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Compound Detail

CHEMBL466586

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CNC(=O)O[C@H]1CN[C@H](C#Cc2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3s2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL466586
Phase Preclinical
Structure Type MOL
InChI Key XNBMKLASHVMECR-UYAOXDASSA-N
5
Targets
9
Activities
2
Assay Types
2
PK Parameters
12
Publications
0
Known Names

Molecular Properties

552.0
MW (Da)
5.24
ALogP
8
HBA
3
HBD
97.4
PSA (Ų)
0.28
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H23ClFN5O3S
MW 552.03
Aromatic Rings 4
Heavy Atoms 38
NP-Likeness -0.98

Activity Summary

IC50 6 meas. best 7.7
EC50 3 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 7.7 7.7 20.0 2
BT-474
CHEMBL614529
 IC50 7.55 7.55 28.0 1
BT-474
CHEMBL614529
 EC50 7.52 7.52 30.0 1
Epidermal growth factor receptor
CHEMBL203
 IC50 7.3 7.3 50.0 2
HN5
CHEMBL614828
 IC50 7.24 7.24 58.0 1
HN5
CHEMBL614828
 EC50 7.22 7.22 60.0 1
HFF
CHEMBL614071
 EC50 5.3 5.3 5000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 18.0 ng.hr.kg/mg/ml Mus musculus
AUC 18.0 ng.hr.kg/mg/ml Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Receptor tyrosine-protein kinase erbB-2 IC50 = 20.0 nM 7.7 Inhibition of ERBb2 by HTRF assay 19028424
Receptor tyrosine-protein kinase erbB-2 IC50 = 20.0 nM 7.7 Inhibition of ErbB2 kinase 18842405
BT-474 IC50 = 28.0 nM 7.55 Antiproliferative activity against human BT474 cells overexpressing ErbB2 after ... 18842405
BT-474 EC50 = 30.0 nM 7.52 Antiproliferative activity against human BT474 cells overexpressing ERBb2 after ... 19028424
Epidermal growth factor receptor IC50 = 50.0 nM 7.3 Inhibition of EGFR by HTRF assay 19028424
Epidermal growth factor receptor IC50 = 50.0 nM 7.3 Inhibition of EGFR kinase 18842405
HN5 IC50 = 58.0 nM 7.24 Antiproliferative activity against human HN5 cells overexpressing EGFR after 3 d... 18842405
HN5 EC50 = 60.0 nM 7.22 Antiproliferative activity against human HN5 cells overexpressing EGFR after 3 d... 19028424
HFF EC50 = 5000.0 nM 5.3 Antiproliferative activity against human HFF cells after 3 days by methylene blu... 19028424

Literature References

PubMed DOI Target Context # Activities
19028424 10.1016/j.bmcl.2008.11.023 Epidermal growth factor receptor 2
18842405 10.1016/j.bmcl.2008.09.090 Epidermal growth factor receptor 2
19028424 10.1016/j.bmcl.2008.11.023 Receptor tyrosine-protein kinase erbB-2 1
19028424 10.1016/j.bmcl.2008.11.023 HN5 1
19028424 10.1016/j.bmcl.2008.11.023 BT-474 1
19028424 10.1016/j.bmcl.2008.11.023 HFF 1
19028424 10.1016/j.bmcl.2008.11.023 Mus musculus 1
18842405 10.1016/j.bmcl.2008.09.090 Receptor tyrosine-protein kinase erbB-2 1
18842405 10.1016/j.bmcl.2008.09.090 HN5 1
18842405 10.1016/j.bmcl.2008.09.090 BT-474 1
18842405 10.1016/j.bmcl.2008.09.090 Mus musculus 1
18842405 10.1016/j.bmcl.2008.09.090 ADMET 1

Data from ChEMBL 36 via Core Engine