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Compound Detail

CHEMBL2103879

GANETESPIB
🧪 Phase III
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🧪 Phase III
CC(C)c1cc(-c2n[nH]c(=O)n2-c2ccc3c(ccn3C)c2)c(O)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2103879
Name GANETESPIB
Phase Phase III
Structure Type MOL
InChI Key RVAQIUULWULRNW-UHFFFAOYSA-N

Known Names

Ganetespib STA 9090 STA-9090
11
Targets
21
Activities
2
Assay Types
1
PK Parameters
20
Publications
3
Known Names
20
Indications
1
Mechanisms

Molecular Properties

364.4
MW (Da)
3.25
ALogP
6
HBA
3
HBD
96.1
PSA (Ų)
0.52
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -espib
USAN Year 2011

Extended Properties

Molecular Formula C20H20N4O3
MW 364.41
Aromatic Rings 4
Heavy Atoms 27
NP-Likeness -0.56

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Heat shock protein HSP90 inhibitor INHIBITOR Heat shock protein HSP90 ✓ ✓

Indications

Adenocarcinoma of Lung Carcinoma, Non-Small-Cell Lung Breast Neoplasms Breast Neoplasms Colonic Neoplasms Gastrointestinal Stromal Tumors Hemangiosarcoma Melanoma Pancreatic Neoplasms Prostatic Neoplasms Rectal Neoplasms Small Cell Lung Carcinoma Stomach Neoplasms Adenocarcinoma Breast Neoplasms, Male Carcinoma, Hepatocellular Esophageal Neoplasms Esophageal Neoplasms Fallopian Tube Neoplasms Leukemia, Myeloid, Acute

Activity Summary

IC50 20 meas. best 8.52
Kd 1 meas. best 4.63

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.52 7.7583 3.0 6
Heat shock protein HSP 90-alpha
CHEMBL3880
 IC50 8.3 7.94 5.0 3
Heat shock protein HSP 90-beta
CHEMBL4303
 IC50 8.3 8.3 5.0 1
PC-3
CHEMBL390
 IC50 8.03 8.03 9.3 1
Endoplasmin
CHEMBL4748
 IC50 8.0 8.0 10.0 1
HeLa
CHEMBL399
 IC50 7.93 7.93 11.7 1
A-375
CHEMBL613859
 IC50 7.82 7.82 15.0 1
Heat shock protein 75 kDa, mitochondrial
CHEMBL1075132
 IC50 7.42 7.355 37.7 2
Endoplasmin
CHEMBL1075323
 IC50 7.42 7.42 37.7 1
Heat shock protein HSP90
CHEMBL2095165
 IC50 7.2 6.235 63.0 2
A549
CHEMBL392
 IC50 5.17 5.17 6840.0 1
Heat shock protein HSP90
CHEMBL2095165
 Kd 4.63 4.63 23565.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 1.487 10'5L/mol Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 3.0 nM 8.52 Antiproliferative activity against mouse GL26 cells assessed as inhibition of ce... 37172473
Heat shock protein HSP 90-beta IC50 = 5.0 nM 8.3 Displacement of 5-(3-(3-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin... 23965125
Heat shock protein HSP 90-alpha IC50 = 5.0 nM 8.3 Displacement of 5-(3-(3-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin... 23965125
Heat shock protein HSP 90-alpha IC50 = 6.0 nM 8.22 Inhibition of human recombinant HSP90alpha preincubated for 30 mins followed by ... 37172473
PC-3 IC50 = 9.3 nM 8.03 Antiproliferative activity against human PC3 cells by MTT assay 31839539
Endoplasmin IC50 = 10.0 nM 8.0 Displacement of 5-(3-(3-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin... 23965125
Unchecked IC50 = 10.0 nM 8.0 Cytotoxicity against human NB39 cells assessed as decrease in cell viability aft... 26844689
Unchecked IC50 = 10.0 nM 8.0 Inhibition of E13;A20 EML4-ALK variant (unknown origin) expressed in human NCI-H... 26844689
Unchecked IC50 = 11.0 nM 7.96 Inhibition of EML4-ALK variant 1 (unknown origin) expressed in BA/F3 cells asses... 26844689
HeLa IC50 = 11.65 nM 7.93 Antiproliferative activity against human HeLa cells by MTT assay 31839539
Unchecked IC50 = 13.0 nM 7.89 Inhibition of E6a/b;A20 EML4-ALK (unknown origin) expressed in human NCI-H2228 c... 26844689
A-375 IC50 = 15.0 nM 7.82 Cytotoxicity against human A375 cells assessed as decrease in cell viability aft... 26844689
Heat shock protein 75 kDa, mitochondrial IC50 = 37.7 nM 7.42 Inhibition of TRAP1 (unknown origin) 31839539
Endoplasmin IC50 = 37.7 nM 7.42 Inhibition of GRP94 (unknown origin) 31839539
Heat shock protein HSP 90-alpha IC50 = 50.45 nM 7.3 Inhibition of recombinant HSP90alpha (unknown origin) incubated for 24 hrs in pr... 31839539
Heat shock protein 75 kDa, mitochondrial IC50 = 51.0 nM 7.29 Displacement of 5-(3-(3-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin... 23965125
Heat shock protein HSP90 IC50 = 63.0 nM 7.2 Inhibition of Hsp90 in human MG63 cells 26844689
Unchecked IC50 = 660.0 nM 6.18 Inhibition of fungal HSP90 incubated for 6 hrs in presence of FITC-Geldanamycin ... 34742014
Heat shock protein HSP90 IC50 = 5390.0 nM 5.27 Inhibition of human HSP90 34742014
A549 IC50 = 6840.0 nM 5.17 Antiproliferative activity against human Temozolomide-sensitive U-251 cells asse... 37172473

Literature References

PubMed DOI Target Context # Activities
26844689 10.1021/acs.jmedchem.5b01106 Unchecked 6
37172473 10.1016/j.ejmech.2023.115459 Unchecked 5
32222339 10.1016/j.bmc.2020.115434 Heat shock protein HSP90 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
34742014 10.1016/j.ejmech.2021.113961 Candida albicans 4
26844689 10.1021/acs.jmedchem.5b01106 A-375 4
34742014 10.1016/j.ejmech.2021.113961 Unchecked 3
- 10.6019/CHEMBL3885741 Heat shock protein HSP 90-alpha 3
31839539 10.1016/j.bmcl.2019.126809 Unchecked 2
38285511 10.1021/acs.jmedchem.3c02053 GBM 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
29537263 10.1021/acs.jnatprod.7b00918 HEK-293T 2
27745993 10.1016/j.bmc.2016.09.067 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
26844689 10.1021/acs.jmedchem.5b01106 NCI-H2228 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
25383915 10.1021/jm5010144 NCI-H1299 1
38971048 10.1016/j.ejmech.2024.116620 Unchecked 1
23965125 10.1021/jm400619b Heat shock protein HSP 90-beta 1

Data from ChEMBL 36 via Core Engine