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CHEBI:29650 - narbonolide

ChEBI IDCHEBI:29650
ChEBI Namenarbonolide
Stars
DefinitionA 14-membererd macrolide containing seven stereocentres carrying one ethyl, one hydroxy and five methyl substituents. It is the aglycone of the antibiotic narbonomycin and an intermediate in the biosynthesis of pikromycin.
Last Modified29 April 2015
DownloadsMolfile
FormulaC20H32O5
Net Charge0
Average Mass352.471
Monoisotopic Mass352.22497
SMILESCC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)C[C@@H](C)C(=O)/C=C/[C@H]1C
InChIInChI=1S/C20H32O5/c1-7-17-11(2)8-9-16(21)12(3)10-13(4)18(22)14(5)19(23)15(6)20(24)25-17/h8-9,11-15,17-18,22H,7,10H2,1-6H3/b9-8+/t11-,12-,13+,14-,15-,17-,18+/m1/s1
InChIKeyYFFOFFWSBYZSOI-HQWJGCFGSA-N
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
narbonolide (CHEBI:29650) has role metabolite (CHEBI:25212)
narbonolide (CHEBI:29650) is a enone (CHEBI:51689)
narbonolide (CHEBI:29650) is a macrolide (CHEBI:25106)
Incoming Relation(s)
narbomycin (CHEBI:29649) has functional parent narbonolide (CHEBI:29650)
neopikromycin (CHEBI:85614) has functional parent narbonolide (CHEBI:29650)
novapikromycin (CHEBI:77648) has functional parent narbonolide (CHEBI:29650)
pikromycin (CHEBI:29665) has functional parent narbonolide (CHEBI:29650)
IUPAC Name 
(3R,5R,6S,7S,9R,11E,13R,14R)-14-ethyl-6-hydroxy-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
Synonym  Source
NarbonolideKEGG COMPOUND
UniProt Name  Source
narbonolideUniProt
Manual XrefsDatabases
C11997KEGG COMPOUND
Registry NumbersSources
Reaxys:4541269Reaxys
Citations