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CHEBI:65437 - arisugacin C

Default Structure
ChEBI IDCHEBI:65437
ChEBI Namearisugacin C
Stars
DefinitionAn organic heterotetracyclic compound that is 4,4,6a,12b-tetramethyl-1,4a,5,6,6a,12,12a,12b-octahydro-2H,11H-benzo[f]pyrano[4,3-b]chromene-3,11(4H)-dione substituted at position 4a by a hydroxy and and at position 9 by 4-methoxyphenyl group (the 4aS,6aR,12aR,12bR stereoisomer). Isolated from the culture broth of Penicillium, it acts as a selective inhibitor of acetylcholinesterase.
Last Modified13 January 2014
DownloadsMolfile
FormulaC27H32O6
Net Charge0
Average Mass452.547
Monoisotopic Mass452.21989
SMILES[H][C@]12Cc3c(cc(-c4ccc(OC)cc4)oc3=O)O[C@]1(C)CC[C@@]1(O)C(C)(C)C(=O)CC[C@]21C
InChIInChI=1S/C27H32O6/c1-24(2)22(28)10-11-25(3)21-14-18-20(33-26(21,4)12-13-27(24,25)30)15-19(32-23(18)29)16-6-8-17(31-5)9-7-16/h6-9,15,21,30H,10-14H2,1-5H3/t21-,25-,26-,27-/m1/s1
InChIKeyXKDGQMPLQPRTCS-HHPVDLARSA-N
Species of MetaboliteComponentSourceComments
Penicillium (ncbitaxon:5073) - PubMed (10724008) UV irradiation induced mutant of Penicillium FO4259 Strain: FO 4259-11
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
EC 3.1.1.7 (acetylcholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
ChEBI Ontology
Outgoing Relation(s)
arisugacin C (CHEBI:65437) has role Penicillium metabolite (CHEBI:76964)
arisugacin C (CHEBI:65437) has role antimicrobial agent (CHEBI:33281)
arisugacin C (CHEBI:65437) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
arisugacin C (CHEBI:65437) is a aromatic ether (CHEBI:35618)
arisugacin C (CHEBI:65437) is a cyclic ketone (CHEBI:3992)
arisugacin C (CHEBI:65437) is a organic heterotetracyclic compound (CHEBI:38163)
arisugacin C (CHEBI:65437) is a tertiary alcohol (CHEBI:26878)
arisugacin C (CHEBI:65437) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4aS,6aR,12aR,12bR)-4a-hydroxy-9-(4-methoxyphenyl)-4,4,6a,12b-tetramethyl-1,4a,5,6,6a,12,12a,12b-octahydro-2H,11H-benzo[f]pyrano[4,3-b]chromene-3,11(4H)-dione
Registry NumbersSources
Reaxys:8521391Reaxys
Citations