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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:11:01 UTC
Update Date2022-03-07 02:53:42 UTC
HMDB IDHMDB0033449
Secondary Accession Numbers
  • HMDB33449
Metabolite Identification
Common NamePipercide
DescriptionPipercide 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 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. Based on a literature review very few articles have been published on Pipercide.
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point114 - 115 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+191.95830932474
DeepCCS[M-H]-189.40830932474
DeepCCS[M-2H]-223.94530932474
DeepCCS[M+Na]+200.00630932474
AllCCS[M+H]+191.432859911
AllCCS[M+H-H2O]+188.632859911
AllCCS[M+NH4]+194.032859911
AllCCS[M+Na]+194.732859911
AllCCS[M-H]-192.032859911
AllCCS[M+Na-2H]-193.032859911
AllCCS[M+HCOO]-194.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PipercideCC(C)CNC(=O)\C=C\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C14637.0Standard polar33892256
PipercideCC(C)CNC(=O)\C=C\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C12956.8Standard non polar33892256
PipercideCC(C)CNC(=O)\C=C\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C13289.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pipercide,1TMS,isomer #1CC(C)CN(C(=O)/C=C/C=C/CCCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C3115.1Semi standard non polar33892256
Pipercide,1TMS,isomer #1CC(C)CN(C(=O)/C=C/C=C/CCCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C3044.7Standard non polar33892256
Pipercide,1TBDMS,isomer #1CC(C)CN(C(=O)/C=C/C=C/CCCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C3305.0Semi standard non polar33892256
Pipercide,1TBDMS,isomer #1CC(C)CN(C(=O)/C=C/C=C/CCCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C3252.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pipercide GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1941000000-959fa274bd750c5657312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pipercide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pipercide 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 - Pipercide 10V, Positive-QTOFsplash10-05fr-9013000000-7acc13c4edcc2e82818f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 20V, Positive-QTOFsplash10-00di-9010000000-bb8cc978eb9788a9fe592016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 40V, Positive-QTOFsplash10-0ab9-9010000000-47667fe1f97e7a04780a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 10V, Negative-QTOFsplash10-0udi-1029000000-7d002fe5c934a70f6c432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 20V, Negative-QTOFsplash10-0pi1-4096000000-4b4a27de826ea7286d7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 40V, Negative-QTOFsplash10-007o-8090000000-d18f0b78a16376d97fd72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 10V, Positive-QTOFsplash10-0a4i-1029000000-df54dacb563f64ec059e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 20V, Positive-QTOFsplash10-0a4i-9384000000-103e2e02d2a916ef71882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 40V, Positive-QTOFsplash10-06vm-3910000000-69ec7070abd7915c98722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 10V, Negative-QTOFsplash10-0udi-0019000000-dfa4a541dc9b56bae5c62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 20V, Negative-QTOFsplash10-0udi-1039000000-87a88193af7f1bd49c652021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipercide 40V, Negative-QTOFsplash10-0007-9231000000-d4d3a34b72fc54aadf3f2021-09-25Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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.. .