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Compound Detail

CHEMBL5423608

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C[C@@H]1COCCN1c1nc(-c2cccc3[nH]ccc23)nc2c1CN(C(=O)c1cccc(S(C)(=O)=O)c1)C2(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5423608
Phase Preclinical
Structure Type MOL
InChI Key LKHMVKNMSWRHJH-GOSISDBHSA-N
16
Targets
26
Activities
1
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

545.7
MW (Da)
4.14
ALogP
7
HBA
1
HBD
108.5
PSA (Ų)
0.41
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H31N5O4S
MW 545.67
Aromatic Rings 4
Heavy Atoms 39
NP-Likeness -1.01

Activity Summary

IC50 26 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 9.0 7.975 1.0 4
Serine/threonine-protein kinase ATR
CHEMBL5024
 IC50 8.52 8.52 3.0 1
A549
CHEMBL392
 IC50 7.89 6.975 13.0 4
Serine/threonine-protein kinase mTOR
CHEMBL2842
 IC50 7.75 7.75 18.0 1
HT-29
CHEMBL384
 IC50 7.72 7.215 19.0 2
LoVo
CHEMBL614721
 IC50 7.4 7.4 40.0 1
SW-620
CHEMBL612262
 IC50 7.02 7.02 95.0 1
OVCAR-3
CHEMBL614213
 IC50 7.01 7.01 98.0 1
MCF7
CHEMBL387
 IC50 6.48 6.27 328.0 2
MDA-MB-231
CHEMBL400
 IC50 6.36 6.165 435.0 2
DNA-dependent protein kinase catalytic subunit
CHEMBL3142
 IC50 6.18 6.18 662.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 6.0 5.5 1000.0 2
Cytochrome P450 2C19
CHEMBL3622
 IC50 6.0 6.0 1000.0 1
Serine-protein kinase ATM
CHEMBL3797
 IC50 6.0 6.0 1000.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 IC50 6.0 6.0 1000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1170.0 ng.hr.mL-1 Rattus norvegicus
AUC 1160.0 ng.hr.mL-1 Rattus norvegicus
AUC 1620.0 ng.hr.mL-1 Rattus norvegicus
AUC 1750.0 ng.hr.mL-1 Rattus norvegicus
CL 385.0 mL.min-1.kg-1 Homo sapiens
CL 119.0 mL.min-1.kg-1 Rattus norvegicus
CL 14.2 mL.min-1.kg-1 Rattus norvegicus
Cmax 516.8 nM Rattus norvegicus
F 30.0 % Rattus norvegicus
MRT 1.45 hr Rattus norvegicus
MRT 4.26 hr Rattus norvegicus
T1/2 0.05667 hr Homo sapiens
T1/2 0.35 hr Rattus norvegicus
T1/2 1.32 hr Rattus norvegicus
T1/2 2.66 hr Rattus norvegicus
Tmax 2.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 1.0 nM 9.0 Antiproliferative activity against ATM-proficient human HCT-116 cells assessed a... 36462444
Serine/threonine-protein kinase ATR IC50 = 3.0 nM 8.52 Inhibition of ATR (unknown origin) using peptide as substrate preincubated for 1... 36462444
A549 IC50 = 13.0 nM 7.89 Antiproliferative activity against ATM-proficient human A549 cells assessed as r... 36462444
HCT-116 IC50 = 13.0 nM 7.89 Synergistic antiproliferative activity against ATM-proficient human HCT-116 cell... 36462444
Serine/threonine-protein kinase mTOR IC50 = 18.0 nM 7.75 Inhibition of mTOR (unknown origin) using peptide as substrate preincubated for ... 36462444
HT-29 IC50 = 19.0 nM 7.72 Antiproliferative activity against ATM-proficient human HT-29 cells assessed as ... 36462444
HCT-116 IC50 = 24.0 nM 7.62 Synergistic antiproliferative activity against ATM-proficient human HCT-116 cell... 36462444
LoVo IC50 = 40.0 nM 7.4 Antiproliferative activity against ATM-deficient human LoVo cells assessed as re... 36462444
HCT-116 IC50 = 41.0 nM 7.39 Antiproliferative activity against ATM-proficient human HCT-116 cells assessed a... 36462444
SW-620 IC50 = 95.0 nM 7.02 Antiproliferative activity against ATM-deficient human SW620 cells assessed as r... 36462444
OVCAR-3 IC50 = 98.0 nM 7.01 Antiproliferative activity against ATM-deficient human OVCAR-3 cells assessed as... 36462444
A549 IC50 = 114.0 nM 6.94 Synergistic antiproliferative activity against ATM-proficient human A549 cells a... 36462444
HT-29 IC50 = 197.0 nM 6.71 Antiproliferative activity against ATM-proficient human HT-29 cells assessed as ... 36462444
A549 IC50 = 280.0 nM 6.55 Synergistic antiproliferative activity against ATM-proficient human A549 cells a... 36462444
A549 IC50 = 302.0 nM 6.52 Antiproliferative activity against ATM-proficient human A549 cells assessed as r... 36462444
MCF7 IC50 = 328.0 nM 6.48 Synergistic antiproliferative activity against human MCF7 cells assessed as redu... 36462444
MDA-MB-231 IC50 = 435.0 nM 6.36 Synergistic antiproliferative activity against human MDA-MB-231 cells assessed a... 36462444
DNA-dependent protein kinase catalytic subunit IC50 = 662.0 nM 6.18 Inhibition of DNA-PK (unknown origin) using peptide as substrate preincubated fo... 36462444
MCF7 IC50 = 873.0 nM 6.06 Antiproliferative activity against human MCF7 cells assessed as reduction in cel... 36462444
Cytochrome P450 2C19 IC50 = 1000.0 nM 6.0 Inhibition of CYP2C19 in human liver microsomes using nootkatone as substrate pr... 36462444

Literature References

PubMed DOI Target Context # Activities
36462444 10.1016/j.ejmech.2022.114945 ADMET 29
36462444 10.1016/j.ejmech.2022.114945 LoVo 5
36462444 10.1016/j.ejmech.2022.114945 A549 4
36462444 10.1016/j.ejmech.2022.114945 HCT-116 4
36462444 10.1016/j.ejmech.2022.114945 HT-29 3
36462444 10.1016/j.ejmech.2022.114945 No relevant target 2
36462444 10.1016/j.ejmech.2022.114945 MDA-MB-231 2
36462444 10.1016/j.ejmech.2022.114945 Cytochrome P450 3A4 2
36462444 10.1016/j.ejmech.2022.114945 MCF7 2
36462444 10.1016/j.ejmech.2022.114945 SW-620 1
36462444 10.1016/j.ejmech.2022.114945 DNA-dependent protein kinase catalytic subunit 1
36462444 10.1016/j.ejmech.2022.114945 Serine-protein kinase ATM 1
36462444 10.1016/j.ejmech.2022.114945 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 1
36462444 10.1016/j.ejmech.2022.114945 OVCAR-3 1
36462444 10.1016/j.ejmech.2022.114945 Serine/threonine-protein kinase ATR 1
36462444 10.1016/j.ejmech.2022.114945 Cytochrome P450 2D6 1
36462444 10.1016/j.ejmech.2022.114945 Cytochrome P450 2C19 1
36462444 10.1016/j.ejmech.2022.114945 Cytochrome P450 2C9 1
36462444 10.1016/j.ejmech.2022.114945 Cytochrome P450 1A2 1
36462444 10.1016/j.ejmech.2022.114945 Serine/threonine-protein kinase mTOR 1

Data from ChEMBL 36 via Core Engine