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Compound Detail

CHEMBL382300

ORTATAXEL
🧪 Phase II
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🧪 Phase II
CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]34OC(=O)O[C@H]3[C@H](OC(=O)[C@H](O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)C(C)=C1C4(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL382300
Name ORTATAXEL
Phase Phase II
Structure Type MOL
InChI Key BWKDAMBGCPRVPI-ZQRPHVBESA-N

Known Names

BAY 59-8862 BAY-59-8862 IDN 5109 IDN-5109 IDN5109 Ortataxel SB-T 101131 SB-T-101131
4
Targets
9
Activities
1
Assay Types
0
PK Parameters
17
Publications
8
Known Names
5
Indications

Molecular Properties

871.9
MW (Da)
3.66
ALogP
17
HBA
3
HBD
245.8
PSA (Ų)
0.17
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -taxel

Extended Properties

Molecular Formula C44H57NO17
MW 871.93
Aromatic Rings 1
Heavy Atoms 62
NP-Likeness 1.82

Indications

Carcinoma, Renal Cell Glioblastoma Kidney Neoplasms Lung Neoplasms Lymphoma

Activity Summary

IC50 9 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 8.96 8.88 1.1 2
A2780
CHEMBL614004
 IC50 8.44 7.8025 3.6 4
MCF7-DOX
CHEMBL614326
 IC50 7.5 7.5 32.0 1
MCF7R
CHEMBL614327
 IC50 7.48 7.46 33.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 1.1 nM 8.96 In vitro cytotoxicity against MCF-7 cell line 14584931
MCF7 IC50 = 1.6 nM 8.8 Cytotoxic potency in MCF7 human mammary carcinoma cell line after 72 hr exposure... 16183281
A2780 IC50 = 3.6 nM 8.44 In vitro cytotoxicity against A2780CIS cell line 14584931
A2780 IC50 = 4.8 nM 8.32 In vitro cytotoxicity against A2780 cell line 14584931
MCF7-DOX IC50 = 32.0 nM 7.5 Cytotoxic potency in doxorubicin resistant MCF7 cell line after 72 hr exposure b... 16183281
MCF7R IC50 = 33.0 nM 7.48 Potency differential in resistant to that of sensitive MCF7-R cell line 14584931
MCF7R IC50 = 36.0 nM 7.44 In vitro cytotoxicity against MCF7-R cell line 14584931
A2780 IC50 = 56.0 nM 7.25 In vitro cytotoxicity against A2780TAX cell line 14584931
A2780 IC50 = 63.0 nM 7.2 In vitro cytotoxicity against A2780ADR cell line 14584931

Literature References

PubMed DOI Target Context # Activities
14584931 10.1021/jm034146v A2780 4
14584931 10.1021/jm034146v Unchecked 3
24332858 10.1016/j.bmc.2013.11.037 Caco-2 3
14584931 10.1021/jm034146v MCF7R 2
16183281 10.1016/j.bmcl.2005.08.066 MCF7 1
16183281 10.1016/j.bmcl.2005.08.066 MCF7-DOX 1
16183281 10.1016/j.bmcl.2005.08.066 Unchecked 1
15060738 10.1007/s00280-003-0745-2 ATP-dependent translocase ABCB1 1
14584931 10.1021/jm034146v MCF7 1
24332858 10.1016/j.bmc.2013.11.037 DU-145 1
24332858 10.1016/j.bmc.2013.11.037 HL-60 1
24332858 10.1016/j.bmc.2013.11.037 HT-29 1
24332858 10.1016/j.bmc.2013.11.037 A-375 1
24332858 10.1016/j.bmc.2013.11.037 NCI-H460 1
24332858 10.1016/j.bmc.2013.11.037 MCF7 1
24332858 10.1016/j.bmc.2013.11.037 HeLa 1
24332858 10.1016/j.bmc.2013.11.037 A2780 1

Data from ChEMBL 36 via Core Engine