[M+HCOO]-160.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MoprololCOC1=CC=CC=C1OCC(O)CNC(C)C2487.4Standard polar33892256
MoprololCOC1=CC=CC=C1OCC(O)CNC(C)C1801.3Standard non polar33892256
MoprololCOC1=CC=CC=C1OCC(O)CNC(C)C1811.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Moprolol,1TMS,isomer #1COC1=CC=CC=C1OCC(CNC(C)C)O[Si](C)(C)C1843.5Semi standard non polar33892256
Moprolol,1TMS,isomer #2COC1=CC=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C1993.1Semi standard non polar33892256
Moprolol,2TMS,isomer #1COC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C2049.7Semi standard non polar33892256
Moprolol,2TMS,isomer #1COC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C2059.4Standard non polar33892256
Moprolol,1TBDMS,isomer #1COC1=CC=CC=C1OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C2066.2Semi standard non polar33892256
Moprolol,1TBDMS,isomer #2COC1=CC=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C2250.8Semi standard non polar33892256
Moprolol,2TBDMS,isomer #1COC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2515.7Semi standard non polar33892256
Moprolol,2TBDMS,isomer #1COC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2490.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Moprolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9310000000-87d01eaf6e0fd37bd5a72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moprolol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9130000000-627c437a9c3a9d00a81e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moprolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moprolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moprolol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moprolol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moprolol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 10V, Positive-QTOFsplash10-0006-1590000000-3a51394e7d52b00c298e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 20V, Positive-QTOFsplash10-00di-7920000000-d12b59adbcd13c2743a82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 40V, Positive-QTOFsplash10-0ab9-9200000000-13764f26d7f7373f397f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 10V, Negative-QTOFsplash10-0079-1690000000-c8d529e99b56f7ff11cc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 20V, Negative-QTOFsplash10-05fr-1900000000-b9edb62dce6b8ec176b62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 40V, Negative-QTOFsplash10-0a4i-6900000000-8a5e7a954c65d02d0cdd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 10V, Negative-QTOFsplash10-01w0-1930000000-4fd04a71e0618d9cf59c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 20V, Negative-QTOFsplash10-0udi-4900000000-37a14a5c470c2c7d655a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 40V, Negative-QTOFsplash10-0a4i-9500000000-ab86a4019be38b3a9c8b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 10V, Positive-QTOFsplash10-0006-2390000000-44349cf8de7e3ec208dc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 20V, Positive-QTOFsplash10-00xr-9400000000-b89dbe46eb69a5797ed12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moprolol 40V, Positive-QTOFsplash10-0603-9200000000-63ce19356f987f6aed0a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID64348
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
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