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Record Information
Version1.0
Created at2012-09-11 17:30:03 UTC
Updated at2021-08-19 20:22:33 UTC
NP-MRD IDNP0000084
Secondary Accession NumbersNone
Natural Product Identification
Common NamePiperine
DescriptionPiperine, also known as fema 2909, 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. Piperine is a pepper tasting compound. Piperine is found in the highest concentration within pepper (Piper nigrum) and many other Piper species. Piperine has also been detected, but not quantified, in dills and herbs and spices. Piperine is responsible for the hot taste of pepper. Piperine has been used in trials studying the treatment of Multiple Myeloma and Deglutition Disorders. It is used to impart pungent taste to brandy.
Structure
Data?1628564077
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
Piperine, (e,Z)-isomerMeSH
Piperine, (Z,e)-isomerMeSH
Piperine, (Z,Z)-isomerMeSH
Piperine, (e,e)-isomerMeSH
((1-5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidineMeSH
(1-(5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidineMeSH
BioperineHMDB
1-Piperoyl-(e,e)-piperidineHMDB
FEMA 2909HMDB
N-(e,e)-Piperoyl-piperidineHMDB
N-Ee-piperoyl-piperidineHMDB
PiperinHMDB
Chemical FormulaC17H19NO3
Average Mass285.3377 Da
Monoisotopic Mass285.13649 Da
IUPAC Name(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Traditional Namebioperine
CAS Registry Number94-62-2
SMILES
[H]\C(\C(\[H])=C(/[H])C1=C([H])C([H])=C2OC([H])([H])OC2=C1[H])=C(\[H])C(=O)N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H]
InChI Identifier
InChI=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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Piper acutisleginumKNApSAcK Database
Piper betleKNApSAcK Database
Piper chabaKNApSAcK Database
Piper guineense Schum.et Thom.KNApSAcK Database
Piper khasianaKNApSAcK Database
Piper longumKNApSAcK Database
Piper nigrumKNApSAcK Database
Piper officinarumKNApSAcK Database
Piper retrofractum Vahl.KNApSAcK Database
Piper thomsoniKNApSAcK Database
Piper trichostachyonKNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling Point498.00 to 499.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.04 mg/mL at 18 °CNot Available
LogP2.656 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP3.38ALOGPS
logP2.78ChemAxon
logS-3.3ALOGPS
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
External Links
HMDB IDHMDB0029377
DrugBank IDDB12582
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000449
KNApSAcK IDC00002065
Chemspider ID553590
KEGG Compound IDC03882
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperine
METLIN IDNot Available
PubChem Compound638024
PDB IDNot Available
ChEBI ID28821
Good Scents IDrw1033851
References
General References
  1. Lin Z, Hoult JR, Bennett DC, Raman A: Stimulation of mouse melanocyte proliferation by Piper nigrum fruit extract and its main alkaloid, piperine. Planta Med. 1999 Oct;65(7):600-3. doi: 10.1055/s-1999-14031. [PubMed:10575373 ]
  2. Pradeep CR, Kuttan G: Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells. Int Immunopharmacol. 2004 Dec 20;4(14):1795-803. doi: 10.1016/j.intimp.2004.08.005. [PubMed:15531295 ]
  3. Wattanathorn J, Chonpathompikunlert P, Muchimapura S, Priprem A, Tankamnerdthai O: Piperine, the potential functional food for mood and cognitive disorders. Food Chem Toxicol. 2008 Sep;46(9):3106-10. doi: 10.1016/j.fct.2008.06.014. Epub 2008 Jun 29. [PubMed:18639606 ]
  4. D'Cruz SC, Vaithinathan S, Saradha B, Mathur PP: Piperine activates testicular apoptosis in adult rats. J Biochem Mol Toxicol. 2008 Nov-Dec;22(6):382-8. doi: 10.1002/jbt.20251. [PubMed:19110999 ]
  5. Lin Y, Xu J, Liao H, Li L, Pan L: Piperine induces apoptosis of lung cancer A549 cells via p53-dependent mitochondrial signaling pathway. Tumour Biol. 2014 Apr;35(4):3305-10. doi: 10.1007/s13277-013-1433-4. Epub 2013 Nov 24. [PubMed:24272201 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .