Piperine (BioCAD00000016377)

blood feces placenta plant natural products microbial natural products

Metabolite Card

Formula: C17H19NO3 (285.1365)
SMILES: O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1

Synonyms [en]

piperine; 1-piperoylpiperidine; 1-Piperoyl-piperidine; 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine; (E,E)-1-piperoylpiperidine; N-[(E,E)-Piperoyl]piperidine

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Piperine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000016377). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Piperine, 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.

Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 495-91-0
  • CAS Registry Number: 7780-20-3
  • CAS Registry Number: 94-62-2
  • PubChem: 4840
  • PubChem: 638024
  • ChEBI: ChEBI:28821
  • HMDB: HMDB0029377
  • KEGG: C03882
  • BioCyc: N-EE-PIPEROYL-PIPERIDINE
  • NCBI MeSH: piperine
  • Wikipedia: Piperine
  • DrugBank: DB12582
  • RefMet: RM0043248
  • MoNA: Alkaloids000084
  • MoNA: Alkaloids000085
  • MoNA: Alkaloids000525
  • MoNA: Alkaloids000526
  • MoNA: Alkaloids000527
  • MoNA: AU252301
  • MoNA: AU252302
  • MoNA: AU252303
  • MoNA: AU252304
  • MoNA: AU252305
  • MoNA: AU252306
  • MoNA: BML01649
  • MoNA: BML01660
  • MoNA: BML01671
  • MoNA: BML81975
  • MoNA: BML81977
  • MoNA: Bruker_HCD_library001476
  • MoNA: CB000031
  • MoNA: CCMSLIB00000081712
  • MoNA: CCMSLIB00005720175
  • MoNA: FiehnHILIC000698
  • MoNA: FiehnHILIC002264
  • MoNA: FiehnLib000828
  • MoNA: FiehnLib000829
  • MoNA: HMDB0029377_c_ms_100298
  • MoNA: HMDB0029377_c_ms_100299
  • MoNA: JP001402
  • MoNA: JP005656
  • MoNA: LU109601
  • MoNA: LU109602
  • MoNA: LU109603
  • MoNA: LU109604
  • MoNA: LU109605
  • MoNA: LU109606
  • MoNA: MoNA009981
  • MoNA: MoNA009982
  • MoNA: MoNA009983
  • MoNA: MoNA009984
  • MoNA: MoNA009985
  • MoNA: MoNA009986
  • MoNA: MoNA_0001647
  • MoNA: MoNA_0001648
  • MoNA: MoNA_0001649
  • MoNA: MT000119
  • MoNA: NA000149
  • MoNA: NA000150
  • MoNA: NA000151
  • MoNA: NA000152
  • MoNA: NA000153
  • MoNA: NA000154
  • MoNA: NA000155
  • MoNA: NA000156
  • MoNA: NA000157
  • MoNA: NA000158
  • MoNA: NA000159
  • MoNA: NA000160
  • MoNA: NA000161
  • MoNA: NA000162
  • MoNA: NA000163
  • MoNA: NA000164
  • MoNA: NA000165
  • MoNA: NA000166
  • MoNA: NA000167
  • MoNA: NA000168
  • MoNA: NGA02813
  • MoNA: NGA02814
  • MoNA: NGA02815
  • MoNA: NGA02816
  • MoNA: PR310562
  • MoNA: RIKENPlaSMA001779
  • MoNA: RIKENPlaSMA001781
  • MoNA: RIKENPlaSMA001784
  • MoNA: RIKENPlaSMA001787
  • MoNA: RIKENPlaSMA001790
  • MoNA: RIKENPlaSMA001792
  • MoNA: RIKENPlaSMA001795
  • MoNA: RIKENPlaSMA001798
  • MoNA: RIKENPlaSMA001801
  • MoNA: RIKENPlaSMA001804
  • MoNA: RIKENPlaSMA001807
  • MoNA: RIKENPlaSMA001810
  • MoNA: TOF_alkaloids_pos000077
  • MoNA: TOF_alkaloids_pos000078
  • MoNA: TOF_alkaloids_pos000437
  • MoNA: TOF_alkaloids_pos000438
  • MoNA: VF-NPL-LTQ000299
  • MoNA: VF-NPL-LTQ000300
  • MoNA: VF-NPL-LTQ000301
  • MoNA: VF-NPL-LTQ000302
  • MoNA: VF-NPL-LTQ007733
  • MoNA: VF-NPL-LTQ007734
  • MoNA: VF-NPL-QEHF000634
  • MoNA: VF-NPL-QEHF000635
  • MoNA: VF-NPL-QEHF000636
  • MoNA: VF-NPL-QEHF000637
  • MoNA: VF-NPL-QEHF000638
  • MoNA: VF-NPL-QEHF000639
  • MoNA: VF-NPL-QEHF028021
  • MoNA: VF-NPL-QEHF028022
  • MoNA: VF-NPL-QEHF028023
  • MoNA: VF-NPL-QEHF028024
  • MoNA: VF-NPL-QEHF028025
  • MoNA: VF-NPL-QEHF028026
  • MoNA: VF-NPL-QEHF028027
  • MoNA: VF-NPL-QEHF028028
  • MoNA: VF-NPL-QEHF028029
  • MoNA: VF-NPL-QEHF028030
  • MoNA: VF-NPL-QEHF028031
  • MoNA: VF-NPL-QEHF028032
  • MoNA: VF-NPL-QEHF028033
  • MoNA: VF-NPL-QEHF028034
  • MoNA: VF-NPL-QEHF028035
  • MoNA: VF-NPL-QTOF009334
  • MoNA: VF-NPL-QTOF009335
  • MoNA: VF-NPL-QTOF009336
  • Metlin: METLIN_43568
  • Coconut NaturalProduct: CNP0193594.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03994 2.3.1.145 (E,E)-piperoyl-CoA:piperidine N-piperoyltransferase
Rhea:RHEA:14562 2.3.1.145 piperidine + (E,E)-piperoyl-CoA => piperine + CoA + H+
Rhea:RHEA:14563 2.3.1.145 piperine + CoA + H+ => piperidine + (E,E)-piperoyl-CoA
Rhea:RHEA:14564 2.3.1.145 piperidine + (E,E)-piperoyl-CoA <=> piperine + CoA + H+
BioCyc:PIPERIDINE-N-PIPEROYLTRANSFERASE-RXN 2.3.1.145 PIPERIDINE + EE-PIPEROYL-COA --> PROTON + N-EE-PIPEROYL-PIPERIDINE + CO-A
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Organism Source

Taxonomy Source

  1. Abies webbiana [ncbi taxid: ]
  2. Agaricus xanthodermus [ncbi taxid: 83518]
  3. Artemisia coerulescens [ncbi taxid: ]
  4. Brickellia longifolia [ncbi taxid: 1550837]
  5. Bupleurum rigidum [ncbi taxid: 199748]
  6. Cannabis sativa [ncbi taxid: 3483]
  7. Carpesium longifolium [ncbi taxid: 2558928]
  8. Chenopodium ambrosioides [ncbi taxid: ]
  9. Cochlearia officinalis [ncbi taxid: 270110]
  10. Coelogyne nitida [ncbi taxid: 466244]
  11. Crocus corsicus [ncbi taxid: 481051]
  12. Dichotomanthes tristaniicarpa [ncbi taxid: 193303]
  13. Didymosphaeria enalia [ncbi taxid: ]
  14. Dracontium loretense [ncbi taxid: ]
  15. Euphorbia wangii [ncbi taxid: ]
  16. Frullania brasiliensis [ncbi taxid: 264464]
  17. Homalium laurifolium [ncbi taxid: ]
  18. Homo sapiens [ncbi taxid: 9606]
  19. Hydrastis canadensis [ncbi taxid: 13569]
  20. Indian beech tree [ncbi taxid: ]
  21. Leifsonia aquatica [ncbi taxid: 144185]
  22. Magnolia officinalis [ncbi taxid: 85864]
  23. Matsumurella chinensis [ncbi taxid: 587663]
  24. Monascus rubropunctatus [ncbi taxid: ]
  25. Mycoplasma mycoides [ncbi taxid: 2102]
  26. Palisota barteri [ncbi taxid: 1415684]
  27. Penicillium tardum [ncbi taxid: 128435]
  28. Periconia sp. [ncbi taxid: 1756127]
  29. Photorhabdus luminescens [ncbi taxid: 29488]
  30. Piper acutisleginum [ncbi taxid: ]
  31. Piper betle [ncbi taxid: 13217]
  32. Piper chaba [ncbi taxid: ]
  33. Piper guineense [ncbi taxid: 511543]
  34. Piper guineense Schum.et Thom. [ncbi taxid: ]
  35. Piper khasiana [ncbi taxid: ]
  36. Piper khasianum [ncbi taxid: 405331]
  37. Piper longum [ncbi taxid: 49511]
  38. Piper nigrum [ncbi taxid: 13216]
  39. Piper novae-hollandiae [ncbi taxid: 2873833]
  40. Piper officinarum [ncbi taxid: ]
  41. Piper retrofractum [ncbi taxid: 130414]
  42. Piper retrofractum Vahl. [ncbi taxid: ]
  43. Piper thomsoni [ncbi taxid: ]
  44. Piper trichostachyon [ncbi taxid: 1595995]
  45. Piper tuberculatum [ncbi taxid: 247704]
  46. Piperaceae [ncbi taxid: 16739]
  47. Podocarpus minor [ncbi taxid: ]
  48. Pothomorphe peltata [ncbi taxid: ]
  49. Pseudomonas stutzeri [ncbi taxid: ]
  50. Rubia cordifolia [ncbi taxid: 339321]
  51. Schefflera venulosa [ncbi taxid: ]
  52. Silene banksia [ncbi taxid: 1137874]
  53. Stolonica socialis [ncbi taxid: 581074]
  54. Tephrosia crassifolia [ncbi taxid: 3091980]
  55. Valeriana officinalis [ncbi taxid: 19953]
  56. Verbesina virginica [ncbi taxid: 1620208]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5752 piperine biosynthesis
PlantCyc:BLACKPEPPER_PWY-5752 piperine biosynthesis
PlantCyc:PLANT_PWY-5752 piperine biosynthesis
View All Pathways