CHEBI:65450 - aspergillide A

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ChEBI Name aspergillide A ChEBI ID CHEBI:65450 Definition A 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). Stars This entity has been manually annotated by the ChEBI Team. Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C14H22O4 Net Charge 0 Average Mass 254.32210 Monoisotopic Mass 254.15181 InChI InChI=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 InChIKey FDJDTDDUDZAAFP-GDHSIMSHSA-N SMILES [H][C@@]12CC[C@H](O)[C@@]([H])(CC(=O)O[C@@H](C)CCC\C=C\1)O2 Metabolite of Species Details Aspergillus ostianus (NCBI:txid138279) of strain 01F313 See: PubMed Roles Classification Biological Role(s): Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . Application(s): antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. View more via ChEBI Ontology ChEBI Ontology Outgoing 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 Number Type Source 19982176 Reaxys Registry Number Reaxys Citations Types Sources 18078344 PubMed citation Europe PMC 20141226 PubMed citation Europe PMC 21064045 PubMed citation Europe PMC 21207589 PubMed citation Europe PMC 21370350 PubMed citation Europe PMC Last Modified 27 October 2016

General Comment 2012-11-15 The stereochemistry of aspergillide A was revised by its total synthesis: Tetrahedron Lett 2010, 51(5), 875-877.