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InChI=1S/C30H29NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,32-34,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t28-,29-,30+/m0/s1
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Nicolaou, K. C.; Hale, Christopher R. H.; Nilewski, Christian; Ioannidou, Heraklidia A.; Elmarrouni, Abdelatif; Nilewski, Lizanne G.; Beabout, Kathryn; Wang, Tim T.; Shamoo, Yousif (2014).
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fungi. A synthetic structure matching that of natural viridicatumtoxin B makes possible synthetic variants that match or surpass its antibiotic potency.
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Nicolaou, K. C.; Nilewski, Christian; Hale, Christopher R. H.; Ioannidou, Heraklidia A.; Elmarrouni, Abdelatif; Koch, Lizanne G. (2013).
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470:"Total Synthesis of Viridicatumtoxin B and Analogues Thereof: Strategy Evolution, Structural Revision, and Biological Evaluation"
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52:)-5',6',7a',10',11a'-Pentahydroxy-3'-methoxy-2,6,6-trimethyl-7',8',12'-trioxo-7',7a',8',11',11a',12'-hexahydro-1'
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Concerns about solubility, biodegradation, availability and other issues must be resolved before
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CC1=CCCC(12Cc3c4c2c(cc(c4c(c5c3C(=O)6(CC(=C(C(=O)6(C5=O)O)C(=O)N)O)O)O)O)OC)(C)C
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426:"Viridicatumtoxin B, a new anti-MRSA agent from Penicillium sp. FR11"
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Except where otherwise noted, data are given for materials in their
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519:"Total Synthesis and Structural Revision of Viridicatumtoxin B"
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data, the substance was originally thought to be the 11a',12'-
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discovered in 2008. It was isolated from small amounts of
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Zheng, C. J.; Yu, H. E.; Kim, E. H.; Kim, W. G. (2008).
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345:, but 8 to 64 times greater than that of tetracycline.
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A complete total synthesis of viridicatumtoxin B, in
252:were even more effective than the original against
341:of 0.5 μg/ml. That effect is similar to that of
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357:form, was completed in 2013 by the group of
316:Viridicatumtoxin B inhibited the growth of
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271:The substance was first isolated from the
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474:Journal of the American Chemical Society
523:Angewandte Chemie International Edition
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126:Key: SSOXEPGCLBSNOP-OIFRRMEBSA-N
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395:"Synthesis produces new antibiotic"
585:. You can help Knowledge (XXG) by
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339:minimum inhibitory concentration
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211:(at 25 °C , 100 kPa).
56:-spirotetracene]-9'-carboxamide
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430:The Journal of Antibiotics
399:Research & Development
302:nuclear magnetic resonance
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632:Tetracycline antibiotics
581:-related article is a
535:10.1002/anie.201304691
324:methicillin resistant
254:Gram-positive bacteria
319:Staphylococcus aureus
261:clinical development
201: g·mol
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17:Viridicatumtoxin B
443:10.1038/ja.2008.84
371:Viridicatumtoxin A
248:Analogs lacking a
227:Viridicatumtoxin B
215:Infobox references
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486:10.1021/ja506472u
298:mass spectrometry
223:Chemical compound
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81:Interactive image
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642:Cyclohexenes
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403:. Retrieved
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235:tetracycline
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62:Identifiers
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333:-resistant
282:Penicillium
243:penicillium
156:Properties
626:Categories
579:antibiotic
405:2015-10-09
377:References
343:vancomycin
275:of liquid
239:antibiotic
194:Molar mass
92:ChemSpider
68:3D model (
37:IUPAC name
335:S. aureus
331:quinolone
326:S. aureus
296:Based on
292:Structure
233:-derived
553:23893651
504:25317739
452:19168978
365:See also
273:mycelium
263:begins.
101:29355821
544:3835450
495:4210137
355:racemic
337:with a
312:Effects
306:epoxide
286:species
267:History
199:563.559
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288:FR11.
237:-like
231:fungus
140:SMILES
31:Names
229:is a
115:InChI
70:JSmol
48:,11a'
583:stub
549:PMID
500:PMID
448:PMID
329:and
300:and
44:,7a'
539:PMC
531:doi
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184:O
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