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CHEMBL1774154

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CN[C@@H](C)C(=O)N[C@H]1CCCC[C@H]2CC[C@@H](C(=O)N[C@@H](c3ccccc3)c3cn(CCCCc4ccc(CCCCn5cc([C@@H](NC(=O)[C@@H]6CC[C@@H]7CCCC[C@H](NC(=O)[C@H](C)NC)C(=O)N76)c6ccccc6)nn5)cc4)nn3)N2C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1774154
Phase Preclinical
Structure Type MOL
InChI Key LGYDZXNSSLRFJS-IOQQVAQYSA-N
5
Targets
24
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

1121.5
MW (Da)

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C62H84N14O6
MW 1121.45

Activity Summary

IC50 14 meas. best 8.48
Ki 8 meas. best 9.3
EC50 2 meas. best 7.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Baculoviral IAP repeat-containing protein 2
CHEMBL5462
 Ki 9.3 9.06 0.5 2
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
 Ki 8.7 8.025 2.0 4
Baculoviral IAP repeat-containing protein 3
CHEMBL5335
 Ki 8.7 8.7 2.0 2
MDA-MB-231
CHEMBL400
 IC50 8.48 8.02 3.3 3
Baculoviral IAP repeat-containing protein 2
CHEMBL5462
 IC50 8.34 8.3067 4.6 3
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
 IC50 8.12 7.452 7.5 5
Baculoviral IAP repeat-containing protein 3
CHEMBL5335
 IC50 8.07 8.07 8.5 2
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
 EC50 7.82 7.06 15.0 2
SK-OV-3
CHEMBL614925
 IC50 7.8 7.8 16.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 221.0 ng.hr.mL-1 Rattus norvegicus
T1/2 0.14 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Baculoviral IAP repeat-containing protein 2 Ki = 0.5 nM 9.3 Binding affinity to BIR3 domain of cIAP1 by fluorescence polarization assay 22148838
Baculoviral IAP repeat-containing protein 2 Ki = 1.5 nM 8.82 Binding affinity to human cIAP1 BIR2-BIR3 domain after 2 to 3 hrs by fluorescenc... 21462933
E3 ubiquitin-protein ligase XIAP Ki = 2.0 nM 8.7 Binding affinity to BIR2-BIR3 domain of XIAP by fluorescence polarization assay 22148838
Baculoviral IAP repeat-containing protein 3 Ki = 2.0 nM 8.7 Binding affinity to human cIAP2 BIR3 domain after 2 to 3 hrs by fluorescence pol... 21462933
E3 ubiquitin-protein ligase XIAP Ki = 2.0 nM 8.7 Binding affinity to human XIAP linker BIR2-BIR3 domain expressed in Escherichia ... 21462933
Baculoviral IAP repeat-containing protein 3 Ki = 2.0 nM 8.7 Binding affinity to BIR3 domain of cIAP2 by fluorescence polarization assay 22148838
MDA-MB-231 IC50 = 3.3 nM 8.48 Growth inhibition of human MDA-MB-231 cells after 2 to 3 hrs by WST8 assay 21462933
Baculoviral IAP repeat-containing protein 2 IC50 = 4.6 nM 8.34 Competitive inhibition of human cIAP1 BIR3 domain after 2 to 3 hrs by fluorescen... 21462933
Baculoviral IAP repeat-containing protein 2 IC50 = 4.6 nM 8.34 Binding affinity to BIR3 domain of cIAP1 by fluorescence polarization assay 22148838
Baculoviral IAP repeat-containing protein 2 IC50 = 5.7 nM 8.24 Competitive inhibition of human cIAP1BIR2-BIR3 domain after 2 to 3 hrs by fluore... 21462933
MDA-MB-231 IC50 = 6.8 nM 8.17 Growth inhibition of human MDA-MB-231 cells after 4 days by WST8 assay 22148838
E3 ubiquitin-protein ligase XIAP IC50 = 7.5 nM 8.12 Competitive inhibition of human XIAP linker BIR2-BIR3 domain expressed in Escher... 21462933
E3 ubiquitin-protein ligase XIAP IC50 = 7.5 nM 8.12 Binding affinity to BIR2-BIR3 domain of XIAP by fluorescence polarization assay 22148838
Baculoviral IAP repeat-containing protein 3 IC50 = 8.5 nM 8.07 Binding affinity to BIR3 domain of cIAP2 by fluorescence polarization assay 22148838
Baculoviral IAP repeat-containing protein 3 IC50 = 8.5 nM 8.07 Competitive inhibition of human cIAP2 BIR3 domain after 2 to 3 hrs by fluorescen... 21462933
E3 ubiquitin-protein ligase XIAP EC50 = 15.0 nM 7.82 Antagonist activity at XIAP linker BIR2-BIR3 domain assessed as induction of cas... 22148838
SK-OV-3 IC50 = 16.0 nM 7.8 Growth inhibition of human SKOV3 cells after 4 days by WST8 assay 22148838
MDA-MB-231 IC50 = 39.0 nM 7.41 Cytotoxicity against human MDA-MB-231 cells after 72 hrs by MTT assay 23062821
E3 ubiquitin-protein ligase XIAP IC50 = 41.2 nM 7.38 Displacement of FITC-Smac from human His-tagged XIAP BIR3 domain (241 to 356 res... 23062821
E3 ubiquitin-protein ligase XIAP Ki = 45.0 nM 7.35 Binding affinity to His-tagged human XIAP BIR3 domain expressed in Escherichia c... 21462933

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058564 HEK-293T 10
- 10.6019/CHEMBL5303304 HEK-293T 9
21462933 10.1021/jm101651b MDA-MB-231 7
- 10.6019/CHEMBL5058564 Fibroblast 7
21462933 10.1021/jm101651b E3 ubiquitin-protein ligase XIAP 6
22148838 10.1021/jm201072x E3 ubiquitin-protein ligase XIAP 6
- 10.6019/CHEMBL5303304 Fibroblast 6
23651223 10.1021/jm400216d MDA-MB-231 6
21462933 10.1021/jm101651b Baculoviral IAP repeat-containing protein 2 4
- 10.6019/CHEMBL5058564 U2OS 4
23651223 10.1021/jm400216d Rattus norvegicus 4
23062821 10.1016/j.bmc.2012.09.041 E3 ubiquitin-protein ligase XIAP 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
23651223 10.1021/jm400216d E3 ubiquitin-protein ligase XIAP 2
- 10.6019/CHEMBL5303304 U2OS 2
23062821 10.1016/j.bmc.2012.09.041 IGROV-1 2
23062821 10.1016/j.bmc.2012.09.041 Mus musculus 2
22148838 10.1021/jm201072x Baculoviral IAP repeat-containing protein 3 2
22148838 10.1021/jm201072x Baculoviral IAP repeat-containing protein 2 2
21462933 10.1021/jm101651b Baculoviral IAP repeat-containing protein 3 2

Data from ChEMBL 36 via Core Engine