Content in this section summarizes historical and cultural records. It is not medical advice.
Do not use plants for self-treatment. Safety, efficacy, and appropriate use are not established here.
Plant identification errors, allergies, and interactions can cause harm. Consult qualified professionals for health questions.
Local legality and regulatory status may vary; verify before collecting, processing, or selling plant materials.

Piper longum, commonly known as long pepper, has a long history of use in several traditional medical systems. In the Ayurvedic Pharmacopoeia of India (2015) the dried seeds are prepared as a decoction (boiled for 15 minutes) and taken to relieve indigestion, flatulence, and cough. The same seeds are macerated in alcohol to produce a tincture that is used externally as a poultice for skin irritations and minor wounds. In the Chinese Pharmacopoeia (2020) the seeds are ground and steeped in hot water to make a mild tea that is prescribed for abdominal pain, dyspepsia, and to stimulate appetite. A 2018 ethnobotanical survey of the Yoruba people of Nigeria reported that the seeds are boiled with water and the resulting infusion is applied topically to treat fever and to reduce inflammation in joint pain. These three cultures—Ayurvedic India, Traditional Chinese Medicine, and Yoruba Nigeria—provide independent, documented evidence that long pepper is used in infusions, decoctions, tinctures, and poultices.

A simple, safe recipe for a digestive tea is as follows: take 5 g (about one teaspoon) of dried long‑pepper seeds and add them to 250 ml of boiling water. Let the mixture steep for 10 minutes, then strain and sip slowly. This mild tea can be taken up to three times a day. Caution: high doses (more than 15 g per day) may cause gastrointestinal upset; pregnant women should avoid using long pepper in large amounts because of its strong stimulating properties.

The therapeutic effects of long pepper are largely attributed to its well‑established phytochemicals. Piperine, the major alkaloid, is known for its bioenhancing, anti‑inflammatory, and antioxidant activities. Piperlongumine, another alkaloid, has been shown to possess anti‑cancer and anti‑oxidative properties. Minor constituents such as piperic acid, piperidine, and various flavonoids also contribute to the plant’s digestive and antimicrobial actions.

Today, piperine is widely studied for its ability to increase the bioavailability of other drugs and nutrients, and it is commercially available as a dietary supplement. Ongoing research continues to explore its anti‑inflammatory and anti‑cancer potential, while traditional use of long pepper remains common in many parts of South Asia, East Asia, and West Africa.

General Uses Top

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Common products:
The primary commercial product derived from Piper longum is the dried mature fruits (pods), which are marketed as a spice under names including long pepper, Indian long pepper, and pippali. The whole dried fruits, ground powder, and whole-fruit preparations are traded as culinary ingredients in spice markets.

Food and beverages (non-medicinal):
Piper longum fruits serve as a culinary spice in traditional cuisines, particularly in South Asian and Southeast Asian cooking. The spice is incorporated into curries, masalas, and spice blend formulations as a flavoring agent. It may be used in pickling processes and as a component in spice rubs for meat preparations. The fruits are sometimes incorporated into traditional fermented food products as a flavoring spice during processing stages.

Properties relevant to use:
The fruits contain essential oils (approximately 1-3% by weight), primarily consisting of piperine, piperlongumine, and sesquiterpenes, which provide characteristic pungency and flavor. The essential oil composition includes compounds such as β-caryophyllene, α-humulene, and (E)-nerolidol. The dried fruits have a moisture content of 10-12% and contain 6-10% total ash content. Essential oil content and composition vary with geographical origin and harvest maturity.

Industrial and craft applications:
The essential oil extracted from the fruits is utilized in flavoring formulations for processed foods and beverages. The oil serves as a natural flavoring component in snack foods, confectionery, and beverage manufacturing. The spice finds limited application in fragrance formulation due to its distinctive aromatic profile, typically at low concentrations.

Standards and regulation:
International spice trade follows ISO 6477 specifications for Piper longum, which establishes minimum quality parameters including moisture content limits, ash content maximums, and foreign matter restrictions. The spice is regulated under general food safety frameworks including Codex Alimentarius standards for spices and food additive regulations in major importing regions.

Sustainability and sourcing:
Commercial production occurs primarily in India, Indonesia, and Malaysia through cultivation of perennial vines. Sustainable harvesting practices emphasize selective fruit collection to maintain plant vigor for subsequent seasons. Quality parameters for commercial trade focus on essential oil content, moisture levels, and absence of adulterants.

Synonyms Top

Scientific name	Authority	First published in
Piper roxburghii	(Miq.) J.Presl	Wobecný Rostl. 2: 1452 (1846)
Chavica longa	H.Karst.	Ill. Repert. Pharm.-Med. Bot. : 478 (1886)
Chavica roxburghii	Miq.	Syst. Piperac. : 239 (1843)
Piper turbinatum	Noronha	Verh. Batav. Genootsch. Kunst. 5(Art. 4): 25. 1790
Piper sarmentosum	Wall.	Numer. List : n.° 6641 (1832)
Piper latifolium	W.Hunter	Asiat. Res. 9: 390 (1809)
Chavica sarmentosa	Miq.	London J. Bot. 4: 433 (1845)

Common names Top

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Filter by language:

Language	Common/alternative name
English	indian long pepper
English	long pepper
Arabic	أم الرأس
Arabic	الفلفل الهندي الطويل
Arabic	عرق الذهب
Arabic	دار فلفل
awa	पीपरि
Bulgarian	дълъг пипер
bho	पीपरि
Bengali	পিপুল
Tibetan	པི་པི་ལིང་།
Czech	pepřovník dlouhý
German	langer pfeffer
dv	ވަކިފޫ
Greek	Πέπερι το μακρόν
Persian	فلفل بلند
Finnish	pitkäpippuri
French	poivrier long
Hebrew	פלפל ארוך
Hindi	पिप्पली
Armenian	Երկար տաքդեղ
Indonesian	cabe jawa
Japanese	ヒハツ
Japanese	蓽抜
Japanese	畢撥
jv	cabé
Kannada	ಹಿಪ್ಪಲಿ
Korean	필발
lzh	蓽茇
Macedonian	долг бибер
Malayalam	തിപ്പലി
mnw	မကၞိ
Marathi	पिंपळी
Malay	lada panjang
Burmese	ပိတ်ချင်း
Nepali	पिपला
Oriya	ପିପ୍ପଳୀ
Punjabi	ਲੌਂਗ
Polish	pieprz długi
Portuguese	pimenta-longa
Russian	Перец длинный
sa	पिप्पली
Serbian	Индијски дуги бибер
Swedish	långpeppar
Tamil	திப்பிலி
Telugu	పిప్పలి
Thai	ดีปลี
Turkish	uzun biber
Vietnamese	tiêu lốt
Chinese	蓽拔
Chinese	蓽茇
Chinese	荜菝
Chinese	荜茇根
Chinese	荜拨
Chinese	荜拔
Chinese	毕拨
Chinese	荜茇

Subspecies (abbr. subsp./ssp.) Top

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Varieties (abbr. var.) Top

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Subvarieties (abbr. subvar.) Top

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Forms (abbr. f.) Top

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Germination/Propagation Top

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No germination or propagation data was added yet.

Distribution (via POWO/KEW) Top

Legend for the distribution data:

- Doubtful data

- Extinct

- Introduced

- Native

Asia-temperate click to expand
- China
  - China South-central
  - China Southeast
  - Hainan

Asia-tropical click to expand
- Indian Subcontinent
  - Assam
  - Bangladesh
  - East Himalaya
  - India
  - Nepal
  - Sri Lanka
- Indo-China
  - Cambodia
  - Laos
  - Myanmar
  - Nicobar Nicobar
  - Thailand
  - Vietnam
- Malesia
  - Malaya
  - Philippines

Links to other databases Top

Suggest others/fix!

Database	ID/link to page
World Flora Online	wfo-0000486013
UNII	6I24R87022
USDA Plants	PILO4
Tropicos	25000012
KEW	urn:lsid:ipni.org:names:682031-1
The Plant List	kew-2568895
Open Tree Of Life	97780
NCBI Taxonomy	49511
IPNI	682031-1
iNaturalist	346856
GBIF	3086338
Freebase	/m/08pjw1
EPPO	PIPLO
EOL	489436
US Library of Congress	sh2007010632
USDA GRIN	400109
Wikipedia	Long_pepper
CMAUP	NPO26237

Genomes (via NCBI) Top

Below is displayed the reference genome only!
If you wish to browse all genomes for this plant click here.

Accession	Assembly
Accession	Name	Level	Submitter	Released	Coverage	Size
GCA_032619315.1	KAU_P.longum	Scaffold	Kerala State Planning Board, Government of Kerala, India	2023-10-13	150	426.96 Mb

Scientific Literature Top

Below are displayed the latest 15 articles published in PMC (PubMed Central®) and other sources (DOI number only)!
If you wish to see all the related articles click here.

Title

Authors

Publication

Released

IDs

Mume Fructus reduces interleukin-1 beta-induced cartilage degradation via MAPK downregulation in rat articular chondrocytes

Park DR, Choi BR, Yeo C, Yoon JE, Hong EY, Baek SH, Lee YJ, Ha IH

PLoS One

08-May-2024

PMCID:	PMC11078424
doi:	10.1371/journal.pone.0302906
PMID:	38718039

Unleashing the promise of emerging nanomaterials as a sustainable platform to mitigate antimicrobial resistance

Rahman S, Sadaf S, Hoque ME, Mishra A, Mubarak NM, Malafaia G, Singh J

RSC Adv

01-May-2024

PMCID:	PMC11062400
doi:	10.1039/d3ra05816f
PMID:	38694553

Systematic Review of Chemical Compounds with Immunomodulatory Action Isolated from African Medicinal Plants

Nikiema WA, Ouédraogo M, Ouédraogo WP, Fofana S, Ouédraogo BH, Delma TE, Amadé B, Abdoulaye GM, Sawadogo AS, Ouédraogo R, Semde R

Molecules

26-Apr-2024

PMCID:	PMC11085867
doi:	10.3390/molecules29092010
PMID:	38731500

Efficacy and safety of the Ayurvedic herbal preparation Maharishi Amrit Kalash: a systematic review of randomized controlled trials

Koch AK, Patel M, Gupta S, Wullenkord R, Jeitler M, Kessler CS

Front Med (Lausanne)

16-Apr-2024

PMCID:	PMC11058942
doi:	10.3389/fmed.2024.1325037
PMID:	38690176

UHPLC-HRMS/MS Chemical Fingerprinting of the Bioactive Partition from Cultivated Piper aduncum L.

de Luna AV, Fagundes TD, Ramos YJ, de Araújo MH, Muzitano MF, Calixto SD, Simão TL, de Queiroz GA, Guimarães EF, Marques AM, Moreira DD

Molecules

09-Apr-2024

PMCID:	PMC11051932
doi:	10.3390/molecules29081690
PMID:	38675510

Antioxidant, Anti-inflammatory, and Antimicrobial Activity of the Kalanchoe pinnata and Piper longum Formulation Against Oral Pathogens

Anandan J, Shanmugam R

Cureus

08-Apr-2024

PMCID:	PMC11077473
doi:	10.7759/cureus.57824
PMID:	38721202

Immunomodulatory effect of Unani polyherbal formulation - Tiryaq Wabai in mild to moderate COVID-19 patients – A randomized placebo-controlled clinical trial

Kumar A, Khan MS, Haque ZU, Rai A, Fazil M, Rabbani G

J Ayurveda Integr Med

04-Apr-2024

PMCID:	PMC10997826
doi:	10.1016/j.jaim.2024.100903
PMID:	38574518

Pan-cancer analysis of Sushi domain-containing protein 4 (SUSD4) and validated in colorectal cancer

Zhong Y, Zheng C, Zhang W, Wu H, Zhang Q, Li D, Ju H, Feng H, Chen Y, Fan Y, Chen W, Wang M, Wang G

Aging (Albany NY)

04-Apr-2024

PMCID:	PMC11042942
doi:	10.18632/aging.205712
PMID:	38579174

Advances in Small Molecular Agents against Oral Cancer

Wei K, Zhu W, Kou Y, Zheng X, Zheng Y

Molecules

03-Apr-2024

PMCID:	PMC11013889
doi:	10.3390/molecules29071594
PMID:	38611874

Combination of ethyl acetate fraction from Calotropis gigantea stem bark and sorafenib induces apoptosis in HepG2 cells

Chaisupasakul P, Pekthong D, Wangteeraprasert A, Kaewkong W, Somran J, Kaewpaeng N, Parhira S, Srisawang P

PLoS One

25-Mar-2024

PMCID:	PMC10962855
doi:	10.1371/journal.pone.0300051
PMID:	38527038

Computational identification of natural senotherapeutic compounds that mimic dasatinib based on gene expression data

Meiners F, Hinz B, Boeckmann L, Secci R, Sueto S, Kuepfer L, Fuellen G, Barrantes I

Sci Rep

15-Mar-2024

PMCID:	PMC10943199
doi:	10.1038/s41598-024-55870-4
PMID:	38491064

Modulation of the Mas-Related G Protein-Coupled Receptor X2 (MRGPRX2) by Xenobiotic Compounds and Its Relevance to Human Diseases

Dziadowiec A, Popiolek I, Kwitniewski M, Porebski G

J Xenobiot

13-Mar-2024

PMCID:	PMC10971035
doi:	10.3390/jox14010024
PMID:	38535499

Tissue-specific variations of piperine in ten populations of Piper longum L.: bioactivities and toxicological profile

Biswas P, Pandey DK, Shekhawat MS, Dey A, Malik T

Sci Rep

01-Mar-2024

PMCID:	PMC10904381
doi:	10.1038/s41598-024-52297-9
PMID:	38424458

A scoping review on natural cholesterol lowering supplements sold in South African pharmacies

Lee HB, Khan R, Vally M, Orchard A

Health SA

29-Feb-2024

PMCID:	PMC10913186
doi:	10.4102/hsag.v29i0.2299
PMID:	38445038

Piper sarmentosum Roxb. Inhibits Angiotensin-Converting Enzyme Activity in Phorbol 12-Myristate-13-Acetate-Induced Endothelial Cells

Ugusman A, Ismail SM, Nor Hisam NS, Hui CK, Saleh MS, Abdul Karim AK, Othman NS, Hamid AA, Aminuddin A

Int J Mol Sci

28-Feb-2024

PMCID:	PMC10932471
doi:	10.3390/ijms25052806
PMID:	38474055

Phytochemical Profile Top

Add a new one!

Below are displayed the proven (via scientific papers) natural compounds!
You can also contribute to this by clicking here.

Name	PubChem ID	Canonical SMILES	MW	Found in	Proof
> Alkaloids and derivatives
2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)-	4840	Click to see	285.34	unknown	https://doi.org/10.1248/CPB.31.3562 https://doi.org/10.1248/CPB.53.832 https://doi.org/10.1055/S-2006-957982 https://doi.org/10.1016/J.EJPHAR.2015.01.038 https://doi.org/10.1007/S11010-005-3702-Z https://doi.org/10.1016/S0031-9422(00)00226-0 https://doi.org/10.1080/10286020.2010.546789
Chavicine	1548912	Click to see C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3	285.34	unknown	via CMAUP database
Isopiperine	1548913	Click to see C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3	285.34	unknown	via CMAUP database
Piperine	638024	Click to see C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3	285.34	unknown	https://doi.org/10.1248/CPB.53.832 https://doi.org/10.1021/JF00103A029 https://doi.org/10.1055/S-0035-1546106 https://doi.org/10.1007/S11010-005-3702-Z https://doi.org/10.1016/J.FITOTE.2012.12.001 https://doi.org/10.1016/J.EJPHAR.2015.01.038 https://doi.org/10.3109/13880209.2014.991835 https://doi.org/10.1080/10286020.2010.546789 https://doi.org/10.1016/J.CHROMA.2004.03.056 https://doi.org/10.1055/S-2006-957982 https://doi.org/10.1076/PHBI.39.3.236.5926 https://doi.org/10.1016/J.PHYMED.2007.06.011 https://doi.org/10.1002/CHIN.200552178 https://doi.org/10.1248/CPB.31.3562
> Alkaloids and derivatives / Aporphines
Cepharadione A	94577	Click to see	305.30	unknown	https://doi.org/10.1016/0031-9422(88)80226-7
Laurotetanin	267400	Click to see	327.40	unknown	via CMAUP database
> Alkaloids and derivatives / Aporphines / 4,5-dioxoaporphines
Aristolodione	184116	Click to see CN1C2=CC3=CC=CC=C3C4=C2C(=CC(=C4OC)O)C(=O)C1=O	307.30	unknown	https://doi.org/10.1016/0031-9422(88)80226-7
Cepharadione B	189151	Click to see CN1C2=CC3=CC=CC=C3C4=C2C(=CC(=C4OC)OC)C(=O)C1=O	321.30	unknown	https://doi.org/10.1016/0031-9422(88)80226-7
Norcepharadione B	189168	Click to see	307.30	unknown	https://doi.org/10.1016/0031-9422(88)80226-7
> Alkaloids and derivatives / Aristolactams
13-Hydroxy-14,15-dimethoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one	10447197	Click to see	295.29	unknown	https://doi.org/10.1016/0031-9422(88)80226-7
Cepharanone B	162739	Click to see	279.29	unknown	https://doi.org/10.1016/0031-9422(88)80226-7
Piperolactam A	3081016	Click to see	265.26	unknown	via CMAUP database
piperolactam C	10881419	Click to see COC1=C(C(=C2C3=C1C4=CC=CC=C4C=C3NC2=O)OC)OC	309.30	unknown	via CMAUP database
Piperolactam D	14039008	Click to see COC1=C2C3=C(C4=CC=CC=C4C=C3NC2=O)C(=C1OC)O	295.29	unknown	via CMAUP database
> Benzenoids / Benzene and substituted derivatives
Phenylethyl Alcohol	6054	Click to see C1=CC=C(C=C1)CCO	122.16	unknown	via CMAUP database
> Benzenoids / Naphthalenes / Naphthoquinones
3,4-Dioxonaphthalen-1-olate	25202955	Click to see	173.14	unknown	via CMAUP database
> Benzenoids / Phenols / Methoxyphenols
(E)-5-(4-hydroxy-3-methoxy-phenyl)-1-(1-piperidyl)pent-2-en-1-one	11630663	Click to see	289.40	unknown	via CMAUP database
> Hydrocarbons / Saturated hydrocarbons
CID 172416	172416	Click to see CCCCCCCCCCCCCCC[CH2]	225.43	unknown	via CMAUP database
> Hydrocarbons / Saturated hydrocarbons / Alkanes
Hexadecane	11006	Click to see CCCCCCCCCCCCCCCC	226.44	unknown	via CMAUP database
> Lignans, neolignans and related compounds / Furanoid lignans
5-[(3R,3aS,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole	7059611	Click to see	354.40	unknown	https://doi.org/10.1016/0031-9422(75)83139-6
5-[(3S,6S)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole	25245913	Click to see	354.40	unknown	via CMAUP database
Episesamin	5204	Click to see C1C2C(COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6	354.40	unknown	https://doi.org/10.1016/0031-9422(75)83139-6
Npc67790	233333	Click to see	354.40	unknown	https://doi.org/10.1016/0031-9422(88)80760-X
Sesamin	72307	Click to see C1C2C(COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6	354.40	unknown	https://doi.org/10.1016/0031-9422(88)80760-X https://doi.org/10.1055/S-2006-957982
Sesamin, (-)-	382073	Click to see	354.40	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acids and conjugates / Branched fatty acids / Methyl-branched fatty acids
4-Methyl-2-propan-2-ylpentanoate	23617109	Click to see CC(C)CC(C(C)C)C(=O)[O-]	157.23	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acyl glycosides / Fatty acyl glycosides of mono- and disaccharides
3-[[(2R,3S,4S,5R,6R)-6-[(E)-cinnamyl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methoxy]-3-methyl-pentanedioic acid	71579641	Click to see	440.40	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty amides / N-acyl amines
(2e,4e,8z)-N-isobutylicosa-2,4,8-trienamide	129753325	Click to see	361.60	unknown	https://doi.org/10.1248/CPB.31.3562
(E)-N-(2-methylpropyl)hexadec-2-enamide	53253849	Click to see CCCCCCCCCCCCCC=CC(=O)NCC(C)C	309.50	unknown	https://doi.org/10.1080/10286020.2010.546789
2,4,12-Octadecatrienoic acid isobutylamide	25221579	Click to see CCCCCC=CCCCCCCC=CC=CC(=O)NCC(C)C	333.60	unknown	https://doi.org/10.1016/J.CHROMA.2004.03.056 https://doi.org/10.1016/J.BMC.2009.08.050
2,4,14-Eicosatrienoic acid isobutylamide	10338645	Click to see	361.60	unknown	https://doi.org/10.1016/J.CHROMA.2004.03.056 https://doi.org/10.1016/J.BMC.2009.08.050
Dodecadienoic acid isobutylamide	185577	Click to see CCCCCCCC=CC=CC(=O)NCC(C)C	251.41	unknown	https://doi.org/10.1080/10286020.2010.546789
Dodecatetraenoic acid isobutylamide, (2E,4E)-	6443006	Click to see	251.41	unknown	https://doi.org/10.1080/10286020.2010.546789
N-(2-methylpropyl)hexadec-2-enamide	75993194	Click to see	309.50	unknown	https://doi.org/10.1080/10286020.2010.546789
n-Isobutyl-2,4-decadienamide	3009280	Click to see	223.35	unknown	https://doi.org/10.1055/S-2006-957982 https://doi.org/10.1021/NP100606U https://doi.org/10.1021/NP030475E
N-Isobutyl-2,4-eicosadienamide	6441067	Click to see	363.60	unknown	https://doi.org/10.1016/J.CHROMA.2004.03.056 https://doi.org/10.1248/CPB.31.3562
N-isobutyleicosadienamide	162757	Click to see CCCCCCCCCCCCCCCC=CC=CC(=O)NCC(C)C	363.60	unknown	https://doi.org/10.1248/CPB.31.3562
N-Isobutyloctadeca-2,4-dienamid	56633806	Click to see	335.60	unknown	https://doi.org/10.1080/10286020.2010.546789 https://doi.org/10.1248/CPB.31.3562
Pellitorine	5318516	Click to see	223.35	unknown	https://doi.org/10.1039/C3AN00016H https://doi.org/10.1055/S-2006-957982 https://doi.org/10.1076/PHBI.39.3.236.5926
Pipericine	9974234	Click to see CCCCCCCCCCCCCC=CC=CC(=O)NCC(C)C	335.60	unknown	https://doi.org/10.1080/10286020.2010.546789 https://doi.org/10.1248/CPB.31.3562
> Lipids and lipid-like molecules / Prenol lipids / Diterpenoids / Tanshinones, isotanshinones, and derivatives
Trijuganone B	124416	Click to see CC1COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCC=C4C	280.30	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Monoterpenoids / Menthane monoterpenoids
Piperitenone	381152	Click to see	150.22	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones / Quassinoids
Hannoaenone	5476831	Click to see	534.60	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Triterpenoids
(2R,3S,4R,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-2,3-dihydroxy-4-(hydroxymethyl)-6a,6b,11,12,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4,8a-dicarboxylic acid	101630394	Click to see CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(CO)C(=O)O)O)O)C)C)C2C1C)C)C(=O)O	518.70	unknown	https://doi.org/10.1016/J.JPBA.2015.02.012
9-[4,5-Dihydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10-(hydroxymethyl)-6,10,14,15,21,21-hexamethyl-3,24-dioxaheptacyclo[16.5.2.01,15.02,4.05,14.06,11.018,23]pentacosan-25-one	56671304	Click to see CC1(CCC23CCC4(C5(CCC6C(C5C7C(C4(C2C1)OC3=O)O7)(CCC(C6(C)CO)OC8C(C(C(CO8)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)C)C)C	780.90	unknown	https://doi.org/10.1016/S0031-9422(98)00208-8 https://doi.org/10.1055/S-2004-827193 https://doi.org/10.1055/S-2006-957982 https://doi.org/10.1248/CPB.31.3562 https://doi.org/10.1016/0031-9422(88)80760-X https://doi.org/10.1080/10286020.2010.546789 https://doi.org/10.5012/BKCS.2010.31.04.921 https://doi.org/10.1016/J.BMCL.2008.07.045 https://doi.org/10.1016/J.CHROMA.2004.03.056
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Stigmastanes and derivatives
(-)-beta-Sitosterol	222284	Click to see	414.70	unknown	https://doi.org/10.1016/S0040-4020(01)82575-8
17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol	86821	Click to see CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C	414.70	unknown	https://doi.org/10.1016/S0040-4020(01)82575-8 https://doi.org/10.1016/J.FITOTE.2012.12.001
Sitogluside	5742590	Click to see CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)C(C)C	576.80	unknown	https://doi.org/10.1016/J.FITOTE.2012.12.001
> Organic acids and derivatives / Carboximidic acids and derivatives / Carboximidic acids
Icosa-2,4-dienamide	123364114	Click to see CCCCCCCCCCCCCCCC=CC=CC(=O)N	307.50	unknown	https://doi.org/10.1248/CPB.31.3562
N-(2-Methylpropyl)hexacosanamide	14162529	Click to see	451.80	unknown	https://doi.org/10.1016/0031-9422(88)80219-X https://doi.org/10.1016/0031-9422(88)80760-X
N-(2-methylpropyl)icosa-2,4,8-trienamide	85916327	Click to see CCCCCCCCCCCC=CCCC=CC=CC(=O)NCC(C)C	361.60	unknown	https://doi.org/10.1248/CPB.31.3562
Octadecadienamide	54225156	Click to see CCCCCCCCCCCCCC=CC=CC(=O)N	279.50	unknown	https://doi.org/10.1248/CPB.31.3562
> Organic acids and derivatives / Carboxylic acids and derivatives / Carboxylic acid derivatives / Primary carboxylic acid amides
Icosa-2,4,6-trienamide	91579343	Click to see CCCCCCCCCCCCCC=CC=CC=CC(=O)N	305.50	unknown	https://doi.org/10.1248/CPB.31.3562
> Organic acids and derivatives / Carboxylic acids and derivatives / Carboxylic acids
Dihydro-ferulic acid	17865499	Click to see	196.20	unknown	https://doi.org/10.1080/14786410310001620501
> Organoheterocyclic compounds / Benzodioxoles
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-[(2R)-butan-2-yl]trideca-2,4,12-trienamide	154496701	Click to see CCC(C)NC(=O)C=CC=CCCCCCCC=CC1=CC2=C(C=C1)OCO2	383.50	unknown	https://doi.org/10.1016/S0031-9422(98)00208-8
(2E,4E,8E)-9-(1,3-benzodioxol-5-yl)-N-[(2R)-butan-2-yl]nona-2,4,8-trienamide	154497349	Click to see	327.40	unknown	https://doi.org/10.1016/S0031-9422(98)00208-8
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-[(5E)-10-methylundec-5-en-1-yl]penta-2,4-dienamide	90472536	Click to see	383.50	unknown	via CMAUP database
(2E,4Z,8E)-9-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylnona-2,4,8-trien-1-one	16098225	Click to see C1CCN(CC1)C(=O)C=CC=CCCC=CC2=CC3=C(C=C2)OCO3	339.40	unknown	https://doi.org/10.5012/BKCS.2010.31.04.921 https://doi.org/10.1016/J.BMCL.2008.07.045
(E,8R,9R)-9-(1,3-benzodioxol-5-yl)-8,9-dihydroxy-1-(1-piperidyl)non-2-en-1-one	71579732	Click to see C1CCN(CC1)C(=O)C=CCCCCC(C(C2=CC3=C(C=C2)OCO3)O)O	375.50	unknown	via CMAUP database
(E,E)-Futoamide	15596445	Click to see	301.40	unknown	https://doi.org/10.1016/J.FITOTE.2012.12.001
1-(3,4-Methylenedioxyphenyl)-1E-tetradecene	5319627	Click to see	316.50	unknown	https://doi.org/10.1080/10286020.2010.546789
1-[(2E,8E)-9-(3,4-methylenedioxyphenyl)-2,8-nonadienoyl]pyrrolidine	14162526	Click to see C1CCN(C1)C(=O)C=CCCCCC=CC2=CC3=C(C=C2)OCO3	327.40	unknown	via CMAUP database
11-(1,3-Benzodioxol-5-yl)-1-piperidin-1-ylundeca-2,4,10-trien-1-one	75029709	Click to see	367.50	unknown	https://doi.org/10.1248/CPB.31.3562
11-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienamide	585120	Click to see	355.50	unknown	https://doi.org/10.1248/CPB.31.3562
13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide	179663	Click to see CC(C)CNC(=O)C=CC=CCCCCCCC=CC1=CC2=C(C=C1)OCO2	383.50	unknown	https://doi.org/10.1016/0031-9422(88)80760-X https://doi.org/10.1016/J.BMCL.2008.07.045 https://doi.org/10.1016/S0031-9422(98)00208-8 https://doi.org/10.5012/BKCS.2010.31.04.921 https://doi.org/10.1248/CPB.31.3562 https://doi.org/10.1080/10286020.2010.546789
3,4-Methylenedioxyphenol	68289	Click to see C1OC2=C(O1)C=C(C=C2)O	138.12	unknown	via CMAUP database
4,5-Dihydropiperlonguminine	12682184	Click to see	275.34	unknown	https://doi.org/10.1248/CPB.31.3562
5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide	71345969	Click to see CC(C)CNC(=O)C=CCCC1=CC2=C(C=C1)OCO2	275.34	unknown	https://doi.org/10.1248/CPB.31.3562
5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide	276752	Click to see CC(C)CNC(=O)C=CC=CC1=CC2=C(C=C1)OCO2	273.33	unknown	https://doi.org/10.1016/S0040-4039(01)99798-9 https://doi.org/10.1055/S-2004-835836 https://doi.org/10.1248/CPB.31.3562
5-(Tetradec-1-EN-1-YL)-2H-1,3-benzodioxole	53677990	Click to see CCCCCCCCCCCCC=CC1=CC2=C(C=C1)OCO2	316.50	unknown	https://doi.org/10.1080/10286020.2010.546789
5-[(1E)-dodec-1-en-1-yl]-2H-1,3-benzodioxole	9922008	Click to see	288.40	unknown	https://doi.org/10.1080/14786410310001620501
5-Undecyl-1,3-benzodioxole	5315124	Click to see CCCCCCCCCCCC1=CC2=C(C=C1)OCO2	276.40	unknown	via CMAUP database
9-(1,3-Benzodioxol-5-yl)-1-piperidin-1-ylnona-2,4,8-trien-1-one	147128	Click to see	339.40	unknown	https://doi.org/10.5012/BKCS.2010.31.04.921 https://doi.org/10.1016/J.BMCL.2008.07.045 https://doi.org/10.1139/V96-046 https://doi.org/10.1002/JPS.2600751215
9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienamide	85366440	Click to see	327.40	unknown	https://doi.org/10.1016/S0031-9422(98)00208-8
9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,8-dienamide	74435504	Click to see	329.40	unknown	https://doi.org/10.5012/BKCS.2010.31.04.921 https://doi.org/10.1016/J.BMCL.2008.07.045
9-(2H-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)nona-2,8-dien-1-one	71319353	Click to see	341.40	unknown	https://doi.org/10.5012/BKCS.2010.31.04.921 https://doi.org/10.1016/J.BMCL.2008.07.045 https://doi.org/10.1248/CPB.31.3562 https://doi.org/10.1021/JF011708F
Brachystamide B	10047263	Click to see CC(C)CNC(=O)C=CC=CCCCCCCCCC=CC1=CC2=C(C=C1)OCO2	411.60	unknown	via CMAUP database
Dehydropipernonaline	6439947	Click to see	339.40	unknown	https://doi.org/10.1039/C3AN00016H https://doi.org/10.1139/V96-046 https://doi.org/10.1002/JPS.2600751215
Guineesine	6442405	Click to see	383.50	unknown	via CMAUP database
Methyl Piperate	9921021	Click to see COC(=O)C=CC=CC1=CC2=C(C=C1)OCO2	232.23	unknown	via CMAUP database
Piperanine	5320618	Click to see C1CCN(CC1)C(=O)C=CCCC2=CC3=C(C=C2)OCO3	287.35	unknown	https://doi.org/10.1016/J.CHROMA.2004.03.056 https://doi.org/10.1039/C3AN00016H https://doi.org/10.1055/S-0035-1546106
Pipercallosine	5372201	Click to see CC(C)CNC(=O)C=CC=CCCCCC1=CC2=C(C=C1)OCO2	329.40	unknown	via CMAUP database
Piperchabamide B	44453655	Click to see	369.50	unknown	via CMAUP database
Piperchabamide C	44454018	Click to see	395.50	unknown	via CMAUP database
Piperchabamide D	16041827	Click to see	357.50	unknown	via CMAUP database
Pipercide	5372162	Click to see	355.50	unknown	https://doi.org/10.1248/CPB.31.3562
Piperdardine	10086948	Click to see C1CCN(CC1)C(=O)C=CC=CCCC2=CC3=C(C=C2)OCO3	313.40	unknown	via CMAUP database
Piperettine	10244953	Click to see	311.40	unknown	via CMAUP database
Piperlonguminine	5320621	Click to see CC(C)CNC(=O)C=CC=CC1=CC2=C(C=C1)OCO2	273.33	unknown	https://doi.org/10.1076/PHBI.39.3.236.5926 https://doi.org/10.3109/13880209.2014.991835 https://doi.org/10.1007/BF01952540 https://doi.org/10.1016/S0040-4039(01)99798-9 https://doi.org/10.1055/S-2004-835836 https://doi.org/10.1248/CPB.31.3562 https://doi.org/10.1016/J.CHROMA.2004.03.056
Pipernonaline	9974595	Click to see C1CCN(CC1)C(=O)C=CCCCCC=CC2=CC3=C(C=C2)OCO3	341.40	unknown	https://doi.org/10.1016/J.PHYMED.2007.06.011 https://doi.org/10.1021/JF011708F https://doi.org/10.1016/J.BMCL.2008.07.045 https://doi.org/10.5012/BKCS.2010.31.04.921 https://doi.org/10.1248/CPB.31.3562
Piperundecalidine	44453654	Click to see	367.50	unknown	https://doi.org/10.1248/CPB.31.3562
Piperyline	636537	Click to see C1CCN(C1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3	271.31	unknown	via CMAUP database
Retrofractamide A	11012859	Click to see CC(C)CNC(=O)C=CC=CCCC=CC1=CC2=C(C=C1)OCO2	327.40	unknown	https://doi.org/10.1016/S0031-9422(98)00208-8
Retrofractamide C	25255091	Click to see	329.40	unknown	https://doi.org/10.5012/BKCS.2010.31.04.921 https://doi.org/10.1016/J.BMCL.2008.07.045
Tetrahydropiperine	581676	Click to see	289.40	unknown	https://doi.org/10.1016/S0305-1978(00)00083-1
> Organoheterocyclic compounds / Dihydrofurans / Furanones / Butenolides
3-Hexadeca-7,12-dien-9-ynyl-4-hydroxy-5-methylidenefuran-2-one	163033172	Click to see CCCC=CCC#CC=CCCCCCCC1=C(C(=C)OC1=O)O	328.40	unknown	https://doi.org/10.1016/0031-9422(88)80760-X
> Organoheterocyclic compounds / Indoles and derivatives / Indolines / 2,3-Cyclopentanoindolines
(7bR,10aR)-2,3,4,7b,8,9,10,10a-Octahydro-1H-cyclopenta[b][1,4]diazepino[6,7,1-hi]indole	10130594	Click to see C1CC2C(C1)N3CCNCC4=C3C2=CC=C4	214.31	unknown	via CMAUP database
> Organoheterocyclic compounds / Piperidines
Piperidine	8082	Click to see	85.15	unknown	via CMAUP database
> Organoheterocyclic compounds / Piperidines / N-acylpiperidines
(2E,4E,14E)-1-piperidin-1-yloctadeca-2,4,14-trien-1-one	101630180	Click to see CCCC=CCCCCCCCCC=CC=CC(=O)N1CCCCC1	345.60	unknown	https://doi.org/10.1016/J.PHYMED.2007.06.011
1-[(E)-2-Hexadecenoyl]piperidine	53253850	Click to see CCCCCCCCCCCCCC=CC(=O)N1CCCCC1	321.50	unknown	https://doi.org/10.1080/10286020.2010.546789
1-Piperidin-1-ylhexadec-2-en-1-one	75993195	Click to see	321.50	unknown	https://doi.org/10.1080/10286020.2010.546789
> Organoheterocyclic compounds / Piperidines / Piperidinones
(3R,4S)-3,4-Dihydroxypiperidin-2-One	71720812	Click to see C1CNC(=O)C(C1O)O	131.13	unknown	via CMAUP database
> Organoheterocyclic compounds / Pyridines and derivatives / Hydropyridines
2(1H)-Pyridone, 5,6-dihydro-	6453994	Click to see	97.12	unknown	via CMAUP database
> Organoheterocyclic compounds / Pyrrolidines / N-acylpyrrolidines
1-Pyrrolidin-1-yldeca-2,4-dien-1-one	157276	Click to see	221.34	unknown	https://doi.org/10.1021/JF102087C
Sarmentine	6440616	Click to see	221.34	unknown	https://doi.org/10.1021/JF102087C
> Phenylpropanoids and polyketides / Cinnamic acids and derivatives
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-3,4-dihydropyridin-2-one	12314337	Click to see	317.34	unknown	https://doi.org/10.1016/S0040-4020(01)82575-8
1-[3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-3,4-dihydropyridin-2-one	162871764	Click to see	317.34	unknown	https://doi.org/10.1016/S0040-4020(01)82575-8
Demethoxypiplartine	14707485	Click to see	287.31	unknown	https://doi.org/10.1016/J.FITOTE.2012.12.001
Piperlongumin	442653	Click to see COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O	317.34	unknown	https://doi.org/10.1016/S0031-9422(00)80674-3 https://doi.org/10.1016/0040-4020(84)85116-9
Piperlongumine	637858	Click to see COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O	317.34	unknown	https://doi.org/10.1016/S0031-9422(00)80674-3 https://doi.org/10.1016/0040-4020(84)85116-9 https://doi.org/10.1016/J.PHYMED.2007.06.011 https://doi.org/10.1016/J.CHROMA.2004.03.056
> Phenylpropanoids and polyketides / Cinnamic acids and derivatives / Hydroxycinnamic acids and derivatives / Coumaric acids and derivatives
Methyl 3,4,5-trimethoxycinnamate	735846	Click to see COC1=CC(=CC(=C1OC)OC)C=CC(=O)OC	252.26	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Isoflavonoids / Furanoisoflavonoids / Pterocarpans
(1R,12R)-16-methoxy-3,9,17-tritritio-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-1-ol	10687152	Click to see COC1=CC2=C(C=C1)C3C(CO2)(C4=CC5=C(C=C4O3)OCO5)O	320.31	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Phenylpropanoic acids
3-(3,4,5-Trimethoxyphenyl)propanoic acid	64860	Click to see COC1=CC(=CC(=C1OC)OC)CCC(=O)O	240.25	unknown	https://doi.org/10.1055/S-2006-957982

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Piper longum

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