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CHEBI:193157 - sceliphrolactam

ChEBI IDCHEBI:193157
ChEBI Namesceliphrolactam
Stars
DefinitionA polyene macrocyclic lactam with formula C28H35NO6. It was isolated from an actinomycete, Streptomyces sp. and displays antifungal activity against amphotericin B-resistant Candida albicans.
Last Modified30 September 2022
DownloadsMolfile
FormulaC28H35NO6
Net Charge0
Average Mass481.589
Monoisotopic Mass481.24644
SMILESCC1=C\C=C\C=C\C(C)CNC(=O)/C=C(O)/C=C/C(C)=C/C=C/C(O)C(O)C(O)C(=O)/C=C\C=C\1
InChIInChI=1S/C28H35NO6/c1-20-10-5-4-6-12-22(3)19-29-26(33)18-23(30)17-16-21(2)13-9-15-25(32)28(35)27(34)24(31)14-8-7-11-20/h4-18,22,25,27-28,30,32,34-35H,19H2,1-3H3,(H,29,33)/b5-4+,11-7+,12-6+,14-8-,15-9+,17-16+,20-10+,21-13+,23-18-
InChIKeyHRAPIHJIKATMEB-GWVUBWKVSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) - PubMed (21247188)
Streptomyces sp. SD85 (ncbitaxon:1849710) - PubMed (29371699)
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
sceliphrolactam (CHEBI:193157) has role antifungal agent (CHEBI:35718)
sceliphrolactam (CHEBI:193157) has role bacterial metabolite (CHEBI:76969)
sceliphrolactam (CHEBI:193157) is a azamacrocycle (CHEBI:52898)
sceliphrolactam (CHEBI:193157) is a enamide (CHEBI:51751)
sceliphrolactam (CHEBI:193157) is a enol (CHEBI:33823)
sceliphrolactam (CHEBI:193157) is a enone (CHEBI:51689)
sceliphrolactam (CHEBI:193157) is a lactam (CHEBI:24995)
sceliphrolactam (CHEBI:193157) is a polyene antibiotic (CHEBI:26177)
sceliphrolactam (CHEBI:193157) is a tetrol (CHEBI:33573)
IUPAC Name 
(3Z,5E,7E,9E,15Z,17E,19E,21E,23E)-4,11,12,13-tetrahydroxy-7,19,25-trimethylazacyclohexacosa-3,5,7,9,15,17,19,21,23-nonaene-2,14-dione
Citations