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Compound Detail

CHEMBL1094366

(S)-1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-N5-((S)-2-PHENYLPROPYL)-N5'-((S)-2-PHENYLPROPYL)-2,2'-BINAPHTHYL-5,5'-DICARBOXAMIDE (ATROPISOMERIC MIX)
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Cc1cc2c(C(=O)NC[C@@H](C)c3ccccc3)c(O)c(O)cc2c(O)c1-c1c(C)cc2c(C(=O)NC[C@@H](C)c3ccccc3)c(O)c(O)cc2c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1094366
Name (S)-1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-N5-((S)-2-PHENYLPROPYL)-N5'-((S)-2-PHENYLPROPYL)-2,2'-BINAPHTHYL-5,5'-DICARBOXAMIDE (ATROPISOMERIC MIX)
Phase Preclinical
Structure Type MOL
InChI Key RAYNZUHYMMLQQA-DNQXCXABSA-N
7
Targets
16
Activities
3
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

700.8
MW (Da)
7.58
ALogP
8
HBA
8
HBD
179.6
PSA (Ų)
0.07
QED
3
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C42H40N2O8
MW 700.79
Aromatic Rings 6
Heavy Atoms 52
NP-Likeness 0.13

Activity Summary

IC50 8 meas. best 6.62
EC50 6 meas. best 6.92
Kd 2 meas. best 6.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 EC50 6.92 6.715 120.0 2
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 IC50 6.62 6.62 240.0 2
Bcl-2-like protein 1
CHEMBL4625
 Kd 6.4 6.05 400.0 2
Apoptosis regulator Bcl-2
CHEMBL4860
 IC50 6.37 6.37 430.0 2
Bcl-2-like protein 1
CHEMBL4625
 IC50 6.36 6.275 440.0 2
PC-3
CHEMBL390
 EC50 6.33 6.06 470.0 2
NCI-H460
CHEMBL396
 EC50 6.25 6.175 560.0 2
Bcl-2-related protein A1
CHEMBL6044
 IC50 6.12 6.115 750.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked EC50 = 120.0 nM 6.92 Induction of apoptosis in human BP3 cells after 1 to 2 days by FITC-conjugated a... 20443627
Induced myeloid leukemia cell differentiation protein Mcl-1 IC50 = 240.0 nM 6.62 Displacement of FITC-labeled Bak BH3 peptide from Mcl-1 after 30 mins by fluores... 20443627
Induced myeloid leukemia cell differentiation protein Mcl-1 IC50 = 240.0 nM 6.62 Displacement of FITC-labeled Bak BH3 peptide from Mcl-1 after 30 mins by fluores... 20443627
Unchecked EC50 = 310.0 nM 6.51 Induction of apoptosis in human BP3 cells after 1 to 2 days by FITC-conjugated a... 20443627
Bcl-2-like protein 1 Kd = 400.0 nM 6.4 Binding affinity to Bcl-XL by isothermal titration calorimetric assay 20443627
Apoptosis regulator Bcl-2 IC50 = 430.0 nM 6.37 Displacement of FITC-labeled Bak BH3 peptide from Bcl-2 after 30 mins by fluores... 20443627
Apoptosis regulator Bcl-2 IC50 = 430.0 nM 6.37 Displacement of FITC-labeled Bak BH3 peptide from Bcl-2 after 30 mins by fluores... 20443627
Bcl-2-like protein 1 IC50 = 440.0 nM 6.36 Displacement of FITC-labeled Bak BH3 peptide from Bcl-XL after 30 mins by fluore... 20443627
PC-3 EC50 = 470.0 nM 6.33 Cytotoxicity against human PC3 cells after 3 days by ATP-LITE assay 20443627
NCI-H460 EC50 = 560.0 nM 6.25 Cytotoxicity against human H460 cells after 3 days by ATP-LITE assay 20443627
Bcl-2-like protein 1 IC50 = 650.0 nM 6.19 Displacement of FITC-labeled Bak BH3 peptide from Bcl-XL after 30 mins by fluore... 20443627
Bcl-2-related protein A1 IC50 = 750.0 nM 6.12 Displacement of FITC-labeled Bak BH3 peptide from Bfl-1 after 30 mins by fluores... 20443627
Bcl-2-related protein A1 IC50 = 770.0 nM 6.11 Displacement of FITC-labeled Bak BH3 peptide from Bfl-1 after 30 mins by fluores... 20443627
NCI-H460 EC50 = 800.0 nM 6.1 Cytotoxicity against human H460 cells after 3 days by ATP-LITE assay 20443627
PC-3 EC50 = 1610.0 nM 5.79 Cytotoxicity against human PC3 cells after 3 days by ATP-LITE assay 20443627
Bcl-2-like protein 1 Kd = 2000.0 nM 5.7 Binding affinity to Bcl-XL by isothermal titration calorimetric assay 20443627

Literature References

PubMed DOI Target Context # Activities
20443627 10.1021/jm1001265 No relevant target 8
20443627 10.1021/jm1001265 Mus musculus 6
20443627 10.1021/jm1001265 Unchecked 4
20443627 10.1021/jm1001265 Bcl-2-like protein 1 4
20443627 10.1021/jm1001265 MEF 2
20443627 10.1021/jm1001265 ADMET 2
20443627 10.1021/jm1001265 Plasma 2
20443627 10.1021/jm1001265 Liver microsomes 2
20443627 10.1021/jm1001265 NCI-H460 2
20443627 10.1021/jm1001265 PC-3 2
20443627 10.1021/jm1001265 Induced myeloid leukemia cell differentiation protein Mcl-1 2
20443627 10.1021/jm1001265 Bcl-2-related protein A1 2
20443627 10.1021/jm1001265 Apoptosis regulator Bcl-2 2

Data from ChEMBL 36 via Core Engine