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CHEBI:90924 - aurachin A

Default Structure
ChEBI IDCHEBI:90924
ChEBI Nameaurachin A
Stars
DefinitionAn A-type aurichin that is 1,2-dihydrofuro[2,3-c]quinoline 5-oxide which is substituted at position 2 by a (6E)-10-hydroxy-2,6-dimethylundeca-2,6-dien-10-yl group and at position 4 by a methyl group (relative configuration shown). Found in the myxobacterium Stigmatella aurantiaca strain Sg a15.
Last Modified12 May 2016
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H33NO3
Net Charge0
Average Mass395.543
Monoisotopic Mass395.24604
SMILES[H][C@]1([C@@](C)(O)CC/C=C(\C)CCC=C(C)C)Cc2c(c(C)[n+]([O-])c3ccccc23)O1
InChIInChI=1S/C25H33NO3/c1-17(2)10-8-11-18(3)12-9-15-25(5,27)23-16-21-20-13-6-7-14-22(20)26(28)19(4)24(21)29-23/h6-7,10,12-14,23,27H,8-9,11,15-16H2,1-5H3/b18-12+/t23-,25+/m1/s1
InChIKeyZEUIHPOXFICJIT-ZVWRMSPBSA-N
Species of MetaboliteComponentSourceComments
Stigmatella aurantiaca (ncbitaxon:41) - PubMed (24367422) Strain: MYX-030
Stigmatella aurantiaca Sg a15 (ncbitaxon:675526) - PubMed (18989924) Strain: Sg a15
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
ChEBI Ontology
Outgoing Relation(s)
aurachin A (CHEBI:90924) has role antibacterial agent (CHEBI:33282)
aurachin A (CHEBI:90924) has role bacterial metabolite (CHEBI:76969)
aurachin A (CHEBI:90924) is a A-type aurachin (CHEBI:90917)
aurachin A (CHEBI:90924) is a furoquinoline (CHEBI:84586)
aurachin A (CHEBI:90924) is a quinoline N-oxide (CHEBI:26508)
aurachin A (CHEBI:90924) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
rel-(2R,5E)-6,10-dimethyl-2-[(2S)4-methyl-5-oxido-1,2-dihydrofuro[2,3-c]quinolin-2-yl]undeca-5,9-dien-2-ol
Synonym  Source
aurichan-AChemIDplus
Manual XrefsDatabases
CPD-15911MetaCyc
Registry NumbersSources
Reaxys:19439470Reaxys
CAS:108354-15-0ChemIDplus
Citations