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CHEBI:65450 - aspergillide A

ChEBI IDCHEBI:65450
ChEBI Nameaspergillide A
Stars
DefinitionA macrolide that is 4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one substituted by a hydroxy group at position 14 and a methyl group at position 5 (the 1R,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
FormulaC14H22O4
Net Charge0
Average Mass254.326
Monoisotopic Mass254.15181
SMILES[H][C@@]12/C=C/CCC[C@H](C)OC(=O)C[C@@]([H])(O1)[C@@H](O)CC2
InChIInChI=1S/C14H22O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6,10-13,15H,2-3,5,7-9H2,1H3/b6-4+/t10-,11-,12-,13+/m0/s1
InChIKeyFDJDTDDUDZAAFP-GDHSIMSHSA-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 A (CHEBI:65450) has role Aspergillus metabolite (CHEBI:76956)
aspergillide A (CHEBI:65450) has role antineoplastic agent (CHEBI:35610)
aspergillide A (CHEBI:65450) is a bridged compound (CHEBI:35990)
aspergillide A (CHEBI:65450) is a cyclic ether (CHEBI:37407)
aspergillide A (CHEBI:65450) is a macrolide (CHEBI:25106)
aspergillide A (CHEBI:65450) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1R,5S,9E,11R,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one
Registry NumbersSources
Reaxys:19982176Reaxys
Citations