aspergillide C (CHEBI:65452)

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ChEBI Name	aspergillide C

ChEBI ID	CHEBI:65452

Definition	A 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).

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C14H20O4

Net Charge

Average Mass

252.30620

Monoisotopic Mass

252.13616

InChI

InChI=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

InChIKey

LXBFWPWKVZPNRA-NPZYAQMBSA-N

SMILES

[H][C@@]12CC(=O)O[C@@H](C)CCC\C=C\[C@]([H])(O1)C=C[C@@H]2O

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.

ChEBI Ontology
Outgoing	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 C	ChEBI

Registry Number	Type	Source
15805982	Reaxys Registry Number	Reaxys

Last Modified

27 October 2016