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Compound Detail

CHEMBL1094250

1,1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-N5-((R)-2-PHENYLPROPYL)-N5'-((R)-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 CHEMBL1094250
Name 1,1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-N5-((R)-2-PHENYLPROPYL)-N5'-((R)-2-PHENYLPROPYL)-2,2'-BINAPHTHYL-5,5'-DICARBOXAMIDE (ATROPISOMERIC MIX)
Phase Preclinical
Structure Type MOL
InChI Key RAYNZUHYMMLQQA-ZEQRLZLVSA-N
7
Targets
20
Activities
3
Assay Types
1
PK Parameters
20
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 12 meas. best 6.75
EC50 6 meas. best 7.31
Kd 2 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 EC50 7.31 7.225 49.0 2
Bcl-2-like protein 1
CHEMBL4625
 Kd 7.0 6.31 100.0 2
PC-3
CHEMBL390
 EC50 6.89 6.11 130.0 2
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 IC50 6.75 6.7167 180.0 3
Bcl-2-like protein 1
CHEMBL4625
 IC50 6.51 6.3967 310.0 3
Apoptosis regulator Bcl-2
CHEMBL4860
 IC50 6.5 6.3133 320.0 3
NCI-H460
CHEMBL396
 EC50 6.38 6.245 420.0 2
Bcl-2-related protein A1
CHEMBL6044
 IC50 6.23 6.2167 590.0 3

Pharmacokinetic Data

Parameter Value Units Species
CL 34.67 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked EC50 = 49.0 nM 7.31 Induction of apoptosis in human BP3 cells after 1 to 2 days by FITC-conjugated a... 20443627
Unchecked EC50 = 72.0 nM 7.14 Induction of apoptosis in human BP3 cells after 1 to 2 days by FITC-conjugated a... 20443627
Bcl-2-like protein 1 Kd = 100.0 nM 7.0 Binding affinity to Bcl-XL by isothermal titration calorimetric assay 20443627
PC-3 EC50 = 130.0 nM 6.89 Cytotoxicity against human PC3 cells after 3 days by ATP-LITE assay 20443627
Induced myeloid leukemia cell differentiation protein Mcl-1 IC50 = 180.0 nM 6.75 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 = 200.0 nM 6.7 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 = 200.0 nM 6.7 Inhibition of BH3 peptide binding to Mcl-1 (unknown origin) 32563811
Bcl-2-like protein 1 IC50 = 310.0 nM 6.51 Inhibition of BH3 peptide binding to Bcl-xL (unknown origin) 32563811
Bcl-2-like protein 1 IC50 = 310.0 nM 6.51 Displacement of FITC-labeled Bak BH3 peptide from Bcl-XL after 30 mins by fluore... 20443627
Apoptosis regulator Bcl-2 IC50 = 320.0 nM 6.5 Displacement of FITC-labeled Bak BH3 peptide from Bcl-2 after 30 mins by fluores... 20443627
Apoptosis regulator Bcl-2 IC50 = 320.0 nM 6.5 Inhibition of BH3 peptide binding to Bcl-2 (unknown origin) 32563811
NCI-H460 EC50 = 420.0 nM 6.38 Cytotoxicity against human H460 cells after 3 days by ATP-LITE assay 20443627
Bcl-2-related protein A1 IC50 = 590.0 nM 6.23 Displacement of FITC-labeled Bak BH3 peptide from Bfl-1 after 30 mins by fluores... 20443627
Bcl-2-related protein A1 IC50 = 620.0 nM 6.21 Displacement of FITC-labeled Bak BH3 peptide from Bfl-1 after 30 mins by fluores... 20443627
Bcl-2-related protein A1 IC50 = 620.0 nM 6.21 Inhibition of BH3 peptide binding to Bfl-1 (unknown origin) 32563811
Bcl-2-like protein 1 IC50 = 680.0 nM 6.17 Displacement of FITC-labeled Bak BH3 peptide from Bcl-XL after 30 mins by fluore... 20443627
NCI-H460 EC50 = 780.0 nM 6.11 Cytotoxicity against human H460 cells after 3 days by ATP-LITE assay 20443627
Apoptosis regulator Bcl-2 IC50 = 1140.0 nM 5.94 Displacement of FITC-labeled Bak BH3 peptide from Bcl-2 after 30 mins by fluores... 20443627
Bcl-2-like protein 1 Kd = 2400.0 nM 5.62 Binding affinity to Bcl-XL by isothermal titration calorimetric assay 20443627
PC-3 EC50 = 4640.0 nM 5.33 Cytotoxicity against human PC3 cells after 3 days by ATP-LITE assay 20443627

Literature References

PubMed DOI Target Context # Activities
20443627 10.1021/jm1001265 No relevant target 8
20443627 10.1021/jm1001265 Mus musculus 7
20443627 10.1021/jm1001265 Unchecked 4
20443627 10.1021/jm1001265 Bcl-2-like protein 1 4
20443627 10.1021/jm1001265 Liver microsomes 3
20443627 10.1021/jm1001265 NON-PROTEIN TARGET 3
20443627 10.1021/jm1001265 Induced myeloid leukemia cell differentiation protein Mcl-1 2
20443627 10.1021/jm1001265 Apoptosis regulator Bcl-2 2
20443627 10.1021/jm1001265 Bcl-2-related protein A1 2
20443627 10.1021/jm1001265 PC-3 2
20443627 10.1021/jm1001265 NCI-H460 2
20443627 10.1021/jm1001265 Plasma 2
20443627 10.1021/jm1001265 ADMET 2
20443627 10.1021/jm1001265 MEF 2
- 10.6019/CHEMBL3301361 ADMET 1
- 10.6019/CHEMBL3301361 No relevant target 1
32563811 10.1016/j.ejmech.2020.112446 Apoptosis regulator Bcl-2 1
32563811 10.1016/j.ejmech.2020.112446 Bcl-2-like protein 1 1
32563811 10.1016/j.ejmech.2020.112446 Induced myeloid leukemia cell differentiation protein Mcl-1 1
32563811 10.1016/j.ejmech.2020.112446 Bcl-2-related protein A1 1

Data from ChEMBL 36 via Core Engine