Compound Detail

CHEMBL249448

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O=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1[C@H](O)C[C@@](O)(C(=O)O)C[C@H]1OC(=O)/C=C/c1ccc(O)c(O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL249448
Phase	Preclinical
Structure Type	MOL
InChI Key	UFCLZKMFXSILNL-PSEXTPKNSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

516.5

MW (Da)

1.03

ALogP

HBA

HBD

211.3

PSA (Å²)

0.16

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 15 meas. best 7.11

EC50 1 meas. best 4.5

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	7.11	7.11	78.0	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	6.62	6.62	240.0	1
Acetylcholinesterase CHEMBL220	IC50	5.67	5.67	2140.0	1
Beta-secretase 1 CHEMBL4822	IC50	5.48	5.48	3310.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	5.33	5.33	4700.0	1
Influenza A virus H3N2 CHEMBL2366902	IC50	4.99	4.99	10200.0	1
Radical scavenging activity CHEMBL613712	IC50	4.54	4.54	28900.0	1
Hepatitis B virus CHEMBL613497	EC50	4.5	4.5	31900.0	1
Unchecked CHEMBL612545	IC50	4.43	4.1867	37200.0	3
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	4.38	4.38	41500.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aldo-keto reductase family 1 member B1	IC50	=	78.0	nM	7.11	Inhibition of human recombinant N-terminus His6-tagged AKR1B1 expressed in Esche...	22236472
Aldo-keto reductase family 1 member B10	IC50	=	240.0	nM	6.62	Inhibition of human recombinant N-terminus His6-tagged AKR1B10 expressed in Esch...	22236472
Acetylcholinesterase	IC50	=	2140.0	nM	5.67	Inhibition of AChE (unknown origin)	33984802
Beta-secretase 1	IC50	=	3310.0	nM	5.48	Inhibition of BACE1 (unknown origin)	33984802
Amyloid-beta precursor protein	IC50	=	4700.0	nM	5.33	Inhibition of human amyloid beta (1 to 42) aggregation after 24 hrs by thioflavi...	22921742
Influenza A virus H3N2	IC50	=	10200.0	nM	4.99	Antiviral activity against Influenza virus A/Hanfang/359/95 (H3N2)	24279769
Radical scavenging activity	IC50	=	28900.0	nM	4.54	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins ...	23356964
Hepatitis B virus	EC50	=	31900.0	nM	4.5	Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as re...	36709647
Unchecked	IC50	=	37200.0	nM	4.43	Inhibition of collagenase type 5	15921434
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	41500.0	nM	4.38	Inhibition of PTP1B (unknown origin)	29525218
Unchecked	IC50	=	80000.0	nM	4.1	Inhibition of A23187-induced 12-hydroxy-5,8,10-heptadecatrienoic acid formation ...	2822857
Unchecked	IC50	=	92500.0	nM	4.03	Inhibition of A23187-induced LTB4 formation in human polymorphonuclear leukocyte...	2822857

PubMed	DOI	Target Context	# Activities
2822857	10.1021/np50051a009	Unchecked	7
24279769	10.1021/np4005773	NON-PROTEIN TARGET	4
36709647	10.1016/j.ejmech.2023.115128	Hepatitis B virus	3
28248102	10.1021/acs.jnatprod.6b01026	SH-SY5Y	3
30030001	10.1016/j.bmc.2018.07.014	B16-F1	2
18029179	10.1016/j.bmcl.2007.10.046	Hepatitis B virus	2
29525218	10.1016/j.bmcl.2018.02.052	Tyrosine-protein phosphatase non-receptor type 1	2
30030001	10.1016/j.bmc.2018.07.014	Unchecked	2
30145372	10.1016/j.ejmech.2018.08.033	Dihydroorotate dehydrogenase (fumarate)	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
22921742	10.1016/j.bmc.2012.08.001	Amyloid-beta precursor protein	2
24279769	10.1021/np4005773	Human immunodeficiency virus 1	1
24279769	10.1021/np4005773	KETR3	1
24279769	10.1021/np4005773	MCF7	1
24279769	10.1021/np4005773	A549	1
24279769	10.1021/np4005773	Influenza A virus H3N2	1
25981689	10.1016/j.bmcl.2015.04.091	Escherichia coli	1
22236472	10.1016/j.ejmech.2011.12.034	Aldo-keto reductase family 1 member B10	1
22236472	10.1016/j.ejmech.2011.12.034	Aldo-keto reductase family 1 member B1	1
15921434	10.1021/np0500631	Jurkat	1

Data from ChEMBL 36 via Core Engine