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:
assay
98% (HPLC)
form
solid
color
light yellow
solubility
DMSO: soluble ~21 mg/mL, H2O: insoluble
SMILES string
C\C(C=C)=C/[C@@]1(C)SC(=O)C(C)=C1O
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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Zbigniew J Witczak et al.
Applied microbiology and biotechnology, 69(3), 237-244 (2005-10-22)
Thiosugars, containing a sulfur atom as heteroatom or a disaccharide linked via a sulfur bridge, possess unique physicochemical properties such as water solubility, which differs from conventional functionalized monosaccharides. The differences in biological activities between thiosugars and their oxygen analogs
Sylvia R Luckner et al.
Structure (London, England : 1993), 17(7), 1004-1013 (2009-07-17)
Mycobacteria have a unique cell wall consisting of mycolic acids, very-long-chain lipids that provide protection and allow the bacteria to persist within human macrophages. Inhibition of cell wall biosynthesis is fatal for the organism and a starting point for the
Thomas Steinbrecher et al.
Bioorganic & medicinal chemistry, 20(11), 3446-3453 (2012-05-09)
Finding novel antibiotics to combat the rise of drug resistance in harmful bacteria is of enormous importance for human health. Computational drug design can be employed to aid synthetic chemists in the search for new potent inhibitors. In recent years
Jill M McFadden et al.
Journal of medicinal chemistry, 48(4), 946-961 (2005-02-18)
Fatty acid synthase (FAS) catalyzes the synthesis of palmitate from the sequential condensation of an acetyl primer with two carbon units added from malonyl-CoA. Inhibition of the beta-ketoacyl synthase domain of mammalian FAS leads to selective cytotoxicity to various cancer
Simon M Jones et al.
Bioorganic & medicinal chemistry, 12(4), 683-692 (2004-02-05)
A series of analogues of the naturally occurring antibiotic thiolactomycin (TLM) have been synthesised and evaluated for their ability to inhibit the growth of the malaria parasite, Plasmodium falciparum. Thiolactomycin is an inhibitor of Type II fatty acid synthase which
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