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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:11:01 UTC
Update Date2019-07-23 06:13:28 UTC
HMDB IDHMDB0033449
Secondary Accession Numbers
  • HMDB33449
Metabolite Identification
Common NamePipercide
DescriptionPipercide, also known as retrofractamide b, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Pipercide is a moderately basic compound (based on its pKa). Outside of the human body, pipercide has been detected, but not quantified in, herbs and spices and pepper (spice). This could make pipercide a potential biomarker for the consumption of these foods.
Structure
Data?1563862408
Synonyms
ValueSource
Retrofractamide bHMDB
(2E,4E,10E)-11-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienimidateGenerator
Chemical FormulaC22H29NO3
Average Molecular Weight355.4706
Monoisotopic Molecular Weight355.214743799
IUPAC Name(2E,4E,10E)-11-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienamide
Traditional Name(2E,4E,10E)-11-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienamide
CAS Registry Number54794-74-0
SMILES
CC(C)CNC(=O)\C=C\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C22H29NO3/c1-18(2)16-23-22(24)12-10-8-6-4-3-5-7-9-11-19-13-14-20-21(15-19)26-17-25-20/h6,8-15,18H,3-5,7,16-17H2,1-2H3,(H,23,24)/b8-6+,11-9+,12-10+
InChI KeyRPOYGOULCHMVBB-ADDDGJNWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Styrene
  • N-acyl-amine
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point114 - 115 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00053 g/LALOGPS
logP5.55ALOGPS
logP5.25ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)16.4ChemAxon
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.33 m³·mol⁻¹ChemAxon
Polarizability42.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1941000000-959fa274bd750c565731Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9013000000-7acc13c4edcc2e82818fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9010000000-bb8cc978eb9788a9fe59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9010000000-47667fe1f97e7a04780aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1029000000-7d002fe5c934a70f6c43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi1-4096000000-4b4a27de826ea7286d7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007o-8090000000-d18f0b78a16376d97fd7Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB011487
KNApSAcK IDC00034631
Chemspider ID4522504
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5372162
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .