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CHEBI:156382 - jawsamycin

ChEBI IDCHEBI:156382
ChEBI Namejawsamycin
Stars
DefinitionA 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.
Last Modified21 August 2020
Submitterrnash
DownloadsMolfile
FormulaC32H43N3O6
Net Charge0
Average Mass565.711
Monoisotopic Mass565.31519
SMILESC[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](N2CCC(=O)NC2=O)[C@H](O)[C@@H]1O
InChIInChI=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
InChIKeyQOOORVUXEUQEKV-KNLYTHMISA-N
Species of MetaboliteComponentSourceComments
Streptoverticillium fervens (ncbitaxon:66429) cell suspension culture (BTO:0000221) PubMed (2387768) Strain: HP-891
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
FR-900848ChemIDplus
FR900848SUBMITTER
FR 900848ChemIDplus
Manual XrefsDatabases
EP0286330Patent
Registry NumbersSources
CAS:120500-69-8ChemIDplus
Citations