Compound Detail

CHEMBL5172138

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O=C1c2ccccc2C(=O)c2oc(-c3cccnc3)nc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL5172138
Phase	Preclinical
Structure Type	MOL
InChI Key	DOYPPVCQHGJUBC-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

276.2

MW (Da)

2.51

ALogP

HBA

HBD

73.1

PSA (Å²)

0.53

QED

Ro5 Violations

Rot. Bonds

Availability	Unknown
Chirality	Unknown

First in Class Prodrug

IC50 11 meas. best 8.77

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Ubiquitin thioesterase OTUB1 CHEMBL4523428	IC50	8.77	8.77	1.7	1
Ubiquitin carboxyl-terminal hydrolase 8 CHEMBL2157854	IC50	8.57	8.57	2.7	1
NCI-H1703 CHEMBL1075522	IC50	7.03	7.03	93.0	1
NCI-H1975 CHEMBL614348	IC50	7.01	7.01	98.0	1
Unchecked CHEMBL612545	IC50	7.0	7.0	100.0	1
EBC-1 CHEMBL4296411	IC50	6.91	6.91	122.0	1
NCI-H23 CHEMBL614997	IC50	6.55	6.55	281.0	1
A549 CHEMBL392	IC50	6.18	6.18	662.0	1
Ubiquitin carboxyl-terminal hydrolase 1 CHEMBL1795087	IC50	6.0	6.0	990.0	1
Ubiquitin carboxyl-terminal hydrolase 36 CHEMBL4630861	IC50	5.41	5.41	3900.0	1
Ubiquitin carboxyl-terminal hydrolase 2 CHEMBL1293227	IC50	5.29	5.29	5100.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Ubiquitin thioesterase OTUB1	IC50	=	1.7	nM	8.77	Inhibition of N-terminal His-6 tagged OTUB1 (40 to 271 residues) (unknown origin...	36221183
Ubiquitin carboxyl-terminal hydrolase 8	IC50	=	2.7	nM	8.57	Inhibition of N-terminal His-6 tagged USP8 (734 to 1110 residues) (unknown origi...	36221183
NCI-H1703	IC50	=	93.0	nM	7.03	Antiproliferative activity against human NCI-H1703 cells harboring wild type KRA...	36221183
NCI-H1975	IC50	=	98.0	nM	7.01	Antiproliferative activity against human NCI-H1975 cells harboring wild type KRA...	36221183
Unchecked	IC50	=	100.0	nM	7.0	Cytotoxicity against human multiple myeloma cells by WST-1 assay	34974338
EBC-1	IC50	=	122.0	nM	6.91	Antiproliferative activity against human EBC-1 cells harboring wild type KRAS in...	36221183
NCI-H23	IC50	=	281.0	nM	6.55	Antiproliferative activity against human NCI-H23 cells harboring KRAS mutant inc...	36221183
A549	IC50	=	662.0	nM	6.18	Antiproliferative activity against human A549 cells harboring KRAS mutant incuba...	36221183
Ubiquitin carboxyl-terminal hydrolase 1	IC50	=	990.0	nM	6.0	Inhibition of USP1 (unknown origin) using Ub-Rho measured after 0.5 to 3 hrs	36221183
Ubiquitin carboxyl-terminal hydrolase 36	IC50	=	3900.0	nM	5.41	Inhibition of USP36 (unknown origin) using Ub-Rho measured after 0.5 to 3 hrs	36221183
Ubiquitin carboxyl-terminal hydrolase 2	IC50	=	5100.0	nM	5.29	Inhibition of USP2 (unknown origin) using Ub-Rho measured after 0.5 to 3 hrs	36221183

PubMed	DOI	Target Context	# Activities
36221183	10.1021/acs.jmedchem.2c00408	Ubiquitin thioesterase OTUB1	5
36221183	10.1021/acs.jmedchem.2c00408	Ubiquitin carboxyl-terminal hydrolase 8	3
-	10.6019/CHEMBL5724796	Bromodomain-containing protein 4	1
-	10.6019/CHEMBL5724796	Fibroblast growth factor receptor 2	1
-	10.6019/CHEMBL5724796	Tyrosine-protein kinase ABL1	1
-	10.6019/CHEMBL5724796	Aurora kinase A	1
-	10.6019/CHEMBL5724796	Mitogen-activated protein kinase 1	1
-	10.6019/CHEMBL5724796	Glycogen synthase kinase-3 beta	1
-	10.6019/CHEMBL5724796	Cyclin-dependent kinase 2	1
-	10.6019/CHEMBL5724796	Casein kinase I isoform delta	1
34974338	10.1016/j.ejmech.2021.114053	Unchecked	1
36221183	10.1021/acs.jmedchem.2c00408	A549	1
36221183	10.1021/acs.jmedchem.2c00408	NCI-H23	1
36221183	10.1021/acs.jmedchem.2c00408	NCI-H1703	1
36221183	10.1021/acs.jmedchem.2c00408	EBC-1	1
36221183	10.1021/acs.jmedchem.2c00408	NCI-H1975	1
36221183	10.1021/acs.jmedchem.2c00408	Ataxin-3	1
36221183	10.1021/acs.jmedchem.2c00408	Ubiquitin carboxyl-terminal hydrolase 36	1
36221183	10.1021/acs.jmedchem.2c00408	Ubiquitin carboxyl-terminal hydrolase 7	1
36221183	10.1021/acs.jmedchem.2c00408	Ubiquitin carboxyl-terminal hydrolase 2	1

Data from ChEMBL 36 via Core Engine