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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 03:47:03 UTC
Update Date2021-09-26 23:00:01 UTC
HMDB IDHMDB0249279
Secondary Accession NumbersNone
Metabolite Identification
Common NameBitolterol
DescriptionBitolterol belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Bitolterol is a drug which is used to dilate air passages in the lungs that have become narrowed as a result of disease or inflammation. it is used in the treatment of asthma and chronic obstructive pulmonary disease (copd). Bitolterol is a very strong basic compound (based on its pKa). The di-4-toluate ester of (+-)-N-tert-butylnoradrenaline (colterol). This compound has been identified in human blood as reported by (PMID: 31557052 ). Bitolterol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bitolterol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
4-(2-(Tert-butylamino)-1-hydroxyethyl)-O-phenylene di-p-toluateChEBI
4-[2-(Tert-butylamino)-1-hydroxyethyl]-O-phenylene di-p-toluateChEBI
Bis(4-methylbenzoic acid) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene esterChEBI
BitolterolumChEBI
4-(2-(Tert-butylamino)-1-hydroxyethyl)-O-phenylene di-p-toluic acidGenerator
4-[2-(Tert-butylamino)-1-hydroxyethyl]-O-phenylene di-p-toluic acidGenerator
Bis(4-methylbenzoate) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene esterGenerator
Dura brand OF bitolterol methanesulfonateMeSH
Bitolterol mesylateMeSH
TornalateMeSH
Bitolterol methanesulfonateMeSH
Chemical FormulaC28H31NO5
Average Molecular Weight461.5494
Monoisotopic Molecular Weight461.220223107
IUPAC Name4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate
Traditional Namebitolterol
CAS Registry NumberNot Available
SMILES
CC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C
InChI Identifier
InChI=1S/C28H31NO5/c1-18-6-10-20(11-7-18)26(31)33-24-15-14-22(23(30)17-29-28(3,4)5)16-25(24)34-27(32)21-12-8-19(2)9-13-21/h6-16,23,29-30H,17H2,1-5H3
InChI KeyFZGVEKPRDOIXJY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • Benzoate ester
  • Phenol ester
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Benzoyl
  • Aralkylamine
  • Toluene
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Secondary amine
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Aromatic alcohol
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP4.69ALOGPS
logP6.3ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity132.76 m³·mol⁻¹ChemAxon
Polarizability50.91 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+209.2130932474
DeepCCS[M-H]-206.81430932474
DeepCCS[M-2H]-239.69830932474
DeepCCS[M+Na]+215.12230932474
AllCCS[M+H]+215.832859911
AllCCS[M+H-H2O]+213.732859911
AllCCS[M+NH4]+217.732859911
AllCCS[M+Na]+218.332859911
AllCCS[M-H]-211.832859911
AllCCS[M+Na-2H]-212.032859911
AllCCS[M+HCOO]-212.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BitolterolCC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C4470.4Standard polar33892256
BitolterolCC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C3498.5Standard non polar33892256
BitolterolCC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C3493.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bitolterol,2TMS,isomer #1CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C13564.2Semi standard non polar33892256
Bitolterol,2TMS,isomer #1CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C13372.7Standard non polar33892256
Bitolterol,2TMS,isomer #1CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C14199.1Standard polar33892256
Bitolterol,2TBDMS,isomer #1CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C14008.9Semi standard non polar33892256
Bitolterol,2TBDMS,isomer #1CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C13658.5Standard non polar33892256
Bitolterol,2TBDMS,isomer #1CC1=CC=C(C(=O)OC2=CC=C(C(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C2OC(=O)C2=CC=C(C)C=C2)C=C14268.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bitolterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-06dr-9515300000-9183ab463ea023a403bf2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bitolterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bitolterol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bitolterol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bitolterol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bitolterol 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 - Bitolterol 10V, Positive-QTOFsplash10-07bf-0206900000-0d2add6387daa82a668a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 20V, Positive-QTOFsplash10-06du-0409400000-bb41c3be88071d157bd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 40V, Positive-QTOFsplash10-014i-5931000000-5bf735cde96a513326c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 10V, Negative-QTOFsplash10-03dl-2203900000-2ae4baeac004d904db772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 20V, Negative-QTOFsplash10-0076-8519700000-66927241cb18ed8105722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 40V, Negative-QTOFsplash10-000l-7931000000-151a6828e2b9760ef5522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 10V, Positive-QTOFsplash10-05n0-0406900000-3abf7d0e232423e8dc9f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 20V, Positive-QTOFsplash10-00kr-3409400000-5ffcffe98e28c353480b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 40V, Positive-QTOFsplash10-0006-9100000000-e6b66fd8168c156913182021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 10V, Negative-QTOFsplash10-03di-0002900000-898b8130cb2475df346a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 20V, Negative-QTOFsplash10-01vo-0029500000-546df6039034f820cc042021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bitolterol 40V, Negative-QTOFsplash10-0006-8379500000-a31b75ebcff1355478502021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00901
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06853
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBitolterol
METLIN IDNot Available
PubChem Compound35330
PDB IDNot Available
ChEBI ID3133
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]