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Compound Detail

CHEMBL8953

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COc1cc(C(=O)c2cc(Cl)ccc2N)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL8953
Phase Preclinical
Structure Type MOL
InChI Key XNXGUYDYCYSOCU-UHFFFAOYSA-N
7
Targets
13
Activities
2
Assay Types
3
PK Parameters
12
Publications
0
Known Names

Molecular Properties

321.8
MW (Da)
3.18
ALogP
5
HBA
1
HBD
70.8
PSA (Ų)
0.68
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H16ClNO4
MW 321.76
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.35

Activity Summary

IC50 12 meas. best 7.22
EC50 1 meas. best 7.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CPT30 cell line
CHEMBL614470
 IC50 7.22 7.22 60.3 1
HONE1 cell line
CHEMBL614830
 IC50 7.19 7.19 64.5 1
KB
CHEMBL398
 IC50 7.15 6.9271 71.0 7
T98G
CHEMBL614775
 EC50 7.05 7.05 90.0 1
Tubulin
CHEMBL2094134
 IC50 7.0 7.0 100.0 1
TSGH
CHEMBL615018
 IC50 6.73 6.73 185.0 1
HT-29
CHEMBL384
 IC50 6.66 6.66 218.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 16200.0 nM Mus musculus
Cmax 100.0 nM Mus musculus
Cmax 100.0 nM Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CPT30 cell line IC50 = 60.3 nM 7.22 Inhibitory concentration against camptothecin (CPT) resistant cell line using te... 12467626
HONE1 cell line IC50 = 64.5 nM 7.19 Inhibitory concentration against human NPC cancer cell line using tetrazolium dy... 12467626
KB IC50 = 71.0 nM 7.15 Inhibitory concentration against taxol resistant cell line (KBs5) at a concentra... 12467626
T98G EC50 = 90.0 nM 7.05 Decrease in PrPc expression on human T98G cell surface after 2 days by ELISA 24530226
KB IC50 = 90.4 nM 7.04 Inhibitory concentration against human oral cancer cell line (KB) using tetrazol... 12467626
KB IC50 = 97.2 nM 7.01 Inhibitory concentration against vincristine-resistant cell line (KB-Vin 10) usi... 12467626
Tubulin IC50 = 100.0 nM 7.0 Inhibitory concentration required against MAP-rich tubulin polymerization 15139768
KB IC50 = 104.0 nM 6.98 Inhibitory concentration against VP16 resistant cell line (KB-7D) using tetrazol... 12467626
KB IC50 = 156.0 nM 6.81 Inhibitory concentration against camptothecin (CPT) resistant cell line (KB-100)... 12467626
KB IC50 = 162.0 nM 6.79 In vitro cytotoxic activity against human KB-VIN10 cell line overexpressing P-gp... 15139768
TSGH IC50 = 185.0 nM 6.73 In vitro cytotoxic activity against human TSGH cell line of stomach carcinoma 15139768
KB IC50 = 195.0 nM 6.71 In vitro cytotoxic activity against human KB cell line of epidermoid carcinoma 15139768
HT-29 IC50 = 218.0 nM 6.66 In vitro cytotoxic activity against human HT-29 cell line of colorectal carcinom... 15139768

Literature References

PubMed DOI Target Context # Activities
12467626 10.1016/s0960-894x(02)00850-8 KB 3-1 12
12467626 10.1016/s0960-894x(02)00850-8 KB 5
15139768 10.1021/jm0305974 KB 2
24530226 10.1016/j.bmc.2014.01.001 Brain 2
12467626 10.1016/s0960-894x(02)00850-8 CPT30 cell line 1
12467626 10.1016/s0960-894x(02)00850-8 HONE1 cell line 1
15139768 10.1021/jm0305974 HT-29 1
15139768 10.1021/jm0305974 TSGH 1
15139768 10.1021/jm0305974 Tubulin 1
24530226 10.1016/j.bmc.2014.01.001 Plasma 1
24530226 10.1016/j.bmc.2014.01.001 T98G 1
- 10.6019/CHEMBL3301361 No relevant target 1

Data from ChEMBL 36 via Core Engine