Oxasetin
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| Category | Antibiotics |
| Catalog number | BBF-02328 |
| CAS | |
| Molecular Weight | 359.46 |
| Molecular Formula | C21H29NO4 |
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Description
It is produced by the strain of Vaginatispora aquatica HK 1821. It has medium activity against gram-positive bacteria, including Methicillin-resistant Staphylococcus aureus and Vancomycin-resistant enterococcus faecalis (MIC is 16 μg/mL). It has no activity against gram-negative bacteria and fungi.
Specification
| IUPAC Name | 3-[(1S,2R,4aS,6R,8aR)-1,3,6-trimethyl-2-propyl-4a,5,6,7,8,8a-hexahydro-2H-naphthalene-1-carbonyl]-4-hydroxypyrrole-2,5-dione |
| Canonical SMILES | CCCC1C(=CC2CC(CCC2C1(C)C(=O)C3=C(C(=O)NC3=O)O)C)C |
| InChI | InChI=1S/C21H29NO4/c1-5-6-14-12(3)10-13-9-11(2)7-8-15(13)21(14,4)18(24)16-17(23)20(26)22-19(16)25/h10-11,13-15H,5-9H2,1-4H3,(H2,22,23,25,26)/t11-,13+,14-,15-,21-/m1/s1 |
| InChI Key | PGUSTONLIMHUIA-PGONBXCCSA-N |
Properties
| Appearance | Colorless Oily Matter |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Methanol |
Reference Reading
1. Phenalenone derivatives and the unusual tricyclic sesterterpene acid from the marine fungus Lophiostoma bipolare BCC25910
Chakapong Intaraudom, Sutichai Nitthithanasilp, Pranee Rachtawee, Tanapong Boonruangprapa, Samran Prabpai, Palangpon Kongsaeree, Pattama Pittayakhajonwut Phytochemistry. 2015 Dec;120:19-27. doi: 10.1016/j.phytochem.2015.11.003. Epub 2015 Nov 12.
Ten compounds including nine phenalenone derivatives (five bipolarides and four bipolarols) and a sesterterpene acid (bipolarenic acid), were isolated from a marine isolated of the fungus Lophiostoma bipolare (BCC25910), along with the known compounds, (-)-scleroderolide, (-)-sclerodin, and oxasetin. Chemical structures were elucidated based on NMR spectroscopic data and HRESIMS analysis. In addition, the absolute configurations of the phenalenones were resolved using specific rotations and chemical means, while the relative configuration of bipolarenic acid was confirmed by X-ray crystallographic analysis. The compounds were evaluated for biological activity against the Plasmodium falciparum K-1 strain, Candida albicans, and Bacillus cereus, and for cytotoxicity against both cancerous and non-cancerous cells.
2. Oxasetin from Lophiostoma sp. of the Baltic Sea: identification, in silico binding mode prediction and antibacterial evaluation against fish pathogenic bacteria
Muftah Ali M Shushni, Faizul Azam, Ulrike Lindequist Nat Prod Commun. 2013 Sep;8(9):1223-6.
Because of the evolving resistance of microorganisms against existing antibiotics, there is an increasing need for new ones, not only in human, but also in veterinary medicine. The dichloromethane extract of a fungal strain of the genus Lophiostoma, isolated from driftwood collected from the coast of the Baltic Sea, displayed antibacterial activity against some fish pathogenic bacteria. Ergosterol epoxide (1), cerebroside C (2) and oxasetin (3) were isolated from the extract and structurally elucidated on the basis of spectroscopic data and chemical evidence. Compound 3 exhibited in vitro activity against Vibrio anguillarum, Flexibacter maritimus and Pseudomonas anguilliseptica with minimal inhibitory concentrations of 12.5, 12.5 and 6.25 microg/mL, respectively. Molecular docking studies were performed to understand the interaction of compound 3 with different macromolecular targets. Analysis of in silico results, together with experimental findings, validates the antimicrobial activity associated with compound 3. These results may be exploited in lead optimization and development of potent antibacterial agents.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
