Compound Detail

CHEMBL66879

COUMARIC ACID

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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL66879
Name	COUMARIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	NGSWKAQJJWESNS-ZZXKWVIFSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

164.2

MW (Da)

1.49

ALogP

HBA

HBD

57.5

PSA (Å²)

0.65

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	C9H8O3
MW	164.16
Aromatic Rings	1
Heavy Atoms	12
NP-Likeness	0.84

Activity Summary

IC50 28 meas. best 6.85

Ki 18 meas. best 6.01

EC50 4 meas. best 5.31

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	6.85	5.485	140.0	2
Mus musculus CHEMBL375	IC50	6.72	6.72	190.0	1
Carbonic anhydrase 2 CHEMBL205	Ki	6.01	6.01	980.0	1
Carbonic anhydrase 1 CHEMBL261	Ki	5.97	5.97	1070.0	1
Tyrosinase CHEMBL1973	IC50	5.7	5.64	2000.0	3
Unchecked CHEMBL612545	IC50	5.64	4.9275	2300.0	4
Unchecked CHEMBL612545	Ki	5.48	5.48	3300.0	1
Estrogen receptor beta CHEMBL242	EC50	5.31	5.31	4890.0	1
Carbonic anhydrase 7 CHEMBL2326	Ki	5.28	5.28	5230.0	1
Carbonic anhydrase 9 CHEMBL3594	Ki	5.27	5.27	5330.0	1
Carbonic anhydrase 5A, mitochondrial CHEMBL4789	Ki	5.22	5.22	5960.0	1
HT-22 CHEMBL614316	EC50	5.19	5.19	6400.0	1
Carbonic anhydrase 6 CHEMBL3025	Ki	5.17	5.17	6720.0	1
Carbonic anhydrase 14 CHEMBL3510	Ki	5.17	5.17	6680.0	2
Carbonic anhydrase 3 CHEMBL2885	Ki	5.12	5.12	7570.0	1
Carbonic anhydrase 5B, mitochondrial CHEMBL3969	Ki	5.11	5.11	7760.0	1
Carbonic anhydrase 12 CHEMBL3242	Ki	5.1	5.1	8010.0	2
Carbonic anhydrase 4 CHEMBL3729	Ki	5.02	5.02	9600.0	1
Carbonic anhydrase 13 CHEMBL2186	Ki	5.0	5.0	10100.0	2
BT-549 CHEMBL614072	IC50	5.0	5.0	10000.0	1
Hydroxycarboxylic acid receptor 2 CHEMBL3785	Ki	4.85	4.85	14000.0	1
Estrogen receptor CHEMBL206	EC50	4.79	4.79	16120.0	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	4.2	4.2	63000.0	1
No relevant target CHEMBL2362975	EC50	4.18	4.18	66290.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.18	4.155	66000.0	2
RAW264.7 CHEMBL612557	IC50	4.13	4.13	73400.0	1
LoVo CHEMBL614721	IC50	4.09	4.09	82000.0	1
Dipeptidyl peptidase 4 CHEMBL284	IC50	4.08	4.08	83180.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aldo-keto reductase family 1 member B1	IC50	=	140.0	nM	6.85	Inhibition of aldose reductase (unknown origin)	-
Mus musculus	IC50	=	190.0	nM	6.72	Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops fl...	21388814
Carbonic anhydrase 2	Ki	=	980.0	nM	6.01	Inhibition of human CA2 by stopped-flow CO2 hydration assay	20185318
Carbonic anhydrase 1	Ki	=	1070.0	nM	5.97	Inhibition of human CA1 by stopped-flow CO2 hydration assay	20185318
Tyrosinase	IC50	=	2000.0	nM	5.7	Inhibition of tyrosinase in neonatal human epidermal melanocytes	32787103
Tyrosinase	IC50	=	2000.0	nM	5.7	Inhibition of human tyrosinase expressed in HEK293 cells	32787103
Unchecked	IC50	=	2300.0	nM	5.64	Inhibition of tyrosinase using L-dihydroxyphenylalanine as substrate preincubate...	23113717
Tyrosinase	IC50	=	3000.0	nM	5.52	Inhibition of human tyrosinase after 120 mins	29763564
Unchecked	Ki	=	3300.0	nM	5.48	Inhibition of Malassezia globosa recombinant beta-carbonic anhydrase preincubate...	28343756
Estrogen receptor beta	EC50	=	4890.0	nM	5.31	Agonist activity at human estrogen receptor-beta by yeast two-hybrid assay in pr...	23608764
Carbonic anhydrase 7	Ki	=	5230.0	nM	5.28	Inhibition of human CA7 by stopped-flow CO2 hydration assay	20185318
Carbonic anhydrase 9	Ki	=	5330.0	nM	5.27	Inhibition of human CA9 by stopped-flow CO2 hydration assay	20185318
Carbonic anhydrase 5A, mitochondrial	Ki	=	5960.0	nM	5.22	Inhibition of human CA5A by stopped-flow CO2 hydration assay	20185318
HT-22	EC50	=	6400.0	nM	5.19	Neuroprotective activity against glutamate-induced cell death in mouse HT-22 cel...	32991171
Carbonic anhydrase 14	Ki	=	6680.0	nM	5.17	Inhibition of human CA14 by stopped-flow CO2 hydration assay	20185318
Carbonic anhydrase 6	Ki	=	6720.0	nM	5.17	Inhibition of human CA6 by stopped-flow CO2 hydration assay	20185318
Carbonic anhydrase 14	Ki	=	6680.0	nM	5.17	Inhibition of human carbonic anhydrase 14 preincubated for 15 mins by stopped-fl...	26498394
Carbonic anhydrase 3	Ki	=	7570.0	nM	5.12	Inhibition of human CA3 by stopped-flow CO2 hydration assay	20185318
Carbonic anhydrase 5B, mitochondrial	Ki	=	7760.0	nM	5.11	Inhibition of human CA5B by stopped-flow CO2 hydration assay	20185318
Carbonic anhydrase 12	Ki	=	8010.0	nM	5.1	Inhibition of human CA12 by stopped-flow CO2 hydration assay	20185318

Literature References

PubMed	DOI	Target Context	# Activities
17400451	10.1016/j.bmcl.2007.03.051	Mus musculus	11
37355024	10.1016/j.bmcl.2023.129386	Unchecked	9
-	10.1007/s00044-012-0419-x	Radical scavenging activity	6
18590964	10.1016/j.bmc.2008.06.010	Radical scavenging activity	6
21870840	10.1021/jf2025538	Root	5
-	10.1016/j.cropro.2012.09.015	Lasiodiplodia theobromae	5
-	10.1039/C4MD00022F	NON-PROTEIN TARGET	5
-	10.1016/j.cropro.2012.09.015	Botryosphaeria dothidea	5
-	10.1016/j.cropro.2012.09.015	Diplodia seriata	4
-	10.1016/j.cropro.2012.09.015	Neofusicoccum ribis	4
23454014	10.1016/j.bmcl.2013.01.091	RAW264.7	4
22925447	10.1016/j.bmc.2012.07.043	U-937	4
11076549	10.1021/np0000318	Raji	4
11076549	10.1021/np0000318	Unchecked	4
21696954	10.1016/j.bmcl.2011.05.089	NON-PROTEIN TARGET	4
21870840	10.1021/jf2025538	Leaf	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
23145924	10.1021/jf303290g	Diplodia seriata	4
28343756	10.1016/j.bmc.2017.03.026	Unchecked	3
28415050	10.1016/j.ejmech.2017.03.061	No relevant target	3

Data from ChEMBL 36 via Core Engine