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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:44:01 UTC
Update Date2019-07-23 14:38:56 UTC
HMDB IDHMDB0240248
Secondary Accession NumbersNone
Metabolite Identification
Common NamePyrrobutamine
DescriptionPyrrobutamine belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Pyrrobutamine is a very strong basic compound (based on its pKa). In humans, pyrrobutamine is involved in pyrrobutamine h1-antihistamine action. Pyrrobutamine is an antihistamine and anticholinergic.
Structure
Data?1563892736
Synonyms
ValueSource
1-(gamma-P-Chlorobenzylcinnamyl)pyrrolidineMeSH, HMDB
PirrobutamineMeSH, HMDB
Pyrrobutamine, (Z)-isomerMeSH, HMDB
Pyrrobutamine, hydrobromide salt, (Z)-isomerMeSH, HMDB
Pyrrobutamine, phosphate (1:2) saltMeSH, HMDB
Pyrrobutamine, phosphate (1:2) salt, (e)-isomerMeSH, HMDB
Pyrrobutamine, phosphate (2:1) salt, (trans)-isomerMeSH, HMDB
Chemical FormulaC20H22ClN
Average Molecular Weight311.85
Monoisotopic Molecular Weight311.1440774
IUPAC Name1-[(2E)-4-(4-chlorophenyl)-3-phenylbut-2-en-1-yl]pyrrolidine
Traditional NameC20H22ClN
CAS Registry Number91-82-7
SMILES
ClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C1
InChI Identifier
InChI=1S/C20H22ClN/c21-20-10-8-17(9-11-20)16-19(18-6-2-1-3-7-18)12-15-22-13-4-5-14-22/h1-3,6-12H,4-5,13-16H2/b19-12+
InChI KeyWDYYVNNRTDZKAZ-XDHOZWIPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Styrene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Benzenoid
  • N-alkylpyrrolidine
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.35ALOGPS
logP5.41ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.24 m³·mol⁻¹ChemAxon
Polarizability35.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0129000000-8a96b4d1f332a08cff78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gl-4983000000-f1d9a2fb9ae99efe57f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-4930000000-ba22a383856747920bc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-9efb2113a2e783168485Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-6019000000-eaae45dae1de66ee61faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9010000000-77bfdd6f2c0ef3ac8010Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
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 LinkPyrrobutamine
METLIN IDNot Available
PubChem Compound5284614
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. MOTHERSILL MH, MILLS J, LEE HM, ANDERSON RC, HARRIS PN: Chemical and pharmacological characteristics of the antihistaminic compound, pyrrobutamine. Ann Allergy. 1953 Nov-Dec;11(6):754-7. [PubMed:13114796 ]