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CHEBI:65436 - arisugacin B

Default Structure
ChEBI IDCHEBI:65436
ChEBI Namearisugacin B
Stars
DefinitionAn 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.
Last Modified13 January 2014
DownloadsMolfile
FormulaC27H30O7
Net Charge0
Average Mass466.530
Monoisotopic Mass466.19915
SMILESCOc1ccc(-c2cc3c(c(=O)o2)C[C@]2(O)[C@@]4(C)C(=O)C=CC(C)(C)[C@]4(O)CC[C@@]2(C)O3)cc1
InChIInChI=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
InChIKeyFNHNBWWIASUEQH-HVWQDESWSA-N
Species of MetaboliteComponentSourceComments
Penicillium (ncbitaxon:5073) - PubMed (7649881) Strain: FO 4259
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 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 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)
arisugacin B (CHEBI:65436) is a δ-lactone (CHEBI:18946)
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 NumbersSources
Reaxys:7629746Reaxys
Citations