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CHEBI:182764 - anisatin

ChEBI IDCHEBI:182764
ChEBI Nameanisatin
Stars
DefinitionA sesquiterpene lactone with formula C15H20O8. It is a neurotoxic natural product found in plants of the family Illiciaceae.
Secondary ChEBI IDCHEBI:2733
Last Modified1 September 2023
SubmitterMetaboLights
DownloadsMolfile
FormulaC15H20O8
Net Charge0
Average Mass328.317
Monoisotopic Mass328.11582
SMILESC[C@@H]1C[C@@H](O)[C@@]2(O)[C@@]13C[C@@H](OC(=O)[C@@H]3O)[C@](C)(O)[C@@]21COC1=O
InChIInChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8-,9+,12+,13+,14+,15-/m1/s1
InChIKeyGEVWHIDSUOMVRI-QWNPAUMXSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Illicium anisatum (ncbitaxon:12479) seed (BTO:0001226) PubMed (6974321)
Illicium fargesii (ncbitaxon:124774) pericarp (BTO:0001017) PubMed (18670129)
Illicium oligandrum (ncbitaxon:145286) pericarp (BTO:0001017) PubMed (19159273)
Illicium religiosum (IPNI:554536-1) seed (BTO:0001226) DOI (10.1016/S0040-4039(01)89037-7)
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
GABA antagonist  A compound that inhibits the action of γ-aminobutyric acid.
neurotoxin  A poison that interferes with the functions of the nervous system.
Applications:
phytogenic insecticide  An insecticide compound naturally occurring in plants.
GABA antagonist  A compound that inhibits the action of γ-aminobutyric acid.
ChEBI Ontology
Outgoing Relation(s)
anisatin (CHEBI:182764) has role GABA antagonist (CHEBI:65259)
anisatin (CHEBI:182764) has role neurotoxin (CHEBI:50910)
anisatin (CHEBI:182764) has role phytogenic insecticide (CHEBI:22917)
anisatin (CHEBI:182764) has role plant metabolite (CHEBI:76924)
anisatin (CHEBI:182764) is a bridged compound (CHEBI:35990)
anisatin (CHEBI:182764) is a organic heterotetracyclic compound (CHEBI:38163)
anisatin (CHEBI:182764) is a secondary alcohol (CHEBI:35681)
anisatin (CHEBI:182764) is a sesquiterpene lactone (CHEBI:37667)
anisatin (CHEBI:182764) is a spiro compound (CHEBI:33599)
anisatin (CHEBI:182764) is a tertiary alcohol (CHEBI:26878)
anisatin (CHEBI:182764) is a tetrol (CHEBI:33573)
IUPAC Name 
(1R,3'S,4R,5R,6aR,7R,9R,9aS)-1,5,6a,7-tetrahydroxy-5,9-dimethylhexahydrospiro[4,9a-methanocyclopenta[d]oxocine-6,3'-oxetane]-2,2'(1H)-dione
Synonyms  Source
AnisatinKEGG COMPOUND
(−)-anisatinChEBI
(1R,3'S,4R,5R,6aR,7R,9R,9aS)-hexahydro-1,5,6a,7-tetrahydroxy-5,9-dimethylspiro[4H-4,9a-methanocyclopent[d]oxocin-6(2H),3'-oxetane]-2,2'-dioneChEBI
Manual XrefsDatabases
C09294KEGG COMPOUND
C00003212KNApSAcK
FDB005800FooDB
HMDB0302686HMDB
AnisatinWikipedia
Registry NumbersSources
CAS:5230-87-5KEGG COMPOUND
Citations