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CHEBI:65436 - arisugacin B

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:
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.
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
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