Compound Detail

CHEMBL105350

BISDEMETHOXYCURCUMIN

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O=C(/C=C/c1ccc(O)cc1)CC(=O)/C=C/c1ccc(O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL105350
Name	BISDEMETHOXYCURCUMIN
Phase	Preclinical
Structure Type	MOL
InChI Key	PREBVFJICNPEKM-YDWXAUTNSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

308.3

MW (Da)

3.35

ALogP

HBA

HBD

74.6

PSA (Å²)

0.63

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	C19H16O4
MW	308.33
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	0.72

Activity Summary

IC50 33 meas. best 7.52

EC50 6 meas. best 5.35

Ki 3 meas. best 6.1

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
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	7.22	7.22	60.0	1
Amine oxidase [flavin-containing] B CHEMBL2039	Ki	6.1	6.1	800.0	1
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	5.59	5.59	2590.0	1
Trypanosoma brucei brucei CHEMBL612851	EC50	5.35	5.16	4500.0	3
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	5.29	5.29	5100.0	1
HT-1080 CHEMBL614580	IC50	5.16	5.16	7000.0	1
Lactoylglutathione lyase CHEMBL2424	Ki	4.75	4.745	18000.0	2
Acetylcholinesterase CHEMBL4078	IC50	4.74	4.74	18270.0	1
LNCaP CHEMBL612518	IC50	4.71	4.71	19700.0	1
KB CHEMBL398	IC50	4.67	4.67	21440.0	1
MDA-MB-231 CHEMBL400	IC50	4.66	4.5667	21900.0	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.65	4.3167	22300.0	3
MCF7 CHEMBL387	IC50	4.61	4.4633	24300.0	3
HL-60 CHEMBL383	IC50	4.6	4.6	25120.0	1
PC-3 CHEMBL390	IC50	4.56	4.56	27300.0	1
DU-145 CHEMBL613508	IC50	4.52	4.52	30100.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	4.44	4.44	36370.0	1
Calcium/calmodulin-dependent protein kinase type II subunit alpha CHEMBL4147	IC50	4.43	4.43	37000.0	1
A549 CHEMBL392	IC50	4.42	4.42	38100.0	1
Multidrug resistance protein CDR1 CHEMBL1163109	IC50	4.4	4.4	40000.0	1
WRL68 CHEMBL612587	IC50	4.34	4.34	45400.0	1
HepG2 CHEMBL395	IC50	4.2	4.16	62900.0	2
Leishmania mexicana CHEMBL612880	EC50	4.2	4.2	63000.0	1
Leishmania major CHEMBL612879	EC50	4.14	4.14	72000.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	4.1	4.05	80000.0	2
NCI-H460 CHEMBL396	IC50	4.05	4.05	88100.0	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
Aldo-keto reductase family 1 member B10	IC50	=	60.0	nM	7.22	Inhibition of AKR1B10 (unknown origin)	28976752
Amine oxidase [flavin-containing] B	Ki	=	800.0	nM	6.1	Inhibition of human MAO-B assessed as inhibition constant using benzylamine as s...	32942081
Amine oxidase [flavin-containing] B	IC50	=	2590.0	nM	5.59	Inhibition of human MAO-B using benzylamine as substrate	32942081
Trypanosoma brucei brucei	EC50	=	4500.0	nM	5.35	Antitrypanosomal activity against multidrug-resistant Trypanosoma brucei brucei ...	20004045
Aldo-keto reductase family 1 member B1	IC50	=	5100.0	nM	5.29	Inhibition of AKR1B1 (unknown origin)	28976752
HT-1080	IC50	=	7000.0	nM	5.16	Decrease in UPA expression in human HT1080 cells	31336310
Trypanosoma brucei brucei	EC50	=	7700.0	nM	5.11	Antitrypanosomal activity against Trypanosoma brucei brucei 427 after 48 hrs by ...	20004045
Trypanosoma brucei brucei	EC50	=	9500.0	nM	5.02	Antitrypanosomal activity against diminazene-resistant Trypanosoma brucei brucei...	20004045
Lactoylglutathione lyase	Ki	=	18000.0	nM	4.75	Inhibition of human recombinant His-tagged glyoxalase 1 expressed in Escherichia...	21237663
Lactoylglutathione lyase	Ki	=	18200.0	nM	4.74	Inhibition of human glyoxalase 1	21689932
Acetylcholinesterase	IC50	=	18270.0	nM	4.74	Inhibition of electric eel AChE using acetylthiocholine iodide as substrate afte...	23583510
LNCaP	IC50	=	19700.0	nM	4.71	Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay	19249204
KB	IC50	=	21440.0	nM	4.67	Cytotoxicity against human KB cells assessed as growth inhibition by resazurin m...	24857542
MDA-MB-231	IC50	=	21900.0	nM	4.66	Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT as...	19249204
NON-PROTEIN TARGET	IC50	=	22300.0	nM	4.65	Cytotoxicity against human EOL-1 cells after 48 hrs by MTT assay	24689857
MDA-MB-231	IC50	=	24000.0	nM	4.62	Inhibition of TGF-beta-induced PTHrP secretion in human MDA-MB-231 cells treated...	23145932
MCF7	IC50	=	24300.0	nM	4.61	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	19249204
HL-60	IC50	=	25120.0	nM	4.6	Cytotoxicity against human HL60	16038556
PC-3	IC50	=	27300.0	nM	4.56	Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay	19249204

Literature References

PubMed	DOI	Target Context	# Activities
23145932	10.1021/np300663v	Mus musculus	14
23145932	10.1021/np300663v	MDA-MB-231	14
27521589	10.1016/j.ejmech.2016.07.017	NON-PROTEIN TARGET	10
27843113	10.1016/j.bmcl.2016.10.068	NON-PROTEIN TARGET	7
9584408	10.1021/np970459f	DNA topoisomerase 1	6
9584408	10.1021/np970459f	DNA topoisomerase 2	6
25666820	10.1016/j.bmcl.2015.01.027	NON-PROTEIN TARGET	6
17652175	10.1073/pnas.0701267104	PBMC	5
9461664	10.1021/np970293i	NON-PROTEIN TARGET	4
27843113	10.1016/j.bmcl.2016.10.068	No relevant target	4
24275249	10.1016/j.ejmech.2013.10.073	Molecular identity unknown	4
27521589	10.1016/j.ejmech.2016.07.017	No relevant target	3
20004045	10.1016/j.ejmech.2009.11.035	Trypanosoma brucei brucei	3
27843113	10.1016/j.bmcl.2016.10.068	HepG2	2
12350137	10.1021/np010039x	PC-12	2
27843113	10.1016/j.bmcl.2016.10.068	Caco-2	2
32942081	10.1016/j.ejmech.2020.112787	Amine oxidase [flavin-containing] B	2
15780608	10.1016/j.bmcl.2005.02.039	Prostaglandin G/H synthase 2	2
27843113	10.1016/j.bmcl.2016.10.068	EA.hy 926	2
24689857	10.1021/np401028h	EOL1	2

Data from ChEMBL 36 via Core Engine