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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015409
Secondary Accession Numbers
  • HMDB15409
Metabolite Identification
Common NameBevantolol
DescriptionBevantolol, also known as (+-)-bevantolol, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. Bevantolol is a drug which is used for the treatment of angina pectoris and hypertension. In humans, bevantolol is involved in the bevantolol action pathway. Bevantolol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Bevantolol.
Structure
Data?1582753293
Synonyms
ValueSource
(+-)-BevantololChEBI
1-((2-(3,4-Dimethoxyphenyl)ethyl)amino)-3-(3-methylphenoxy)-2-propanolChEBI
1-(3,4-Dimethoxyphenethylamino)-3-(m-tolyloxy)-2-propanolChEBI
1-(3,4-Dimethoxyphenethylamino)-3-m-tolyloxy-propan-2-olChEBI
1-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-3-m-tolyloxy-propan-2-olChEBI
BevantololumChEBI
Bevantolol hydrochlorideHMDB
Chemical FormulaC20H27NO4
Average Molecular Weight345.4327
Monoisotopic Molecular Weight345.194008357
IUPAC Name1-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-(3-methylphenoxy)propan-2-ol
Traditional Name1-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-(3-methylphenoxy)propan-2-ol
CAS Registry Number59170-23-9
SMILES
COC1=C(OC)C=C(CCNCC(O)COC2=CC=CC(C)=C2)C=C1
InChI Identifier
InChI=1S/C20H27NO4/c1-15-5-4-6-18(11-15)25-14-17(22)13-21-10-9-16-7-8-19(23-2)20(12-16)24-3/h4-8,11-12,17,21-22H,9-10,13-14H2,1-3H3
InChI KeyHXLAFSUPPDYFEO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Phenethylamine
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Alkyl aryl ether
  • Aralkylamine
  • Toluene
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Ether
  • Secondary aliphatic amine
  • Secondary amine
  • Alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point137 - 138 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogP3.00HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP2.83ALOGPS
logP3.03ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area59.95 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity98.54 m³·mol⁻¹ChemAxon
Polarizability39.75 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]+182.36531661259
DarkChem[M-H]-184.13331661259
DeepCCS[M+H]+184.77530932474
DeepCCS[M-H]-182.41730932474
DeepCCS[M-2H]-215.78730932474
DeepCCS[M+Na]+191.13830932474
AllCCS[M+H]+186.732859911
AllCCS[M+H-H2O]+183.632859911
AllCCS[M+NH4]+189.432859911
AllCCS[M+Na]+190.232859911
AllCCS[M-H]-188.832859911
AllCCS[M+Na-2H]-189.132859911
AllCCS[M+HCOO]-189.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BevantololCOC1=C(OC)C=C(CCNCC(O)COC2=CC=CC(C)=C2)C=C13561.8Standard polar33892256
BevantololCOC1=C(OC)C=C(CCNCC(O)COC2=CC=CC(C)=C2)C=C12800.9Standard non polar33892256
BevantololCOC1=C(OC)C=C(CCNCC(O)COC2=CC=CC(C)=C2)C=C12806.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bevantolol,1TMS,isomer #1COC1=CC=C(CCNCC(COC2=CC=CC(C)=C2)O[Si](C)(C)C)C=C1OC2737.1Semi standard non polar33892256
Bevantolol,1TMS,isomer #2COC1=CC=C(CCN(CC(O)COC2=CC=CC(C)=C2)[Si](C)(C)C)C=C1OC2875.6Semi standard non polar33892256
Bevantolol,2TMS,isomer #1COC1=CC=C(CCN(CC(COC2=CC=CC(C)=C2)O[Si](C)(C)C)[Si](C)(C)C)C=C1OC2879.0Semi standard non polar33892256
Bevantolol,2TMS,isomer #1COC1=CC=C(CCN(CC(COC2=CC=CC(C)=C2)O[Si](C)(C)C)[Si](C)(C)C)C=C1OC2827.3Standard non polar33892256
Bevantolol,2TMS,isomer #1COC1=CC=C(CCN(CC(COC2=CC=CC(C)=C2)O[Si](C)(C)C)[Si](C)(C)C)C=C1OC3476.1Standard polar33892256
Bevantolol,1TBDMS,isomer #1COC1=CC=C(CCNCC(COC2=CC=CC(C)=C2)O[Si](C)(C)C(C)(C)C)C=C1OC2994.2Semi standard non polar33892256
Bevantolol,1TBDMS,isomer #2COC1=CC=C(CCN(CC(O)COC2=CC=CC(C)=C2)[Si](C)(C)C(C)(C)C)C=C1OC3131.7Semi standard non polar33892256
Bevantolol,2TBDMS,isomer #1COC1=CC=C(CCN(CC(COC2=CC=CC(C)=C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC3352.7Semi standard non polar33892256
Bevantolol,2TBDMS,isomer #1COC1=CC=C(CCN(CC(COC2=CC=CC(C)=C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC3187.2Standard non polar33892256
Bevantolol,2TBDMS,isomer #1COC1=CC=C(CCN(CC(COC2=CC=CC(C)=C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC3599.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bevantolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-0910000000-8aa5d780fe28a27f24462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bevantolol GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-4920100000-07c281447cef757587bc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bevantolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bevantolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bevantolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bevantolol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bevantolol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bevantolol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 10V, Positive-QTOFsplash10-0002-0619000000-c80a361c12fa3b4032ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 20V, Positive-QTOFsplash10-014i-0911000000-6ad65562f40d6b5e4dc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 40V, Positive-QTOFsplash10-014i-2900000000-b6b1aef6064426fc5de02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 10V, Negative-QTOFsplash10-052f-0709000000-05c7a169bb694a3af1af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 20V, Negative-QTOFsplash10-0a4i-0900000000-f7b79906c5a458973ce52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 40V, Negative-QTOFsplash10-0a4i-2900000000-f995f6e0c34da79b66fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 10V, Positive-QTOFsplash10-0002-0139000000-a92bb5486118787290122021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 20V, Positive-QTOFsplash10-00rb-0985000000-b58c7ce7a2156157d6002021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 40V, Positive-QTOFsplash10-00kf-3901000000-b6060247ae27237ffa9d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 10V, Negative-QTOFsplash10-052f-0339000000-0b2d0d2752aa5578825c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 20V, Negative-QTOFsplash10-0a4i-0900000000-2f22028bf76e61e934f52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bevantolol 40V, Negative-QTOFsplash10-0a4i-2900000000-f56bc729abb4bfc544b32021-10-11Wishart 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 DB01295 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01295 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01295
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2282
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBevantolol
METLIN IDNot Available
PubChem Compound2372
PDB IDNot Available
ChEBI ID238698
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 References
  1. Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. [PubMed:2888789 ]

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. Hino T, Sakai K, Ichihara K, Abiko Y: Attenuation of ischaemia-induced regional myocardial acidosis by bevantolol, a beta 1-adrenoceptor antagonist, in dogs. Pharmacol Toxicol. 1989 Apr;64(4):324-8. [PubMed:2568629 ]
  2. Dukes ID, Vaughan Williams EM: Cardiovascular effects of bevantolol, a selective beta 1-adrenoceptor antagonist with a novel pharmacological profile. Br J Pharmacol. 1985 Feb;84(2):365-80. [PubMed:2858236 ]
  3. Lofdahl CG, Svedmyr K, Svedmyr N: Selectivity of bevantolol hydrochloride, a beta 1-adrenoceptor antagonist, in asthmatic patients. Pharmacotherapy. 1984 Jul-Aug;4(4):205-10. [PubMed:6148733 ]
  4. Vaughan Williams EM: Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions. J Clin Pharmacol. 1987 Jul;27(7):450-60. [PubMed:2888789 ]
  5. Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. [PubMed:17628611 ]
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. Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. [PubMed:17628611 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Shiraishi K, Moriya M, Miyake N, Takayanagi I: Alpha 1-adrenoceptor blocking activities of bevantolol hydrochloride(NC-1400) and labetalol in rat isolated thoracic aorta--do they distinguish between subtypes? Gen Pharmacol. 1992 Sep;23(5):843-5. [PubMed:1358746 ]