Showing metabocard for Fexofenadine (BMDB0005030)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:48 UTC
Update Date2020-05-11 20:24:33 UTC
BMDB IDBMDB0005030
Secondary Accession Numbers
  • BMDB05030
Metabolite Identification
Common NameFexofenadine
Descriptionfexofenadine, also known as terfenadine-COOH or telfast, 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. fexofenadine 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 very few articles have been published on fexofenadine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acidChEBI
CarboxyterfenadineChEBI
Terfenadine acid metaboliteChEBI
Terfenadine carboxylateChEBI
Terfenadine-COOHChEBI
TelfastKegg
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetateGenerator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetic acidGenerator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetateGenerator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetateGenerator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetic acidGenerator
Terfenadine carboxylic acidGenerator
AllegraHMDB, MeSH
Fexofenadine hydrochlorideHMDB, MeSH
Aventis pharma brand OF fexofenadine hydrochlorideMeSH, HMDB
MDL 16,455aMeSH, HMDB
alpha-(4-(1-Carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanolMeSH, HMDB
Aventis behring brand OF fexofenadine hydrochlorideMeSH, HMDB
Aventis brand OF fexofenadine hydrochlorideMeSH, HMDB
Hoechst brand OF fexofenadine hydrochlorideMeSH, HMDB
Chemical FormulaC32H39NO4
Average Molecular Weight501.6564
Monoisotopic Molecular Weight501.287908741
IUPAC Name2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid
Traditional Namefexofenadine
CAS Registry Number83799-24-0
SMILES
CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)
InChI KeyRWTNPBWLLIMQHL-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
  • Phenylbutylamine
  • Phenylpropane
  • Aralkylamine
  • Piperidine
  • Tertiary alcohol
  • Amino acid or derivatives
  • Secondary alcohol
  • Amino acid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Carbonyl group
  • Aromatic alcohol
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.02ALOGPS
logP2.94ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity147.98 m³·mol⁻¹ChemAxon
Polarizability57.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0912400000-d47ca5514638bcd48093View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1931153000-7fd2e3b3cc17ae068da6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a6r-0005900000-17ae091cc3d9ba9c62f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a6r-0396000000-be2d6fedab983b50c280View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-1970000000-c78b1c745afc54f58e01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4r-0920000000-9ad3dc88e743866c23caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0btj-0900000000-66a31911b29382b93745View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-1900000000-ce2d00bbddc284806cb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0000090000-2622c1f2ddb4bff3f93dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0159-0000910000-0afa1079fbe9a822e35cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00xr-1920200000-1163d721ce08480aea71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-1910000000-c593678096415da5efb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002f-2900000000-01de1f32826ab5569301View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002f-3900000000-72f624b2d6e05d29cb72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a6r-0296000000-08bc8f52b1adac426d92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-1970000000-7a763967a0e22ba5aee4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a6r-0004900000-264e1e3683f099cd4d18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00xr-1920200000-f89d210776b04ca1a4f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0159-0000910000-e86af4100fbcd4806c84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0udi-0000090000-9d409ff3e4f83806f5acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0001930000-b9b7ff78564293a249b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0541-0212900000-ab3069ba65212a7da302View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-1985500000-f990cf713f3191736f10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100690000-e140f2c9a1bcece115e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zj0-4223930000-8c8b81776964fc2cb368View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004u-9651000000-b823e5714fa6afb8f50fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0000980000-811ef09a2d84417ca55cView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Brain
  • Epidermis
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3231
KEGG Compound IDC06999
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFexofenadine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID5050
References
Synthesis ReferenceCarr, Albert A.; Dolfini, Joseph E.; Wright, George J. Piperidine derivatives with antihistamine action. Ger. Offen. (1980), 39 pp. CODEN: GWXXBX DE 3007498 19801023 CAN 94:156758 AN 1981:156758
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available