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CHEBI:65437 - arisugacin C

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:
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
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.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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