CHEBI:65436 - arisugacin B

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ChEBI Name arisugacin B
ChEBI ID CHEBI:65436
Definition An organic heterotetracyclic compound that is 4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-benzo[f]pyrano[4,3-b]chromene-1,11(5H)-dione substituted by a 4-methoxyphenyl group at position 9 (the 4aR,6aR,12aS,12bS steroisomer). 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 C27H30O7
Net Charge 0
Average Mass 466.52290
Monoisotopic Mass 466.19915
InChI InChI=1S/C27H30O7/c1-23(2)11-10-21(28)25(4)26(23,30)13-12-24(3)27(25,31)15-18-20(34-24)14-19(33-22(18)29)16-6-8-17(32-5)9-7-16/h6-11,14,30-31H,12-13,15H2,1-5H3/t24-,25+,26-,27-/m1/s1
InChIKey FNHNBWWIASUEQH-HVWQDESWSA-N
SMILES COc1ccc(cc1)-c1cc2O[C@]3(C)CC[C@@]4(O)C(C)(C)C=CC(=O)[C@]4(C)[C@@]3(O)Cc2c(=O)o1
Metabolite of Species Details
Penicillium (NCBI:txid5073) of strain FO 4259 See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing arisugacin B (CHEBI:65436) has role Penicillium metabolite (CHEBI:76964)
arisugacin B (CHEBI:65436) has role antimicrobial agent (CHEBI:33281)
arisugacin B (CHEBI:65436) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
arisugacin B (CHEBI:65436) is a δ-lactone (CHEBI:18946)
arisugacin B (CHEBI:65436) is a aromatic ether (CHEBI:35618)
arisugacin B (CHEBI:65436) is a enone (CHEBI:51689)
arisugacin B (CHEBI:65436) is a organic heterotetracyclic compound (CHEBI:38163)
arisugacin B (CHEBI:65436) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(4aR,6aR,12aS,12bS)-4a,12a-dihydroxy-9-(4-methoxyphenyl)-4,4,6a,12b-tetramethyl-4a,6,6a,12,12a,12b-hexahydro-4H,11H-benzo[f]pyrano[4,3-b]chromene-1,11(5H)-dione
Registry Number Type Source
7629746 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
7649881 PubMed citation Europe PMC
Last Modified
13 January 2014