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jawsamycin |
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CHEBI:156382 |
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A polyketide that is 5'-amino-5'-deoxy-3,4,5,6-tetrahydrouridine in which one of the hydrogens of the amino group is substituted by a (1E,3E)-1-[(1R,1'R,1''R,1'''R,2S,2'R,2''R,2'''S)-2'''-{(E)-2-[(1R,2R)-2-methylcyclopropyl]ethenyl}[1,1':2',1'':2'',1'''-quater(cyclopropan)]-2-yl]-5-oxopenta-1,3-dien-5-yl group. It is a metabolite isolated from the bacterium, Streptoverticillium fervens and targets the catalytic subunit of the fungal UDP-glycosyltransferase, the first step in the biosynthesis of glycosylphosphatidylinositol (GPI) anchors. It exhibits broad spectrum antifungal activity against several pathogenic fungi including Mucorales. |
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This entity has been manually annotated by the ChEBI Team.
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Rob Nash
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Molfile
XML
SDF
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more structures >>
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InChI=1S/C32H43N3O6/c1-16-10-17(16)6-7-19-12-21(19)23-14-25(23)24-13-22(24)20-11-18(20)4-2-3-5-27(36)33-15-26-29(38)30(39)31(41-26)35-9-8-28(37)34-32(35)40/h2-7,16-26,29-31,38-39H,8-15H2,1H3,(H,33,36)(H,34,37,40)/b4-2+,5-3+,7-6+/t16-,17-,18-,19-,20-,21-,22+,23+,24-,25-,26-,29-,30-,31-/m1/s1 |
QOOORVUXEUQEKV-KNLYTHMISA-N |
C[C@@H]1C[C@H]1\C=C\[C@@H]1C[C@H]1[C@@H]1C[C@H]1[C@@H]1C[C@H]1[C@@H]1C[C@H]1\C=C\C=C\C(=O)NC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1CCC(=O)NC1=O |
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Streptoverticillium fervens
(NCBI:txid66429)
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Found in
cell suspension culture
(BTO:0000221).
of strain
HP-891
See:
PubMed
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bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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View more via ChEBI Ontology
5'-deoxy-5'-({(2E,4E)-5-[(1R,1'R,1''R,1'''R,2S,2'R,2''R,2'''S)-2'''-{(E)-2-[(1R,2R)-2-methylcyclopropyl]ethenyl}[1,1':2',1'':2'',1'''-quater(cyclopropan)]-2-yl]penta-2,4-dienoyl}amino)-5,6-dihydrouridine
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FR 900848
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ChemIDplus
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FR-900848
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ChemIDplus
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FR900848
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SUBMITTER
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120500-69-8
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CAS Registry Number
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ChemIDplus
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17136894
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PubMed citation
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Europe PMC
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19030571
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PubMed citation
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Europe PMC
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2387768
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PubMed citation
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SUBMITTER
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24756819
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PubMed citation
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Europe PMC
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28059412
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PubMed citation
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Europe PMC
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32636417
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PubMed citation
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SUBMITTER
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32737318
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PubMed citation
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Europe PMC
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