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CHEBI:48080 - brefeldin A

Default Structure
ChEBI IDCHEBI:48080
ChEBI Namebrefeldin A
Stars
DefinitionA metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity.
Last Modified12 April 2017
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC16H24O4
Net Charge0
Average Mass280.364
Monoisotopic Mass280.16746
SMILES[H][C@@]12C[C@@H](O)C[C@@]1([H])/C=C/CCC[C@H](C)OC(=O)/C=C/[C@H]2O
InChIInChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1
InChIKeyKQNZDYYTLMIZCT-KQPMLPITSA-N
Roles Classification
Biological Roles:
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
brefeldin A (CHEBI:48080) has role Penicillium metabolite (CHEBI:76964)
brefeldin A (CHEBI:48080) is a macrolide antibiotic (CHEBI:25105)
Incoming Relation(s)
TX-1875 (CHEBI:134260) has functional parent brefeldin A (CHEBI:48080)
IUPAC Name 
(1R,2E,6S,10E,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
Synonyms  Source
ascotoxinChemIDplus
Brefeldin AChemIDplus
cyaneinChemIDplus
decumbinChemIDplus
Registry NumbersSources
Beilstein:25191Beilstein
Beilstein:5282047Beilstein
CAS:20350-15-6ChemIDplus