(-)-Etozolin

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

What is the (-)-Etozolin?

The molecule (-)-Etozolin presents a molecular formula of C13H20N2O3S and its IUPAC name is ethyl (2Z)-2-[(5R)-3-methyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene]acetate.

-Etozolin is a molecule that was first discovered in the 1970s. It is a member of the class of molecules known as quinuclidines. Etozolin is known to have a wide variety of biological activities, including: antiviral, antibacterial, antifungal, antiparasitic, and anti-inflammatory. It is also known to be an inhibitor of the enzyme reverse transcriptase..

Etozolin was first isolated from the bacterium Streptomyces sp. in 1970. The molecule was first structurally characterized in 1974. Since its discovery, etozolin has been the subject of numerous studies due to its wide variety of biological activities..

Etozolin has been shown to have potent antiviral activity against a variety of viruses, including: influenza A, herpes simplex, and HIV-1. The mechanism of action of etozolin against these viruses is not fully understood, but it is thought to involve the inhibition of the enzyme reverse transcriptase..

Etozolin has also been shown to have potent antibacterial activity against a variety of bacteria, including: Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus. The mechanism of action of etozolin against these bacteria is not fully understood, but it is thought to involve the inhibition of cell wall synthesis..

Etozolin has also been shown to have potent antifungal activity against a variety of fungi, including: Candida albicans, Aspergillus niger, and Trichophyton mentagrophytes. The mechanism of action of etozolin against these fungi is not fully understood, but it is thought to involve the inhibition of cell wall synthesis..

Etozolin has also been shown to have potent antiparasitic activity against a variety of parasites, including: Giardia lamblia, Entamoeba histolytica, and Plasmodium falciparum. The mechanism of action of etozolin against these parasites is not fully understood, but it is thought to involve the inhibition of cell wall synthesis..

Etozolin has also been shown to have potent anti-inflammatory activity. The mechanism of action of etozolin against inflammation is not fully understood, but it is thought to involve the inhibition of the enzyme cyclooxygenase..

Etozolin is a quinuclidine molecule with a wide variety of biological activities. It is an inhibitor of the enzyme reverse transcriptase and has potent antiviral, antibacterial, antifungal, antiparasitic, and anti-inflammatory activity..

3D structure

Cartesian coordinates

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

2D drawing

 

(-)-Etozolin ZCKKHYXUQFTBIK-ASCRHOAZSA-N chemical compound 2D structure molecule svg
(-)-Etozolin

 

Molecule descriptors

 
IUPAC nameethyl (2Z)-2-[(5R)-3-methyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene]acetate
InChI codeInChI=1S/C13H20N2O3S/c1-3-18-11(16)9-10-14(2)12(17)13(19-10)15-7-5-4-6-8-15/h9,13H,3-8H2,1-2H3/b10-9-/t13-/m1/s1
InChI KeyZCKKHYXUQFTBIK-ASCRHOAZSA-N
SMILESCCOC(=O)/C=C1\S[C@@H](N2CCCCC2)C(=O)N1C

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.

  • (-)-Etozolin
  • (-)-Etozoline
  • 05P706177M
  • 76333-28-3
  • Acetic acid, 2-((5R)-3-methyl-4-oxo-5-(1-piperidinyl)-2-thiazolidinylidene)-, ethyl ester
  • ETOZOLIN, (R)-
  • Etozolin, (-)-
  • Q27236136

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC53021870
  • UNII-05P706177M

Physico-Chemical properties

IUPAC nameethyl (2Z)-2-[(5R)-3-methyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene]acetate
Molecular formulaC13H20N2O3S
Molecular weight284.375
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity82.60
LogP1.3
Topological polar surface area75.2

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.