Compound Detail

CHEMBL43185

PIPERINE

🧪 Phase II

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🧪 Phase II

O=C(/C=C/C=C/c1ccc2c(c1)OCO2)N1CCCCC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL43185
Name	PIPERINE
Phase	Phase II
Structure Type	MOL
InChI Key	MXXWOMGUGJBKIW-YPCIICBESA-N

Known Names

Bioperine FEMA NO. 2909 NSC-21727 Piperine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

285.3

MW (Da)

3.00

ALogP

HBA

HBD

38.8

PSA (Å²)

0.63

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C17H19NO3
MW	285.34
Aromatic Rings	1
Heavy Atoms	21
NP-Likeness	0.13

Indications

Lupus Erythematosus, Systemic Deglutition Disorders Pain

Activity Summary

IC50 38 meas. best 6.58

Ki 5 meas. best 6.15

EC50 4 meas. best 5.5

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Amine oxidase [flavin-containing] B CHEMBL2993	IC50	6.58	6.58	260.0	1
Amine oxidase [flavin-containing] A CHEMBL3358	IC50	6.39	6.39	404.0	1
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	6.32	6.15	483.0	2
Dihydroorotate dehydrogenase (quinone), mitochondrial CHEMBL1966	Ki	6.15	6.15	710.0	1
Dihydroorotate dehydrogenase (quinone), mitochondrial CHEMBL1966	IC50	6.06	6.06	880.0	1
HeLa CHEMBL399	IC50	6.02	5.37	950.0	2
MCF7 CHEMBL387	IC50	6.0	4.9633	990.0	3
Histone deacetylase 6 CHEMBL1865	IC50	5.98	5.98	1044.0	1
Transient receptor potential cation channel subfamily V member 1 CHEMBL4794	EC50	5.5	5.5	3162.3	1
Amine oxidase [flavin-containing] B CHEMBL3050	Ki	5.5	5.5	3190.0	1
Trypanosoma cruzi CHEMBL368	IC50	5.31	5.238	4910.0	5
GABA-A receptor; alpha-1/beta-2/gamma-2 CHEMBL2095172	EC50	5.24	4.76	5800.0	2
WI-38 CHEMBL614391	IC50	5.06	5.06	8800.0	1
IMR-32 CHEMBL614585	IC50	4.99	4.52	10190.0	2
Hepatocyte CHEMBL3140324	IC50	4.92	4.92	12000.0	1
A549 CHEMBL392	IC50	4.92	4.92	11890.0	1
Leishmania amazonensis CHEMBL612877	IC50	4.84	4.84	14500.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	4.81	4.47	15500.0	2
Amine oxidase [flavin-containing] A CHEMBL3681	Ki	4.72	4.72	19000.0	1
L929 CHEMBL612267	IC50	4.38	4.38	42000.0	1
Cathepsin D CHEMBL2581	IC50	4.37	4.37	42300.0	1
COLO 205 CHEMBL614561	IC50	4.34	4.34	46000.0	1
Amine oxidase [flavin-containing] A CHEMBL3358	Ki	4.31	4.31	49300.0	1
Unchecked CHEMBL612545	EC50	4.28	4.28	52000.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	4.27	4.27	54000.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	4.23	4.23	58980.0	1
HEp-2 CHEMBL614735	IC50	4.16	4.16	70000.0	1
Staphylococcus aureus CHEMBL352	IC50	4.14	4.14	72300.0	1
Amine oxidase [flavin-containing] B CHEMBL2993	Ki	4.04	4.04	91300.0	1
HUVEC CHEMBL613979	IC50	4.0	4.0	100000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	3370.0	ng.hr.mL-1	Homo sapiens
AUC	5300.0	ng.hr.mL-1	Homo sapiens
Cmax	1401.84	nM	Homo sapiens
Cmax	19170.11	nM	Mus musculus
ka	1.41	/hr	Homo sapiens
Tmax	2.5	hr	Homo sapiens
Tmax	6.0	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Amine oxidase [flavin-containing] B	IC50	=	260.0	nM	6.58	Inhibition of MAO-B in Sprague-Dawley rat brain homogenate using kynuramine as s...	22475561
Amine oxidase [flavin-containing] A	IC50	=	404.0	nM	6.39	Inhibition of MAO-A in Sprague-Dawley rat brain homogenate using kynuramine as s...	22475561
Amine oxidase [flavin-containing] B	IC50	=	483.0	nM	6.32	Inhibition of MAO-B assessed as inhibition of kyneuramine conversion to 4-hydrox...	23102654
Dihydroorotate dehydrogenase (quinone), mitochondrial	Ki	=	710.0	nM	6.15	Binding affinity to N-terminal 6His-tagged recombinant human DHODH expressed in ...	35151222
Dihydroorotate dehydrogenase (quinone), mitochondrial	IC50	=	880.0	nM	6.06	Inhibition of N-terminal 6His-tagged recombinant human DHODH expressed in Escher...	35151222
HeLa	IC50	=	950.0	nM	6.02	Cytotoxicity against Homo sapiens (human) HeLa cells after 48 hr by MTT assay	-
MCF7	IC50	=	990.0	nM	6.0	Cytotoxicity against Homo sapiens (human) MCF7 cells after 48 hr by MTT assay	-
Histone deacetylase 6	IC50	=	1044.0	nM	5.98	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Amine oxidase [flavin-containing] B	IC50	=	1050.0	nM	5.98	Inhibition of human microsomal MAO-B expressed in baculovirus infected BTI-TN-5B...	31711793
Transient receptor potential cation channel subfamily V member 1	EC50	=	3162.28	nM	5.5	Agonist activity at human TRPV1 expressed in tetracycline-stimulated HEK293 cell...	20381363
Amine oxidase [flavin-containing] B	Ki	=	3190.0	nM	5.5	Inhibition of mouse brain MAOB	19969454
Trypanosoma cruzi	IC50	=	4910.0	nM	5.31	In vitro growth inhibition of amastigotes of Trypanosoma cruzi	15177472
Trypanosoma cruzi	IC50	=	4910.0	nM	5.31	Antiparasitic activity against Trypanosoma cruzi Y amastigotes	18226906
Trypanosoma cruzi	IC50	=	5000.0	nM	5.3	Antimicrobial activity against Trypanosoma cruzi	20185316
GABA-A receptor; alpha-1/beta-2/gamma-2	EC50	=	5800.0	nM	5.24	Positive allosteric modulation of GABAA alpha1beta2gamma2 receptor (unknown orig...	35475609
Trypanosoma cruzi	IC50	=	7310.0	nM	5.14	Antiparasitic activity against Trypanosoma cruzi Y epimastigote	18226906
Trypanosoma cruzi	IC50	=	7360.0	nM	5.13	In vitro growth inhibition of epimastigotes of Trypanosoma cruzi	15177472
WI-38	IC50	=	8800.0	nM	5.06	Induction of senescence in human WI-38 cells	38436272
IMR-32	IC50	=	10190.0	nM	4.99	Antiproliferative activity in human IMR32 cells assessed as reduction in cell nu...	30108756
A549	IC50	=	11890.0	nM	4.92	Antiproliferative activity in human A549 cells assessed as reduction in cell num...	30108756

Literature References

PubMed	DOI	Target Context	# Activities
33492139	10.1021/acs.jnatprod.0c01018	Unchecked	22
33492139	10.1021/acs.jnatprod.0c01018	Mus musculus	13
25740159	10.1016/j.bmcl.2015.02.013	No relevant target	9
18289853	10.1016/j.bmcl.2008.01.101	Mus musculus	9
18289853	10.1016/j.bmcl.2008.01.101	Hepatocyte	9
19775895	10.1016/j.bmc.2009.08.050	Mus musculus	9
33492139	10.1021/acs.jnatprod.0c01018	ADMET	9
20085307	10.1021/np900656g	Unchecked	9
27810594	10.1016/j.ejmech.2016.10.047	Unchecked	8
19775895	10.1016/j.bmc.2009.08.050	Hepatocyte	8
11808866	10.1007/bf03226378	Homo sapiens	6
-	10.1016/0960-894X(95)00272-U	Nucleic Acid	6
27503686	10.1016/j.bmcl.2016.07.062	Quinolone resistance protein NorA	6
19523722	10.1016/j.ejmech.2009.05.004	Quinolone resistance protein NorA	5
19775895	10.1016/j.bmc.2009.08.050	L929	5
25596479	10.1016/j.ejmech.2015.01.001	Rattus norvegicus	5
20381363	10.1016/j.bmc.2010.03.013	Transient receptor potential cation channel subfamily V member 1	4
20159656	10.1016/j.bmc.2010.01.047	L929	4
19775895	10.1016/j.bmc.2009.08.050	Peritoneal macrophage cell	4
18477507	10.1016/j.bmcl.2008.04.052	3T3-L1	4

Data from ChEMBL 36 via Core Engine