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CHEBI:195288 - xyloketal A

ChEBI IDCHEBI:195288
ChEBI Namexyloketal A
Stars
DefinitionA xyloketal with formula C27H36O6. It was initially isolated from the mangrove fungus Xylaria sp. from the South China sea coast.
Last Modified8 June 2023
SubmitterAdnan
DownloadsMolfile
FormulaC27H36O6
Net Charge0
Average Mass456.579
Monoisotopic Mass456.25119
SMILES[H][C@]12Cc3c(c4c(c5c3O[C@@]3(C)OC[C@H](C)[C@@]3([H])C5)O[C@@]3(C)OC[C@H](C)[C@@]3([H])C4)O[C@@]1(C)OC[C@@H]2C
InChIInChI=1S/C27H36O6/c1-13-10-28-25(4)19(13)7-16-22(31-25)17-8-20-14(2)12-30-27(20,6)33-24(17)18-9-21-15(3)11-29-26(21,5)32-23(16)18/h13-15,19-21H,7-12H2,1-6H3/t13-,14-,15-,19+,20+,21+,25+,26+,27+/m0/s1
InChIKeyHFZTVRRNBDAJIS-PERNPGNGSA-N
Species of MetaboliteComponentSourceComments
Xylaria sp. 2508 (ncbitaxon:598750) - PubMed (11559170)
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.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
ChEBI Ontology
Outgoing Relation(s)
xyloketal A (CHEBI:195288) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
xyloketal A (CHEBI:195288) is a organic heteroheptacyclic compound (CHEBI:52157)
xyloketal A (CHEBI:195288) is a xyloketal (CHEBI:195287)
IUPAC Name 
(3R,3aR,5aR,8R,8aR,10aR,13R,13aR,15aR)-3,5a,8,10a,13,15a-hexamethyl-2,3,3a,7,8,8a,9,12,13,13a,14,15a-dodecahydro-4H,5aH,10aH-furo[2,3-b]bisfuro[3',2':5,6]pyrano[2,3-f:2',3'-h]chromene
Synonyms  Source
(3R,3aR,5aR,8R,8aR,10aR,13R,13aR,15aR)-3,5a,8,10a,13,15a-hexamethyl-2,3,3a,7,8,8a,9,12,13,13a,14,15a-dodecahydro-4H,5aH,10aH-trifuro[3,2-e:3,2-e':3,2-e'']benzo[1,6-b:3,2-b':5,4-b'']tripyranIUPAC
(−)-xyloketal AChEBI
Citations