EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:2439 - acroptilin

ChEBI IDCHEBI:2439
ChEBI Nameacroptilin
Stars
DefinitionA sesquiterpene lactone that is isolated from Acroptilon repens and displays anti-allergic properties.
Last Modified30 January 2015
DownloadsMolfile
FormulaC19H23ClO7
Net Charge0
Average Mass398.839
Monoisotopic Mass398.11323
SMILES[H][C@]12OC(=O)C(=C)[C@]1([H])[C@@H](OC(=O)[C@](C)(O)CCl)CC(=C)[C@]1([H])C[C@H](O)[C@@]3(CO3)[C@]21[H]
InChIInChI=1S/C19H23ClO7/c1-8-4-11(26-17(23)18(3,24)6-20)13-9(2)16(22)27-15(13)14-10(8)5-12(21)19(14)7-25-19/h10-15,21,24H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18+,19-/m0/s1
InChIKeyRFRUYYQMUJRBAN-LKUPFZQBSA-N
Species of MetaboliteComponentSourceComments
Centaurea (ncbitaxon:41503) - Article (Chemistry of Natural Compounds, 1973, Volume 9, pp 156-161)
Acroptilon (ncbitaxon:41465) leaf (BTO:0000713) Article (Chemistry of Natural Compounds, 1973, Volume 9, pp 156-161)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
anti-allergic agent  A drug used to treat allergic reactions.
ChEBI Ontology
Outgoing Relation(s)
acroptilin (CHEBI:2439) has role anti-allergic agent (CHEBI:50857)
acroptilin (CHEBI:2439) has role plant metabolite (CHEBI:76924)
acroptilin (CHEBI:2439) is a azulenofuran (CHEBI:39433)
acroptilin (CHEBI:2439) is a epoxide (CHEBI:32955)
acroptilin (CHEBI:2439) is a olefinic compound (CHEBI:78840)
acroptilin (CHEBI:2439) is a organic heterotetracyclic compound (CHEBI:38163)
acroptilin (CHEBI:2439) is a organochlorine compound (CHEBI:36683)
acroptilin (CHEBI:2439) is a secondary alcohol (CHEBI:35681)
acroptilin (CHEBI:2439) is a sesquiterpene lactone (CHEBI:37667)
acroptilin (CHEBI:2439) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(3aR,4S,6aR,8S,9S,9aS,9bS)-8-hydroxy-3,6-bis(methylidene)-2-oxodecahydro-2H-spiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl (2S)-3-chloro-2-hydroxy-2-methylpropanoate
Synonyms  Source
AcroptilinKEGG COMPOUND
Chlorohyssopifolin CKEGG COMPOUND
Manual XrefsDatabases
C09288KEGG COMPOUND
C00003206KNApSAcK
Registry NumbersSources
CAS:41787-75-1KEGG COMPOUND
CAS:41787-75-1ChemIDplus