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CHEBI:171741 - cerulenin

Default Structure
ChEBI IDCHEBI:171741
ChEBI Namecerulenin
Stars
DefinitionAn epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.
Secondary ChEBI IDCHEBI:29552
Last Modified22 February 2017
DownloadsMolfile
FormulaC12H17NO3
Net Charge0
Average Mass223.272
Monoisotopic Mass223.12084
SMILES[H][C@@]1(C(N)=O)O[C@]1([H])C(=O)CC/C=C/C/C=C/C
InChIInChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
InChIKeyGVEZIHKRYBHEFX-NQQPLRFYSA-N
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
fatty acid synthesis inhibitor  Any pathway inhibitor that inhibits the synthesis of fatty acids.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Applications:
antilipemic drug  A substance used to treat hyperlipidemia (an excess of lipids in the blood).
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
ChEBI Ontology
Outgoing Relation(s)
cerulenin (CHEBI:171741) has role antifungal agent (CHEBI:35718)
cerulenin (CHEBI:171741) has role antiinfective agent (CHEBI:35441)
cerulenin (CHEBI:171741) has role antilipemic drug (CHEBI:35679)
cerulenin (CHEBI:171741) has role antimetabolite (CHEBI:35221)
cerulenin (CHEBI:171741) has role antimicrobial agent (CHEBI:33281)
cerulenin (CHEBI:171741) has role fatty acid synthesis inhibitor (CHEBI:50185)
cerulenin (CHEBI:171741) is a epoxide (CHEBI:32955)
cerulenin (CHEBI:171741) is a monocarboxylic acid amide (CHEBI:29347)
IUPAC Name 
(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
Synonyms  Source
(2R,3S)-3-((4E,7E)-nona-4,7-dienoyl)oxirane-2-carboxamideChEMBL
(2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amideChEMBL
(+)-ceruleninChEBI
CeruleninKEGG COMPOUND
Manual XrefsDatabases
578DrugCentral
C00018711KNApSAcK
C12058KEGG COMPOUND
DB01034DrugBank
Registry NumbersSources
Beilstein:4807182Beilstein
CAS:17397-89-6KEGG COMPOUND
CAS:17397-89-6ChemIDplus
Citations