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CHEBI:65438 - arisugacin D

Default Structure
ChEBI IDCHEBI:65438
ChEBI Namearisugacin D
Stars
DefinitionAn organic heterotetracyclic compound that is 4,4,6a,12b-tetramethyl-11-oxo-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-3-yl acetate substituted by hydroxy groups at positions 4a and 12a and by a 4-methoxyphenyl group at position 9 (the 3R,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
FormulaC29H36O8
Net Charge0
Average Mass512.599
Monoisotopic Mass512.24102
SMILESCOc1ccc(-c2cc3c(c(=O)o2)C[C@]2(O)[C@@]4(C)CC[C@@H](OC(C)=O)C(C)(C)[C@]4(O)CC[C@@]2(C)O3)cc1
InChIInChI=1S/C29H36O8/c1-17(30)35-23-11-12-26(4)28(32,25(23,2)3)14-13-27(5)29(26,33)16-20-22(37-27)15-21(36-24(20)31)18-7-9-19(34-6)10-8-18/h7-10,15,23,32-33H,11-14,16H2,1-6H3/t23-,26+,27-,28-,29+/m1/s1
InChIKeyLHKWCVMCNOROFZ-MCPFUKIPSA-N
Species of MetaboliteComponentSourceComments
Penicillium (ncbitaxon:5073) - PubMed (10724008) UV irradiation induced mutant of Penicillium FO4259 Strain: FO 4259-11
Roles Classification
Biological Roles:
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.
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
ChEBI Ontology
Outgoing Relation(s)
arisugacin D (CHEBI:65438) has role Penicillium metabolite (CHEBI:76964)
arisugacin D (CHEBI:65438) has role antimicrobial agent (CHEBI:33281)
arisugacin D (CHEBI:65438) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
arisugacin D (CHEBI:65438) is a acetate ester (CHEBI:47622)
arisugacin D (CHEBI:65438) is a aromatic ether (CHEBI:35618)
arisugacin D (CHEBI:65438) is a cyclic ketone (CHEBI:3992)
arisugacin D (CHEBI:65438) is a organic heterotetracyclic compound (CHEBI:38163)
arisugacin D (CHEBI:65438) is a tertiary alcohol (CHEBI:26878)
arisugacin D (CHEBI:65438) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(3R,4aR,6aR,12aS,12bS)-4a,12a-dihydroxy-9-(4-methoxyphenyl)-4,4,6a,12b-tetramethyl-11-oxo-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-3-yl acetate
Registry NumbersSources
Reaxys:8525638Reaxys
Citations