Compound Detail

CHEMBL484853

CARNOSIC ACID

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CC(C)c1cc2c(c(O)c1O)[C@@]1(C(=O)O)CCCC(C)(C)[C@@H]1CC2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL484853
Name	CARNOSIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	QRYRORQUOLYVBU-VBKZILBWSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

332.4

MW (Da)

4.32

ALogP

HBA

HBD

77.8

PSA (Å²)

0.71

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	C20H28O4
MW	332.44
Aromatic Rings	1
Heavy Atoms	24
NP-Likeness	2.17

Activity Summary

IC50 16 meas. best 6.62

Ki 8 meas. best 5.52

EC50 4 meas. best 5.26

Kd 1 meas. best 4.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Protease CHEMBL2366517	IC50	6.62	6.62	240.0	1
beta-catenin-B-cell lymphoma 9 protein complex CHEMBL3885525	Ki	5.52	5.392	3000.0	5
Cytochrome P450 3A4 CHEMBL340	Ki	5.37	5.37	4300.0	1
Prostaglandin E synthase CHEMBL5658	IC50	5.3	5.3	5000.0	2
beta-catenin-B-cell lymphoma 9 protein complex CHEMBL3885525	IC50	5.28	5.28	5213.0	1
MIA PaCa-2 CHEMBL614725	EC50	5.26	5.26	5500.0	1
HCT-116 CHEMBL394	IC50	5.06	5.06	8670.0	1
Cytochrome P450 2C9 CHEMBL3397	Ki	5.04	5.04	9200.0	1
SW480 CHEMBL612544	IC50	4.98	4.98	10490.0	1
Farnesyl pyrophosphate synthase CHEMBL1782	IC50	4.7	4.7	20000.0	1
HT-29 CHEMBL384	IC50	4.7	4.7	20190.0	1
Catenin beta-1 CHEMBL5866	Kd	4.7	4.7	20000.0	1
MRC5 CHEMBL614181	IC50	4.66	4.66	21800.0	1
Metallo-beta-lactamase type 2 CHEMBL5465386	IC50	4.57	4.57	27070.0	1
Unchecked CHEMBL612545	IC50	4.57	4.57	27070.0	1
Pancreatic triacylglycerol lipase CHEMBL1812	IC50	4.44	4.44	36000.0	1
HepG2 CHEMBL395	IC50	4.38	4.38	41300.0	1
Radical scavenging activity CHEMBL613712	IC50	4.27	4.27	53300.0	1
Glutathione S-transferase omega-1 CHEMBL3174	IC50	4.21	4.21	62000.0	1
AGS CHEMBL613860	IC50	4.05	4.05	89800.0	1
Hepatocyte CHEMBL613690	EC50	4.02	4.02	94800.0	2

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Protease	IC50	=	240.0	nM	6.62	Inhibition of HIV1 protease	19813754
beta-catenin-B-cell lymphoma 9 protein complex	Ki	=	3000.0	nM	5.52	Binding affinity to N-terminal FLAG tagged beta catenin (134 to 671 residues)/FL...	35581674
beta-catenin-B-cell lymphoma 9 protein complex	Ki	=	3300.0	nM	5.48	Inhibition of FLAG tagged human beta-catenin/FLAG-tagged human BCL9 HD2 (343 to ...	36630177
beta-catenin-B-cell lymphoma 9 protein complex	Ki	=	3300.0	nM	5.48	Inhibition of beta-catenin (unknown origin)/BCL9 (unknown origin) protein-protei...	38912577
Cytochrome P450 3A4	Ki	=	4300.0	nM	5.37	Inhibition of CYP3A4 activity in human hepatocytes after 30 mins by liquid chrom...	22531045
Prostaglandin E synthase	IC50	=	5000.0	nM	5.3	Inhibition of microsomal PGES1 in ILbeta-stimulated human A549 cells using PGH2 ...	-
Prostaglandin E synthase	IC50	=	5000.0	nM	5.3	Inhibition of mPGES1 in human A549 cell microsomal membrane using pGH2 as substr...	29329790
beta-catenin-B-cell lymphoma 9 protein complex	IC50	=	5213.0	nM	5.28	Inhibition of beta-catenin/BCL9 in Wnt-activated human SW480 cells assessed as r...	-
beta-catenin-B-cell lymphoma 9 protein complex	Ki	=	5300.0	nM	5.28	Competitive inhibition of wild type beta-catenin (unknown origin) expressed in E...	27190602
MIA PaCa-2	EC50	=	5500.0	nM	5.26	Cytotoxicity against human MIAPaCa2 cells assessed as decrease in cell growth me...	31725297
beta-catenin-B-cell lymphoma 9 protein complex	Ki	=	6334.0	nM	5.2	Inhibition of C-terminal 6x-histidine tagged beta-catenin (138 to 686 residues) ...	-
HCT-116	IC50	=	8670.0	nM	5.06	Cytotoxicity in human HCT116 cells assessed as reduction in cell viability incub...	-
Cytochrome P450 2C9	Ki	=	9200.0	nM	5.04	Inhibition of CYP2C9 activity in human hepatocytes after 30 mins by liquid chrom...	22531045
SW480	IC50	=	10490.0	nM	4.98	Cytotoxicity in human SW480 cells assessed as reduction in cell viability incuba...	-
Catenin beta-1	Kd	=	20000.0	nM	4.7	Binding affinity to N-terminal FLAG tagged beta catenin alpha helix (H1 - 141 to...	35581674
HT-29	IC50	=	20190.0	nM	4.7	Cytotoxicity in human HT-29 cells assessed as reduction in cell viability incuba...	-
Farnesyl pyrophosphate synthase	IC50	=	20000.0	nM	4.7	Inhibition of human N-terminal TEV protease cleavage site-fused-His6-tagged FPPS...	31725297
MRC5	IC50	=	21800.0	nM	4.66	Cytotoxicity against human MRC5 cells after 24 hrs by neutral red uptake assay	20359186
Metallo-beta-lactamase type 2	IC50	=	27070.0	nM	4.57	Inhibition of bacterial NDM-1 (unknown origin)	37360393
Unchecked	IC50	=	27070.0	nM	4.57	Inhibition of NDM-1 (unknown origin)	34391033

Literature References

PubMed	DOI	Target Context	# Activities
22531045	10.1124/dmd.112.044909	Hepatocyte	11
33378620	10.1021/acs.jnatprod.0c00832	Listeria monocytogenes	4
33378620	10.1021/acs.jnatprod.0c00832	Pseudomonas aeruginosa	4
33378620	10.1021/acs.jnatprod.0c00832	Acinetobacter baumannii	4
33378620	10.1021/acs.jnatprod.0c00832	Escherichia coli	4
33378620	10.1021/acs.jnatprod.0c00832	Staphylococcus aureus	4
33378620	10.1021/acs.jnatprod.0c00832	Pectobacterium carotovorum	4
22531045	10.1124/dmd.112.044909	Cytochrome P450 2C9	2
18524600	10.1016/j.bmc.2008.05.030	Quinolone resistance protein NorA	2
18848780	10.1016/j.bmc.2008.09.042	Quinolone resistance protein NorA	2
22531045	10.1124/dmd.112.044909	Cytochrome P450 3A4	2
35581674	10.1021/acs.jmedchem.2c00228	Catenin beta-1	2
23507152	10.1016/j.bmc.2013.02.019	Nuclear factor erythroid 2-related factor 2	2
20359186	10.1021/np900822x	MRC5	1
20359186	10.1021/np900822x	HepG2	1
20359186	10.1021/np900822x	AGS	1
12350144	10.1021/np020189n	Radical scavenging activity	1
8229021	10.1021/np50098a031	H9	1
8229021	10.1021/np50098a031	Human immunodeficiency virus 1	1
38912577	10.1021/acs.jmedchem.3c02079	beta-catenin-B-cell lymphoma 9 protein complex	1

Data from ChEMBL 36 via Core Engine