Piperine

Details

• Internal ID: c70db00b-a446-4077-b843-6961c976afdf
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
• SMILES (Canonical): C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3
• SMILES (Isomeric): C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
• InChI: 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 Key: MXXWOMGUGJBKIW-YPCIICBESA-N
• Popularity: 2,795 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.34 g/mol
• Exact Mass: 285.13649347 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 94-62-2
• 1-Piperoylpiperidine
• Piperin
• Bioperine
• 7780-20-3
• Piperoylpiperidine
• FEMA No. 2909
• (E,E)-1-piperoylpiperidine
• Piperidine, 1-piperoyl-, (E,E)-
• (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• CCRIS 5572
• N-[(E,E)-Piperoyl]piperidine
• 1-Piperoylpiperidine, (E,E)-
• AI 3-01439
• EINECS 202-348-0
• UNII-U71XL721QK
• NSC 21727
• NSC-21727
• Piperine [USP]
• N-(E,E)-piperoyl-piperidine
• Piperine (aliphatic)
• U71XL721QK
• 1-Piperoyl-piperidine
• DTXSID3021805
• CHEBI:28821
• piperidine, 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-
• (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• Piperidine, 1-piperoyl-
• 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine
• (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
• 1,3-Benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperine
• CHEMBL43185
• Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (E,E)-
• DTXCID701805
• 1-(5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine, (E,E)-
• NSC21727
• NSC 242267
• AI3-01439
• Piperidine, 1-(5-(3,4-methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)-
• PIPERINE (USP-RS)
• PIPERINE [USP-RS]
• 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
• Piperidine, 1-((2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-
• Piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (E,E)-
• N-((E,E)-Piperoyl)piperidine
• 1-(5-(3,4-Methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)piperidine
• 1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine
• (E,E)-1-(5-(1,3-BENZODIOXOL-5-YL)-2,4-PENTADIENOYL)PIPERIDINE
• 5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• SMR000112278
• SR-01000638580
• Bioperine;1-Piperoylpiperidine
• piperine, (E,E)-isomer
• piperin-
• 1-((2E,4E)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl)piperidine
• 1-((2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl)piperidine
• 1-((2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine
• (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• (2E,4E)-5-(BENZO(D)(1,3)DIOXOL-5-YL)-1-(PIPERIDIN-1-YL)PENTA-2,4-DIEN-1-ONE
• CAS-94-62-2
• Piperine,(S)
• 1-Piperylpiperidine
• Prestwick_398
• MFCD00005839
• Piperine, >=97%
• ST079380
• starbld0008505
• Piperidine, (E,E)-
• PIPERINE [FHFI]
• PIPERINE [INCI]
• PIPERINE [MI]
• Prestwick2_000474
• Prestwick3_000474
• Spectrum5_001507
• D0H7PW
• PIPERINE [WHO-DD]
• Piperine, >=97%, FG
• SCHEMBL94058
• SCHEMBL94059
• BSPBio_000608
• BSPBio_002515
• Piperine, analytical standard
• MLS002153830
• MLS002473213
• BIDD:ER0675
• SPECTRUM1500873
• BPBio1_000670
• GTPL2489
• N-EE-PIPEROYL-PIPERIDINE
• Piperine (1-Piperoylpiperidine)
• CHEBI:93043
• FEMA 2909
• HMS502P16
• 2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)-
• HMS1569O10
• HMS1921M12
• HMS2092M22
• HMS2096O10
• HMS2270M18
• Pharmakon1600-01500873
• 1-trans,trans-piperinoyl-piperidine
• AMY40672
• BCP18901
• HY-N0144
• Tox21_201990
• Tox21_302746
• ((1-5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine
• (1-(5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine
• 1-PIPEROYL-(E,E)-PIPERIDINE
• BBL027541
• BDBM50148573
• CCG-39991
• NSC757803
• s2344
• STL377909
• (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(1-piperidyl)penta-2,4-dien-1-one
• AKOS003369047
• AKOS040750229
• CS-6155
• DB12582
• LS-2194
• NSC-757803
• SDCCGMLS-0066693.P001
• IDI1_000954
• (piperidin-1-yl)penta-2,4-dien-1-one
• NCGC00094872-01
• NCGC00094872-02
• NCGC00094872-03
• NCGC00094872-04
• NCGC00094872-05
• NCGC00094872-06
• NCGC00094872-09
• NCGC00256392-01
• NCGC00259539-01
• AC-11746
• AS-17442
• SBI-0051621.P002
• CS-0368434
• P0460
• SW196642-2
• EN300-20100
• PIPERINE (CONSTITUENT OF BLACK PEPPER)
• C03882
• P-6920
• AB00052185_08
• EN300-7392817
• AG-205/01792022
• Q414501
• (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-
• SR-01000638580-1
• SR-01000638580-2
• SR-01000638580-5
• SR-01000638580-6
• BRD-K59522102-001-08-8
• PIPERINE (CONSTITUENT OF BLACK PEPPER) [DSC]
• Q27164772
• 1,3-Benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperidine
• Piperine, European Pharmacopoeia (EP) Reference Standard
• Z104476830
• 1-[5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine
• 4-(1,3-Benzodioxole-5-yl)-1,3-butenylpiperidino ketone
• Piperine, United States Pharmacopeia (USP) Reference Standard
• 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-1-penta-2,4-dienone
• 5-(1,3-dioxaindan-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• Piperidine,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (E,E)-
• (E,E) 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
• 1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine #
• (2E,4E)-5-(1,3-dioxaindan-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• Piperidine, 1-[5-(1,3-benzodioxol-5-yl) -1-oxo-2,4-pentadienyl]-, (E,E)-
• 147030-08-8
• InChI=1/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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	+	0.8147	81.47%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6869	68.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9543	95.43%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6539	65.39%
P-glycoprotein inhibitior	-	0.4563	45.63%
P-glycoprotein substrate	-	0.9175	91.75%
CYP3A4 substrate	-	0.5856	58.56%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.8586	85.86%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.7067	70.67%
CYP2D6 inhibition	+	0.8307	83.07%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8658	86.58%
CYP inhibitory promiscuity	+	0.8136	81.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5912	59.12%
Eye corrosion	-	0.9821	98.21%
Eye irritation	-	0.5667	56.67%
Skin irritation	-	0.7202	72.02%
Skin corrosion	-	0.8834	88.34%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8415	84.15%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.9250	92.50%
skin sensitisation	-	0.8223	82.23%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7287	72.87%
Acute Oral Toxicity (c)	III	0.8002	80.02%
Estrogen receptor binding	+	0.7116	71.16%
Androgen receptor binding	+	0.9000	90.00%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	-	0.7247	72.47%
Aromatase binding	+	0.9037	90.37%
PPAR gamma	+	0.6922	69.22%
Honey bee toxicity	-	0.9389	93.89%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5952	59.52%
Fish aquatic toxicity	+	0.8498	84.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL2581	P07339	Cathepsin D	42300 nM	IC50	DOI: 10.1007/s00044-012-0397-z
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL2039	P27338	Monoamine oxidase B	483 nM	IC50	PMID: 23102654
CHEMBL1293277	O15118	Niemann-Pick C1 protein	2511.9 nM	Potency	via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	74100 nM; 15500 nM	IC50; IC50	PMID: 12130727; PMID: 12130727
CHEMBL1293235	P02545	Prelamin-A/C	631 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	2511.9 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	14125.4 nM	Potency	via CMAUP
CHEMBL4794	Q8NER1	Vanilloid receptor	3162.28 nM	EC50	PMID: 20381363

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.73%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.91%	86.33%
CHEMBL2039	P27338	Monoamine oxidase B	93.49%	92.51%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.25%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.04%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.02%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.91%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.88%	96.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.42%	83.57%
CHEMBL2581	P07339	Cathepsin D	87.33%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.32%	94.80%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.03%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.86%	96.09%
CHEMBL4208	P20618	Proteasome component C5	83.58%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.54%	90.71%

Plants that contains it

• Aglaia perviridis
• Artemisia sericea
• Brickellia longifolia
• Bupleurum rigidum
• Capsicum annuum
• Carpesium longifolium
• Centaurea aegyptiaca
• Cochlearia officinalis
• Coelogyne nitida
• Crocus corsicus
• Dichotomanthes tristaniicarpa
• Dracontium spruceanum
• Euphorbia micractina
• Frullania brasiliensis
• Heptapleurum venulosum
• Homalium laurifolium
• Lychnis coronata
• Matsumurella chinensis
• Palisota barteri
• Piper attenuatum
• Piper betle
• Piper boehmeriifolium
• Piper capense
• Piper guineense
• Piper longum
• Piper nigrum
• Piper pedicellatum
• Piper retrofractum
• Piper suipigua
• Piper thomsonii
• Piper trichostachyon
• Piper tuberculatum
• Retrophyllum minus
• Rubia cordifolia
• Verbesina virginica

Cross-Links

• PubChem: 638024
• NPASS: NPC136330
• ChEMBL: CHEMBL43185
• LOTUS: LTS0014461
• wikiData: Q414501