Dioxamycin

Dioxamycin
Names
IUPAC name
(2S,4S,5S)-4-[(1E,3E,5E)-7-[(2R,6R)-6-[(2R,3S,4aR,12bS)-2,3,4a,8,12b-pentahydroxy-3-methyl-1,7,12-trioxo-2,4-dihydrobenzo[a]anthracen-9-yl]-2-methyloxan-3-yl]oxy-7-oxohepta-1,3,5-trienyl]-2,5-dimethyl-1,3-dioxolane-2-carboxylic acid[1]
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C38H40O15/c1-18-23(51-26(39)10-8-6-5-7-9-24-19(2)52-36(4,53-24)34(45)46)13-14-25(50-18)20-11-12-21-27(29(20)40)30(41)22-15-16-37(48)17-35(3,47)32(43)33(44)38(37,49)28(22)31(21)42/h5-12,15-16,18-19,23-25,32,40,43,47-49H,13-14,17H2,1-4H3,(H,45,46)/b6-5+,9-7+,10-8+/t18-,19+,23?,24+,25-,32+,35+,36+,37+,38-/m1/s1
    Key: HWMMBHOXHRVLCU-QOUANJGESA-N
  • C[C@H]1[C@@H](O[C@@](O1)(C)C(=O)O)/C=C/C=C/C=C/C(=O)OC2CC[C@@H](O[C@@H]2C)C3=C(C4=C(C=C3)C(=O)C5=C(C4=O)C=C[C@]6([C@@]5(C(=O)[C@@H]([C@@](C6)(C)O)O)O)O)O
Properties
C38H40O15
Molar mass 736.723 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dioxamycin is a benz[a]anthraquinone antibiotic and kinase inhibitor with the molecular formula C38H40O15.[1][2][3] Dioxamycin is produced by the bacterium Streptomyces cocklensis and Streptomyces xantholiticus.[2][4]

References

  1. ^ a b "Dioxamycin". Pubchem.ncbi.NLM.nih.gov.
  2. ^ a b Rahman, Atta-ur (20 January 2015). Studies in Natural Products Chemistry. Elsevier. p. 422. ISBN 978-0-444-63470-2.
  3. ^ Sawa, Ryuichi; Matsuda, Naoko; Uchida, Takeshi; Ikeda, Takako; Sawa, Tsutomu; Naganawa, Hiroshi; Hamada, Masa; Takeuchi, Tomio (1991). "Dioxamycin, a new benz(a)anthraquinone antibiotic". The Journal of Antibiotics. 44 (4): 396–402. doi:10.7164/antibiotics.44.396. PMID 2032948.
  4. ^ Kim, Byung-Yong; Zucchi, Tiago Domingues; Fiedler, Hans-Peter; Goodfellow, Michael (1 February 2012). "Streptomyces cocklensis sp. nov., a dioxamycin-producing actinomycete". International Journal of Systematic and Evolutionary Microbiology. 62 (2): 279–283. doi:10.1099/ijs.0.029983-0. PMID 21398501.

Further reading

  • Thomson, R. H. (6 December 2012). Naturally Occurring Quinones IV: Recent advances. Springer Science & Business Media. p. 544. ISBN 978-94-009-1551-0.


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