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Compound Detail

CHEMBL109480

TANESPIMYCIN
🧪 Phase III
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🧪 Phase III
C=CCNC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O

Basic Information

ChEMBL ID CHEMBL109480
Name TANESPIMYCIN
Phase Phase III
Structure Type MOL
InChI Key AYUNIORJHRXIBJ-TXHRRWQRSA-N

Known Names

17-AAG 17aag BMS-722782 CNF-1010 CNF1010 KOS-953 NSC-330507 Tanespimicina Tanespimycin Tanespimycine
605
Targets
762
Activities
4
Assay Types
22
PK Parameters
20
Publications
10
Known Names
20
Indications
1
Mechanisms

Molecular Properties

585.7
MW (Da)
2.54
ALogP
9
HBA
4
HBD
166.3
PSA (Ų)
0.27
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -mycin
USAN Year 2006

Extended Properties

Molecular Formula C31H43N3O8
MW 585.70
Aromatic Rings 0
Heavy Atoms 42
NP-Likeness 2.38

Mechanism of Action

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

Indications

Multiple Myeloma Adenocarcinoma, Follicular Breast Neoplasms Carcinoma, Medullary Hodgkin Disease Kidney Neoplasms Leukemia Lymphoma Lymphoma, Large-Cell, Anaplastic Lymphoma, Mantle-Cell Melanoma Melanoma Myeloproliferative Disorders Neoplasms Neoplasms Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Thyroid Neoplasms Burkitt Lymphoma Chondrosarcoma

Activity Summary

IC50 728 meas. best 10.0
EC50 15 meas. best 7.92
Kd 15 meas. best 10.06
Ki 4 meas. best 8.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Kd 10.06 7.835 0.1 2
HT-29
CHEMBL384
IC50 10.0 8.465 0.1 4
MCF7
CHEMBL387
IC50 9.52 7.638 0.3 10
A549
CHEMBL392
IC50 9.52 8.305 0.3 2
IST-MEL1
CHEMBL2366094
IC50 9.39 9.39 0.4 1
FaDu
CHEMBL612250
IC50 8.68 8.68 2.1 1
SNU1
CHEMBL614931
IC50 8.68 8.68 2.1 1
C32
CHEMBL1075401
IC50 8.52 8.52 3.0 1
Heat shock protein HSP90
CHEMBL2095165
IC50 8.52 6.5741 3.0 22
D-566MG
CHEMBL2366336
IC50 8.41 8.41 3.9 1
SK-BR-3
CHEMBL613834
IC50 8.4 7.4711 4.0 9
LXF-289 cell line
CHEMBL614107
IC50 8.38 8.38 4.2 1
Heat shock protein HSP 90-alpha
CHEMBL3880
Ki 8.34 7.94 4.6 2
Heat shock protein HSP 90-alpha
CHEMBL3880
IC50 8.3 6.3779 5.0 14
Unchecked
CHEMBL612545
IC50 8.3 6.5175 5.0 4
HGC-27
CHEMBL1075463
IC50 8.29 8.29 5.1 1
Heat shock protein HSP 90-beta
CHEMBL4303
IC50 8.15 6.9113 7.0 8
Heat shock protein HSP 90-beta
CHEMBL4303
Kd 8.14 6.6933 7.3 3
RPMI-7951
CHEMBL612447
IC50 8.14 8.14 7.2 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 8.11 6.625 7.7 10
PC-3
CHEMBL390
IC50 8.05 7.11 9.0 4
Heat shock protein HSP 90-beta
CHEMBL4303
Ki 8.05 7.165 9.0 2
HSC-3
CHEMBL612279
IC50 8.03 8.03 9.3 1
NCI-H460
CHEMBL396
IC50 8.0 7.455 10.0 4
BT-474
CHEMBL614529
IC50 8.0 7.675 10.0 2
MIA PaCa-2
CHEMBL614725
IC50 8.0 8.0 10.1 1
Heat shock protein HSP 90-alpha
CHEMBL3880
EC50 7.92 7.05 12.0 5
KS-1
CHEMBL2366228
IC50 7.87 7.87 13.6 1
CAL-51
CHEMBL1075411
IC50 7.85 7.85 14.1 1
MDA-MB-361
CHEMBL614129
IC50 7.83 7.83 14.9 1
TI-73
CHEMBL2366158
IC50 7.75 7.75 18.0 1
Heat shock protein HSP90
CHEMBL2095165
EC50 7.72 7.2957 19.0 7
AGS
CHEMBL613860
IC50 7.71 7.71 19.4 1
CHL-1
CHEMBL1075422
IC50 7.65 7.65 22.5 1
DU-4475
CHEMBL2366246
IC50 7.65 7.65 22.6 1
A204
CHEMBL614514
IC50 7.65 7.65 22.5 1
CGTH-W-1
CHEMBL2366300
IC50 7.63 7.63 23.5 1
HCC2218
CHEMBL2366221
IC50 7.6 7.6 24.9 1
SK-BR-3
CHEMBL613834
EC50 7.6 7.6 25.0 1
A2780
CHEMBL614004
IC50 7.6 7.6 25.3 1
NCI-H720
CHEMBL2366105
IC50 7.59 7.59 25.5 1
NCI-N87
CHEMBL614197
IC50 7.59 7.59 25.9 1
CHP-212
CHEMBL1075423
IC50 7.58 7.58 26.3 1
NCI-H23
CHEMBL614997
IC50 7.57 7.57 26.6 1
D-263MG
CHEMBL2366183
IC50 7.55 7.55 27.9 1
ME-180
CHEMBL1075499
IC50 7.54 7.54 28.9 1
SW982
CHEMBL2366238
IC50 7.52 7.52 30.0 1
H4
CHEMBL1075452
IC50 7.51 7.51 30.9 1
OE19
CHEMBL1075555
IC50 7.51 7.51 30.8 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
IC50 7.51 7.51 31.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 154039.1 ng.hr.mL-1 Mus musculus
AUC 46856.0 ng.hr.mL-1 Mus musculus
AUC 39827.6 ng.hr.mL-1 Mus musculus
AUC 12885.4 ng.hr.mL-1 Homo sapiens
CL 0.01 L/hr Mus musculus
CL 0.03 L/hr Mus musculus
CL 0.04 L/hr Mus musculus
CL 42.0 L/hr Homo sapiens
CL 36.0 L/hr Homo sapiens
Cmax 126000.0 nM Mus musculus
Cmax 35000.0 nM Mus musculus
Cmax 7500.0 nM Homo sapiens
Ka 1.2 10'4/M/s Homo sapiens
T1/2 0.86 hr Mus musculus
T1/2 7.5 hr Mus musculus
T1/2 0.88 hr Mus musculus
T1/2 9.8 hr -
T1/2 3.8 hr Homo sapiens
T1/2 4.0 hr Homo sapiens
Vz 0.01 l Mus musculus
Vz 0.34 l Mus musculus
Vz 0.05 l Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 0.087 nM 10.06 Binding affinity to pig spleen Hsp90 ATPase pocket by Bradford assay 19552433
HT-29 IC50 = 0.1 nM 10.0 Antiproliferative activity against human HT-29 cells after 72 to 144 hrs by cyqu... 19552433
A549 IC50 = 0.3029 nM 9.52 SANGER: Inhibition of human A549 cell growth in a cell viability assay. -
MCF7 IC50 = 0.3 nM 9.52 Antiproliferative activity against human MCF7 cells after 72 to 144 hrs by cyqua... 19552433
IST-MEL1 IC50 = 0.4075 nM 9.39 SANGER: Inhibition of human IST-MEL1 cell growth in a cell viability assay. -
HT-29 IC50 = 2.0 nM 8.7 Antiproliferative activity against human HT29 cells 17488003
FaDu IC50 = 2.093 nM 8.68 SANGER: Inhibition of human FADU cell growth in a cell viability assay. -
SNU1 IC50 = 2.068 nM 8.68 SANGER: Inhibition of human NCI-SNU-1 cell growth in a cell viability assay. -
Heat shock protein HSP90 IC50 = 3.0 nM 8.52 Inhibition of Hsp90 in human AU565 cells assessed as Her2 degradation after 24 h... 19552433
C32 IC50 = 3.045 nM 8.52 SANGER: Inhibition of human C32 cell growth in a cell viability assay. -
D-566MG IC50 = 3.904 nM 8.41 SANGER: Inhibition of human D-566MG cell growth in a cell viability assay. -
SK-BR-3 IC50 = 4.0 nM 8.4 Antitumor activity against human SK-BR-3 cells assessed as cell growth inhibitio... 36858050
Heat shock protein HSP90 IC50 = 4.0 nM 8.4 Inhibition of Hsp90 in human A375 cells assessed as Hsp70 induction after 24 hrs... 19552433
LXF-289 cell line IC50 = 4.192 nM 8.38 SANGER: Inhibition of human LXF-289 cell growth in a cell viability assay. -
Heat shock protein HSP 90-alpha Ki = 4.6 nM 8.34 Inhibition of HSP90alpha 20055425
Unchecked IC50 = 5.0 nM 8.3 Inhibition of Hsp90 (unknown origin) 37839344
MCF7 IC50 = 5.0 nM 8.3 Antitumor activity against human MCF7 cells assessed as cell growth inhibition 36858050
Heat shock protein HSP 90-alpha IC50 = 5.0 nM 8.3 Inhibition of human N-terminal Hsp90alpha (9 to 236 residues) expressed in Esche... 38232464
MCF7 IC50 = 5.0 nM 8.3 Antiproliferative activity against human MCF7 cells measured after 5 days by MTS... 27153346
HGC-27 IC50 = 5.099 nM 8.29 SANGER: Inhibition of human HGC-27 cell growth in a cell viability assay. -

Literature References

PubMed DOI Target Context # Activities
19410458 10.1016/j.bmcl.2009.04.030 Mus musculus 20
17603540 10.1038/nchembio.2007.10 Heat shock protein HSP 90-beta 17
20014866 10.1021/jm901566c NON-PROTEIN TARGET 14
25050163 10.1021/ml500114p ADMET 10
26254279 10.18632/oncotarget.4214 Heat shock protein HSP90 9
20055425 10.1021/jm9004708 ADMET 7
32663707 10.1016/j.ejmech.2020.112624 Unchecked 7
20055425 10.1021/jm9004708 Homo sapiens 7
20014866 10.1021/jm901566c HCT-116 6
30035186 10.18632/oncoscience.420 Hep 3B2 5
34469710 10.1016/j.bmcl.2021.128338 ADMET 5
20055425 10.1021/jm9004708 Plasma 5
21106457 10.1016/j.bmcl.2010.10.010 Heat shock protein HSP 90-alpha 5
20055425 10.1021/jm9004708 Heat shock protein HSP 90-beta 5
20055425 10.1021/jm9004708 Liver 5
17488003 10.1021/jm050752+ Heat shock protein HSP90 5
25105924 10.1016/j.ejmech.2014.07.101 Heat shock protein HSP 90-beta 5
21972823 10.1021/jm200784m Heat shock protein HSP 90-beta 4
19552433 10.1021/jm900230j Heat shock protein HSP90 4
18024584 10.1073/pnas.0709695104 H4 4

Data from ChEMBL 36 via Core Engine