Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL94657

PATUPILONE
🧪 Phase III
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
🧪 Phase III
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[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 CHEMBL94657
Name PATUPILONE
Phase Phase III
Structure Type MOL
InChI Key QXRSDHAAWVKZLJ-PVYNADRNSA-N

Known Names

(-)-epothilone b Epithilone b EPO 906 EPO 906A Epo b EPO-906 EPO-906A EPO906 EPO906A Epothilone b GNF-PF-193 Patupilona +1 more
683
Targets
746
Activities
3
Assay Types
1
PK Parameters
20
Publications
13
Known Names
18
Indications
1
Mechanisms

Molecular Properties

507.7
MW (Da)
4.48
ALogP
8
HBA
2
HBD
109.2
PSA (Ų)
0.45
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C27H41NO6S
MW 507.69
Aromatic Rings 1
Heavy Atoms 35
NP-Likeness 2.23

Mechanism of Action

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

Indications

Fallopian Tube Neoplasms Ovarian Neoplasms Peritoneal Neoplasms Breast Neoplasms Breast Neoplasms Carcinoid Tumor Carcinoma, Hepatocellular Colonic Neoplasms Colonic Neoplasms Kidney Neoplasms Melanoma Neuroendocrine Tumors Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Carcinoma, Non-Small-Cell Lung Glioblastoma Neoplasms Neoplasms

Activity Summary

IC50 738 meas. best 10.67
EC50 7 meas. best 8.4
Kd 1 meas. best 8.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SW1710
CHEMBL1075590
 IC50 10.67 10.67 0.0 1
SK-OV-3
CHEMBL614925
 IC50 10.63 9.655 0.0 4
Daoy
CHEMBL612519
 IC50 10.56 10.56 0.0 1
BFTC-905
CHEMBL1075396
 IC50 10.3 10.3 0.0 1
A-375
CHEMBL613859
 IC50 10.3 10.3 0.0 1
KB 3-1
CHEMBL614590
 IC50 10.28 8.8278 0.1 9
1A9
CHEMBL614075
 IC50 10.22 10.0 0.1 3
RKO
CHEMBL614879
 IC50 10.19 10.19 0.1 1
A549
CHEMBL392
 IC50 10.16 8.11 0.1 4
A-431
CHEMBL614069
 IC50 10.14 8.1367 0.1 3
MCF7
CHEMBL387
 IC50 10.13 8.5233 0.1 6
KYSE-510
CHEMBL613868
 IC50 10.13 10.13 0.1 1
HLE
CHEMBL1075464
 IC50 10.08 10.08 0.1 1
U2OS
CHEMBL615023
 IC50 9.98 7.84 0.1 2
786-0
CHEMBL613102
 IC50 9.96 9.96 0.1 1
TE-8
CHEMBL2366182
 IC50 9.95 9.95 0.1 1
PANC-03-27
CHEMBL1075557
 IC50 9.88 9.88 0.1 1
VMRC-RCZ
CHEMBL1075610
 IC50 9.87 9.87 0.1 1
IGROV-1
CHEMBL613984
 IC50 9.81 9.81 0.2 1
MG-63
CHEMBL614347
 IC50 9.78 9.78 0.2 1
NCI-H650
CHEMBL1075543
 IC50 9.77 9.77 0.2 1
SIG-M5
CHEMBL2366251
 IC50 9.77 9.77 0.2 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.77 8.2113 0.2 8
PSN1
CHEMBL614241
 IC50 9.76 9.76 0.2 1
PA-1
CHEMBL614949
 IC50 9.76 9.76 0.2 1
KB
CHEMBL398
 IC50 9.74 9.74 0.2 1
BHY
CHEMBL1075399
 IC50 9.71 9.71 0.2 1
BB30-HNC
CHEMBL2366271
 IC50 9.7 9.7 0.2 1
HOS
CHEMBL614736
 IC50 9.67 9.67 0.2 1
639-V
CHEMBL1075383
 IC50 9.66 9.66 0.2 1
TE-15
CHEMBL2366086
 IC50 9.65 9.65 0.2 1
ES1
CHEMBL2366146
 IC50 9.65 9.65 0.2 1
LXF-289 cell line
CHEMBL614107
 IC50 9.64 9.64 0.2 1
CAL-12T
CHEMBL1075406
 IC50 9.62 9.62 0.2 1
T84
CHEMBL613531
 IC50 9.62 9.62 0.2 1
PC-3
CHEMBL390
 IC50 9.6 7.768 0.2 5
KYSE-450
CHEMBL1075488
 IC50 9.57 9.57 0.3 1
1A9/ptx-22
CHEMBL613858
 IC50 9.51 9.51 0.3 2
LCLC-103H cell line
CHEMBL614066
 IC50 9.51 9.51 0.3 1
NCI-H810
CHEMBL1075546
 IC50 9.49 9.49 0.3 1
NCI-H460
CHEMBL396
 IC50 9.48 9.48 0.3 1
HuTu80
CHEMBL614582
 IC50 9.48 9.48 0.3 1
HGC-27
CHEMBL1075463
 IC50 9.47 9.47 0.3 1
HSC-2
CHEMBL1075468
 IC50 9.44 9.44 0.4 1
IA-LM
CHEMBL2366366
 IC50 9.41 9.41 0.4 1
COLO-679
CHEMBL1075426
 IC50 9.4 9.4 0.4 1
HMV-2 cell line
CHEMBL614826
 IC50 9.4 9.4 0.4 1
CAL-39
CHEMBL1075410
 IC50 9.39 9.39 0.4 1
NCI-H2122
CHEMBL1075533
 IC50 9.39 9.39 0.4 1
SW 954
CHEMBL614943
 IC50 9.36 9.36 0.4 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 7.5 10'8/M -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SW1710 IC50 = 0.02135 nM 10.67 SANGER: Inhibition of human SW1710 cell growth in a cell viability assay. -
SK-OV-3 IC50 = 0.0236 nM 10.63 Cytotoxicity against human SKOV3 cells assessed as reduction in cell viability a... 28398049
Daoy IC50 = 0.02733 nM 10.56 SANGER: Inhibition of human Daoy cell growth in a cell viability assay. -
BFTC-905 IC50 = 0.04994 nM 10.3 SANGER: Inhibition of human BFTC-905 cell growth in a cell viability assay. -
A-375 IC50 = 0.04997 nM 10.3 SANGER: Inhibition of human A375 cell growth in a cell viability assay. -
KB 3-1 IC50 = 0.053 nM 10.28 Cytotoxicity against human KB3-1 cells measured after 5 days by MTT assay 31021629
1A9 IC50 = 0.06 nM 10.22 Cytotoxicity against human 1A9 cells 28850227
KB 3-1 IC50 = 0.061 nM 10.21 Cytotoxicity against human KB3-1 cells assessed as reduction in cell viability a... 28398049
KB 3-1 IC50 = 0.065 nM 10.19 Cytotoxicity in human KB 3.1 cells 31001977
RKO IC50 = 0.06474 nM 10.19 SANGER: Inhibition of human RKO cell growth in a cell viability assay. -
A549 IC50 = 0.069 nM 10.16 Cytotoxicity against human A549 cells assessed as reduction in cell growth incub... 31599583
A-431 IC50 = 0.073 nM 10.14 Cytotoxicity against human A431 cells assessed as reduction in cell viability af... 28398049
KYSE-510 IC50 = 0.07379 nM 10.13 SANGER: Inhibition of human KYSE-510 cell growth in a cell viability assay. -
MCF7 IC50 = 0.074 nM 10.13 Cytotoxicity against human MCF7 cells measured after 5 days by MTT assay 31021629
A-431 IC50 = 0.079 nM 10.1 Cytotoxicity against human A431 cells assessed as reduction in cell growth incub... 31599583
HLE IC50 = 0.08261 nM 10.08 SANGER: Inhibition of human HLE cell growth in a cell viability assay. -
MCF7 IC50 = 0.08657 nM 10.06 SANGER: Inhibition of human MCF7 cell growth in a cell viability assay. -
KB 3-1 IC50 = 0.089 nM 10.05 Cytotoxicity against human KB3-1 cells assessed as reduction in cell growth incu... 31599583
U2OS IC50 = 0.104 nM 9.98 Cytotoxicity against human U2OS cells assessed as reduction in cell viability af... 28398049
786-0 IC50 = 0.1104 nM 9.96 SANGER: Inhibition of human 786-0 cell growth in a cell viability assay. -

Literature References

PubMed DOI Target Context # Activities
22320354 10.1021/jm200848t NON-PROTEIN TARGET 8
20966043 10.1124/dmd.110.035105 Nuclear receptor subfamily 1 group I member 2 7
17206139 10.1038/nchembio853 Unchecked 7
22320354 10.1021/jm200848t SNU-398 5
30149324 10.1016/j.ejmech.2018.08.055 Unchecked 4
37531745 10.1016/j.ejmech.2023.115693 MCF7 4
22320354 10.1021/jm200848t Molecular identity unknown 3
30318441 10.1016/j.bmc.2018.10.005 MCF7 3
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
25872984 10.1016/j.bmcl.2015.03.081 HCC1937 2
31047749 10.1016/j.bmcl.2019.04.035 A2780 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37531745 10.1016/j.ejmech.2023.115693 ADMET 2
16134928 10.1021/jm050524f 1A9/ptx-22 2
16134928 10.1021/jm050524f 1A9/ptx-10 2
16134928 10.1021/jm050524f 1A9 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
11133086 10.1016/s0960-894x(00)00555-2 Sus scrofa 2
18579783 10.1073/pnas.0802982105 Huh-7 1
9873670 10.1016/s0960-894x(98)00546-0 NON-PROTEIN TARGET 1

Data from ChEMBL 36 via Core Engine