Compound Detail

CHEMBL140

CURCUMIN

🧪 Phase III

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🧪 Phase III

COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(O)c(OC)c2)ccc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL140
Name	CURCUMIN
Phase	Phase III
Structure Type	MOL
InChI Key	VFLDPWHFBUODDF-FCXRPNKRSA-N

Known Names

C.i. 75300 C.i. natural yellow 3 Ci 75300 Ci-75300 Curcumin Curcumin e100 Diferuloylmethane E 100 E-100 E100 Haldar INS NO. 100(I) +10 more

253

Targets

941

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

368.4

MW (Da)

3.37

ALogP

HBA

HBD

93.1

PSA (Å²)

0.55

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C21H20O6
MW	368.39
Aromatic Rings	2
Heavy Atoms	27
NP-Likeness	0.72

Indications

Colitis, Ulcerative Colonic Neoplasms Colonic Neoplasms Crohn Disease Optic Atrophy, Hereditary, Leber Pancreatic Neoplasms Periodontitis Prostatic Neoplasms, Castration-Resistant Proteinuria Renal Insufficiency, Chronic Stomatitis Tobacco Use Disorder Adenomatous Polyposis Coli Alzheimer Disease Asthma Bipolar Disorder Breast Neoplasms Cognition Cognitive Dysfunction Colorectal Neoplasms

Activity Summary

IC50 843 meas. best 8.6

EC50 49 meas. best 8.0

Ki 30 meas. best 9.68

Kd 19 meas. best 6.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Amyloid-beta precursor protein CHEMBL2487	Ki	9.68	9.68	0.2	1
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	IC50	8.6	7.72	2.5	4
Unchecked CHEMBL612545	Ki	8.45	7.875	3.6	2
Lactoylglutathione lyase CHEMBL2424	Ki	8.3	6.0967	5.0	3
Transcription factor AP1 CHEMBL2111421	IC50	8.16	8.16	6.9	1
Human alphaherpesvirus 2 CHEMBL370	EC50	8.0	8.0	10.0	1
Human alphaherpesvirus 1 CHEMBL377	EC50	8.0	8.0	10.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	8.0	5.4729	10.0	7
Vaccinia virus CHEMBL613493	EC50	8.0	8.0	10.0	1
Vesicular stomatitis virus CHEMBL613739	EC50	8.0	8.0	10.0	1
Human gammaherpesvirus 4 CHEMBL613124	IC50	7.99	7.99	10.2	1
Tissue factor CHEMBL4081	IC50	7.88	7.0933	13.2	3
Orphan methyltransferase M.SssI CHEMBL4373	IC50	7.52	7.52	30.0	1
Human immunodeficiency virus 1 CHEMBL378	IC50	7.43	7.43	37.0	1
Human immunodeficiency virus 2 CHEMBL380	IC50	7.43	7.43	37.0	1
Rattus norvegicus CHEMBL376	IC50	7.27	7.27	53.4	1
Glycogen synthase kinase-3 beta CHEMBL3669	IC50	7.18	7.18	66.0	1
MCF7 CHEMBL387	IC50	7.06	4.6989	88.0	37
CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168	Ki	7.0	7.0	101.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	6.97	5.2703	107.0	37
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	IC50	6.83	6.83	147.7	1
Prostaglandin E synthase CHEMBL5658	IC50	6.7	6.404	200.0	5
Alpha-synuclein CHEMBL6152	IC50	6.66	6.07	220.0	2
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	6.52	6.52	300.0	1
DU-145 CHEMBL613508	IC50	6.52	4.7473	300.0	15
Carbonic anhydrase 2 CHEMBL205	Ki	6.42	6.42	380.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.38	4.7979	420.0	61
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	6.3	5.7129	500.0	7
Unchecked CHEMBL612545	IC50	6.3	4.888	500.0	71
BV-2 CHEMBL614781	IC50	6.3	5.585	500.0	12
Alpha-synuclein CHEMBL6152	Kd	6.3	5.6225	500.0	4
Unchecked CHEMBL612545	Kd	6.29	5.4591	507.0	11
Histone deacetylase CHEMBL2093865	Ki	6.27	6.27	539.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	Ki	6.15	6.15	710.0	1
Nitric oxide synthase, inducible CHEMBL3464	IC50	6.1	6.1	800.0	1
RAW264.7 CHEMBL612557	IC50	6.1	5.0579	800.0	24
MDA-MB-231 CHEMBL400	IC50	6.06	4.672	880.0	15
Potassium channel subfamily K member 2 CHEMBL1075183	IC50	6.03	6.03	930.0	1
Thymocyte CHEMBL613302	IC50	5.99	5.99	1020.0	1
D-amino-acid oxidase CHEMBL6172	IC50	5.97	5.97	1070.0	2
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL2903	IC50	5.92	5.92	1200.0	1
Monocyte CHEMBL614076	IC50	5.92	5.92	1200.0	2
THP-1 CHEMBL614245	IC50	5.92	5.285	1210.0	2
NCI-H1975 CHEMBL614348	IC50	5.85	5.85	1400.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	5.79	5.79	1630.0	1
17-beta-hydroxysteroid dehydrogenase type 2 CHEMBL2789	IC50	5.76	5.76	1730.0	1
No relevant target CHEMBL2362975	IC50	5.75	4.6782	1800.0	11
Trypanosoma brucei CHEMBL612849	EC50	5.75	5.75	1780.0	1
Glutathione S-transferase Mu 2 CHEMBL4589	IC50	5.74	5.74	1810.0	1
U-937 CHEMBL612794	IC50	5.73	5.73	1880.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	275.0	ng.hr.mL-1	Rattus norvegicus
AUC	672.0	ng.hr.mL-1	Rattus norvegicus
AUC	2.43	ng.hr.mL-1	Mus musculus
AUC	179553.29	ng.hr.mL-1	Mus musculus
AUC	17682.72	ng.hr.mL-1	Mus musculus
AUC	179590.12	ng.hr.mL-1	Mus musculus
AUC	17793.24	ng.hr.mL-1	Mus musculus
CL	161.2	mL.min-1.kg-1	Rattus norvegicus
CL	3039.83	mL.min-1.kg-1	Not specified
Cmax	247.02	nM	Rattus norvegicus
Cmax	1.547	nM	Mus musculus
Cmax	154.73	nM	Homo sapiens
Cmax	6243.38	nM	Homo sapiens
Cmax	4696.11	nM	Homo sapiens
Cmax	60.0	nM	Mus musculus
Cmax	156.36	nM	Homo sapiens
Cmax	27000.0	nM	Mus musculus
Cmax	81000.0	nM	Mus musculus
Cmax	1770.0	nM	Homo sapiens
Cmax	106100.0	nM	Mus musculus
Cmax	5900.0	nM	Mus musculus
Cmax	6.379	nM	Mesocricetus auratus
F	1.0	%	Rattus norvegicus
F	2000.0	%	Homo sapiens
F	1.0	%	Rattus norvegicus
F	1.0	%	Rattus norvegicus
Ka	4.5	10'5/M	Capra hircus
Ka	2664.0	/s	Influenza A virus (A/WSN/1933(H1N1))
MRT	3.436	hr	Rattus norvegicus
MRT	22.69	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Amyloid-beta precursor protein	Ki	=	0.208	nM	9.68	Displacement of [125I]IMSB from beta amyloid protein 40	17004725
Dual specificity tyrosine-phosphorylation-regulated kinase 2	IC50	=	2.5	nM	8.6	Inhibition of human GST-tagged DYRK2 expressed in Escherichia coli BL21 (DE3) us...	36800260
Unchecked	Ki	=	3.57	nM	8.45	Binding affinity to amyloid beta (1 to 42) after 3 hrs using [125I]IMSB by gamma...	21885280
Dual specificity tyrosine-phosphorylation-regulated kinase 2	IC50	=	5.0	nM	8.3	Inhibition of N-terminal 6his tagged/ TEV fused full length human DYRK2 expresse...	38033250
Lactoylglutathione lyase	Ki	=	5.0	nM	8.3	Inhibition of human erythrocyte Glyoxalase-1 using GSH and MGO as substrate by D...	31879183
Transcription factor AP1	IC50	=	6.9	nM	8.16	Inhibition of Fos-Jun dimer formation (unknown origin)	24831826
Human alphaherpesvirus 2	EC50	=	10.0	nM	8.0	Antiviral activity against Herpes simplex virus 2 G infected in HEL cells assess...	20034711
Dual specificity tyrosine-phosphorylation-regulated kinase 2	IC50	=	10.0	nM	8.0	Inhibition of human recombinant DYRK2 using KKISGRLSPIMTEQ as substrate incubate...	38746900
NON-PROTEIN TARGET	EC50	=	10.0	nM	8.0	Antiprion activity against Scrapie prion protein-mediated scrapie in mouse ScNB ...	19842664
Vaccinia virus	EC50	=	10.0	nM	8.0	Antiviral activity against Vaccinia virus infected in HEL cells assessed as prot...	20034711
Vesicular stomatitis virus	EC50	=	10.0	nM	8.0	Antiviral activity against VSV infected in HEL cells assessed as protection from...	20034711
Human alphaherpesvirus 1	EC50	=	10.0	nM	8.0	Antiviral activity against acyclovir-sensitive Herpes simplex virus 1 KOS infect...	20034711
Human gammaherpesvirus 4	IC50	=	10.2	nM	7.99	Inhibition of TPA-induced Epstein-Barr virus early antigen activation in Raji ce...	17503850
Tissue factor	IC50	=	13.16	nM	7.88	Inhibition of LPS-induced tissue factor procoagulant activity in human THP1 cell...	28109788
Orphan methyltransferase M.SssI	IC50	=	30.0	nM	7.52	Inhibition of Spiroplasma sp. MQ-1 M.SssI	19112019
Human immunodeficiency virus 2	IC50	=	37.0	nM	7.43	Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as prot...	20034711
Human immunodeficiency virus 1	IC50	=	37.0	nM	7.43	Antiviral activity against HIV1 3B-infected in human MT4 cells assessed as prote...	20034711
Unchecked	Ki	=	49.8	nM	7.3	Displacement of [125I]IMPY from amyloid beta (1 to 42) aggregate after 2 hrs by ...	21417461
Rattus norvegicus	IC50	=	53.4	nM	7.27	Antiinflammatory activity in carrageenan induced rat paw edema model assessed in...	32795767
Glycogen synthase kinase-3 beta	IC50	=	66.0	nM	7.18	Inhibition of recombinant rat N-terminal GST-tagged GSK3beta expressed in Escher...	28074653

Literature References

PubMed	DOI	Target Context	# Activities
30794412	10.1021/acs.jnatprod.8b00873	ADMET	37
21504179	10.1021/jm200017g	NCI-H460	27
24960549	10.1021/jm401352a	Molecular identity unknown	26
17145789	10.1128/aac.01238-06	Plasmodium falciparum	21
19388706	10.1021/np8007123	Xanthine dehydrogenase/oxidase	19
28523093	10.1021/acsmedchemlett.7b00139	Homo sapiens	19
18284200	10.1021/jf072591j	Pseudomonas aeruginosa	17
19653644	10.1021/np900227x	Unchecked	16
27295561	10.1021/acs.jnatprod.6b00286	Acinetobacter baumannii	15
27295561	10.1021/acs.jnatprod.6b00286	Pseudomonas aeruginosa	15
23145932	10.1021/np300663v	MDA-MB-231	14
23145932	10.1021/np300663v	Mus musculus	14
19204190	10.1128/aac.01242-08	Helicobacter pylori	12
27295561	10.1021/acs.jnatprod.6b00286	Staphylococcus aureus	12
27295561	10.1021/acs.jnatprod.6b00286	Stenotrophomonas maltophilia	12
26810315	10.1016/j.bmcl.2015.12.013	No relevant target	12
32311607	10.1016/j.ejmech.2020.112293	Mus musculus	12
27521589	10.1016/j.ejmech.2016.07.017	NON-PROTEIN TARGET	11
20227282	10.1016/j.bmc.2010.02.029	Unchecked	11
32311607	10.1016/j.ejmech.2020.112293	Rattus norvegicus	11

Data from ChEMBL 36 via Core Engine