CHEBI:65443 - AS-186a

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ChEBI Name AS-186a
ChEBI ID CHEBI:65443
Definition A dibenzodioxocine that is 5H,7H-dibenzo[b,g][1,5]dioxocin-5-one substituted by a hydroxy group at position 11, a (1S)-1-hydroxy-3-methylbutyl group at position 3 and a methoxy and a methyl group at positions 4 and 9 respectively. It is isolated from the culture broth of Penicillium asperosporum and acts as an acyl-CoA:cholesterol acyltransferase inhibitor.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H24O6
Net Charge 0
Average Mass 372.41170
Monoisotopic Mass 372.15729
InChI InChI=1S/C21H24O6/c1-11(2)7-15(22)14-5-6-17-18(20(14)25-4)21(24)26-10-13-8-12(3)9-16(23)19(13)27-17/h5-6,8-9,11,15,22-23H,7,10H2,1-4H3/t15-/m0/s1
InChIKey UOWGLBYIKHMCIS-HNNXBMFYSA-N
SMILES COc1c(ccc2Oc3c(O)cc(C)cc3COC(=O)c12)[C@@H](O)CC(C)C
Metabolite of Species Details
Penicillium asperosporum (NCBI:txid70097) of strain KY 1635 See: DOI
Roles Classification
Biological Role(s): Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
EC 2.3.1.26 (sterol O-acyltransferase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of acyl-CoA:cholesterol acyltransferase (EC 2.3.1.26).
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing AS-186a (CHEBI:65443) has role Penicillium metabolite (CHEBI:76964)
AS-186a (CHEBI:65443) has role antimicrobial agent (CHEBI:33281)
AS-186a (CHEBI:65443) has role EC 2.3.1.26 (sterol O-acyltransferase) inhibitor (CHEBI:64696)
AS-186a (CHEBI:65443) is a aromatic ether (CHEBI:35618)
AS-186a (CHEBI:65443) is a dibenzodioxocine (CHEBI:71064)
AS-186a (CHEBI:65443) is a lactone (CHEBI:25000)
AS-186a (CHEBI:65443) is a phenols (CHEBI:33853)
AS-186a (CHEBI:65443) is a secondary alcohol (CHEBI:35681)
Incoming AS-186b (CHEBI:65444) has functional parent AS-186a (CHEBI:65443)
IUPAC Name
11-hydroxy-3-[(1S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one
Synonyms Sources
penicillide ChEBI
vermixocin A ChEBI
Registry Number Type Source
4767683 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
8119857 PubMed citation Europe PMC
Last Modified
13 January 2014
General Comment
2012-11-15 The absolute configuration of penicillide is based on the structural revision; Phytochemistry, Volume 30, Issue 6, 1991, Pages 2096-2098.