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Compound Detail

CHEMBL278315

GELDANAMYCIN
🧪 Phase II
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🧪 Phase II
COC1=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
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL278315
Name GELDANAMYCIN
Phase Phase II
Structure Type MOL
InChI Key QTQAWLPCGQOSGP-KSRBKZBZSA-N

Known Names

Geldanamycin NSC-122750
58
Targets
178
Activities
3
Assay Types
4
PK Parameters
20
Publications
2
Known Names
3
Indications

Molecular Properties

560.6
MW (Da)
2.41
ALogP
9
HBA
3
HBD
163.5
PSA (Ų)
0.35
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -mycin

Extended Properties

Molecular Formula C29H40N2O9
MW 560.64
Aromatic Rings 0
Heavy Atoms 40
NP-Likeness 2.76

Indications

Hodgkin Disease Kidney Neoplasms von Hippel-Lindau Disease

Activity Summary

IC50 151 meas. best 8.47
Kd 19 meas. best 6.99
EC50 8 meas. best 9.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 9.6 9.26 0.2 2
A2780
CHEMBL614004
 IC50 8.47 7.815 3.4 2
K562
CHEMBL385
 IC50 8.46 8.06 3.5 2
SK-BR-3
CHEMBL613834
 IC50 8.4 7.2 4.0 10
A549
CHEMBL392
 IC50 8.36 7.0971 4.4 7
MDA-MB-231
CHEMBL400
 IC50 8.25 6.9725 5.6 8
SW-620
CHEMBL612262
 IC50 8.21 8.21 6.2 1
HL-60
CHEMBL383
 IC50 8.21 8.21 6.1 1
MCF7
CHEMBL387
 IC50 8.19 7.3618 6.5 11
Endoplasmin
CHEMBL4748
 IC50 8.0 8.0 10.0 1
Heat shock protein HSP 90-alpha
CHEMBL3880
 IC50 7.89 7.332 13.0 20
Unchecked
CHEMBL612545
 IC50 7.84 6.437 14.4 10
Heat shock protein HSP90
CHEMBL2095165
 IC50 7.8 7.2725 16.0 4
HeLa
CHEMBL399
 IC50 7.75 6.925 18.0 2
HUVEC
CHEMBL613979
 IC50 7.72 7.72 19.0 1
Heat shock protein HSP 90-beta
CHEMBL4303
 IC50 7.7 7.2733 20.0 3
Plasmodium falciparum
CHEMBL364
 IC50 7.7 6.7871 20.0 7
HT-29
CHEMBL384
 IC50 7.61 7.61 24.5 1
BT-474
CHEMBL614529
 IC50 7.57 7.57 27.0 1
ES-2
CHEMBL5058622
 IC50 7.54 7.54 28.7 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.52 7.2543 30.0 7
HCT-116
CHEMBL394
 EC50 7.52 7.52 30.0 2
HCT-116
CHEMBL394
 IC50 7.52 7.26 30.0 2
MDA-MB-468
CHEMBL614335
 IC50 7.48 7.48 33.0 1
Heat shock protein HSP90
CHEMBL2095165
 EC50 7.46 7.46 35.0 1
NCI-H1975
CHEMBL614348
 IC50 7.44 7.44 36.0 1
A-431
CHEMBL614069
 IC50 7.4 7.05 40.0 2
HepG2
CHEMBL395
 IC50 7.4 6.5275 40.0 4
SH-SY5Y
CHEMBL614910
 EC50 7.37 7.37 42.7 1
Unchecked
CHEMBL612545
 EC50 7.24 7.24 57.0 1
A-375
CHEMBL613859
 IC50 7.22 7.22 60.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.05 7.05 89.0 1
P19
CHEMBL614064
 IC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
 Kd 6.99 6.0017 103.0 6
SMMC-7721
CHEMBL613831
 IC50 6.96 6.96 110.0 1
BGC-823
CHEMBL614526
 IC50 6.96 6.96 110.0 1
HCC1806
CHEMBL1075457
 IC50 6.92 6.92 120.0 1
Lysine-specific demethylase 5A
CHEMBL2424504
 IC50 6.89 6.89 130.0 1
ADMET
CHEMBL612558
 IC50 6.85 6.3 141.0 2
Heat shock protein HSP 90-beta
CHEMBL4303
 Kd 6.82 6.4475 152.0 4
HSP90
CHEMBL1795086
 Kd 6.77 6.635 169.0 2
Heat shock protein HSP 90
CHEMBL1667702
 IC50 6.55 6.125 282.0 2
SW1990
CHEMBL1075592
 IC50 6.54 6.54 290.0 1
CNE2Z
CHEMBL4632328
 IC50 6.51 6.51 310.0 1
SW480
CHEMBL612544
 IC50 6.51 6.4 310.0 2
Lysine-specific demethylase 6B
CHEMBL1938211
 IC50 6.4 6.4 400.0 1
LNCaP
CHEMBL612518
 IC50 6.37 6.37 430.0 1
LS174T
CHEMBL614097
 IC50 6.35 6.35 450.0 1
LNCaP C4-2B
CHEMBL4296461
 IC50 6.3 6.3 500.0 1
HEK-293T
CHEMBL3706568
 IC50 6.28 6.28 530.0 1

Pharmacokinetic Data

Parameter Value Units Species
t1/2 - - Rattus norvegicus
t1/2 - - Homo sapiens
t1/2 - - Mus musculus
t1/2 - - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 0.25 nM 9.6 Antiviral activity against Hepatitis C virus genotype 1b Con1 infected in human ... 18936191
Hepatitis C virus EC50 = 1.2 nM 8.92 Antiviral activity against Hepatitis C virus genotype 1b Con1 infected in human ... 18936191
A2780 IC50 = 3.4 nM 8.47 Compound was evaluated for antiproliferative activity against human ovarian carc... 11514145
K562 IC50 = 3.5 nM 8.46 Cytotoxicity against human K562 cells assessed as reduction in cell viability 32273216
SK-BR-3 IC50 = 4.0 nM 8.4 Antitumor activity against human SK-BR-3 cells assessed as cell growth inhibitio... 36858050
A549 IC50 = 4.4 nM 8.36 Cytotoxicity against human A549 cells assessed as reduction in cell viability 32273216
MDA-MB-231 IC50 = 5.57 nM 8.25 Cytotoxicity against human MDA-MB-231 cells by MTT assay 37315698
HL-60 IC50 = 6.1 nM 8.21 Cytotoxicity against human HL60 cells assessed as reduction in cell viability 32273216
SW-620 IC50 = 6.2 nM 8.21 Inhibitory concentration against human colorectal carcinoma SW620 cell lines 15658879
MCF7 IC50 = 6.5 nM 8.19 Inhibitory concentration against human breast cancer MCF-7 cell lines 15658879
MCF7 IC50 = 7.7 nM 8.11 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability 32273216
SK-BR-3 IC50 = 8.5 nM 8.07 Antiproliferative activity against estrogen receptor deficient human SKBR3 cells... 23648180
MCF7 IC50 = 9.8 nM 8.01 Antiproliferative activity against human MCF7 cells expressing estrogen receptor... 23648180
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
MCF7 IC50 = 11.0 nM 7.96 Antitumor activity against human MCF7 cells assessed as cell growth inhibition 36858050
Heat shock protein HSP 90-alpha IC50 = 13.0 nM 7.89 Inhibition of human recombinant HSP90alpha preincubated for 30 mins followed by ... 37172473
Heat shock protein HSP 90-alpha IC50 = 14.0 nM 7.85 Inhibition of FITC-geldanamycin binding to N-terminal domain of recombinant full... 29202402
Heat shock protein HSP 90-alpha IC50 = 14.0 nM 7.85 Inhibition of fluorescein isothiocyanate labeled geldanamycin binding to N-termi... 27783977
Unchecked IC50 = 14.4 nM 7.84 Cytotoxicity against human 95-D cells by MTT assay 37315698
Heat shock protein HSP90 IC50 = 16.0 nM 7.8 Inhibition of geldanamycin-based probe binding to HSP90 (unknown origin) by fluo... 29545103

Literature References

PubMed DOI Target Context # Activities
37315698 10.1016/j.bmcl.2023.129375 A549 17
18024584 10.1073/pnas.0709695104 H4 11
26642769 10.1016/j.bmcl.2015.11.073 PC-12 10
25756299 10.1021/acs.jnatprod.5b00054 Heat shock protein HSP90 9
32663707 10.1016/j.ejmech.2020.112624 Unchecked 8
28038472 10.18632/oncotarget.14252 Unchecked 8
37042709 10.1021/acs.jnatprod.2c01151 Staphylococcus aureus 8
31591016 10.1016/j.bmcl.2019.126676 Heat shock protein HSP90 6
27476419 10.1016/j.bmcl.2016.07.040 Heat shock protein HSP 90-alpha 5
37669603 10.1016/j.bmc.2023.117463 Unchecked 5
37210951 10.1016/j.ejmech.2023.115450 Heat shock protein HSP 90-alpha 5
24914738 10.1021/jm500535j Plasmodium falciparum 5
23859777 10.1016/j.bmc.2013.06.042 SK-BR-3 4
21177985 10.1124/dmd.110.036418 Liver microsome 4
21129982 10.1016/j.bmc.2010.10.029 Heat shock protein HSP 90-beta 4
7562911 10.1021/jm00019a010 Mus musculus 4
21273068 10.1016/j.bmcl.2010.12.088 Heat shock protein HSP90 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19138859 10.1016/j.bmc.2008.12.047 SH-SY5Y 4
21486005 10.1021/np200029q Unchecked 4

Data from ChEMBL 36 via Core Engine