Compound Detail

CHEMBL15193

LAPACHOL

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CC(C)=CCC1=C(O)C(=O)c2ccccc2C1=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL15193
Name	LAPACHOL
Phase	Preclinical
Structure Type	MOL
InChI Key	CIEYTVIYYGTCCI-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

242.3

MW (Da)

3.23

ALogP

HBA

HBD

54.4

PSA (Å²)

0.81

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	C15H14O3
MW	242.27
Aromatic Rings	1
Heavy Atoms	18
NP-Likeness	1.56

Activity Summary

IC50 37 meas. best 7.72

EC50 5 meas. best 5.71

Ki 1 meas. best 4.43

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dihydroorotate dehydrogenase (quinone), mitochondrial CHEMBL4523950	IC50	7.72	7.72	19.0	1
DU-145 CHEMBL613508	IC50	7.19	7.19	64.6	1
Dihydroorotate dehydrogenase (quinone), mitochondrial CHEMBL1966	IC50	7.0	7.0	100.0	1
Pyruvate kinase PKM CHEMBL1075189	IC50	5.85	5.85	1400.0	1
PC-3 CHEMBL390	EC50	5.71	5.71	1970.0	1
Ribosomal protein S6 kinase alpha-3 CHEMBL2345	IC50	5.7	5.7	2000.0	1
PBMC CHEMBL613107	IC50	5.68	5.68	2100.0	1
G-protein coupled receptor 35 CHEMBL1293267	EC50	5.55	4.935	2840.0	2
HL-60 CHEMBL383	IC50	5.5	5.5	3180.0	1
C6 CHEMBL614657	IC50	5.43	5.43	3700.0	1
PC-3 CHEMBL390	IC50	5.4	5.4	4000.0	1
G-protein coupled receptor 35 CHEMBL1293267	IC50	5.33	5.33	4660.0	1
A549 CHEMBL392	EC50	5.32	5.32	4780.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.1	4.8267	8000.0	6
A549 CHEMBL392	IC50	5.1	5.1	8000.0	1
SK-MEL-28 CHEMBL614919	IC50	5.1	5.1	8000.0	1
LoVo CHEMBL614721	IC50	5.05	5.05	9000.0	1
MCF7 CHEMBL387	EC50	4.99	4.99	10150.0	1
Unchecked CHEMBL612545	IC50	4.72	4.72	19000.0	1
Trypanosoma cruzi CHEMBL368	IC50	4.5	4.5	31300.0	1
M-phase inducer phosphatase 1 CHEMBL3775	IC50	4.48	4.48	33200.0	1
Leishmania infantum CHEMBL612848	IC50	4.46	4.23	34720.0	2
Lactoylglutathione lyase CHEMBL2424	Ki	4.43	4.43	37153.5	1
M-phase inducer phosphatase 2 CHEMBL4804	IC50	4.37	4.37	42700.0	1
Rhodesain CHEMBL4188	IC50	4.24	4.24	58000.0	1
Leishmania amazonensis CHEMBL612877	IC50	4.2	4.2	63280.0	1
Plasmodium falciparum CHEMBL364	IC50	4.1	4.095	80000.0	2

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dihydroorotate dehydrogenase (quinone), mitochondrial	IC50	=	19.0	nM	7.72	Inhibition of Schistosoma mansoni DHODH using DHO as substrate measured at 4 sec...	30776695
DU-145	IC50	=	64.59	nM	7.19	Anticancer activity against human DU145 cells after 72 hrs by XTT assay	18829316
Dihydroorotate dehydrogenase (quinone), mitochondrial	IC50	=	100.0	nM	7.0	Inhibition of human DHODH using DHO as substrate measured at 4 secs interval for...	30776695
Pyruvate kinase PKM	IC50	=	1400.0	nM	5.85	Inhibition of PKM2 (unknown origin)	34355179
PC-3	EC50	=	1970.0	nM	5.71	Antiproliferative activity against human PC3 cells after 72 hrs by trypan blue e...	19674905
Ribosomal protein S6 kinase alpha-3	IC50	=	2000.0	nM	5.7	Inhibition of RSK2 (unknown origin)	36898330
PBMC	IC50	=	2100.0	nM	5.68	Cytotoxicity against human PBMC after 72 hrs by alamar blue assay	20378360
G-protein coupled receptor 35	EC50	=	2840.0	nM	5.55	Agonist activity at GPR35 receptor in human HT-29 cells after 10 mins by dynamic...	24900447
HL-60	IC50	=	3180.0	nM	5.5	Cytotoxicity against human promyelocytic leukemia HL60 cell line by MTT assay	17249647
C6	IC50	=	3700.0	nM	5.43	Antiproliferative activity against rat C6 cells assessed as inhibition of cell g...	38458106
PC-3	IC50	=	4000.0	nM	5.4	Growth inhibition of human PC3 cells by MTT assay	24374273
G-protein coupled receptor 35	IC50	=	4660.0	nM	5.33	Desensitization of GPR35 receptor in human HT-29 cells assessed as inhibition of...	24900447
A549	EC50	=	4780.0	nM	5.32	Antiproliferative activity against human A549 cells after 72 hrs by trypan blue ...	19674905
NON-PROTEIN TARGET	IC50	=	8000.0	nM	5.1	Growth inhibition of human U373 cells by MTT assay	24374273
A549	IC50	=	8000.0	nM	5.1	Growth inhibition of human A549 cells by MTT assay	24374273
SK-MEL-28	IC50	=	8000.0	nM	5.1	Growth inhibition of human SK-MEL-28 cells by MTT assay	24374273
LoVo	IC50	=	9000.0	nM	5.05	Growth inhibition of human LoVo cells by MTT assay	24374273
MCF7	EC50	=	10150.0	nM	4.99	Antiproliferative activity against human MCF7 cells after 72 hrs by trypan blue ...	19674905
NON-PROTEIN TARGET	IC50	=	11000.0	nM	4.96	Growth inhibition of human Hs683 cells by MTT assay	24374273
NON-PROTEIN TARGET	IC50	=	12560.0	nM	4.9	Cytotoxicity against human ECA109 cells assessed as decrease in cell proliferati...	27667553

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1007/s00044-012-0284-7	Mus musculus	7
24900447	10.1021/ml2003058	G-protein coupled receptor 35	6
33992862	10.1016/j.bmc.2021.116213	Rhodesain	6
22796040	10.1016/j.ejmech.2012.06.042	Plasma	6
19674905	10.1016/j.bmc.2009.07.039	Unchecked	5
17950604	10.1016/j.bmcl.2007.10.005	Human gammaherpesvirus 4	5
23535320	10.1016/j.ejmech.2013.02.038	Unchecked	4
17950604	10.1016/j.bmcl.2007.10.005	Raji	4
18029184	10.1016/j.bmc.2007.10.038	Trypanosoma cruzi	4
30776695	10.1016/j.ejmech.2019.02.018	Dihydroorotate dehydrogenase (quinone), mitochondrial	3
21820768	10.1016/j.ejmech.2011.07.026	Mycobacterium tuberculosis	3
27667553	10.1016/j.bmc.2016.09.034	NON-PROTEIN TARGET	3
14980653	10.1016/j.bmcl.2003.12.069	Plasmodium berghei	3
-	10.1007/s00044-011-9788-9	Mycobacterium tuberculosis	2
18829316	10.1016/j.bmcl.2008.09.053	DU-145	2
10479319	10.1021/np990139r	HaCaT	2
-	10.1016/j.cropro.2011.09.009	Trichoplusia ni	2
23535320	10.1016/j.ejmech.2013.02.038	Leishmania amazonensis	2
24374273	10.1016/j.bmcl.2013.12.049	NON-PROTEIN TARGET	2
19674905	10.1016/j.bmc.2009.07.039	Raji	2

Data from ChEMBL 36 via Core Engine