WS-5995 C
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| Category | Antibiotics |
| Catalog number | BBF-01645 |
| CAS | |
| Molecular Weight | 354.3 |
| Molecular Formula | C19H14O7 |
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Description
WS-5995 C is an anticoccidial antibiotic produced by Streptomyces auranticolor.
Specification
| Synonyms | Antibiotic WS5995C |
| IUPAC Name | 2-(1,5-dihydroxy-3,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid |
| Canonical SMILES | CC1=CC(=C(C(=C1)OC)C2=C(C3=C(C(=CC=C3)O)C(=O)C2=O)O)C(=O)O |
| InChI | InChI=1S/C19H14O7/c1-8-6-10(19(24)25)14(12(7-8)26-2)15-16(21)9-4-3-5-11(20)13(9)17(22)18(15)23/h3-7,20-21H,1-2H3,(H,24,25) |
| InChI Key | CPRXVUOMCYXPHA-UHFFFAOYSA-N |
Properties
| Appearance | Orange Needle Crystal |
| Antibiotic Activity Spectrum | parasites |
| Melting Point | 288-290°C |
Reference Reading
1. A brief and convergent synthetic route to defucogilvocarcin M chromophore: the formal synthesis of WS-5995 A and C
Asit Patra, Pallab Pahari, Sutapa Ray, Dipakranjan Mal J Org Chem. 2005 Oct 28;70(22):9017-20. doi: 10.1021/jo0512960.
[reaction: see text] Densely substituted styryl sulfone 20 is shown to undergo double annulation with phthalide 21 to give, in one-pot operation and in excellent yield, the benzonaphthopyranone scaffold 22 of gilvocarcins.
2. Annulation strategies for benzo[b]fluorene synthesis: efficient routes to the kinafluorenone and WS-5995 antibiotics
G Qabaja, G B Jones J Org Chem. 2000 Oct 20;65(21):7187-94. doi: 10.1021/jo0056186.
Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative to Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.
3. Auxofuran, a novel metabolite that stimulates the growth of fly agaric, is produced by the mycorrhiza helper bacterium Streptomyces strain AcH 505
Julia Riedlinger, Silvia D Schrey, Mika T Tarkka, Rüdiger Hampp, Manmohan Kapur, Hans-Peter Fiedler Appl Environ Microbiol. 2006 May;72(5):3550-7. doi: 10.1128/AEM.72.5.3550-3557.2006.
The mycorrhiza helper bacterium Streptomyces strain AcH 505 improves mycelial growth of ectomycorrhizal fungi and formation of ectomycorrhizas between Amanita muscaria and spruce but suppresses the growth of plant-pathogenic fungi, suggesting that it produces both fungal growth-stimulating and -suppressing compounds. The dominant fungal-growth-promoting substance produced by strain AcH 505, auxofuran, was isolated, and its effect on the levels of gene expression of A. muscaria was investigated. Auxofuran and its synthetic analogue 7-dehydroxy-auxofuran were most effective at a concentration of 15 microM, and application of these compounds led to increased lipid metabolism-related gene expression. Cocultivation of strain AcH 505 and A. muscaria stimulated auxofuran production by the streptomycete. The antifungal substances produced by strain AcH 505 were identified as the antibiotics WS-5995 B and C. WS-5995 B completely blocked mycelial growth at a concentration of 60 microM and caused a cell stress-related gene expression response in A. muscaria. Characterization of these compounds provides the foundation for molecular analysis of the fungus-bacterium interaction in the ectomycorrhizal symbiosis between fly agaric and spruce.
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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 ╳
