CHEBI:90924 - aurachin A

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ChEBI Name aurachin A
ChEBI ID CHEBI:90924
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C25H33NO3
Net Charge 0
Average Mass 395.535
Monoisotopic Mass 395.24604
InChI InChI=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
InChIKey ZEUIHPOXFICJIT-ZVWRMSPBSA-N
SMILES C1=CC=2C(C=C1)=[N+](C(=C3C2C[C@@](O3)([C@](CC/C=C(/CCC=C(C)C)\C)(O)C)[H])C)[O-]
Metabolite of Species Details
Stigmatella aurantiaca (NCBI:txid41) of strain MYX-030 See: PubMed
Stigmatella aurantiaca Sg a15 (NCBI:txid675526) of strain Sg a15 See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-A ChemIDplus
Manual Xref Database
CPD-15911 MetaCyc
View more database links
Registry Numbers Types Sources
108354-15-0 CAS Registry Number ChemIDplus
19439470 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18989924 PubMed citation Europe PMC
21979787 PubMed citation Europe PMC
24367422 PubMed citation Europe PMC
3106289 PubMed citation Europe PMC
Last Modified
12 May 2016