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CHEBI:65443 - AS-186a

ChEBI IDCHEBI:65443
ChEBI NameAS-186a
Stars
DefinitionA 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.
Last Modified13 January 2014
DownloadsMolfile
FormulaC21H24O6
Net Charge0
Average Mass372.417
Monoisotopic Mass372.15729
SMILESCOc1c([C@@H](O)CC(C)C)ccc2c1C(=O)OCc1cc(C)cc(O)c1O2
InChIInChI=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
InChIKeyUOWGLBYIKHMCIS-HNNXBMFYSA-N
Species of MetaboliteComponentSourceComments
Penicillium asperosporum (ncbitaxon:70097) - DOI (10.1016/S0040-4039(01)92051-9) Strain: KY 1635
Roles Classification
Biological Roles:
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).
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
penicillideChEBI
vermixocin AChEBI
Registry NumbersSources
Reaxys:4767683Reaxys
Citations