CHEBI:65435 - arisugacin A

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ChEBI Name arisugacin A
ChEBI ID CHEBI:65435
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 3,4-dimethoxyphenyl 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 C28H32O8
Net Charge 0
Average Mass 496.54890
Monoisotopic Mass 496.20972
InChI InChI=1S/C28H32O8/c1-24(2)10-9-22(29)26(4)27(24,31)12-11-25(3)28(26,32)15-17-20(36-25)14-19(35-23(17)30)16-7-8-18(33-5)21(13-16)34-6/h7-10,13-14,31-32H,11-12,15H2,1-6H3/t25-,26+,27-,28-/m1/s1
InChIKey MIHBCQWIBJDVPX-JUDWXZBOSA-N
SMILES COc1ccc(cc1OC)-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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 A (CHEBI:65435) has role Penicillium metabolite (CHEBI:76964)
arisugacin A (CHEBI:65435) has role antimicrobial agent (CHEBI:33281)
arisugacin A (CHEBI:65435) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
arisugacin A (CHEBI:65435) has role metabolite (CHEBI:25212)
arisugacin A (CHEBI:65435) is a δ-lactone (CHEBI:18946)
arisugacin A (CHEBI:65435) is a aromatic ether (CHEBI:35618)
arisugacin A (CHEBI:65435) is a enone (CHEBI:51689)
arisugacin A (CHEBI:65435) is a organic heterotetracyclic compound (CHEBI:38163)
arisugacin A (CHEBI:65435) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(4aR,6aR,12aS,12bS)-9-(3,4-dimethoxyphenyl)-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
Registry Number Type Source
7450892 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
7649881 PubMed citation Europe PMC
Last Modified
06 November 2013