Compound Detail

CHEMBL244743

ESCULETIN

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O=c1ccc2cc(O)c(O)cc2o1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL244743
Name	ESCULETIN
Phase	Preclinical
Structure Type	MOL
InChI Key	ILEDWLMCKZNDJK-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

178.1

MW (Da)

1.20

ALogP

HBA

HBD

70.7

PSA (Å²)

0.47

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	C9H6O4
MW	178.14
Aromatic Rings	2
Heavy Atoms	13
NP-Likeness	1.03

Activity Summary

IC50 22 meas. best 6.02

Ki 4 meas. best 8.03

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 12 CHEMBL3242	Ki	8.03	8.03	9.3	1
Carbonic anhydrase 9 CHEMBL3594	Ki	7.44	7.44	36.4	1
SK-MEL-28 CHEMBL614919	IC50	6.02	6.02	960.0	1
Induced myeloid leukemia cell differentiation protein Mcl-1 CHEMBL4361	Ki	5.83	5.83	1490.0	1
SK-MEL3 CHEMBL614920	IC50	5.77	5.77	1700.0	1
Mushroom tyrosinase CHEMBL6066154	IC50	5.37	5.37	4300.0	1
Lysine-specific demethylase 5B CHEMBL3774295	IC50	5.34	5.34	4600.0	1
MDA-MB-231 CHEMBL400	IC50	5.13	5.13	7470.0	1
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	5.09	5.09	8200.0	1
Induced myeloid leukemia cell differentiation protein Mcl-1 CHEMBL4361	IC50	5.06	5.06	8770.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.96	4.855	11000.0	2
Unchecked CHEMBL612545	IC50	4.95	4.66	11330.0	3
No relevant target CHEMBL2362975	IC50	4.6	4.6	25180.0	1
U-937 CHEMBL612794	IC50	4.5	4.5	31330.0	1
Sortase A CHEMBL5362	IC50	4.44	4.44	36160.0	1
Prostaglandin G/H synthase 1 CHEMBL221	IC50	4.24	4.24	57000.0	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	4.17	4.17	67200.0	1
Sorbitol dehydrogenase CHEMBL2275	IC50	4.08	4.08	82900.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 12	Ki	=	9.3	nM	8.03	Inhibition of human carbonic anhydrase 12 incubated for 15 mins prior to testing...	29197732
Carbonic anhydrase 9	Ki	=	36.4	nM	7.44	Inhibition of human carbonic anhydrase 9 incubated for 15 mins prior to testing ...	29197732
SK-MEL-28	IC50	=	960.0	nM	6.02	Anticancer activity against human SK-MEL-28 cells assessed as reduction in cell ...	37197457
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	1490.0	nM	5.83	Displacement of FAM-Bid peptide from recombinant N-terminal His6x-tagged human M...	33218896
SK-MEL3	IC50	=	1700.0	nM	5.77	Anticancer activity against human SK-MEL3 cells assessed as reduction in cell vi...	37197457
Mushroom tyrosinase	IC50	=	4300.0	nM	5.37	Inhibition of mushroom tyrosinase using L-tyrosine as substrate	32787103
Lysine-specific demethylase 5B	IC50	=	4600.0	nM	5.34	Inhibition of KDM5B (unknown origin)	32883639
MDA-MB-231	IC50	=	7470.0	nM	5.13	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition...	37602711
Xanthine dehydrogenase/oxidase	IC50	=	8200.0	nM	5.09	Inhibition of xanthine oxidase	17316915
Induced myeloid leukemia cell differentiation protein Mcl-1	IC50	=	8770.0	nM	5.06	Displacement of FAM-Bid peptide from recombinant N-terminal His6x-tagged human M...	33218896
NON-PROTEIN TARGET	IC50	=	11000.0	nM	4.96	Antiinflammatory activity in NMRI mouse macrophages assessed as inhibition of A2...	8988605
Unchecked	IC50	=	11330.0	nM	4.95	PUBCHEM_BIOASSAY: A biochemical assay using the ADP-Hunter methodology, purified...	-
NON-PROTEIN TARGET	IC50	=	18000.0	nM	4.75	Antiinflammatory activity in NMRI mouse macrophages assessed as inhibition of A2...	8988605
No relevant target	IC50	=	25180.0	nM	4.6	Antioxidant activity assessed as DPPH radical scavenging activity measured at 50...	37252094
Unchecked	IC50	=	25840.0	nM	4.59	Cytotoxicity against human C3PV cells assessed as reduction in cell viability in...	37197457
U-937	IC50	=	31330.0	nM	4.5	Growth inhibition of human U937 cells by [3H]thymidine incorporation assay	18060791
Unchecked	IC50	=	36500.0	nM	4.44	Inhibition kidney aldose reductase 2 by spectrophotometric analysis	20805028
Sortase A	IC50	=	36160.0	nM	4.44	Inhibition of Staphylococcus aureus SrtA using FRET substrate incubated for 1 hr...	34516107
Prostaglandin G/H synthase 1	IC50	=	57000.0	nM	4.24	Inhibition of COX1	16038536
Aldo-keto reductase family 1 member B1	IC50	=	67200.0	nM	4.17	Inhibition human recombinant aldose reductase 1 by spectrophotometric analysis	20805028

Literature References

PubMed	DOI	Target Context	# Activities
22925447	10.1016/j.bmc.2012.07.043	U-937	8
15387675	10.1021/np040129c	Unchecked	7
34758374	10.1016/j.bmcl.2021.128445	Macrophage migration inhibitory factor	6
-	10.1007/s00044-010-9426-y	Radical scavenging activity	5
23306152	10.3390/ijms14011293	Aspergillus fumigatus	5
18060791	10.1016/j.bmc.2007.11.038	U-937	4
-	10.1007/s00044-010-9426-y	NON-PROTEIN TARGET	4
8988605	10.1021/np960422f	NON-PROTEIN TARGET	4
23306152	10.3390/ijms14011293	Aspergillus flavus	4
20805028	10.1016/j.bmcl.2010.08.038	Unchecked	3
22222157	10.1016/j.bmc.2011.12.002	Beta-secretase 1	2
22925447	10.1016/j.bmc.2012.07.043	No relevant target	2
24681028	10.1016/j.ejmech.2014.03.029	NON-PROTEIN TARGET	2
37197457	10.1021/acsmedchemlett.3c00019	Unchecked	2
37602711	10.1021/acs.jmedchem.3c00954	MDA-MB-231	2
-	10.1007/s00044-010-9426-y	HT-29	2
33218896	10.1016/j.bmc.2020.115851	Induced myeloid leukemia cell differentiation protein Mcl-1	2
6736971	10.1021/np50032a019	NON-PROTEIN TARGET	2
36183504	10.1016/j.ejmech.2022.114789	HCT-116	2
38340509	10.1016/j.ejmech.2024.116179	MCF7	1

Data from ChEMBL 36 via Core Engine