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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:32:28 UTC
Update Date2019-01-11 19:47:20 UTC
HMDB IDHMDB0033779
Secondary Accession Numbers
  • HMDB33779
Metabolite Identification
Common NamePiperic acid
DescriptionPiperic acid is found in herbs and spices. Piperic acid is obtained from black pepper (Piper nigrum), from Minthostachys verticillata, peppermint (Mentha piperita) and others.
Structure
Data?1547236040
Synonyms
ValueSource
2,4-Pentadienoic acid, 5-(1,3-benzodioxol-5-yl)- (9ci)HMDB
5-(1,3-Benzenedioxol-5-yl)-2,4-pentadienoic acid, 9ciHMDB
5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoic acidHMDB
5-(1,3-Benzodioxol-5-yl)penta-2,4-dienoic acidHMDB
Piperic acid (8ci)HMDB
Piperic acid, 8ciHMDB
Piperinic acidHMDB
Piperonic acidHMDB
Chemical FormulaC12H10O4
Average Molecular Weight218.2054
Monoisotopic Molecular Weight218.057908808
IUPAC Name(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid
Traditional Name(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid
CAS Registry Number5285-18-7
SMILES
OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1-,4-2+
InChI KeyRHBGITBPARBDPH-HSFFGMMNSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Unsaturated fatty acid
  • Benzenoid
  • Fatty acid
  • Fatty acyl
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point215 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP2.79ALOGPS
logP2.29ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.15 m³·mol⁻¹ChemAxon
Polarizability21.47 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1930000000-b89f6f6e141be7a35250JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6590000000-00f335d6958aff048805JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0290000000-754ab183d5924e215f42JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2970000000-98c9a65a7364bbc669a7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-5900000000-842d5fe0cc2f2f0aa750JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-fdd952a8dad85ffb328aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-0970000000-272641c3b38064a63a3aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-2900000000-e5ab3b143eac4f82ef30JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • 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
FoodDB IDFDB011933
KNApSAcK IDNot Available
Chemspider ID22902400
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperic acid
METLIN IDNot Available
PubChem Compound13001421
PDB IDNot Available
ChEBI 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.. .