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Compound Detail

CHEMBL1236460

THIOSTREPTON
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C=C(NC(=O)C(=C)NC(=O)c1csc(C2=N[C@@H]3c4csc(n4)[C@H]4NC(=O)c5csc(n5)[C@H]([C@](C)(O)[C@@H](C)O)NC(=O)[C@H]5CSC(=N5)/C(=C/C)NC(=O)[C@H]([C@@H](C)O)NC(=O)c5csc(n5)[C@]3(CC2)NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)CC)N[C@@H]2C=Cc3c([C@H](C)O)cc(nc3[C@H]2O)C(=O)O[C@@H]4C)n1)C(N)=O

Basic Information

ChEMBL ID CHEMBL1236460
Name THIOSTREPTON
Phase Preclinical
Structure Type MOL
InChI Key NSFFHOGKXHRQEW-AIHSUZKVSA-N
12
Targets
21
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

1664.9
MW (Da)

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C72H85N19O18S5
MW 1664.92

Activity Summary

IC50 20 meas. best 7.0
Kd 1 meas. best 5.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Escherichia coli
CHEMBL354
IC50 7.0 7.0 100.0 1
Plasmodium falciparum
CHEMBL364
IC50 6.76 6.2163 174.7 8
SNU-638
CHEMBL614935
IC50 6.52 6.52 300.0 1
AGS
CHEMBL613860
IC50 6.4 6.4 400.0 1
Unchecked
CHEMBL612545
IC50 6.39 6.39 410.0 1
HepG2
CHEMBL395
IC50 6.15 6.15 710.0 1
SK-HEP1
CHEMBL614912
IC50 6.13 6.13 740.0 1
Hep 3B2
CHEMBL4296437
IC50 6.09 6.09 820.0 1
Nucleic Acid
CHEMBL345
Kd 5.89 5.89 1300.0 1
MKN-74
CHEMBL614048
IC50 5.38 5.38 4200.0 1
GroEL/GroES
CHEMBL4106139
IC50 5.17 4.985 6800.0 2
HSP60/HSP10
CHEMBL4106131
IC50 4.89 4.89 13000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Escherichia coli IC50 = 100.0 nM 7.0 Inhibitory concentration of compound against Escherichia coli in vitro protein t... 12852942
Plasmodium falciparum IC50 = 174.7 nM 6.76 Antimalarial activity after 96 hrs against azithromycin-resistant Plasmodium fal... 17110371
Plasmodium falciparum IC50 = 217.4 nM 6.66 Antimalarial activity after 96 hrs against azithromycin-resistant Plasmodium fal... 17110371
Plasmodium falciparum IC50 = 292.5 nM 6.53 Antimalarial activity after 96 hrs against Plasmodium falciparum Dd2 by [3H]hypo... 17110371
SNU-638 IC50 = 300.0 nM 6.52 Cytotoxicity against human SNU-638 cells 31926469
AGS IC50 = 400.0 nM 6.4 Cytotoxicity against human AGS cells 31926469
Unchecked IC50 = 410.0 nM 6.39 Cytotoxicity against human SNU-216 cells 31926469
Plasmodium falciparum IC50 = 554.8 nM 6.26 Antimalarial activity after 96hrs against Plasmodium falciparum 7G8 by [3H]hypox... 17110371
Plasmodium falciparum IC50 = 688.5 nM 6.16 Antimalarial activity after 48 hrs against Plasmodium falciparum 7G8 by [3H]hypo... 17110371
HepG2 IC50 = 710.0 nM 6.15 Cytotoxicity against human HepG2 cells 31926469
SK-HEP1 IC50 = 740.0 nM 6.13 Cytotoxicity against human SK-HEP1 cells 31926469
Hep 3B2 IC50 = 820.0 nM 6.09 Cytotoxicity against human Hep3B cells 31926469
Plasmodium falciparum IC50 = 916.5 nM 6.04 Antimalarial activity after 96 hrs against Plasmodium falciparum GCO3 by [3H]hyp... 17110371
Nucleic Acid Kd = 1300.0 nM 5.89 Binding affinity to Escherichia coli 23S rRNA L11 binding domain 19445516
Plasmodium falciparum IC50 = 2107.0 nM 5.68 Antimalarial activity after 48 hrs against Plasmodium falciparum Dd2 by [3H]hypo... 17110371
Plasmodium falciparum IC50 = 2277.0 nM 5.64 Antimalarial activity after 48 hrs against Plasmodium falciparum GCO3 by [3H]hyp... 17110371
MKN-74 IC50 = 4200.0 nM 5.38 Cytotoxicity against human MKN-74 cells 31926469
GroEL/GroES IC50 = 6800.0 nM 5.17 Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Esche... 30852084
HSP60/HSP10 IC50 = 13000.0 nM 4.89 Inhibition of human N-terminal octa-His-tagged HSP60 expressed in Escherichia co... 30852084
GroEL/GroES IC50 = 16000.0 nM 4.8 Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Esch... 30852084

Literature References

PubMed DOI Target Context # Activities
17110371 10.1074/jbc.m608615200 Plasmodium falciparum 8
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
- 10.1584/jpestics.28.183 Streptomyces acidiscabies 4
- 10.1584/jpestics.28.183 Streptomyces alboniger 4
12852942 10.1016/s0960-894x(03)00495-5 Escherichia coli 3
- 10.1584/jpestics.28.183 Streptomyces scabiei 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19001112 10.1128/aac.00873-08 Bacillus subtilis 2
20510619 10.1016/j.bmc.2010.04.098 Escherichia coli 2
19445516 10.1021/jm9000659 Nucleic Acid 2
23075290 10.1021/jm3005898 Plasmodium falciparum 1
20510619 10.1016/j.bmc.2010.04.098 Staphylococcus aureus 1
20510619 10.1016/j.bmc.2010.04.098 Bacillus subtilis 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
30852084 10.1016/j.bmcl.2019.02.028 Thiosulfate sulfurtransferase 1
30852084 10.1016/j.bmcl.2019.02.028 Unchecked 1
30852084 10.1016/j.bmcl.2019.02.028 HSP60/HSP10 1
30852084 10.1016/j.bmcl.2019.02.028 Chaperonin GroEL 1
31926469 10.1016/j.ejmech.2019.112016 SK-HEP1 1

Data from ChEMBL 36 via Core Engine