Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:09:40 UTC
Update Date2021-09-14 15:43:40 UTC
HMDB IDHMDB0060961
Secondary Accession Numbers
  • HMDB60961
Metabolite Identification
Common NameN-desisopropylpropranolol
DescriptionN-desisopropylpropranolol 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
Data?1563866128
Synonyms
ValueSource
N-Desisopropylpropranolol hydrochloride, (+-)-isomerHMDB
N-Desisopropylpropranolol, (+-)-isomerHMDB
N-Desisopropylpropranolol hydrochlorideHMDB
N-DesisopropylpropranololMeSH
Chemical FormulaC13H15NO2
Average Molecular Weight217.2637
Monoisotopic Molecular Weight217.110278729
IUPAC Name1-amino-3-(naphthalen-1-yloxy)propan-2-ol
Traditional Name1-amino-3-(naphthalen-1-yloxy)propan-2-ol
CAS Registry NumberNot Available
SMILES
NCC(O)COC1=CC=CC2=CC=CC=C12
InChI Identifier
InChI=1S/C13H15NO2/c14-8-11(15)9-16-13-7-3-5-10-4-1-2-6-12(10)13/h1-7,11,15H,8-9,14H2
InChI KeyZFMCITCRZXLMDJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Alkyl aryl ether
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Ether
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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 Solubility0.55 g/LALOGPS
logP1.48ALOGPS
logP1.38ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)14.1ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.88 m³·mol⁻¹ChemAxon
Polarizability23.81 ųChemAxon
Number of Rings2ChemAxon
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]+149.0131661259
DarkChem[M-H]-146.77231661259
DeepCCS[M-2H]-179.56530932474
DeepCCS[M+Na]+155.10330932474
AllCCS[M+H]+150.032859911
AllCCS[M+H-H2O]+146.132859911
AllCCS[M+NH4]+153.632859911
AllCCS[M+Na]+154.732859911
AllCCS[M-H]-152.432859911
AllCCS[M+Na-2H]-152.532859911
AllCCS[M+HCOO]-152.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-desisopropylpropranololNCC(O)COC1=CC=CC2=CC=CC=C122824.1Standard polar33892256
N-desisopropylpropranololNCC(O)COC1=CC=CC2=CC=CC=C121973.1Standard non polar33892256
N-desisopropylpropranololNCC(O)COC1=CC=CC2=CC=CC=C122065.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-desisopropylpropranolol,1TMS,isomer #1C[Si](C)(C)OC(CN)COC1=CC=CC2=CC=CC=C122102.4Semi standard non polar33892256
N-desisopropylpropranolol,1TMS,isomer #2C[Si](C)(C)NCC(O)COC1=CC=CC2=CC=CC=C122156.2Semi standard non polar33892256
N-desisopropylpropranolol,2TMS,isomer #1C[Si](C)(C)NCC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C2147.5Semi standard non polar33892256
N-desisopropylpropranolol,2TMS,isomer #1C[Si](C)(C)NCC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C2203.2Standard non polar33892256
N-desisopropylpropranolol,2TMS,isomer #1C[Si](C)(C)NCC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C2678.8Standard polar33892256
N-desisopropylpropranolol,2TMS,isomer #2C[Si](C)(C)N(CC(O)COC1=CC=CC2=CC=CC=C12)[Si](C)(C)C2364.2Semi standard non polar33892256
N-desisopropylpropranolol,2TMS,isomer #2C[Si](C)(C)N(CC(O)COC1=CC=CC2=CC=CC=C12)[Si](C)(C)C2345.3Standard non polar33892256
N-desisopropylpropranolol,2TMS,isomer #2C[Si](C)(C)N(CC(O)COC1=CC=CC2=CC=CC=C12)[Si](C)(C)C2824.5Standard polar33892256
N-desisopropylpropranolol,3TMS,isomer #1C[Si](C)(C)OC(COC1=CC=CC2=CC=CC=C12)CN([Si](C)(C)C)[Si](C)(C)C2412.5Semi standard non polar33892256
N-desisopropylpropranolol,3TMS,isomer #1C[Si](C)(C)OC(COC1=CC=CC2=CC=CC=C12)CN([Si](C)(C)C)[Si](C)(C)C2395.1Standard non polar33892256
N-desisopropylpropranolol,3TMS,isomer #1C[Si](C)(C)OC(COC1=CC=CC2=CC=CC=C12)CN([Si](C)(C)C)[Si](C)(C)C2606.0Standard polar33892256
N-desisopropylpropranolol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CN)COC1=CC=CC2=CC=CC=C122350.8Semi standard non polar33892256
N-desisopropylpropranolol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCC(O)COC1=CC=CC2=CC=CC=C122415.5Semi standard non polar33892256
N-desisopropylpropranolol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2622.0Semi standard non polar33892256
N-desisopropylpropranolol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2611.3Standard non polar33892256
N-desisopropylpropranolol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC(COC1=CC=CC2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2861.8Standard polar33892256
N-desisopropylpropranolol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(O)COC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C2833.0Semi standard non polar33892256
N-desisopropylpropranolol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(O)COC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C2712.8Standard non polar33892256
N-desisopropylpropranolol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(O)COC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C2928.8Standard polar33892256
N-desisopropylpropranolol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(COC1=CC=CC2=CC=CC=C12)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3061.2Semi standard non polar33892256
N-desisopropylpropranolol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(COC1=CC=CC2=CC=CC=C12)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2974.9Standard non polar33892256
N-desisopropylpropranolol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(COC1=CC=CC2=CC=CC=C12)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2854.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-desisopropylpropranolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9500000000-a6aa9f51151ac8c611782017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-desisopropylpropranolol GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9410000000-5bb8e83efd3123d735072017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-desisopropylpropranolol 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 - N-desisopropylpropranolol 10V, Positive-QTOFsplash10-014i-0190000000-88648197fd7da2268d852017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 20V, Positive-QTOFsplash10-0v59-7690000000-23257dff5ee1f8e269f62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 40V, Positive-QTOFsplash10-066s-5900000000-3d9efafe27b54d3e08702017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 10V, Negative-QTOFsplash10-014l-0690000000-cc3a095fd358c2c3423c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 20V, Negative-QTOFsplash10-0006-0900000000-ad93d36947eadae0911e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 40V, Negative-QTOFsplash10-0006-0900000000-3659ebd0c5ae1936eee22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 10V, Negative-QTOFsplash10-0006-0930000000-0a574bd2b49b149ff0942021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 20V, Negative-QTOFsplash10-0006-0900000000-aa1606dd90a27cbad6182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 40V, Negative-QTOFsplash10-0006-0900000000-2cf9fbc8c646237a416a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 10V, Positive-QTOFsplash10-014i-0190000000-7edaa7049380d67d70282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 20V, Positive-QTOFsplash10-066r-5950000000-40e130139e64b90caa642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desisopropylpropranolol 40V, Positive-QTOFsplash10-00mo-5900000000-18b9194983917ea2acb82021-09-24Wishart 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 Compound159899
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