PIPERINE (CED0002980)

Record Information
Version1.0
Creation Date2016-05-19 02:22:43 UTC
Update Date2026-08-19 20:26:13 UTC
Accession NumberCHEM007217
Identification
Common NamePIPERINE
ClassSmall Molecule
Description
PIPERINE belongs to the alkaloids and derivatives, a superclass within the organic compounds. It has the chemical formula C17H19NO3 and an average molecular weight of 285.34 g/mol. Biologically, it functions as an alkaloid (PMC10922816). Industrially, the compound is utilized as a fragrance as well as a nutrient and flavouring (PMC10922816). The compound is found in or released from 26 recorded sources. These include drinking water, indoor air, and synthetic textiles, carpets and rugs. It is also associated with food, food processing and cookware, specifically the treatment of hops, processing meats, food packaging, and the preparation of wine, sparkling wine, or vinegar. Additionally, it is found in household cleaning and consumer products such as tobacco product cases, pipe accessories, other smoking requisites, and non electric simulated smoking devices. It is also recorded in electrical and electronic equipment, including batteries, capacitors, cell phones, printed circuit boards, wires and cables, and four other sources. Exposure routes for PIPERINE include touch, oral, and inhalation. At a molecular level, PIPERINE has three recorded protein targets, acting as an inhibitor of Amine oxidase [flavin-containing] A (MAOA), Amine oxidase [flavin-containing] B (MAOB), and Nuclear receptor subfamily 1 group I member 2 (NR1I2). Regarding health effects, PIPERINE has a therapeutic effect on inflammation (PMC12981716).
Contaminant Type
  • PFAS
Chemical Structure
Synonyms
ValueSource
(e,e)-1-PiperoylpiperidineChEBI
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidineChEBI
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidineChEBI
1-Piperoyl-piperidineChEBI
1-PiperoylpiperidineChEBI
N-[(e,e)-Piperoyl]piperidineChEBI
BioperineHMDB
1-Piperoyl-(e,e)-piperidineHMDB
FEMA 2909HMDB
N-(e,e)-Piperoyl-piperidineHMDB
N-Ee-piperoyl-piperidineHMDB
PiperinHMDB
Piperine, (e,Z)-isomerMeSH, HMDB
Piperine, (Z,e)-isomerMeSH, HMDB
Piperine, (Z,Z)-isomerMeSH, HMDB
((1-5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidineMeSH, HMDB
(1-(5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidineMeSH, HMDB
Piperine, (e,e)-isomerMeSH, HMDB
Chemical FormulaC17H19NO3
Average Molecular Mass285.338 g/mol
Monoisotopic Mass285.136 g/mol
CAS Registry Number94-62-2
IUPAC Name(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Traditional Namebioperine
SMILESO=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1
InChI IdentifierInChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
InChI KeyMXXWOMGUGJBKIW-YPCIICBESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Benzodioxole
  • N-acyl-piperidine
  • Alkaloid or derivatives
  • Styrene
  • Piperidine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP2.78ChemAxon
pKa (Strongest Basic)-0.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.9 m³·mol⁻¹ChemAxon
Polarizability32.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0fe0-0590000000-49115b64f9d288ede20bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uki-1980000000-0d80d5bd56077694f4abNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0fe0-0590000000-49115b64f9d288ede20bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uki-1980000000-0d80d5bd56077694f4abNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ru3-5490000000-47caa063ebe950468c83Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0910000000-28987f355a39728ed8e4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0090000000-6221df9a927cf5dae43fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0090000000-f586ee65972a8599fb3eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0190000000-9f77f056ac9f2e385656Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0090000000-d91bf95f43f53499a538Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0190000000-1f5b570135a2c33d60cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0190000000-c67e35d994bd1857d3b3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0190000000-38727bddc27cc1f12b21Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0032950000-09b8545ba31f6fbf5243Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ti-0044970000-8efb835b518a1f9d631eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0033960000-0ebcac3b31c8914732a9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0009700000-45fc15cfc95d4cb7619cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0009500000-356adf7cecbec3f587a1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0022950000-438f2d66c26e4fad4df9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uxr-0930000000-08188c35582e879e867fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-8556d96344dd58005484Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gbl-0910000000-0cc6374f3392d452f5faNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udr-0190000000-1fd31902ba916f49f5c0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-d9688e24ce807650b12cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-4a93b018b8572b204527Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-635969cde45ef523af52Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0590000000-6a9a3ae7c355d0e7f528Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c53c54dc8c0dabd5af85Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f79-0390000000-625f8167c95eb43080d0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-87da84829202db92a1e0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1890000000-3eda5c4e5ad453fb46f1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-9b72a28a9caf41f3eb76Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f79-0390000000-d1bda5d88754a9ed9dcdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0v4l-0920000000-0082a1a68a0582e5f812Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0v4l-0920000000-0dbb7304f4cce0cbd629Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0790000000-3e4efa0d155e1daf5dbfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-a94f240288c62a9a761fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f79-0390000000-f55fb6779b1fa0af60bbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udr-0090000000-ca7d77d5ba255ab20b5eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0v4u-0920000000-f89720f6c68f12513bf2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0v4l-0920000000-0f04c6d94b14669feb30Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-a0b0db8e1422db91df83Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-84019257089ff88830b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-68e45efbdcd5fb753534Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-3e83e83a06556c5f346eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0v4l-0920000000-7198b9f9657968953291Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-299f3dce3870115e5e5aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-5fa9382c0128e4ba66a6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f79-0390000000-d3c96906282efb5b4386Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f79-0960000000-7be9463bd4371a93e81bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-3bc902f8361547db54d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0v4u-0920000000-5b16bb53472088d8c491Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2290000000-12a3336a15ec4f2d04adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-6960000000-cfbbefb16249f62a712dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05q3-9300000000-e0c13b92ad036042aa06Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0190000000-2e45c46d9e273a3e57f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-6490000000-03ac1126cea4a744d034Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9200000000-b9bed611c188499924d5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-793f02ff50658d83401dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0590000000-910c03e63d1f7eda07c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-1490000000-98a19b77e5512da2277aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-b18834fe9a0472cd5189Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01p9-0490000000-de8057fff1c880e40591Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2910000000-407860037b5ea3527793Not AvailableView Spectrum
MSMS Spectrumsplash10-0v4r-4970000000-d7ea6f47f4b46495acb4Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
714.0Log mg/kg[400:1300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationhas_therapeutic_effect_onNot AvailablePMC12981716
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
115Drinking waterDrinking water & water supplyNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
597ChemosterilantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAmine oxidase [flavin-containing] BP19643Rattus norvegicusPredicted (SEA)1.63483
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)11.2881
Click to view 3D structureAmine oxidase [flavin-containing] AP21396Rattus norvegicusPredicted (SEA)2.88042
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)9.10836
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)65.4712
Click to view 3D structureAmine oxidase [flavin-containing] BQ8BW75Mus musculusPredicted (SEA)0.0778492
Dual specificity tyrosine-phosphorylation-regulated kinase 2 structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 2Q92630HumansPredicted (SEA)65.2376
Dihydroorotate dehydrogenase (quinone), mitochondrial structureClick to view 3D structureDihydroorotate dehydrogenase (quinone), mitochondrialQ02127HumansPredicted (SEA)4.67095
Click to view 3D structureDual specificity protein kinase CLK1P22518Mus musculusPredicted (SEA)8.79696
Dual specificity tyrosine-phosphorylation-regulated kinase 1B structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1BQ9Y463HumansPredicted (SEA)219.768
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)469.742
Click to view 3D structureDual specificity protein kinase CLK4O35493Mus musculusPredicted (SEA)5.13805
Click to view 3D structureDual specificity protein kinase CLK2O35491Mus musculusPredicted (SEA)5.0602
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)61.1895
Dual specificity tyrosine-phosphorylation-regulated kinase 3 structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 3O43781HumansPredicted (SEA)216.187
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)572.347
Dual specificity protein kinase CLK1 structureClick to view 3D structureDual specificity protein kinase CLK1P49759HumansPredicted (SEA)192.988
Click to view 3D structureDual specificity protein kinase CLK3O35492Mus musculusPredicted (SEA)4.20386
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)549.693
G-protein coupled receptor 183 structureClick to view 3D structureG-protein coupled receptor 183P32249HumansPredicted (SEA)16.8154
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)133.278
Click to view 3D structureCasein kinase II subunit alphaQ60737Mus musculusPredicted (SEA)4.35956
Click to view 3D structure1-phosphatidylinositol 3-phosphate 5-kinaseQ9Z1T6Mus musculusPredicted (SEA)4.35956
Click to view 3D structureCasein kinase II subunit betaP67871Mus musculusPredicted (SEA)4.35956
Click to view 3D structureGlycogen synthase kinase-3 alphaQ2NL51Mus musculusPredicted (SEA)4.35956
Concentrations
Not Available
External Links
DrugBank IDDB12582
HMDB IDHMDB0029377
FooDB IDFDB000449
Phenol Explorer IDNot Available
KNApSAcK IDC00002065
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPiperine
Chemspider ID553590
ChEBI ID28821
PubChem Compound ID638024
Kegg Compound IDC03882
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10575373
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15531295
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18639606
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19110999
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24272201
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25645812
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=8347144
8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.