2D Structure

3D Structure

Piperine


Properties
PID PID00004
Mol. Weight 285.343 g/mol
LogP 2.78
Water solubility 0.04 mg/mL at 18 °C
Hydrogen Bond Donor 0
Hydrogen Bond Acceptor 3
Rotatable Bonds 3
XLogP3 3.5

Piperine

Identifiers
Formula C17H19NO3
PubChem CID 638024
FEMA 2909
Flavor Profile Spice,pungency
Smiles C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3
InChl Key MXXWOMGUGJBKIW-YPCIICBESA-N
InChl 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+
CAS Registry Number 94-62-2
IUPAC Systematic Name (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one

Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets


Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)


Related Pungent TCM

English Name Pinyin Name (Chinese Name) Latin Name Properties in TCM merdians View Graph
Black PepperHu Jiao (胡椒)Piperis FructusHot,PungentLarge Intestine, StomachView Graph
Long PepperBi Ba (荜茇)Piperis Longi FructusHot,PungentLarge Intestine, StomachView Graph

Pharmacological action

Piperine is known to possess anti-inflammatory activity, antipyretic activity, antifungal activity, antidiarrheal activity, antioxidant activity,

antithyroid activity, antimutagenic activity, antitumor activity, antidepressant activity, analgesic activity, hepatoprotective activity, antihypertensive

activity, hypolipidemic effect, neuroprotective effect etc.



Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.

References

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26. Lee S A, Hong S S, Han X H, et al. Piperine from the fruits of Piper longum with inhibitory effect on monoamine oxidase and antidepressant-like activityJ.. Chemical and pharmaceutical bulletin, 2005, 53(7): 832-835.

27. Li S, Wang C, Wang M, et al. Antidepressant like effects of piperine in chronic mild stress treated mice and its possible mechanismsJ.. Life sciences, 2007, 80(15): 1373-1381.

28. Wattanathorn J, Chonpathompikunlert P, Muchimapura S, et al. Piperine, the potential functional food for mood and cognitive disordersJ.. Food and Chemical Toxicology, 2008, 46(9): 3106-3110.

29. Matsuda H, Ninomiya K, Morikawa T, et al. Protective effects of amide constituents from the fruit of Piper chaba on d-galactosamine/TNF--induced cell death in mouse hepatocytesJ.. Bioorganic & medicinal chemistry letters, 2008, 18(6): 2038-2042.

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31. Capasso R, Izzo A A, Borrelli F, et al. Effect of piperine, the active ingredient of black pepper, on intestinal secretion in miceJ.. Life sciences, 2002, 71(19): 2311-2317.

32. Chen C Y, Li W, Qu K P, et al. Piperine exerts anti-seizure effects via the TRPV1 receptor in miceJ.. European journal of pharmacology, 2013, 714(1-3): 288-294.

33. Booranasubkajorn S, Huabprasert S, Wattanarangsan J, et al. Vasculoprotective and vasodilatation effects of herbal formula (Sahatsatara) and piperine in spontaneously hypertensive ratsJ.. Phytomedicine, 2017, 24: 148-156.

34. Hu D, Wang Y, Chen Z, et al. The protective effect of piperine on dextran sulfate sodium induced inflammatory bowel disease and its relation with pregnane X receptor activationJ.. Journal of ethnopharmacology, 2015, 169: 109-123.

35. Song X Y, Xu S, Hu J F, et al. Piperine prevents cholesterol gallstones formation in miceJ.. European journal of pharmacology, 2015, 751: 112-117.

36. Chithra S, Jasim B, Sachidanandan P, et al. Piperine production by endophytic fungus Colletotrichum gloeosporioides isolated from Piper nigrumJ.. Phytomedicine, 2014, 21(4): 534-540.

37. Bi X, Yuan Z, Qu B, et al. Piperine enhances the bioavailability of silybin via inhibition of efflux transporters BCRP and MRP2J.. Phytomedicine, 2018.

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40. Jwa H, Choi Y, Park U H, et al. Piperine, an LXR antagonist, protects against hepatic steatosis and improves insulin signaling in mice fed a high-fat dietJ.. Biochemical pharmacology, 2012, 84(11): 1501-1510.

41. Samra Y A, Said H S, Elsherbiny N M, et al. Cepharanthine and Piperine ameliorate diabetic nephropathy in rats: role of NF-B and NLRP3 inflammasomeJ.. Life sciences, 2016, 157: 187-199.

42. Gupta R A, Motiwala M N, Dumore N G, et al. Effect of piperine on inhibition of FFA induced TLR4 mediated inflammation and amelioration of acetic acid induced ulcerative colitis in miceJ.. Journal of ethnopharmacology, 2015, 164: 239-246.

43. Lai L, Fu Q, Liu Y, et al. Piperine suppresses tumor growth and metastasis in vitro and in vivo in a 4T1 murine breast cancer modelJ.. Acta Pharmacologica Sinica, 2012, 33(4): 523.

44. Liu Y, Zhang Y, Lin K, et al. Protective effect of piperine on electrophysiology abnormalities of left atrial myocytes induced by hydrogen peroxide in rabbitsJ.. Life sciences, 2014, 94(2): 99-105.

45. Selvendiran K, Senthilnathan P, Magesh V, et al. Modulatory effect of Piperine on mitochondrial antioxidant system in Benzo (a) pyrene-induced experimental lung carcinogenesisJ.. Phytomedicine, 2004, 11(1): 85.

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