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MetaCyc Compound: thiolactomycin

Synonyms: antibiotic 2-200, (+)-thiolactomycin, (R)-(+)-thiolactomycin, (2R)-5-hydroxy-2,4-dimethyl-2-[(1E)-2-methylbuta-1,3-dien-1-yl]-2,3-dihydrothiophen-3-one

Superclasses: a secondary metabolitea xenobiotican antibiotic

Chemical Formula: C11H14O2S

Molecular Weight: 210.29 Daltons

Monoisotopic Molecular Weight: 210.0714503836 Daltons

thiolactomycin compound structure

SMILES: C=CC(C)=CC1(SC(O)=C(C)C(=O)1)(C)

InChI: InChI=1S/C11H14O2S/c1-5-7(2)6-11(4)9(12)8(3)10(13)14-11/h5-6,13H,1H2,2-4H3/b7-6+/t11-/m1/s1

InChIKey: InChIKey=HGCGJTZCWZFGBT-XUIVZRPNSA-N

Unification Links: ChEBI:398495, ChemSpider:16744232, DrugBank:DB04302, KEGG:C11165, PubChem:445629

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 110.93569Inferred by computational analysis [Latendresse13]

In Transport reactions:
a xenobiotic[cytosol] + ATP + H2O ↔ a xenobiotic[extracellular space] + ADP + phosphate

Enzymes inhibited by thiolactomycin, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: acetyl-CoA:ACP transacylase [Tsay92], β-ketoacyl-ACP synthase [Jackowski89], β-ketoacyl-ACP synthase [Jackowski89], acetoacetyl-[acp] synthase [Jackowski89], β-ketoacyl-ACP synthase [Jackowski89], acetoacetyl-[acp] synthase [Jackowski89]

References

Jackowski89: Jackowski S, Murphy CM, Cronan JE, Rock CO (1989). "Acetoacetyl-acyl carrier protein synthase. A target for the antibiotic thiolactomycin." J Biol Chem 1989;264(13);7624-9. PMID: 2651445

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Tsay92: Tsay JT, Oh W, Larson TJ, Jackowski S, Rock CO (1992). "Isolation and characterization of the beta-ketoacyl-acyl carrier protein synthase III gene (fabH) from Escherichia coli K-12." J Biol Chem 1992;267(10);6807-14. PMID: 1551888


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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