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Compound Detail

CHEMBL4446378

TAPOTOCLAX
Phase I
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Phase I
CO[C@H]1/C=C/C[C@H](C)[C@@H](C)S(=O)(=O)NC(=O)c2ccc3c(c2)N(C[C@@H]2CC[C@H]21)C[C@@]1(CCCc2cc(Cl)ccc21)CO3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4446378
Name TAPOTOCLAX
Phase Phase I
Structure Type MOL
InChI Key JQNINBDKGLWYMU-GEAQBIRJSA-N

Known Names

Amg 176 AMG-176 AMG176 Mcl-1 inhibitor amg 176 Mcl-1 inhibitor amg-176 Tapotoclax
6
Targets
15
Activities
2
Assay Types
18
PK Parameters
20
Publications
6
Known Names
2
Indications

Molecular Properties

613.2
MW (Da)
5.90
ALogP
6
HBA
1
HBD
84.9
PSA (Ų)
0.40
QED
2
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Chemical Probe
USAN Stem -toclax
USAN Year 2020

Extended Properties

Molecular Formula C33H41ClN2O5S
MW 613.22
Aromatic Rings 2
Heavy Atoms 42
NP-Likeness 0.45

Indications

Leukemia, Myeloid, Acute Multiple Myeloma

Activity Summary

Ki 10 meas. best 10.22
IC50 5 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
G1/S-specific cyclin-D1
CHEMBL3610
 Ki 10.22 10.22 0.1 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 Ki 10.22 10.195 0.1 4
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 IC50 9.52 9.52 0.3 1
Unchecked
CHEMBL612545
 Ki 9.49 9.49 0.3 1
OPM-2
CHEMBL2366353
 IC50 7.8 7.21 16.0 2
Bcl-2-like protein 1
CHEMBL4625
 Ki 6.16 6.16 700.0 2
Apoptosis regulator Bcl-2
CHEMBL4860
 Ki 6.02 6.02 950.0 2
Bcl-2-like protein 1
CHEMBL4625
 IC50 5.85 5.85 1420.0 1
Apoptosis regulator Bcl-2
CHEMBL4860
 IC50 5.71 5.71 1930.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.0 mL.min-1.kg-1 Rattus norvegicus
CL 0.5 mL.min-1.kg-1 Mus musculus
CL 66.67 mL.min-1.kg-1 Mus musculus
CL 0.3333 mL.min-1.kg-1 Canis lupus familiaris
CL 22.33 mL.min-1.kg-1 Canis lupus familiaris
CL 138.33 mL.min-1.kg-1 Rattus norvegicus
CL 39.0 mL.min-1.g-1 Homo sapiens
CL 9.4 mL.min-1.g-1 Mus musculus
F 31.0 % Mus musculus
F 27.0 % Canis lupus familiaris
F 34.0 % Rattus norvegicus
F 32.0 % Mus musculus
Fu 0.0007 - Homo sapiens
Fu 0.0003 - Mus musculus
T1/2 13.8 hr Mus musculus
T1/2 10.8 hr Canis lupus familiaris
T1/2 18.2 hr Rattus norvegicus
T1/2 14.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Induced myeloid leukemia cell differentiation protein Mcl-1 Ki = 0.06 nM 10.22 Inhibition of human Biotin-DMRPEIWIAQELRRIGDEFNAYYARR peptide binding to 6XHis-t... 31129454
Induced myeloid leukemia cell differentiation protein Mcl-1 Ki = 0.06 nM 10.22 Inhibition of recombinant His6-tagged human MCL1 (171 to 327 residues) expressed... 33253879
Induced myeloid leukemia cell differentiation protein Mcl-1 Ki = 0.06 nM 10.22 Binding affinity to Mcl-1 (unknown origin) 34530384
G1/S-specific cyclin-D1 Ki = 0.06 nM 10.22 Binding affinity to human BCL1 assessed as inhibition constant 39171975
Induced myeloid leukemia cell differentiation protein Mcl-1 Ki = 0.076 nM 10.12 Inhibition of recombinant C-terminal His6x-tagged human Mcl-1 (171 to 327 residu... 31736296
Induced myeloid leukemia cell differentiation protein Mcl-1 IC50 = 0.3 nM 9.52 Inhibition of recombinant C-terminal His6x-tagged human Mcl-1 (171 to 327 residu... 31736296
Unchecked Ki = 0.32 nM 9.49 Inhibition of terbium-labelled Mcl-1 (unknown origin)/Bim BH3 peptide (H3N-(C/Cy... 37114951
OPM-2 IC50 = 16.0 nM 7.8 Antiproliferative activity against human OPM2 cells assessed as reduction in cel... 31736296
OPM-2 IC50 = 240.0 nM 6.62 Anticancer activity against human OPM-2 cells assessed as inhibition of cell via... 33253879
Bcl-2-like protein 1 Ki = 700.0 nM 6.16 Inhibition of human Biotin-DMRPEIWIAQELRRIGDEFNAYYARR peptide binding to Bcl-xL ... 31129454
Bcl-2-like protein 1 Ki = 700.0 nM 6.16 Inhibition of recombinant His6-tagged human Bcl-xL (1 to 196 residues) expressed... 33253879
Apoptosis regulator Bcl-2 Ki = 950.0 nM 6.02 Inhibition of human Biotin-DMRPEIWIAQELRRIGDEFNAYYARR peptide binding to recombi... 31129454
Apoptosis regulator Bcl-2 Ki = 950.0 nM 6.02 Inhibition of recombinant His10-tagged human Bcl-2 (2 to 211 residues) using bio... 33253879
Bcl-2-like protein 1 IC50 = 1420.0 nM 5.85 Inhibition of recombinant C-terminal His6x-tagged human Bcl-xL (1 to 196 residue... 31736296
Apoptosis regulator Bcl-2 IC50 = 1930.0 nM 5.71 Inhibition of recombinant C-terminal His10x-tagged human Bcl-2 (2 to 211 residue... 31736296

Literature References

PubMed DOI Target Context # Activities
31736296 10.1021/acs.jmedchem.9b01310 ADMET 18
37114951 10.1021/acs.jmedchem.2c01953 ADMET 6
37114951 10.1021/acs.jmedchem.2c01953 No relevant target 4
31736296 10.1021/acs.jmedchem.9b01310 No relevant target 4
31736296 10.1021/acs.jmedchem.9b01310 Mus musculus 2
31736296 10.1021/acs.jmedchem.9b01310 Unchecked 2
34530384 10.1016/j.ejmech.2021.113837 ADMET 2
31736296 10.1021/acs.jmedchem.9b01310 Induced myeloid leukemia cell differentiation protein Mcl-1 2
39171975 10.1021/acs.jmedchem.4c01163 No relevant target 2
33253879 10.1016/j.bmcl.2020.127717 Unchecked 2
31129454 10.1016/j.ejmech.2019.05.019 Bcl-2-like protein 1 1
34530384 10.1016/j.ejmech.2021.113837 OPM-2 1
34530384 10.1016/j.ejmech.2021.113837 Induced myeloid leukemia cell differentiation protein Mcl-1 1
33253879 10.1016/j.bmcl.2020.127717 Apoptosis regulator Bcl-2 1
33253879 10.1016/j.bmcl.2020.127717 OPM-2 1
33253879 10.1016/j.bmcl.2020.127717 Induced myeloid leukemia cell differentiation protein Mcl-1 1
31129454 10.1016/j.ejmech.2019.05.019 Apoptosis regulator Bcl-2 1
31129454 10.1016/j.ejmech.2019.05.019 Induced myeloid leukemia cell differentiation protein Mcl-1 1
31736296 10.1021/acs.jmedchem.9b01310 Bcl-2-like protein 1 1
31736296 10.1021/acs.jmedchem.9b01310 Apoptosis regulator Bcl-2 1

Data from ChEMBL 36 via Core Engine