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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:30 UTC
HMDB IDHMDB0014366
Secondary Accession Numbers
  • HMDB14366
Metabolite Identification
Common NameIsoetharine
DescriptionIsoetharine is only found in individuals that have used or taken this drug. It is a selective adrenergic beta-2 agonist used as fast acting bronchodilator for emphysema, bronchitis and asthma. [PubChem]The pharmacologic effects of isoetharine are attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.18 g/LNot Available
LogP2.2Not Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi9-8910000000-2dec3cb38f1785532521Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001l-3691400000-c6578f4b0c80ccb45b36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0290000000-fc1a6304dd95aed2f163Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-1950000000-fc1d8b52614f35e926efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9500000000-b9bf58e7a8a585cf7af9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-d5704f9094a81975e6fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1590000000-d7aed48ac13d87b1fec2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8910000000-93d0bfe1f914510a4da8Spectrum
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 ID
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 ]