EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:65435 - arisugacin A

Default Structure
ChEBI IDCHEBI:65435
ChEBI Namearisugacin A
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 3,4-dimethoxyphenyl 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 Modified6 November 2013
DownloadsMolfile
FormulaC28H32O8
Net Charge0
Average Mass496.556
Monoisotopic Mass496.20972
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)cc1OC
InChIInChI=1S/C28H32O8/c1-24(2)10-9-22(29)26(4)27(24,31)12-11-25(3)28(26,32)15-17-20(36-25)14-19(35-23(17)30)16-7-8-18(33-5)21(13-16)34-6/h7-10,13-14,31-32H,11-12,15H2,1-6H3/t25-,26+,27-,28-/m1/s1
InChIKeyMIHBCQWIBJDVPX-JUDWXZBOSA-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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 A (CHEBI:65435) has role Penicillium metabolite (CHEBI:76964)
arisugacin A (CHEBI:65435) has role antimicrobial agent (CHEBI:33281)
arisugacin A (CHEBI:65435) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
arisugacin A (CHEBI:65435) has role metabolite (CHEBI:25212)
arisugacin A (CHEBI:65435) is a aromatic ether (CHEBI:35618)
arisugacin A (CHEBI:65435) is a enone (CHEBI:51689)
arisugacin A (CHEBI:65435) is a organic heterotetracyclic compound (CHEBI:38163)
arisugacin A (CHEBI:65435) is a tertiary alcohol (CHEBI:26878)
arisugacin A (CHEBI:65435) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4aR,6aR,12aS,12bS)-9-(3,4-dimethoxyphenyl)-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
Registry NumbersSources
Reaxys:7450892Reaxys
Citations