CHEBI:65445 - AS-186c

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ChEBI Name AS-186c
ChEBI ID CHEBI:65445
Definition A dibenzodioxonine isolated from the culture broth of Penicillium asperosporum that acts as an acyl-CoA:cholesterol acyltransferase inhibitor.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB21387988, ZINC000006090922
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Formula C43H46O12
Net Charge 0
Average Mass 754.81810
Monoisotopic Mass 754.29893
InChI InChI=1S/C43H46O12/c1-20(2)9-10-25-11-13-29(45)35(37(25)48)39(50)34-27(16-22(5)18-30(34)46)42-38(49)28-17-23(6)19-31(47)40(28)54-32-14-12-26(33(15-21(3)4)53-24(7)44)41(52-8)36(32)43(51)55-42/h9,11-14,16-19,21,33,38,42,45-49H,10,15H2,1-8H3
InChIKey MQLUFEFCCDNPMA-UHFFFAOYSA-N
SMILES COc1c(ccc2Oc3c(O)cc(C)cc3C(O)C(OC(=O)c12)c1cc(C)cc(O)c1C(=O)c1c(O)ccc(CC=C(C)C)c1O)C(CC(C)C)OC(C)=O
Metabolite of Species Details
Penicillium asperosporum (NCBI:txid70097) of strain KY 1635 See: PubMed
Roles Classification
Biological Role(s): Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing AS-186c (CHEBI:65445) has role Penicillium metabolite (CHEBI:76964)
AS-186c (CHEBI:65445) has role antimicrobial agent (CHEBI:33281)
AS-186c (CHEBI:65445) has role EC 2.3.1.26 (sterol O-acyltransferase) inhibitor (CHEBI:64696)
AS-186c (CHEBI:65445) is a acetate ester (CHEBI:47622)
AS-186c (CHEBI:65445) is a aromatic ether (CHEBI:35618)
AS-186c (CHEBI:65445) is a benzophenones (CHEBI:22726)
AS-186c (CHEBI:65445) is a dibenzodioxonine (CHEBI:71155)
AS-186c (CHEBI:65445) is a lactone (CHEBI:25000)
AS-186c (CHEBI:65445) is a polyphenol (CHEBI:26195)
IUPAC Name
1-(7-{2-[2,6-dihydroxy-3-(3-methylbut-2-en-1-yl)benzoyl]-3-hydroxy-5-methylphenyl}-8,12-dihydroxy-4-methoxy-10-methyl-5-oxo-7,8-dihydro-5H-dibenzo[b,h][1,5]dioxonin-3-yl)-3-methylbutyl acetate
Registry Number Type Source
6839532 Reaxys Registry Number Reaxys
Citation Type Source
8119857 PubMed citation Europe PMC
Last Modified
13 January 2014
General Comment
2012-11-15 The exact stereochemistry of AS-186c is unknown.