EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:65438 - arisugacin D

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:
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 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