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Merck
CN

T9567

Thiolactomycin

98% (HPLC), solid

Synonym(s):

(5R)-4-Hydroxy-3,5-dimethyl-5-[(1E)-2-methyl-1,3-butadienyl]-2(5H)-thiophenone, Antibiotic 2-200, [R-(E)]-4-Hydroxy-3,5-dimethyl-5-(2-methyl-1,3-butadienyl)-2(5H)-thiophenone

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About This Item

Empirical Formula (Hill Notation):
C11H14O2S
CAS Number:
Molecular Weight:
210.29
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
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SMILES string

C\C(C=C)=C/[C@@]1(C)SC(=O)C(C)=C1O

assay

98% (HPLC)

form

solid

color

light yellow

solubility

DMSO: soluble ~21 mg/mL, H2O: insoluble

Gene Information

human ... FASN(2194)

Biochem/physiol Actions

Inhibitor of bacterial myristate synthesis. Does not inhibit eukaryotic myristate synthesis; antibiotic; antitrypanosomal. Shown to be effective against human sleeping sickness parasite, Trypanosoma brucei, as well as malaria parasite and toxoplasma.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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John G Ondeyka et al.
Journal of natural products, 69(3), 377-380 (2006-03-28)
Fatty acids are essential for bacterial growth and viability, with the type II fatty acid synthesis (FAS II) pathway being a potential antibacterial target. A new, selective, and highly sensitive whole cell-based antisense strategy has been designed to screen for
Simon M Jones et al.
Journal of medicinal chemistry, 48(19), 5932-5941 (2005-09-16)
Analogues of the natural antibiotic thiolactomycin (TLM), an inhibitor of the condensing reactions of type II fatty acid synthase, were synthesized and evaluated for their ability to inhibit the growth of the malaria parasite Plasmodium falciparum. Alkylation of the C4
Sudharsan Sridharan et al.
Journal of molecular biology, 366(2), 469-480 (2006-12-19)
Mycolic acids are long chain alpha-alkyl branched, beta-hydroxy fatty acids that represent a characteristic component of the Mycobacterium tuberculosis cell wall. Through their covalent attachment to peptidoglycan via an arabinogalactan polysaccharide, they provide the basis for an essential outer envelope
M L Merrill L Schaeffer et al.
Tuberculosis (Edinburgh, Scotland), 84(6), 353-360 (2004-11-05)
Tuberculosis remains a global health problem, and programs dedicated to discovery of novel compounds against Mycobacterium tuberculosis require robust assays for high-throughput screening of chemical and natural product libraries. Enzymes involved in the biosynthesis of mycolic acids, vital components of
Kanishk Kapilashrami et al.
The Journal of biological chemistry, 288(9), 6045-6052 (2013-01-12)
Thiolactomycin (TLM) is a natural product inhibitor of KasA, the β-ketoacyl synthase A from Mycobacterium tuberculosis. To improve the affinity of TLM for KasA, a series of TLM analogs have been synthesized based on interligand NOEs between TLM and a

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