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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-05-09 20:59:27 UTC
Update Date2020-11-09 23:30:05 UTC
HMDB IDHMDB0060159
Secondary Accession Numbers
  • HMDB60159
Metabolite Identification
Common NameEbastine
DescriptionEbastine (trade names Evastin, Kestine, Ebastel, Aleva) is a non-sedating H1 antihistamine. It does not penetrate the blood–brain barrier and thus allows an effective block of the H1 receptor in peripheral tissue without a central side effect, i. e not causing sedation or drowsiness. The basic patent for ebastine in Europe is EP-B-134124. It is often provided in micronised form, due to poor water solubility. (Wikipedia ) CYP2J2, an arachidonic acid epoxygenase, is recognized for its role in the first-pass metabolism of astemizole and ebastine. (PMID: 22328583 )
Structure
Data?1563866022
Synonyms
ValueSource
KestineKegg
KestinHMDB
4-Diphenylmethoxy-1-(3-(4-tert-butylbenzoyl)propyl)piperidineHMDB
BactilHMDB
BusidrilHMDB
EbastelHMDB
EvastelHMDB
LAS W-090HMDB
1-[4-(1,1-Dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanoneHMDB
AlevaHMDB
BastelHMDB
EbastinHMDB
EbatrolHMDB
ErostinHMDB
EvastinHMDB
LAS-W 090HMDB
RP 64305HMDB
EbastineSMPDB
Chemical FormulaC32H39NO2
Average Molecular Weight469.6576
Monoisotopic Molecular Weight469.298079497
IUPAC Name1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
Traditional Namekestin
CAS Registry Number90729-43-4
SMILES
CC(C)(C)C1=CC=C(C=C1)C(=O)CCCN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C32H39NO2/c1-32(2,3)28-18-16-25(17-19-28)30(34)15-10-22-33-23-20-29(21-24-33)35-31(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-9,11-14,16-19,29,31H,10,15,20-24H2,1-3H3
InChI KeyMJJALKDDGIKVBE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Alkyl-phenylketone
  • Butyrophenone
  • Phenylbutylamine
  • Benzylether
  • Phenylketone
  • Phenylpropane
  • Benzoyl
  • Aryl alkyl ketone
  • Aryl ketone
  • Gamma-aminoketone
  • Piperidine
  • Ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.5e-05 g/LALOGPS
logP6.89ALOGPS
logP6.96ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity145.38 m³·mol⁻¹ChemAxon
Polarizability55.41 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available212.48531661259
DarkChem[M-H]-PredictedNot Available205.01731661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1941000000-bcc59998a2c37520b0d82017-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gi0-0930400000-a3b7001dd8bec489cf922017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0100900000-8cfcd306e418b8c87cff2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-df385226323e9fac05b12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0gi0-0970600000-3ef3f7d6597ce1f3ff252021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0970000000-f4aa490a91255a25791f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0i00-0940000000-d3846e501976868bfb262021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0gi0-0970600000-d27d23cebfd737c49a852021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0970000000-6af0ad480149b5206e3d2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0gi0-0930400000-aaca6e84e4e592528ccf2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0130900000-d87c3180806d2efe676e2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi9-0983500000-a76fa5e83260410a58142016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-3940000000-492eb62bc79baf0463e42016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0110900000-6ae36965d1edc6b0f2aa2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-0622900000-e92cb58fb2500c21490f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-6910000000-b7147b6ba5db0334baab2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11742
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEbastine
METLIN IDNot Available
PubChem Compound3191
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDEBASTINE
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Lee CA, Jones JP 3rd, Katayama J, Kaspera R, Jiang Y, Freiwald S, Smith E, Walker GS, Totah RA: Identifying a selective substrate and inhibitor pair for the evaluation of CYP2J2 activity. Drug Metab Dispos. 2012 May;40(5):943-51. doi: 10.1124/dmd.111.043505. Epub 2012 Feb 10. [PubMed:22328583 ]