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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:35 UTC
HMDB IDHMDB0014366
Secondary Accession Numbers
  • HMDB14366
Metabolite Identification
Common NameIsoetharine
DescriptionIsoetharine, also known as etyprenalinum or bronkometer, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Isoetharine is a drug which is used for the treatment of asthma, wheezing, and chronic asthmatic bronchitis. It can be called the "granddaughter of adrenalin" in the line of β2 agonists that gave quick relief for bronchospasm and asthma. All of the early β2 agonist catecholamines used for bronchospasm had strong side effects, with increase in heart rate as the most common and most problematic. Isoetharine is a very strong basic compound (based on its pKa). Thus they see a continued specialty role in treatment of severe shortness of breath that does not improve in the first five minutes of salbutamol treatment. Orciprenaline in turn was replaced by salbutamol (albuterol). With isoetarine this effect tended to be transient and usually went away within a matter of minutes after the end of the treatment. Epinephrine (adrenalin) was the first of these, and next came isoprenaline (isoproterenol). It generally gave sharp relief of shortness of breath, starting within two to five minutes after the patient began breathing the nebulized mist.
Structure
Data?1582753170
Synonyms
ValueSource
IsoetarineKegg
Mesylate, isoetharineHMDB
EtyprenalinumHMDB
IsoetarinHMDB
Isoetharine mesylateHMDB
BronkometerHMDB
Chemical FormulaC13H21NO3
Average Molecular Weight239.3107
Monoisotopic Molecular Weight239.152143543
IUPAC Name4-{1-hydroxy-2-[(propan-2-yl)amino]butyl}benzene-1,2-diol
Traditional Nameisoetharine
CAS Registry Number530-08-5
SMILES
CCC(NC(C)C)C(O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C13H21NO3/c1-4-10(14-8(2)3)13(17)9-5-6-11(15)12(16)7-9/h5-8,10,13-17H,4H2,1-3H3
InChI KeyHUYWAWARQUIQLE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Aromatic alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.18 g/LNot Available
LogP2.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.18 g/LALOGPS
logP0.63ALOGPS
logP1.05ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.34 m³·mol⁻¹ChemAxon
Polarizability26.39 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]+158.60631661259
DarkChem[M-H]-155.37131661259
DeepCCS[M+H]+162.10730932474
DeepCCS[M-H]-159.74930932474
DeepCCS[M-2H]-192.63530932474
DeepCCS[M+Na]+168.230932474
AllCCS[M+H]+158.832859911
AllCCS[M+H-H2O]+155.232859911
AllCCS[M+NH4]+162.232859911
AllCCS[M+Na]+163.132859911
AllCCS[M-H]-159.432859911
AllCCS[M+Na-2H]-160.132859911
AllCCS[M+HCOO]-160.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsoetharineCCC(NC(C)C)C(O)C1=CC(O)=C(O)C=C13422.8Standard polar33892256
IsoetharineCCC(NC(C)C)C(O)C1=CC(O)=C(O)C=C11886.1Standard non polar33892256
IsoetharineCCC(NC(C)C)C(O)C1=CC(O)=C(O)C=C12006.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoetharine,1TMS,isomer #1CCC(NC(C)C)C(O[Si](C)(C)C)C1=CC=C(O)C(O)=C11970.8Semi standard non polar33892256
Isoetharine,1TMS,isomer #2CCC(NC(C)C)C(O)C1=CC=C(O)C(O[Si](C)(C)C)=C11973.2Semi standard non polar33892256
Isoetharine,1TMS,isomer #3CCC(NC(C)C)C(O)C1=CC=C(O[Si](C)(C)C)C(O)=C11969.3Semi standard non polar33892256
Isoetharine,1TMS,isomer #4CCC(C(O)C1=CC=C(O)C(O)=C1)N(C(C)C)[Si](C)(C)C2193.5Semi standard non polar33892256
Isoetharine,2TMS,isomer #1CCC(NC(C)C)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C11899.0Semi standard non polar33892256
Isoetharine,2TMS,isomer #2CCC(NC(C)C)C(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C11898.8Semi standard non polar33892256
Isoetharine,2TMS,isomer #3CCC(C(O[Si](C)(C)C)C1=CC=C(O)C(O)=C1)N(C(C)C)[Si](C)(C)C2182.1Semi standard non polar33892256
Isoetharine,2TMS,isomer #4CCC(NC(C)C)C(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12022.5Semi standard non polar33892256
Isoetharine,2TMS,isomer #5CCC(C(O)C1=CC=C(O)C(O[Si](C)(C)C)=C1)N(C(C)C)[Si](C)(C)C2121.2Semi standard non polar33892256
Isoetharine,2TMS,isomer #6CCC(C(O)C1=CC=C(O[Si](C)(C)C)C(O)=C1)N(C(C)C)[Si](C)(C)C2130.3Semi standard non polar33892256
Isoetharine,3TMS,isomer #1CCC(NC(C)C)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11968.2Semi standard non polar33892256
Isoetharine,3TMS,isomer #2CCC(C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1)N(C(C)C)[Si](C)(C)C2178.2Semi standard non polar33892256
Isoetharine,3TMS,isomer #3CCC(C(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1)N(C(C)C)[Si](C)(C)C2174.3Semi standard non polar33892256
Isoetharine,3TMS,isomer #4CCC(C(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N(C(C)C)[Si](C)(C)C2181.6Semi standard non polar33892256
Isoetharine,4TMS,isomer #1CCC(C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N(C(C)C)[Si](C)(C)C2254.2Semi standard non polar33892256
Isoetharine,4TMS,isomer #1CCC(C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N(C(C)C)[Si](C)(C)C2133.3Standard non polar33892256
Isoetharine,4TMS,isomer #1CCC(C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N(C(C)C)[Si](C)(C)C2156.6Standard polar33892256
Isoetharine,1TBDMS,isomer #1CCC(NC(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12203.6Semi standard non polar33892256
Isoetharine,1TBDMS,isomer #2CCC(NC(C)C)C(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12229.9Semi standard non polar33892256
Isoetharine,1TBDMS,isomer #3CCC(NC(C)C)C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12234.4Semi standard non polar33892256
Isoetharine,1TBDMS,isomer #4CCC(C(O)C1=CC=C(O)C(O)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2431.4Semi standard non polar33892256
Isoetharine,2TBDMS,isomer #1CCC(NC(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12397.5Semi standard non polar33892256
Isoetharine,2TBDMS,isomer #2CCC(NC(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12400.1Semi standard non polar33892256
Isoetharine,2TBDMS,isomer #3CCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2654.2Semi standard non polar33892256
Isoetharine,2TBDMS,isomer #4CCC(NC(C)C)C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12530.3Semi standard non polar33892256
Isoetharine,2TBDMS,isomer #5CCC(C(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2618.0Semi standard non polar33892256
Isoetharine,2TBDMS,isomer #6CCC(C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2638.3Semi standard non polar33892256
Isoetharine,3TBDMS,isomer #1CCC(NC(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12644.5Semi standard non polar33892256
Isoetharine,3TBDMS,isomer #2CCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2823.3Semi standard non polar33892256
Isoetharine,3TBDMS,isomer #3CCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2813.4Semi standard non polar33892256
Isoetharine,3TBDMS,isomer #4CCC(C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2882.9Semi standard non polar33892256
Isoetharine,4TBDMS,isomer #1CCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C3053.7Semi standard non polar33892256
Isoetharine,4TBDMS,isomer #1CCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2876.4Standard non polar33892256
Isoetharine,4TBDMS,isomer #1CCC(C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N(C(C)C)[Si](C)(C)C(C)(C)C2589.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoetharine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi9-8910000000-2dec3cb38f17855325212017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoetharine GC-MS (3 TMS) - 70eV, Positivesplash10-001l-3691400000-c6578f4b0c80ccb45b362017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoetharine 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 - Isoetharine 10V, Positive-QTOFsplash10-00dl-0290000000-fc1a6304dd95aed2f1632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 20V, Positive-QTOFsplash10-00e9-1950000000-fc1d8b52614f35e926ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 40V, Positive-QTOFsplash10-0a4l-9500000000-b9bf58e7a8a585cf7af92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 10V, Negative-QTOFsplash10-000i-0190000000-d5704f9094a81975e6fc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 20V, Negative-QTOFsplash10-0079-1590000000-d7aed48ac13d87b1fec22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 40V, Negative-QTOFsplash10-0a4i-8910000000-93d0bfe1f914510a4da82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 10V, Negative-QTOFsplash10-000i-0190000000-2baf6ac5f4effe13ceb62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 20V, Negative-QTOFsplash10-0079-0940000000-3483e975160749dead572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 40V, Negative-QTOFsplash10-05g0-5910000000-b841b41a417e004cc14f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 10V, Positive-QTOFsplash10-00dl-0190000000-bef509235248803f4ed62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 20V, Positive-QTOFsplash10-001i-1910000000-e7afceba0ab25786ac492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoetharine 40V, Positive-QTOFsplash10-03k9-2900000000-ea75a06c48e46921c1902021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 DB00221 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00221 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00221
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3630
KEGG Compound IDC07053
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoetarine
METLIN IDNot Available
PubChem Compound3762
PDB IDNot Available
ChEBI ID775164
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. Emerman CL, Cydulka RK, Effron D, Lukens TW, Gershman H, Boehm SP: A randomized, controlled comparison of isoetharine and albuterol in the treatment of acute asthma. Ann Emerg Med. 1991 Oct;20(10):1090-3. [PubMed:1928879 ]

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. Rodrigues LL, Oliveira MC, Pelegrini-da-Silva A, de Arruda Veiga MC, Parada CA, Tambeli CH: Peripheral sympathetic component of the temporomandibular joint inflammatory pain in rats. J Pain. 2006 Dec;7(12):929-36. [PubMed:17157779 ]
  2. 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 ]
  3. Terra SG, McGorray SP, Wu R, McNamara DM, Cavallari LH, Walker JR, Wallace MR, Johnson BD, Bairey Merz CN, Sopko G, Pepine CJ, Johnson JA: Association between beta-adrenergic receptor polymorphisms and their G-protein-coupled receptors with body mass index and obesity in women: a report from the NHLBI-sponsored WISE study. Int J Obes (Lond). 2005 Jul;29(7):746-54. [PubMed:15917856 ]
  4. Burniston JG, Tan LB, Goldspink DF: Relative myotoxic and haemodynamic effects of the beta-agonists fenoterol and clenbuterol measured in conscious unrestrained rats. Exp Physiol. 2006 Nov;91(6):1041-9. Epub 2006 Sep 14. [PubMed:16973691 ]
  5. Muszkat M: Interethnic differences in drug response: the contribution of genetic variability in beta adrenergic receptor and cytochrome P4502C9. Clin Pharmacol Ther. 2007 Aug;82(2):215-8. Epub 2007 Feb 28. [PubMed:17329986 ]