Structure via PubChem · Public domain (PubChem)
nonactin
Sign in to saveNonactin is a member of a family of naturally occurring cyclic ionophores known as the macrotetrolide antibiotics. The other members of this homologous family are monactin, dinactin, trinactin and tetranactin which are all neutral ionophoric substances and higher homologs of nonactin. Collectively, this class is known as the nactins. Nonactin is soluble in acetone, dichloromethane, ethyl acetate and DMSO, but insoluble in water.
Chemical data
- Formula
- C40H64O12
- Molecular weight
- 736.9 g/mol
- IUPAC name
- (1S,2S,5S,7S,10R,11R,14R,16R,19S,20S,23S,25S,28R,29R,32R,34R)-2,5,11,14,20,23,29,32-octamethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
- SMILES
- C[C@@H]1C[C@H]2CC[C@H](O2)[C@@H](C(=O)O[C@H](C[C@@H]3CC[C@@H](O3)[C@H](C(=O)O[C@@H](C[C@H]4CC[C@H](O4)[C@@H](C(=O)O[C@H](C[C@@H]5CC[C@@H](O5)[C@H](C(=O)O1)C)C)C)C)C)C)C
- InChIKey
- RMIXHJPMNBXMBU-QIIXEHPYSA-N
- XLogP
- 6.6
- Polar surface area
- 142 Ų
- H-bond donors
- 0
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- macrolides
- Mass
- 736.44
Show 4 more facts
- canonical SMILES
- CC1CC2CCC(O2)C(C(=O)OC(CC3CCC(O3)C(C(=O)OC(CC4CCC(O4)C(C(=O)OC(CC5CCC(O5)C(C(=O)O1)C)C)C)C)C)C)C
- chemical formula
- C₄₀H₆₄O₁₂
- isomeric SMILES
- C[C@@H]1C[C@H]2CC[C@H](O2)[C@@H](C(=O)O[C@H](C[C@@H]3CC[C@@H](O3)[C@H](C(=O)O[C@@H](C[C@H]4CC[C@H](O4)[C@@H](C(=O)O[C@H](C[C@@H]5CC[C@@H](O5)[C@H](C(=O)O1)C)C)C)C)C)C)C
- found in taxon
- Streptomyces griseus
Sources (1)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Sources
- Structure and properties
- Reactions
- Biological effects
- Applications
- References
- Further reading
Nonactin is a member of a family of naturally occurring cyclic ionophores known as the macrotetrolide antibiotics. The other members of this homologous family are monactin, dinactin, trinactin and tetranactin which are all neutral ionophoric substances and higher homologs of nonactin. Collectively, this class is known as the nactins. Nonactin is soluble in acetone, dichloromethane, ethyl acetate and DMSO, but insoluble in water.
==Sources== Nonactin is commercially available; as of 2006, these bacterial species produce nonactin: Streptomyces tsukubensis, Streptomyces griseus, Streptomyces chrysomallus and Streptomyces werraensis. Total syntheses have been reported.
Excerpted from Wikipedia’s “nonactin” article, available under the CC BY-SA 4.0 licence.