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Compound Detail

CHEMBL481422

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CN[C@@H](C)C(=O)N[C@H]1CCCC[C@H]2CC[C@@H](C(=O)NC(c3ccccc3)c3ccccc3)N2C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL481422
Phase Preclinical
Structure Type MOL
InChI Key XBTLZUHJBOBKRG-HCUBDLJJSA-N
9
Targets
46
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

476.6
MW (Da)
2.92
ALogP
4
HBA
3
HBD
90.5
PSA (Ų)
0.57
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H36N4O3
MW 476.62
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness -0.52

Activity Summary

IC50 23 meas. best 7.42
Ki 20 meas. best 9.1
EC50 2 meas. best 6.2
Kd 1 meas. best 7.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Baculoviral IAP repeat-containing protein 2
CHEMBL5462
 Ki 9.1 8.3933 0.8 6
Baculoviral IAP repeat-containing protein 8
CHEMBL5851
 Ki 8.74 8.74 1.8 1
Baculoviral IAP repeat-containing protein 3
CHEMBL5335
 Ki 8.73 7.99 1.8 4
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
 Kd 7.58 7.58 26.0 1
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
 Ki 7.58 6.635 26.0 8
Unchecked
CHEMBL612545
 Ki 7.58 7.58 26.0 1
Baculoviral IAP repeat-containing protein 2
CHEMBL5462
 IC50 7.42 7.325 38.0 4
Baculoviral IAP repeat-containing protein 3
CHEMBL5335
 IC50 7.16 7.14 70.0 3
Nonstructural protein 3
CHEMBL4523954
 IC50 7.0 7.0 100.0 1
MDA-MB-231
CHEMBL400
 IC50 6.59 6.4425 259.0 4
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
 IC50 6.36 5.8889 438.0 9
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
 EC50 6.2 6.2 630.0 1
SK-OV-3
CHEMBL614925
 IC50 6.05 6.05 900.0 1
Unchecked
CHEMBL612545
 EC50 5.99 5.99 1030.0 1
HL-60
CHEMBL383
 IC50 5.85 5.85 1400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Baculoviral IAP repeat-containing protein 2 Ki = 0.8 nM 9.1 Displacement of fluorescent SM5F peptide from His-tagged human cIAP1 BIR3 domain... 19138149
Baculoviral IAP repeat-containing protein 2 Ki = 1.0 nM 9.0 Displacement of fluorescently tagged SM5F from human cIAP-1 BIR3 expressed in Es... 19049347
Baculoviral IAP repeat-containing protein 8 Ki = 1.8 nM 8.74 Displacement of fluorescently tagged SM5F from human cIAP-2 BIR3 expressed in Es... 19049347
Baculoviral IAP repeat-containing protein 3 Ki = 1.84 nM 8.73 Displacement of fluorescent SM5F peptide from His-tagged human cIAP2 BIR3 domain... 19138149
Baculoviral IAP repeat-containing protein 2 Ki = 6.7 nM 8.17 Displacement of fluorescent SM5F peptide from His-tagged human cIAP1 BIR3 domain... 20684551
Baculoviral IAP repeat-containing protein 2 Ki = 6.8 nM 8.17 Binding affinity to human cIAP1 BIR3 domain after 2 to 3 hrs by fluorescence pol... 21462933
Baculoviral IAP repeat-containing protein 2 Ki = 6.7 nM 8.17 Binding affinity to BIR3 domain of cIAP1 by fluorescence polarization assay 22148838
Baculoviral IAP repeat-containing protein 2 Ki = 18.0 nM 7.75 Binding affinity to human cIAP1 BIR2-BIR3 domain after 2 to 3 hrs by fluorescenc... 21462933
Baculoviral IAP repeat-containing protein 3 Ki = 18.0 nM 7.75 Binding affinity to human cIAP2 BIR3 domain after 2 to 3 hrs by fluorescence pol... 21462933
Baculoviral IAP repeat-containing protein 3 Ki = 18.3 nM 7.74 Displacement of fluorescent SM5F peptide from His-tagged human cIAP2 BIR3 domain... 20684551
Baculoviral IAP repeat-containing protein 3 Ki = 18.3 nM 7.74 Binding affinity to BIR3 domain of cIAP2 by fluorescence polarization assay 22148838
E3 ubiquitin-protein ligase XIAP Kd = 26.0 nM 7.58 Binding affinity to XIAP-BIR3 domain (unknown origin) 30676015
E3 ubiquitin-protein ligase XIAP Ki = 26.0 nM 7.58 Displacement of fluorescent SM5F peptide from His-tagged human XIAP BIR3 domain ... 19138149
Unchecked Ki = 26.0 nM 7.58 Displacement of fluorescently tagged SM5F from human XIAP BIR3 expressed in Esch... 19049347
E3 ubiquitin-protein ligase XIAP Ki = 26.0 nM 7.58 Binding affinity to N-terminal 6xHis-tagged human cloned XIAP BIR3 domain expres... 18954041
Baculoviral IAP repeat-containing protein 2 IC50 = 38.0 nM 7.42 Competitive inhibition of human cIAP1 BIR3 domain after 2 to 3 hrs by fluorescen... 21462933
Baculoviral IAP repeat-containing protein 2 IC50 = 46.2 nM 7.33 Binding affinity to BIR3 domain of cIAP1 by fluorescence polarization assay 22148838
Baculoviral IAP repeat-containing protein 2 IC50 = 46.2 nM 7.33 Displacement of fluorescent SM5F peptide from His-tagged human cIAP1 BIR3 domain... 20684551
Baculoviral IAP repeat-containing protein 2 IC50 = 60.0 nM 7.22 Competitive inhibition of human cIAP1BIR2-BIR3 domain after 2 to 3 hrs by fluore... 21462933
Baculoviral IAP repeat-containing protein 3 IC50 = 70.0 nM 7.16 Competitive inhibition of human cIAP2 BIR3 domain after 2 to 3 hrs by fluorescen... 21462933

Literature References

PubMed DOI Target Context # Activities
18954041 10.1021/jm8006849 MDA-MB-231 11
22148838 10.1021/jm201072x E3 ubiquitin-protein ligase XIAP 6
21462933 10.1021/jm101651b E3 ubiquitin-protein ligase XIAP 6
19138149 10.1021/jm801101z MDA-MB-231 5
30676015 10.1021/acs.jmedchem.8b01668 E3 ubiquitin-protein ligase XIAP 4
21462933 10.1021/jm101651b Baculoviral IAP repeat-containing protein 2 4
18954041 10.1021/jm8006849 SK-OV-3 3
18954041 10.1021/jm8006849 E3 ubiquitin-protein ligase XIAP 3
20684551 10.1021/jm100487z MDA-MB-231 3
22148838 10.1021/jm201072x Baculoviral IAP repeat-containing protein 2 2
22148838 10.1021/jm201072x Baculoviral IAP repeat-containing protein 3 2
21462933 10.1021/jm101651b Baculoviral IAP repeat-containing protein 3 2
20684551 10.1021/jm100487z E3 ubiquitin-protein ligase XIAP 2
20684551 10.1021/jm100487z Baculoviral IAP repeat-containing protein 2 2
20684551 10.1021/jm100487z Baculoviral IAP repeat-containing protein 3 2
23651223 10.1021/jm400216d E3 ubiquitin-protein ligase XIAP 2
19049347 10.1021/jm801254r Unchecked 2
19138149 10.1021/jm801101z E3 ubiquitin-protein ligase XIAP 2
31980339 10.1016/j.bmcl.2020.126965 Nonstructural protein 3 1
19138149 10.1021/jm801101z Baculoviral IAP repeat-containing protein 3 1

Data from ChEMBL 36 via Core Engine