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Compound Detail

CHEMBL5425498

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C[C@@H]1COCCN1c1nc(-c2cccc3[nH]ccc23)nc2c1CN(C(=O)c1ccc3c(c1)OCO3)C2(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5425498
Phase Preclinical
Structure Type MOL
InChI Key MFZAHAAVYSHLCP-QGZVFWFLSA-N
16
Targets
26
Activities
1
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

511.6
MW (Da)
4.47
ALogP
7
HBA
1
HBD
92.8
PSA (Ų)
0.43
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H29N5O4
MW 511.58
Aromatic Rings 4
Heavy Atoms 38
NP-Likeness -0.59

Activity Summary

IC50 26 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase ATR
CHEMBL5024
 IC50 8.3 8.3 5.0 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
 IC50 7.48 7.48 33.0 1
HT-29
CHEMBL384
 IC50 7.35 6.865 45.0 2
HCT-116
CHEMBL394
 IC50 7.17 6.9975 67.0 4
LoVo
CHEMBL614721
 IC50 7.11 7.11 78.0 1
A549
CHEMBL392
 IC50 6.9 6.465 127.0 4
OVCAR-3
CHEMBL614213
 IC50 6.9 6.9 127.0 1
SW-620
CHEMBL612262
 IC50 6.84 6.84 145.0 1
MDA-MB-231
CHEMBL400
 IC50 6.55 6.07 279.0 2
MCF7
CHEMBL387
 IC50 6.46 6.3 347.0 2
Serine-protein kinase ATM
CHEMBL3797
 IC50 6.29 6.29 516.0 1
DNA-dependent protein kinase catalytic subunit
CHEMBL3142
 IC50 6.0 6.0 1000.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 6.0 6.0 1000.0 2
Cytochrome P450 2C19
CHEMBL3622
 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 2810.0 ng.hr.mL-1 Rattus norvegicus
AUC 2740.0 ng.hr.mL-1 Rattus norvegicus
AUC 5700.0 ng.hr.mL-1 Rattus norvegicus
AUC 6170.0 ng.hr.mL-1 Rattus norvegicus
CL 50.3 mL.min-1.kg-1 Homo sapiens
CL 63.6 mL.min-1.kg-1 Rattus norvegicus
CL 5.97 mL.min-1.kg-1 Rattus norvegicus
Cmax 2521.6 nM Rattus norvegicus
F 41.6 % Rattus norvegicus
MRT 2.19 hr Rattus norvegicus
MRT 4.21 hr Rattus norvegicus
T1/2 0.435 hr Homo sapiens
T1/2 0.655 hr Rattus norvegicus
T1/2 1.59 hr Rattus norvegicus
T1/2 3.81 hr Rattus norvegicus
Tmax 1.67 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 = 5.0 nM 8.3 Inhibition of ATR (unknown origin) using peptide as substrate preincubated for 1... 36462444
Serine/threonine-protein kinase mTOR IC50 = 33.0 nM 7.48 Inhibition of mTOR (unknown origin) using peptide as substrate preincubated for ... 36462444
HT-29 IC50 = 45.0 nM 7.35 Antiproliferative activity against ATM-proficient human HT-29 cells assessed as ... 36462444
HCT-116 IC50 = 67.0 nM 7.17 Synergistic antiproliferative activity against ATM-proficient human HCT-116 cell... 36462444
LoVo IC50 = 78.0 nM 7.11 Antiproliferative activity against ATM-deficient human LoVo cells assessed as re... 36462444
HCT-116 IC50 = 84.0 nM 7.08 Antiproliferative activity against ATM-proficient human HCT-116 cells assessed a... 36462444
HCT-116 IC50 = 93.0 nM 7.03 Synergistic antiproliferative activity against ATM-proficient human HCT-116 cell... 36462444
OVCAR-3 IC50 = 127.0 nM 6.9 Antiproliferative activity against ATM-deficient human OVCAR-3 cells assessed as... 36462444
A549 IC50 = 127.0 nM 6.9 Antiproliferative activity against ATM-proficient human A549 cells assessed as r... 36462444
SW-620 IC50 = 145.0 nM 6.84 Antiproliferative activity against ATM-deficient human SW620 cells assessed as r... 36462444
HCT-116 IC50 = 196.0 nM 6.71 Antiproliferative activity against ATM-proficient human HCT-116 cells assessed a... 36462444
MDA-MB-231 IC50 = 279.0 nM 6.55 Synergistic antiproliferative activity against human MDA-MB-231 cells assessed a... 36462444
A549 IC50 = 337.0 nM 6.47 Synergistic antiproliferative activity against ATM-proficient human A549 cells a... 36462444
MCF7 IC50 = 347.0 nM 6.46 Synergistic antiproliferative activity against human MCF7 cells assessed as redu... 36462444
HT-29 IC50 = 421.0 nM 6.38 Antiproliferative activity against ATM-proficient human HT-29 cells assessed as ... 36462444
A549 IC50 = 439.0 nM 6.36 Synergistic antiproliferative activity against ATM-proficient human A549 cells a... 36462444
Serine-protein kinase ATM IC50 = 516.0 nM 6.29 Inhibition of ATM (unknown origin) using peptide as substrate preincubated for 1... 36462444
MCF7 IC50 = 730.0 nM 6.14 Antiproliferative activity against human MCF7 cells assessed as reduction in cel... 36462444
A549 IC50 = 741.0 nM 6.13 Antiproliferative activity against ATM-proficient human A549 cells assessed as r... 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 A549 4
36462444 10.1016/j.ejmech.2022.114945 HCT-116 4
36462444 10.1016/j.ejmech.2022.114945 LoVo 3
36462444 10.1016/j.ejmech.2022.114945 HT-29 2
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