Compound Detail

CHEMBL2325697

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C[C@@H]1COCCN1c1cc(C2(S(C)(=O)=O)CC2)nc(-c2cccc3[nH]ccc23)n1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2325697
Phase	Preclinical
Structure Type	MOL
InChI Key	SCGCBAAYLFTIJU-CQSZACIVSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

412.5

MW (Da)

2.88

ALogP

HBA

HBD

88.2

PSA (Å²)

0.71

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C21H24N4O3S
MW	412.52
Aromatic Rings	3
Heavy Atoms	29
NP-Likeness	-0.74

Activity Summary

IC50 54 meas. best 8.52

Kd 1 meas. best 5.21

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Serine/threonine-protein kinase ATR CHEMBL5024	IC50	8.52	7.8244	3.0	9
ATR/ATRIP CHEMBL4106138	IC50	8.35	8.325	4.5	2
Unchecked CHEMBL612545	IC50	8.0	8.0	10.0	1
Serine/threonine-protein kinase mTOR CHEMBL2842	IC50	7.42	6.5857	38.0	7
HT-29 CHEMBL384	IC50	7.14	6.2867	72.0	3
HCT-116 CHEMBL394	IC50	7.04	6.626	92.0	5
LoVo CHEMBL614721	IC50	6.64	6.355	231.0	2
MDA-MB-231 CHEMBL400	IC50	6.59	6.06	254.0	2
A549 CHEMBL392	IC50	6.48	6.278	333.0	5
A2780 CHEMBL614004	IC50	6.34	6.34	460.0	1
Granta-519 CHEMBL4483240	IC50	6.3	6.3	500.0	1
OVCAR-3 CHEMBL614213	IC50	6.25	6.25	563.0	1
SW-620 CHEMBL612262	IC50	6.14	6.14	727.0	1
OCI-Ly10 CHEMBL4483285	IC50	5.99	5.99	1030.0	1
MCF7 CHEMBL387	IC50	5.91	5.775	1221.0	2
DNA-dependent protein kinase catalytic subunit CHEMBL3142	IC50	5.89	5.89	1300.0	1
Phosphatidylinositol 3-kinase regulatory subunit alpha CHEMBL2506	IC50	5.89	5.89	1300.0	1
SUD4 CHEMBL613711	IC50	5.62	5.62	2380.0	1
DLD-1 CHEMBL614285	IC50	5.46	5.46	3470.0	1
NCI-H446 CHEMBL612440	IC50	5.41	5.41	3900.0	1
Transcription initiation factor TFIID subunit 1 CHEMBL3217390	Kd	5.21	5.21	6167.0	1
CAPAN-1 CHEMBL614536	IC50	5.15	5.15	7050.0	1
Serine-protein kinase ATM CHEMBL3797	IC50	5.15	5.15	7100.0	1
PC-3 CHEMBL390	IC50	5.07	5.07	8430.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	IC50	4.89	4.89	13000.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	4.3	4.3	50000.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	7.41	mL.min-1.g-1	Homo sapiens
CL	622.0	mL.min-1.kg-1	Homo sapiens
CL	600.0	mL.min-1.kg-1	Rattus norvegicus
F	62.0	%	Rattus norvegicus
Fu	0.15	-	Rattus norvegicus
Fu	0.092	-	Homo sapiens
Fu	0.14	-	Mus musculus
T1/2	0.03517	hr	Homo sapiens
T1/2	0.063	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Serine/threonine-protein kinase ATR	IC50	=	3.0	nM	8.52	Inhibition of 5'-TAMRA-labeled tracer 3',6'-bis(dimethylamino)-N-(4-{[2(1H-indol...	32502336
Serine/threonine-protein kinase ATR	IC50	=	4.1	nM	8.39	Inhibition of ATR (unknown origin)	37130473
ATR/ATRIP	IC50	=	4.5	nM	8.35	Inhibition of ATR/ATRIP (unknown origin) using 5-FAM-AK-17 as substrate preincub...	39053006
Serine/threonine-protein kinase ATR	IC50	=	5.0	nM	8.3	Inhibition of ATR in human HeLa cell nuclear extracts using glutathione S-transf...	23394205
Serine/threonine-protein kinase ATR	IC50	=	5.0	nM	8.3	Inhibition of ATR in human HeLa cell nuclear extract using GST-fused p53N66 as s...	30346772
Serine/threonine-protein kinase ATR	IC50	=	5.0	nM	8.3	Inhibition of ATR (unknown origin) using peptide as substrate preincubated for 1...	36462444
ATR/ATRIP	IC50	=	5.0	nM	8.3	Inhibition of human ATR/ATRIP using GST-tagged p53 as substrate in presence of 3...	38299539
Unchecked	IC50	=	10.0	nM	8.0	Inhibition of human full length recombinant ATR M211T mutant using GST-c-Myc-p53...	38299539
Serine/threonine-protein kinase mTOR	IC50	=	38.0	nM	7.42	Inhibition of mTOR (unknown origin) using peptide as substrate preincubated for ...	36462444
Serine/threonine-protein kinase mTOR	IC50	=	38.0	nM	7.42	Inhibition of mTOR (unknown origin)	30346772
Serine/threonine-protein kinase mTOR	IC50	=	38.0	nM	7.42	Inhibition of recombinant mTOR (unknown origin)	23394205
Serine/threonine-protein kinase ATR	IC50	=	50.0	nM	7.3	Inhibition of ATR-mediated CHK1 phosphorylation at serine 345 in human HT29 cell...	23394205
Serine/threonine-protein kinase ATR	IC50	=	61.0	nM	7.21	Inhibition of ATR in human HT29 cells after 60 mins by Hoechst 33258 staining-ba...	30346772
Serine/threonine-protein kinase ATR	IC50	=	61.0	nM	7.21	Inhibition of ATR (unknown origin)	35033884
HT-29	IC50	=	72.0	nM	7.14	Antiproliferative activity against ATM-proficient human HT-29 cells assessed as ...	36462444
HCT-116	IC50	=	92.0	nM	7.04	Synergistic antiproliferative activity against ATM-proficient human HCT-116 cell...	36462444
Serine/threonine-protein kinase ATR	IC50	=	130.0	nM	6.89	Inhibition of ATR in human HeLa S3 cells assessed as decrease in CHK1 phosphoryl...	38299539
HCT-116	IC50	=	137.0	nM	6.86	Synergistic antiproliferative activity against ATM-proficient human HCT-116 cell...	36462444
HCT-116	IC50	=	151.0	nM	6.82	Antiproliferative activity against ATM-proficient human HCT-116 cells assessed a...	36462444
LoVo	IC50	=	231.0	nM	6.64	Antiproliferative activity against ATM-deficient human LoVo cells assessed as re...	36462444

Literature References

PubMed	DOI	Target Context	# Activities
39053006	10.1021/acs.jmedchem.4c00734	Granta-519	8
35191694	10.1021/acs.jmedchem.1c01999	Transcription initiation factor TFIID subunit 1	7
30346772	10.1021/acs.jmedchem.8b01187	ADMET	6
36462444	10.1016/j.ejmech.2022.114945	ADMET	6
30346772	10.1021/acs.jmedchem.8b01187	LoVo	5
36462444	10.1016/j.ejmech.2022.114945	A549	4
36462444	10.1016/j.ejmech.2022.114945	HCT-116	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
23394205	10.1021/jm301859s	LoVo	3
23394205	10.1021/jm301859s	No relevant target	3
35191694	10.1021/acs.jmedchem.1c01999	Unchecked	3
30346772	10.1021/acs.jmedchem.8b01187	No relevant target	3
23394205	10.1021/jm301859s	Serine/threonine-protein kinase mTOR	3
23394205	10.1021/jm301859s	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	3
30346772	10.1021/acs.jmedchem.8b01187	Serine/threonine-protein kinase mTOR	3
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
23394205	10.1021/jm301859s	Cytochrome P450 3A4	2
23394205	10.1021/jm301859s	Mus musculus	2
-	10.6019/CHEMBL3301361	No relevant target	2
30346772	10.1021/acs.jmedchem.8b01187	Serine/threonine-protein kinase ATR	2

Data from ChEMBL 36 via Core Engine