CHEBI:65438 - arisugacin D

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ChEBI Name arisugacin D
ChEBI ID CHEBI:65438
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H36O8
Net Charge 0
Average Mass 512.59130
Monoisotopic Mass 512.24102
InChI InChI=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
InChIKey LHKWCVMCNOROFZ-MCPFUKIPSA-N
SMILES COc1ccc(cc1)-c1cc2O[C@]3(C)CC[C@@]4(O)C(C)(C)[C@@H](CC[C@]4(C)[C@@]3(O)Cc2c(=O)o1)OC(C)=O
Metabolite of Species Details
Penicillium (NCBI:txid5073) UV irradiation induced mutant of Penicillium FO4259 of strain FO 4259-11 See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
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)
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 Number Type Source
8525638 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10724008 PubMed citation Europe PMC
Last Modified
13 January 2014