CHEBI:156382 - jawsamycin

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ChEBI Name jawsamycin
ChEBI ID CHEBI:156382
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Rob Nash
Supplier Information
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Formula C32H43N3O6
Net Charge 0
Average Mass 565.711
Monoisotopic Mass 565.31519
InChI 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
InChIKey QOOORVUXEUQEKV-KNLYTHMISA-N
SMILES 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
Metabolite of Species Details
Streptoverticillium fervens (NCBI:txid66429) Found in cell suspension culture (BTO:0000221). of strain HP-891 See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing jawsamycin (CHEBI:156382) has role antifungal agent (CHEBI:35718)
jawsamycin (CHEBI:156382) has role bacterial metabolite (CHEBI:76969)
jawsamycin (CHEBI:156382) is a cyclopropanes (CHEBI:51454)
jawsamycin (CHEBI:156382) is a nucleoside analogue (CHEBI:60783)
jawsamycin (CHEBI:156382) is a olefinic compound (CHEBI:78840)
jawsamycin (CHEBI:156382) is a polyketide (CHEBI:26188)
jawsamycin (CHEBI:156382) is a secondary carboxamide (CHEBI:140325)
IUPAC Name
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
Synonyms Sources
FR 900848 ChemIDplus
FR-900848 ChemIDplus
FR900848 SUBMITTER
Manual Xref Database
EP0286330 Patent
View more database links
Registry Number Type Source
120500-69-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17136894 PubMed citation Europe PMC
19030571 PubMed citation Europe PMC
2387768 PubMed citation SUBMITTER
24756819 PubMed citation Europe PMC
28059412 PubMed citation Europe PMC
32636417 PubMed citation SUBMITTER
32737318 PubMed citation Europe PMC
Last Modified
21 August 2020