CHEBI:65437 - arisugacin C

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ChEBI Name arisugacin C
ChEBI ID CHEBI:65437
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H32O6
Net Charge 0
Average Mass 452.53940
Monoisotopic Mass 452.21989
InChI InChI=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
InChIKey XKDGQMPLQPRTCS-HHPVDLARSA-N
SMILES [H][C@]12Cc3c(O[C@]1(C)CC[C@@]1(O)C(C)(C)C(=O)CC[C@]21C)cc(oc3=O)-c1ccc(OC)cc1
Metabolite of Species Details
Penicillium (NCBI:txid5073) UV irradiation induced mutant of Penicillium FO4259 of strain FO 4259-11 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 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
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)
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 Number Type Source
8521391 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10724008 PubMed citation Europe PMC
Last Modified
13 January 2014