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CHEBI:65452 - aspergillide C

ChEBI IDCHEBI:65452
ChEBI Nameaspergillide C
Stars
DefinitionA macrolide that is 4,15-dioxabicyclo[9.3.1]pentadeca-9,12-dien-3-one substituted by a hydroxy group at position 14 and a methyl group at position 5 (the 1S,5S,9E,11R,14S stereoisomer). It is isolated from the marine-derived fungus Aspergillus ostianus and exhibits cytotoxic activity against mouse lymphocytic leukemia cells (L1210).
Last Modified27 October 2016
DownloadsMolfile
FormulaC14H20O4
Net Charge0
Average Mass252.310
Monoisotopic Mass252.13616
SMILES[H][C@@]12C=C[C@H](O)[C@]([H])(CC(=O)O[C@@H](C)CCC/C=C/1)O2
InChIInChI=1S/C14H20O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6-8,10-13,15H,2-3,5,9H2,1H3/b6-4+/t10-,11-,12-,13-/m0/s1
InChIKeyLXBFWPWKVZPNRA-NPZYAQMBSA-N
Species of MetaboliteComponentSourceComments
Aspergillus ostianus (ncbitaxon:138279) - PubMed (18078344) Strain: 01F313
Roles Classification
Biological Role:
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
aspergillide C (CHEBI:65452) has role Aspergillus metabolite (CHEBI:76956)
aspergillide C (CHEBI:65452) has role antineoplastic agent (CHEBI:35610)
aspergillide C (CHEBI:65452) is a bridged compound (CHEBI:35990)
aspergillide C (CHEBI:65452) is a cyclic ether (CHEBI:37407)
aspergillide C (CHEBI:65452) is a macrolide (CHEBI:25106)
aspergillide C (CHEBI:65452) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1S,5S,9E,11S,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadeca-9,12-dien-3-one
Synonym  Source
(+)-asperigillide CChEBI
Registry NumbersSources
Reaxys:15805982Reaxys
Citations