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Compound Detail

CHEMBL399043

THIOLACTOMYCIN
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C=C/C(C)=C/[C@@]1(C)SC(=O)C(C)=C1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL399043
Name THIOLACTOMYCIN
Phase Preclinical
Structure Type MOL
InChI Key SYQNUQSGEWNWKV-XUIVZRPNSA-N
8
Targets
18
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

210.3
MW (Da)
2.98
ALogP
3
HBA
1
HBD
37.3
PSA (Ų)
0.71
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H14O2S
MW 210.30
Aromatic Rings 0
Heavy Atoms 14
NP-Likeness 2.23

Activity Summary

IC50 12 meas. best 6.0
Kd 4 meas. best 4.26
Ki 2 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DNA repair nuclease/redox regulator APEX1
CHEMBL5619
 IC50 6.0 6.0 1000.0 1
Unchecked
CHEMBL612545
 IC50 5.72 4.925 1900.0 2
Mycobacterial beta-ketoacyl-[acyl-carrier-protein] synthase III
CHEMBL3640
 IC50 5.4 4.5267 4000.0 3
3-oxoacyl-[acyl-carrier-protein] synthase 2
CHEMBL4543
 IC50 5.22 5.22 6000.0 1
3-oxoacyl-[acyl-carrier-protein] synthase 1
CHEMBL4913
 IC50 4.92 4.92 12000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.31 4.3033 49000.0 3
Unchecked
CHEMBL612545
 Kd 4.26 4.26 55400.0 1
3-oxoacyl-[acyl-carrier-protein] synthase 2
CHEMBL5341
 Kd 4.06 4.06 88000.0 1
Fatty acid synthase
CHEMBL4158
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DNA repair nuclease/redox regulator APEX1 IC50 = 1000.0 nM 6.0 Inhibition of human APE1 preincubated for 15 mins followed by substrate addition... 28161249
Unchecked IC50 = 1900.0 nM 5.72 Inhibition of Escherichia coli FabB 21726077
Mycobacterial beta-ketoacyl-[acyl-carrier-protein] synthase III IC50 = 4000.0 nM 5.4 Inhibitory activity against KasA from Mycobacterium tuberculosis H37Rv 16392800
3-oxoacyl-[acyl-carrier-protein] synthase 2 IC50 = 6000.0 nM 5.22 Inhibitory activity against KasB from Mycobacterium tuberculosis H37Rv 16392800
3-oxoacyl-[acyl-carrier-protein] synthase 1 IC50 = 12000.0 nM 4.92 Inhibitory activity against FabB from Escherichia coli ANSI 16392800
Plasmodium falciparum IC50 = 49000.0 nM 4.31 Antimicrobial activity against Plasmodium falciparum 20185316
Plasmodium falciparum IC50 = 50000.0 nM 4.3 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum W2 by ... 19191586
Plasmodium falciparum IC50 = 50000.0 nM 4.3 Antimalarial activity against chloroquine-resistant Plasmodium falciparum D6 by ... 19191586
Unchecked Kd = 55400.0 nM 4.26 Inhibition of Staphylococcus aureus recombinant GST-tagged KAS3 expressed in Esc... 22104972
Unchecked IC50 = 74900.0 nM 4.13 Inhibitory activity against recombinant Mycobacterium tuberculosis beta-ketoacyl... 14698162
Mycobacterial beta-ketoacyl-[acyl-carrier-protein] synthase III IC50 = 75000.0 nM 4.12 Inhibition of Mycobacterium tuberculosis FabH 17766110
Mycobacterial beta-ketoacyl-[acyl-carrier-protein] synthase III IC50 = 87000.0 nM 4.06 Inhibitory activity against FabH from Mycobacterium tuberculosis H37Rv 16392800
3-oxoacyl-[acyl-carrier-protein] synthase 2 Kd = 88000.0 nM 4.06 Binding affinity to Staphylococcus aureus FabF C165Q mutant expressed in Escheri... 27187871
Fatty acid synthase IC50 = 100000.0 nM 4.0 Inhibitory activity against human FAS1 16392800

Literature References

PubMed DOI Target Context # Activities
21376591 10.1016/j.bmcl.2011.02.008 Mycobacterium tuberculosis 4
15715465 10.1021/jm049389h MCF7 4
27187871 10.1021/acs.jmedchem.6b00236 Staphylococcus aureus 3
27187871 10.1021/acs.jmedchem.6b00236 Unchecked 3
16562839 10.1021/np050416w Escherichia coli 2
19191586 10.1021/jm8008103 Plasmodium falciparum 2
19185501 10.1016/j.bmc.2009.01.004 Staphylococcus aureus 2
19595597 10.1016/j.bmc.2009.06.059 Staphylococcus aureus 2
21726077 10.1021/jm2005805 Fatty acid synthase 2
19595597 10.1016/j.bmc.2009.06.059 Enterococcus faecalis 2
16392800 10.1021/jm050825p Mycobacterial beta-ketoacyl-[acyl-carrier-protein] synthase III 2
27187871 10.1021/acs.jmedchem.6b00236 3-oxoacyl-[acyl-carrier-protein] synthase 2 2
15715465 10.1021/jm049389h Fatty acid synthase 2
16392800 10.1021/jm050825p Mycobacterium tuberculosis 1
16392800 10.1021/jm050825p 3-oxoacyl-[acyl-carrier-protein] synthase 3 1
17507223 10.1016/j.bmcl.2007.04.067 Staphylococcus aureus 1
17507223 10.1016/j.bmcl.2007.04.067 Moraxella catarrhalis 1
16392800 10.1021/jm050825p 3-oxoacyl-[acyl-carrier-protein] synthase 1 1
16392800 10.1021/jm050825p Escherichia coli 1
15715465 10.1021/jm049389h Mus musculus 1

Data from ChEMBL 36 via Core Engine