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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:05 UTC
HMDB IDHMDB0015697
Secondary Accession Numbers
  • HMDB15697
Metabolite Identification
Common NameBupranolol
DescriptionBupranolol, also known as KL-255 or b 1312, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. The main metabolite is carboxybupranolol, 4-chloro-3-benzoic acid, of which 88% are eliminated renally within 24 hours. Bupranolol is a drug which is used to manage hypertension and tachycardia. also used to treat glaucoma. Bupranolol is a non-selective beta blocker with potency similar to . Bupranolol is a very strong basic compound (based on its pKa). Its potency is similar to 'propranolol':http://www.drugbank.ca/drugs/DB00571. Bupranolol is a competitive, nonselective beta-blocker similar to propanolol without intrinsic sympathomimetic activity. It is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. In humans, bupranolol is involved in bupranolol action pathway. Over 90% undergoes first-pass metabolism. Bupranolol is only found in individuals that have used or taken this drug. It does not have intrinsic sympathomimetic activity (ISA), but does have strong membrane stabilizing activity.
Structure
Data?1582753324
Synonyms
ValueSource
BUPRANOLOL hydrochlorideHMDB
KL-255HMDB
BUPRANOLHMDB
b 1312HMDB
BupranololumHMDB
Desma brand OF bupranolol hydrochlorideHMDB
BetadrenolHMDB
Chemical FormulaC14H22ClNO2
Average Molecular Weight271.783
Monoisotopic Molecular Weight271.13390666
IUPAC Name1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
Traditional Name1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
CAS Registry Number23284-25-5
SMILES
CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1
InChI Identifier
InChI=1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3
InChI KeyHQIRNZOQPUAHHV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Toluene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organohalogen compound
  • Organochloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
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 Solubility0.14 g/LALOGPS
logP3.14ALOGPS
logP2.99ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity74.86 m³·mol⁻¹ChemAxon
Polarizability30.35 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
DeepCCS[M+H]+165.60430932474
DeepCCS[M-H]-163.24630932474
DeepCCS[M-2H]-196.13330932474
DeepCCS[M+Na]+171.69830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BupranololCC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C12739.5Standard polar33892256
BupranololCC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C11907.8Standard non polar33892256
BupranololCC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C11950.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bupranolol,1TMS,isomer #1CC1=CC=C(Cl)C(OCC(CNC(C)(C)C)O[Si](C)(C)C)=C11909.6Semi standard non polar33892256
Bupranolol,1TMS,isomer #2CC1=CC=C(Cl)C(OCC(O)CN(C(C)(C)C)[Si](C)(C)C)=C12121.1Semi standard non polar33892256
Bupranolol,2TMS,isomer #1CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C12149.5Semi standard non polar33892256
Bupranolol,2TMS,isomer #1CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C12181.8Standard non polar33892256
Bupranolol,2TMS,isomer #1CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C12295.0Standard polar33892256
Bupranolol,1TBDMS,isomer #1CC1=CC=C(Cl)C(OCC(CNC(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12141.4Semi standard non polar33892256
Bupranolol,1TBDMS,isomer #2CC1=CC=C(Cl)C(OCC(O)CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12377.5Semi standard non polar33892256
Bupranolol,2TBDMS,isomer #1CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12624.9Semi standard non polar33892256
Bupranolol,2TBDMS,isomer #1CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12602.3Standard non polar33892256
Bupranolol,2TBDMS,isomer #1CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12495.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bupranolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9410000000-4fb6e56fbfc20d328e012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bupranolol GC-MS (1 TMS) - 70eV, Positivesplash10-052r-9211000000-af03417e0faa422d8dab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bupranolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bupranolol 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 - Bupranolol 10V, Positive-QTOFsplash10-00di-1390000000-a50fbc36e0a70a4174d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 20V, Positive-QTOFsplash10-00sd-7950000000-c35211adf59d6f487bc52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 40V, Positive-QTOFsplash10-00du-9500000000-45c62fb606c1ef738a012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 10V, Negative-QTOFsplash10-00dl-1690000000-1bcf21cb4e7773e99e3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 20V, Negative-QTOFsplash10-0006-0900000000-87210d97bc0e2d6d01292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 40V, Negative-QTOFsplash10-0006-2900000000-9864230af101317a562a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 10V, Positive-QTOFsplash10-00di-0090000000-0b8a60993730440137912021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 20V, Positive-QTOFsplash10-05fr-9830000000-68ae42e1fc1233fddace2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 40V, Positive-QTOFsplash10-0a4i-8900000000-43ed85ee1afba8adfc072021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 10V, Negative-QTOFsplash10-0096-2930000000-ba5e95e24f16f97db4322021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 20V, Negative-QTOFsplash10-0006-3900000000-a5db325c0590832c3c7d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupranolol 40V, Negative-QTOFsplash10-001i-9300000000-5ba3afed8bc3d8638c602021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08808 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08808 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08808
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2381
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBupranolol
METLIN IDNot Available
PubChem Compound2475
PDB IDNot Available
ChEBI ID200929
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

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
References
  1. Zelaszczyk D, Kozlowska H, Baranowska U, Baranowska M, Reutelsterz A, Kiec-Kononowicz K, Malinowska B, Schlicker E: Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors. J Physiol Pharmacol. 2009 Mar;60(1):51-60. [PubMed:19439807 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
References
  1. Lenard NR, Gettys TW, Dunn AJ: Activation of beta2- and beta3-adrenergic receptors increases brain tryptophan. J Pharmacol Exp Ther. 2003 May;305(2):653-9. Epub 2003 Jan 24. [PubMed:12606631 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis
Gene Name:
ADRB3
Uniprot ID:
P13945
Molecular weight:
43518.6
References
  1. Lenard NR, Gettys TW, Dunn AJ: Activation of beta2- and beta3-adrenergic receptors increases brain tryptophan. J Pharmacol Exp Ther. 2003 May;305(2):653-9. Epub 2003 Jan 24. [PubMed:12606631 ]
  2. Matsushita M, Horinouchi T, Tanaka Y, Tsuru H, Koike K: Characterization of beta 3-adrenoceptor-mediated relaxation in rat abdominal aorta smooth muscle. Eur J Pharmacol. 2003 Dec 15;482(1-3):235-44. [PubMed:14660028 ]