Compound Detail

CHEMBL180239

CURCUMIN PYRAZOLE

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COc1cc(/C=C/c2cc(/C=C/c3ccc(O)c(OC)c3)[nH]n2)ccc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL180239
Name	CURCUMIN PYRAZOLE
Phase	Preclinical
Structure Type	MOL
InChI Key	LKLASFRCXLTNMY-FCXRPNKRSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

364.4

MW (Da)

4.18

ALogP

HBA

HBD

87.6

PSA (Å²)

0.61

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C21H20N2O4
MW	364.40
Aromatic Rings	3
Heavy Atoms	27
NP-Likeness	0.21

Activity Summary

IC50 35 meas. best 7.89

EC50 3 meas. best 5.14

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	7.89	7.398	13.0	5
SK-BR-3 CHEMBL613834	IC50	6.59	6.59	258.0	1
Calcium/calmodulin-dependent protein kinase type II subunit alpha CHEMBL4147	IC50	6.54	5.69	290.0	4
Unchecked CHEMBL612545	IC50	6.47	5.4325	340.0	8
Plasmodium falciparum CHEMBL364	IC50	6.35	6.335	450.0	2
Amyloid-beta precursor protein CHEMBL2487	IC50	6.32	5.4633	476.0	3
LNCaP CHEMBL612518	IC50	5.47	5.47	3400.0	1
MCF7 CHEMBL387	IC50	5.38	5.305	4190.0	2
PC-3 CHEMBL390	IC50	5.25	5.25	5600.0	1
MDA-MB-231 CHEMBL400	IC50	5.18	5.18	6600.0	1
Polyunsaturated fatty acid lipoxygenase ALOX12 CHEMBL3687	IC50	5.14	5.14	7300.0	1
Protein kinase C theta type CHEMBL3920	EC50	5.14	5.14	7250.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	5.01	5.01	9700.0	1
Protein kinase C delta type CHEMBL2996	EC50	4.83	4.83	14970.0	1
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	4.79	4.79	16200.0	1
Protein kinase C epsilon type CHEMBL3582	EC50	4.73	4.73	18810.0	1
Matrix metalloproteinase-9 CHEMBL321	IC50	4.71	4.71	19400.0	1
Nuclear factor NF-kappa-B complex CHEMBL2094258	IC50	4.53	4.53	29800.0	1
Microtubule-associated protein tau CHEMBL1293224	IC50	4.47	4.47	34000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	13.0	nM	7.89	Inhibition of 5-LO-mediated LTB4 formation in LPS-stimulated human monocytes pre...	24920381
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	13.0	nM	7.89	Inhibition of 5-LO-mediated 5-HETE formation in LPS-stimulated human monocytes p...	24920381
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	13.0	nM	7.89	Inhibition of 5-LO-mediated 5,12-DiHETE formation in LPS-stimulated human monocy...	24920381
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	70.0	nM	7.16	Inhibition of human recombinant 5-LO expressed in Escherichia coli Bl21 (DE3) us...	24920381
SK-BR-3	IC50	=	258.0	nM	6.59	Antiproliferative activity against human SKBR3 cells after 72 hrs by MTS-PMS ass...	19019687
Calcium/calmodulin-dependent protein kinase type II subunit alpha	IC50	=	290.0	nM	6.54	Inhibition of autophosphorylated alphaCaMK2 using GST-NR2A as substrate incubate...	22989913
Unchecked	IC50	=	340.0	nM	6.47	Inhibition of Albino Wistar rat CaMK2 in postsynaptic density fraction using GST...	22989913
Unchecked	IC50	=	440.0	nM	6.36	Inhibition of Albino Wistar rat CaMK2 in brain cytosolic fraction using GST-NR2A...	22989913
Plasmodium falciparum	IC50	=	450.0	nM	6.35	Antimalarial activity against chloroquine-resistant Plasmodium falciparum MP14	18194869
Plasmodium falciparum	IC50	=	480.0	nM	6.32	Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCK2	18194869
Amyloid-beta precursor protein	IC50	=	476.0	nM	6.32	Inhibition of amyloid beta 42 transfected in human H4 cells incubated for 20 to ...	33548635
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	700.0	nM	6.16	Inhibition of 5-LO in human neutrophils using arachidonic acid as substrate prei...	24920381
Calcium/calmodulin-dependent protein kinase type II subunit alpha	IC50	=	1490.0	nM	5.83	Inhibition of alphaCaMK2 using GST-NR2A as substrate incubated for 1 min prior t...	22989913
LNCaP	IC50	=	3400.0	nM	5.47	Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay	19249204
Unchecked	IC50	=	3600.0	nM	5.44	Inhibition of Albino Wistar rat CaMK2 in postsynaptic density fraction using GST...	22989913
MCF7	IC50	=	4190.0	nM	5.38	Antiproliferative activity against human MCF7 cells after 72 hrs by MTS-PMS assa...	19019687
Unchecked	IC50	=	4400.0	nM	5.36	Inhibition of Albino Wistar rat CaMK2 in brain cytosolic fraction using GST-NR2A...	22989913
Unchecked	IC50	=	5200.0	nM	5.28	Inhibition of amyloid beta 38 secretion transfected in human H4 cells incubated ...	33548635
PC-3	IC50	=	5600.0	nM	5.25	Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay	19249204
MCF7	IC50	=	5900.0	nM	5.23	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	19249204

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1007/s00044-009-9199-3	NON-PROTEIN TARGET	8
24920381	10.1021/jm500308c	Polyunsaturated fatty acid 5-lipoxygenase	8
22989913	10.1016/j.bmc.2012.08.029	Unchecked	6
18194869	10.1016/j.bmc.2007.12.054	Plasmodium falciparum	4
22989913	10.1016/j.bmc.2012.08.029	Calcium/calmodulin-dependent protein kinase type II subunit alpha	4
30031653	10.1016/j.bmc.2018.07.027	Amyloid-beta precursor protein	4
24920381	10.1021/jm500308c	Prostaglandin G/H synthase 1	4
31336310	10.1016/j.ejmech.2019.07.034	Unchecked	3
24920381	10.1021/jm500308c	Prostaglandin G/H synthase 2	3
33548635	10.1016/j.ejmech.2021.113209	Amyloid-beta precursor protein	3
15780608	10.1016/j.bmcl.2005.02.039	Prostaglandin G/H synthase 2	3
19249204	10.1016/j.bmcl.2009.01.104	MDA-MB-231	2
19128977	10.1016/j.bmc.2008.12.029	Matrix metalloproteinase-9	2
33548635	10.1016/j.ejmech.2021.113209	Microtubule-associated protein tau	2
19249204	10.1016/j.bmcl.2009.01.104	MCF7	2
19249204	10.1016/j.bmcl.2009.01.104	LNCaP	2
24920381	10.1021/jm500308c	Prostaglandin E synthase	2
21975067	10.1016/j.bmc.2011.09.011	Unchecked	2
19249204	10.1016/j.bmcl.2009.01.104	ADMET	1
20691508	10.1016/j.ejmech.2010.07.003	Mycobacterium tuberculosis	1

Data from ChEMBL 36 via Core Engine