Compound Detail

CHEMBL179512

DEMETHOXYCURCUMIN

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COc1cc(/C=C/C(O)=C/C(=O)/C=C/c2ccc(O)cc2)ccc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL179512
Name	DEMETHOXYCURCUMIN
Phase	Preclinical
Structure Type	MOL
InChI Key	UEPVWRDHSPMIAZ-IZTHOABVSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

338.4

MW (Da)

3.84

ALogP

HBA

HBD

87.0

PSA (Å²)

0.42

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	C20H18O5
MW	338.36
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	1.14

Activity Summary

IC50 31 meas. best 7.52

EC50 6 meas. best 5.66

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Orphan methyltransferase M.SssI CHEMBL4373	IC50	7.52	7.52	30.0	1
Trypanosoma brucei brucei CHEMBL612851	EC50	5.66	5.41	2200.0	3
Beta Lactamase CHEMBL1293246	IC50	5.09	5.09	8095.0	1
Intestinal-type alkaline phosphatase CHEMBL3151	IC50	5.08	5.08	8380.0	1
Toll-like receptor 9 CHEMBL5804	IC50	5.04	5.04	9127.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.81	4.81	15600.0	1
MCF7 CHEMBL387	IC50	4.73	4.425	18510.0	2
HT-29 CHEMBL384	IC50	4.71	4.71	19380.0	1
Unchecked CHEMBL612545	IC50	4.7	4.7	20000.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	4.67	4.67	21360.0	1
DU-145 CHEMBL613508	IC50	4.66	4.49	21700.0	2
HL-60 CHEMBL383	IC50	4.62	4.62	24210.0	1
BXPC-3 CHEMBL614530	IC50	4.62	4.62	24140.0	1
MDA-MB-231 CHEMBL400	IC50	4.62	4.3433	24000.0	3
Calcium/calmodulin-dependent protein kinase type II subunit alpha CHEMBL4147	IC50	4.62	4.62	24000.0	1
NCI-H460 CHEMBL396	IC50	4.59	4.59	25700.0	1
KB CHEMBL398	IC50	4.58	4.58	26450.0	1
Leishmania mexicana CHEMBL612880	EC50	4.43	4.43	37000.0	1
Leishmania major CHEMBL612879	EC50	4.43	4.43	37000.0	1
Acetylcholinesterase CHEMBL4078	IC50	4.42	4.42	37740.0	1
A549 CHEMBL392	IC50	4.42	4.275	38100.0	2
CHO CHEMBL613853	IC50	4.41	4.41	39345.0	1
HEK293 CHEMBL614818	EC50	4.4	4.4	40000.0	1
Multidrug resistance protein CDR1 CHEMBL1163109	IC50	4.35	4.35	45000.0	1
HepG2 CHEMBL395	IC50	4.24	4.17	58100.0	2
SK-MEL-5 CHEMBL614922	IC50	4.21	4.21	61410.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Orphan methyltransferase M.SssI	IC50	=	30.0	nM	7.52	Inhibition of Spiroplasma sp. MQ-1 M.SssI	19112019
Trypanosoma brucei brucei	EC50	=	2200.0	nM	5.66	Antitrypanosomal activity against multidrug-resistant Trypanosoma brucei brucei ...	20004045
Trypanosoma brucei brucei	EC50	=	4600.0	nM	5.34	Antitrypanosomal activity against Trypanosoma brucei brucei 427 after 48 hrs by ...	20004045
Trypanosoma brucei brucei	EC50	=	5900.0	nM	5.23	Antitrypanosomal activity against diminazene-resistant Trypanosoma brucei brucei...	20004045
Beta Lactamase	IC50	=	8095.0	nM	5.09	PUBCHEM_BIOASSAY: Counterscreen for inhibitors of TLR9-MyD88 binding: fluorescen...	-
Intestinal-type alkaline phosphatase	IC50	=	8380.0	nM	5.08	PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS hits from a small molecule ...	-
Toll-like receptor 9	IC50	=	9127.0	nM	5.04	PUBCHEM_BIOASSAY: Fluorescence-based cell-based high throughput dose response as...	-
NON-PROTEIN TARGET	IC50	=	15600.0	nM	4.81	Cytotoxicity against human EOL-1 cells after 48 hrs by MTT assay	24689857
MCF7	IC50	=	18510.0	nM	4.73	Cytotoxicity against human MCF7	16038556
HT-29	IC50	=	19380.0	nM	4.71	Antiproliferative activity against human HT-29 cells after 48 hrs by MTS assay	22546674
Unchecked	IC50	=	20000.0	nM	4.7	Inhibition of TrxR preincuabatd for 2 mins	18678491
Prostaglandin G/H synthase 2	IC50	=	21360.0	nM	4.67	Anti-oxidant activity in DPPH radicak scavenging assay; n=3-4	15780608
DU-145	IC50	=	21700.0	nM	4.66	Cytotoxicity against human DU145	16038556
BXPC-3	IC50	=	24140.0	nM	4.62	Antiproliferative activity against human BxPC3 cells after 48 hrs by MTS assay	22546674
MDA-MB-231	IC50	=	24000.0	nM	4.62	Inhibition of TGF-beta-induced PTHrP secretion in human MDA-MB-231 cells treated...	23145932
Calcium/calmodulin-dependent protein kinase type II subunit alpha	IC50	=	24000.0	nM	4.62	Inhibition of alphaCaMK2 using GST-NR2A as substrate incubated for 1 min prior t...	22989913
HL-60	IC50	=	24210.0	nM	4.62	Cytotoxicity against human HL60	16038556
NCI-H460	IC50	=	25700.0	nM	4.59	Cytotoxicity against human NCI-H460	16038556
KB	IC50	=	26450.0	nM	4.58	Cytotoxicity against human KB cells assessed as growth inhibition by resazurin m...	24857542
Leishmania mexicana	EC50	=	37000.0	nM	4.43	Antileishmanial activity against Leishmania mexicana MNYC/BZ/62/M379 amastigotes...	20004045

Literature References

PubMed	DOI	Target Context	# Activities
23145932	10.1021/np300663v	MDA-MB-231	14
23145932	10.1021/np300663v	Mus musculus	14
24689857	10.1021/np401028h	EOL1	3
20004045	10.1016/j.ejmech.2009.11.035	Trypanosoma brucei brucei	3
9584408	10.1021/np970459f	DNA topoisomerase 2	3
9584408	10.1021/np970459f	DNA topoisomerase 1	3
15780608	10.1016/j.bmcl.2005.02.039	Prostaglandin G/H synthase 2	2
25313922	10.1021/np500396y	HT-22	2
25753330	10.1016/j.bmc.2015.02.003	Epidermal growth factor receptor	2
24360557	10.1016/j.bmcl.2013.11.039	Beta-secretase 1	2
12350137	10.1021/np010039x	PC-12	2
9301668	10.1021/jm970190x	Human immunodeficiency virus type 1 integrase	2
16038556	10.1021/np0500171	HL-60	1
16038556	10.1021/np0500171	HepG2	1
16038556	10.1021/np0500171	MCF7	1
16038556	10.1021/np0500171	DU-145	1
19112019	10.1016/j.bmcl.2008.12.041	Orphan methyltransferase M.SssI	1
19112019	10.1016/j.bmcl.2008.12.041	DNA (cytosine-5)-methyltransferase 1	1
16180819	10.1021/np049743e	No relevant target	1
9868158	10.1021/np980269k	OVCAR-3	1

Data from ChEMBL 36 via Core Engine