Thiolactomycin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Thiolactomycin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Thiolactomycin?

The molecule Thiolactomycin presents a molecular formula of C11H14O2S and its IUPAC name is (5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dienyl]thiophen-2-one.

Thiolactomycin (TLM) is a thioester-containing antibiotic produced by Streptomyces bacteria. It has potent activity against Gram-positive bacteria, including methicillin-resistant strains. TLM inhibits bacterial cell growth by blocking the synthesis of essential cell wall components..

TLM was first isolated in the 1960s and its structure was determined in the 1970s. The molecule consists of a thioester group linked to a lactone ring. The thioester group is essential for TLM's antibacterial activity..

TLM has been shown to be effective against a variety of Gram-positive bacteria, including methicillin-resistant strains. TLM is also active against Gram-negative bacteria, although its activity against these bacteria is weaker..

TLM has a relatively low toxicity in animals and humans. A few side effects, such as diarrhea and vomiting, have been reported in humans..

TLM is currently being investigated as a potential treatment for infections caused by Gram-positive bacteria, including methicillin-resistant strains..

3D structure

Cartesian coordinates

Geometry of Thiolactomycin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Thiolactomycin SYQNUQSGEWNWKV-XUIVZRPNSA-N chemical compound 2D structure molecule svg
Thiolactomycin

 

Molecule descriptors

 
IUPAC name(5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dienyl]thiophen-2-one
InChI codeInChI=1S/C11H14O2S/c1-5-7(2)6-11(4)9(12)8(3)10(13)14-11/h5-6,12H,1H2,2-4H3/b7-6+/t11-/m1/s1
InChI KeySYQNUQSGEWNWKV-XUIVZRPNSA-N
SMILESC=C/C(C)=C/[C@@]1(C)SC(=O)C(C)=C1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Thiolactomycin
  • (2R)-5-hydroxy-2,4-dimethyl-2-[(1E)-2-methylbuta-1,3-dien-1-yl]-2,3-dihydrothiophen-3-one
  • (2R)-5-hydroxy-2,4-dimethyl-2-[(1E)-2-methylbuta-1,3-dienyl]thiophen-3-one
  • (4-R)(2E,5E)-2,4,6-Trimethyl-3-hydroxy-2,5,7-octatriene-4-thiolide
  • (5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2,5-dihydrothiophen-2-one
  • (5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
  • (5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dienyl]thiophen-2-one
  • (5R)-Thiolactomycin
  • (R)-(+)-Thiolactomycin
  • (R)-THIOLACTOMYCIN
  • (R,E)-4-Hydroxy-3,5-dimethyl-5-(2-methylbuta-1,3-dien-1-yl)thiophen-2(5H)-one
  • (R-(E))-3,5-Dimethyl-4-hydroxy-5-(2-methyl-1,3-butadienyl)-2(5H)-thiophenone
  • 1fj4
  • 2(5H)-Thiophenone, 3,5-dimethyl-4-hydroxy-5-(2-methyl-1,3-butadienyl)-, (R-(E))-
  • 2(5H)-Thiophenone, 4-hydroxy-3,5-dimethyl-5-(2-methyl-1,3-butadienyl)-, (S-(E))-
  • 2vb8
  • 4-HYDROXY-3,5-DIMETHYL-5-(2-METHYL-BUTA-1,3-DIENYL)-5H-THIOPHEN-2-ONE
  • 4c6x
  • 82079-32-1
  • Antibiotic 2-200
  • BRN 4423670
  • CCG-204990
  • DB04302
  • EU-0100908
  • HMS3262F18
  • LP00908
  • Lopac0_000908
  • NCGC00094221-01
  • NCGC00094221-02
  • NCGC00261593-01
  • Q27095124
  • SDCCGSBI-0050883.P002
  • SR-01000076067
  • SR-01000076067-1
  • T 9567
  • TLM
  • Thiolactomycin
  • [R-(E)]-4-Hydroxy-3,5-dimethyl-5-(2-methyl-1,3-butadienyl)-2(5H)-thiophenone
  • thiolactomycine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4099011
  • DTXSID6041139
  • Tox21_500908
  • SCHEMBL12099108
  • SCHEMBL13332161

Physico-Chemical properties

IUPAC name(5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dienyl]thiophen-2-one
Molecular formulaC11H14O2S
Molecular weight210.293
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity60.86
LogP3.0
Topological polar surface area62.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.