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Compound Detail

CHEMBL96172

EPOTHILONE D
🧪 Phase II
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🧪 Phase II
C/C1=C/C[C@@H](/C(C)=C/c2csc(C)n2)OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL96172
Name EPOTHILONE D
Phase Phase II
Structure Type MOL
InChI Key XOZIUKBZLSUILX-GIQCAXHBSA-N

Known Names

(-)-desoxyepothilone b 12,13-desoxyepothilone b 12,13-desoxyepothilone b, cis Desoxyepothilone b Epothilone d KOS-862 NSC-703147 R-1492 R1492
10
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
9
Known Names
5
Indications
1
Mechanisms

Molecular Properties

491.7
MW (Da)
5.27
ALogP
7
HBA
2
HBD
96.7
PSA (Ų)
0.43
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C27H41NO5S
MW 491.69
Aromatic Rings 1
Heavy Atoms 34
NP-Likeness 2.04

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tubulin stabiliser STABILISER Tubulin ✓ ✓

Indications

Colorectal Neoplasms Lung Neoplasms Prostatic Neoplasms, Castration-Resistant Breast Neoplasms Neoplasms

Activity Summary

IC50 16 meas. best 8.84
EC50 1 meas. best 6.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 8.84 8.84 1.4 1
KB 3-1
CHEMBL614590
 IC50 8.57 8.57 2.7 1
HL-60
CHEMBL383
 IC50 8.1 8.05 8.0 2
MCF7
CHEMBL387
 IC50 8.1 7.9167 8.0 3
NCI-H460
CHEMBL396
 IC50 8.1 7.81 8.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.0 7.68 10.0 2
SF-268
CHEMBL613977
 IC50 7.85 7.8 14.0 2
CCRF-CEM
CHEMBL382
 IC50 7.82 7.74 15.0 2
NCI/ADR-RES
CHEMBL613829
 IC50 7.52 7.52 30.0 1
Sus scrofa
CHEMBL613488
 EC50 6.06 6.06 880.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 1.44 nM 8.84 Concentration required to inhibit the growth of paclitaxel-resistant human epide... 11133086
KB 3-1 IC50 = 2.7 nM 8.57 Concentration required to inhibit the growth of paclitaxel-sensitive human epide... 11133086
MCF7 IC50 = 8.0 nM 8.1 Cytotoxicity against human MCF7 cells after 3 days by SRB assay 12141877
NCI-H460 IC50 = 8.0 nM 8.1 Cytotoxicity against human NCI-H460 cells after 3 days by SRB assay 12141877
HL-60 IC50 = 8.0 nM 8.1 Cytotoxicity against human HL60 cells after 3 days by SRB assay 12141877
HL-60 IC50 = 10.0 nM 8.0 Cytotoxicity against mitoxantrone-resistant human HL60 cells after 3 days by SRB... 12141877
NON-PROTEIN TARGET IC50 = 10.0 nM 8.0 Cytotoxicity against human MCF7/ADR cells after 72 hrs 23994325
SF-268 IC50 = 14.0 nM 7.85 Cytotoxicity against human SF268 cells after 3 days by SRB assay 12141877
MCF7 IC50 = 14.0 nM 7.85 Cytotoxicity against human MCF7 cells after 72 hrs 23994325
CCRF-CEM IC50 = 15.0 nM 7.82 Cytotoxicity against camptothecin-resistant human CCRF-CEM cells after 3 days by... 12141877
MCF7 IC50 = 16.0 nM 7.8 Cytotoxicity against human MCF7 cells after 3 days by SRB assay 14575429
SF-268 IC50 = 18.0 nM 7.75 Cytotoxicity against human SF268 cells after 3 days by SRB assay 14575429
CCRF-CEM IC50 = 22.0 nM 7.66 Cytotoxicity against human CCRF-CEM cells after 3 days by SRB assay 12141877
NCI/ADR-RES IC50 = 30.0 nM 7.52 Cytotoxicity against human NCI/ADR-RES cells after 3 days by SRB assay 12141877
NCI-H460 IC50 = 30.0 nM 7.52 Cytotoxicity against human NCI-H460 cells after 3 days by SRB assay 14575429
NON-PROTEIN TARGET IC50 = 44.0 nM 7.36 Cytotoxicity against human NCI/ADR cells after 3 days by SRB assay 14575429
Sus scrofa EC50 = 880.0 nM 6.06 Concentrations required to induce 50 percent polymerization of porcine brain-der... 11133086

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
24900764 10.1021/ml400233e Unchecked 2
24900764 10.1021/ml400233e Plasma 2
24900764 10.1021/ml400233e Brain 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
12141877 10.1021/np020120f HL-60 2
12141877 10.1021/np020120f CCRF-CEM 2
11133086 10.1016/s0960-894x(00)00555-2 Sus scrofa 2
14575429 10.1021/np030218+ MCF7 1
23994325 10.1016/j.ejmech.2013.08.003 NON-PROTEIN TARGET 1
14575429 10.1021/np030218+ NCI-H460 1
14575429 10.1021/np030218+ SF-268 1
14575429 10.1021/np030218+ NON-PROTEIN TARGET 1
12141877 10.1021/np020120f NCI-H460 1
12141877 10.1021/np020120f SF-268 1
12141877 10.1021/np020120f NCI/ADR-RES 1
12141877 10.1021/np020120f MCF7 1
11473410 10.1021/np000629f L929 1
11133086 10.1016/s0960-894x(00)00555-2 KB 1

Data from ChEMBL 36 via Core Engine