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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:44:01 UTC
Update Date2022-03-07 03:18:14 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. In humans, pyrrobutamine is involved in the pyrrobutamine h1-antihistamine action pathway. Pyrrobutamine 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 Pyrrobutamine.
Structure
Data?1563892736
Synonyms
ValueSource
Pyrrobutamine, (Z)-isomerMeSH
Pyrrobutamine, phosphate (1:2) salt, (e)-isomerMeSH
1-(gamma-p-Chlorobenzylcinnamyl)pyrrolidineMeSH
PirrobutamineMeSH
Pyrrobutamine, hydrobromide salt, (Z)-isomerMeSH
Pyrrobutamine, phosphate (1:2) saltMeSH
Pyrrobutamine, phosphate (2:1) salt, (trans)-isomerMeSH
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 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
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+174.56431661259
AllCCS[M-H]-179.07531661259
DeepCCS[M+H]+177.22830932474
DeepCCS[M-H]-174.8730932474
DeepCCS[M-2H]-207.75530932474
DeepCCS[M+Na]+183.32130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PyrrobutamineClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C13279.5Standard polar33892256
PyrrobutamineClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C12460.4Standard non polar33892256
PyrrobutamineClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C12474.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrobutamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrobutamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 10V, Positive-QTOFsplash10-03di-0129000000-8a96b4d1f332a08cff782019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 20V, Positive-QTOFsplash10-03gl-4983000000-f1d9a2fb9ae99efe57f72019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 40V, Positive-QTOFsplash10-0fi0-4930000000-ba22a383856747920bc72019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 10V, Negative-QTOFsplash10-03di-0009000000-9efb2113a2e7831684852019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 20V, Negative-QTOFsplash10-03k9-6019000000-eaae45dae1de66ee61fa2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 40V, Negative-QTOFsplash10-00di-9010000000-77bfdd6f2c0ef3ac80102019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 10V, Negative-QTOFsplash10-004i-0093000000-1b979f80a163c36dd3412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 20V, Negative-QTOFsplash10-03di-4098000000-aed83a3b69138b29e5052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 40V, Negative-QTOFsplash10-001i-9350000000-f4131d9fcd062dec7d442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 10V, Positive-QTOFsplash10-03dl-0079000000-467b4fd79ab98c330a7a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 20V, Positive-QTOFsplash10-01tc-5696000000-f6450bf975e596f9184f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrobutamine 40V, Positive-QTOFsplash10-004i-4931000000-f4eb7364c8ac3bffdf052021-09-23Wishart LabView Spectrum
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 ID4447659
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
MarkerDB IDNot Available
Good Scents 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 ]