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Compound Detail

CHEMBL329993

EPOTHILONE A
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C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL329993
Name EPOTHILONE A
Phase Preclinical
Structure Type MOL
InChI Key HESCAJZNRMSMJG-KKQRBIROSA-N
14
Targets
29
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

493.7
MW (Da)
4.09
ALogP
8
HBA
2
HBD
109.2
PSA (Ų)
0.47
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C26H39NO6S
MW 493.67
Aromatic Rings 1
Heavy Atoms 34
NP-Likeness 1.93

Activity Summary

IC50 26 meas. best 9.15
EC50 2 meas. best 5.95
Kd 1 meas. best 7.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ADMET
CHEMBL612558
 IC50 9.15 9.15 0.7 1
MCF7
CHEMBL387
 IC50 9.1 8.7567 0.8 6
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.89 8.176 1.3 5
HT-1080
CHEMBL614580
 IC50 8.89 8.89 1.3 1
KB
CHEMBL398
 IC50 8.72 8.72 1.9 1
KB 3-1
CHEMBL614590
 IC50 8.67 8.67 2.1 1
A549
CHEMBL392
 IC50 8.66 8.625 2.2 2
1A9
CHEMBL614075
 IC50 8.66 8.66 2.2 2
HCT-116
CHEMBL394
 IC50 8.55 8.55 2.8 1
L929
CHEMBL612267
 IC50 8.42 8.265 3.8 2
1A9/ptx-22
CHEMBL613858
 IC50 8.23 8.23 5.9 2
1A9/ptx-10
CHEMBL614509
 IC50 7.7 7.7 20.0 2
Unchecked
CHEMBL612545
 Kd 7.55 7.55 28.0 1
Sus scrofa
CHEMBL613488
 EC50 5.95 5.95 1120.0 1
Unchecked
CHEMBL612545
 EC50 5.34 5.34 4600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ADMET IC50 = 0.7 nM 9.15 Cytotoxicity against BAEC 19804980
MCF7 IC50 = 0.8 nM 9.1 Cytotoxicity against human MCF7 cells in presence of 10 mM DTT after 48 hrs by S... 25084144
MCF7 IC50 = 0.9 nM 9.05 Cytotoxicity against human MCF7 cells after 48 hrs by SRB assay 25084144
HT-1080 IC50 = 1.3 nM 8.89 Cytotoxicity against human HT1080 cells after 3 days by MTT assay 19804980
NON-PROTEIN TARGET IC50 = 1.3 nM 8.89 Cytotoxicity against human SKOV3 cells by MTT assay 25397992
KB IC50 = 1.91 nM 8.72 Concentration required to inhibit the growth of paclitaxel-resistant human epide... 11133086
KB 3-1 IC50 = 2.15 nM 8.67 Concentration required to inhibit the growth of paclitaxel-sensitive human epide... 11133086
1A9 IC50 = 2.2 nM 8.66 Inhibitory concentration against ovarian carcinoma 1A9 cell growth 16134928
1A9 IC50 = 2.2 nM 8.66 Inhibitory concentration against ovarian carcinoma 1A9 cell growth 16134928
A549 IC50 = 2.2 nM 8.66 Antiproliferative activity against human A549 cells after 72 hrs 19433359
MCF7 IC50 = 2.2 nM 8.66 Cytotoxicity against human MCF7 cells by MTT assay 25397992
NON-PROTEIN TARGET IC50 = 2.4 nM 8.62 Cytotoxicity against human PC3 cells by MTT assay 25397992
MCF7 IC50 = 2.5 nM 8.6 Cytotoxicity against human MCF7 cells after 72 hrs by methylene blue assay 19804980
A549 IC50 = 2.6 nM 8.59 Cytotoxicity against human A549 cells after 72 hrs by methylene blue assay 19804980
MCF7 IC50 = 2.6 nM 8.59 Antiproliferative activity against human MCF7 cells after 72 hrs 19433359
HCT-116 IC50 = 2.8 nM 8.55 Antiproliferative activity against human HCT116 cells after 72 hrs by methylene ... 18271516
MCF7 IC50 = 2.9 nM 8.54 Antiproliferative activity against human MCF7 cells after 72 hrs by methylene bl... 18271516
L929 IC50 = 3.8 nM 8.42 Cytotoxicity against mouse L929 cells after 5 days by MTT assay 27231731
1A9/ptx-22 IC50 = 5.9 nM 8.23 Inhibitory concentration against beta-tubulin mutant 1A9PTX22 cell line 16134928
1A9/ptx-22 IC50 = 5.9 nM 8.23 Inhibitory concentration against beta-tubulin mutant 1A9PTX22 cell line 16134928

Literature References

PubMed DOI Target Context # Activities
17206139 10.1038/nchembio853 Unchecked 7
19804980 10.1016/j.bmc.2009.09.032 NON-PROTEIN TARGET 3
25397992 10.1021/np500632c NON-PROTEIN TARGET 3
25084144 10.1016/j.ejmech.2014.07.035 Unchecked 3
11133086 10.1016/s0960-894x(00)00555-2 Sus scrofa 2
19804980 10.1016/j.bmc.2009.09.032 Tubulin 2
25084144 10.1016/j.ejmech.2014.07.035 MCF7 2
19433359 10.1016/j.bmcl.2009.04.112 Unchecked 2
16134928 10.1021/jm050524f 1A9/ptx-22 2
16134928 10.1021/jm050524f 1A9/ptx-10 2
16134928 10.1021/jm050524f 1A9 2
18271516 10.1021/jm7013452 MCF7 1
18271516 10.1021/jm7013452 NON-PROTEIN TARGET 1
18271516 10.1021/jm7013452 HCT-116 1
18271516 10.1021/jm7013452 Unchecked 1
11473410 10.1021/np000629f L929 1
16134928 10.1021/jm050524f Tubulin beta-4B chain 1
37490800 10.1016/j.ejmech.2023.115668 Unchecked 1
19804980 10.1016/j.bmc.2009.09.032 A549 1
11133086 10.1016/s0960-894x(00)00555-2 KB 3-1 1

Data from ChEMBL 36 via Core Engine