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CHEBI:145066 - stemphyloxin II

ChEBI IDCHEBI:145066
ChEBI Namestemphyloxin II
Stars
DefinitionA carbotricyclic compound that is betaenone A in which the butan-2-yl side-chain has been hydroxylated at position 1. A phytotoxin isolated from the endophytic fungus Stemphylium botryosum, it shows high affinity for ferric (but not ferrous) ions.
Last Modified27 January 2020
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC21H34O6
Net Charge0
Average Mass382.497
Monoisotopic Mass382.23554
SMILES[H][C@]12C[C@](C)(O)C[C@@]([H])(C)[C@]1([H])[C@@]1(C)C(=O)/C(=C\O)[C@]2(O)[C@@](C)(O)[C@]1([H])[C@@H](CC)CO
InChIInChI=1S/C21H34O6/c1-6-12(9-22)16-19(4)15-11(2)7-18(3,25)8-13(15)21(27,20(16,5)26)14(10-23)17(19)24/h10-13,15-16,22-23,25-27H,6-9H2,1-5H3/b14-10+/t11-,12+,13+,15+,16-,18-,19-,20+,21+/m1/s1
InChIKeyJTFGPTHCAAUOQL-RNPLJHCFSA-N
Roles Classification
Chemical Role:
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
phytotoxin  Any toxin produced by a plant.
ChEBI Ontology
Outgoing Relation(s)
stemphyloxin II (CHEBI:145066) has functional parent betaenone A (CHEBI:145055)
stemphyloxin II (CHEBI:145066) has role fungal metabolite (CHEBI:76946)
stemphyloxin II (CHEBI:145066) has role iron chelator (CHEBI:38157)
stemphyloxin II (CHEBI:145066) has role phytotoxin (CHEBI:38231)
stemphyloxin II (CHEBI:145066) is a 3-oxo aldehyde (CHEBI:145078)
stemphyloxin II (CHEBI:145066) is a bridged compound (CHEBI:35990)
stemphyloxin II (CHEBI:145066) is a carbotricyclic compound (CHEBI:38032)
stemphyloxin II (CHEBI:145066) is a primary alcohol (CHEBI:15734)
stemphyloxin II (CHEBI:145066) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(1S,2S,4R,6R,7S,8R,10Z,11S,12R)-1,4,11-trihydroxy-12-[(2R)-1-hydroxybutan-2-yl]-10-(hydroxymethylene)-4,6,8,11-tetramethyltricyclo[6.2.2.02,7]dodecan-9-one
Synonym  Source
(1R,3Z,4S,4aS,6R,8R,8aS,9S,10R)-4,6,9-trihydroxy-10-[(2R)-1-hydroxybutan-2-yl]-3-(hydroxymethylidene)-1,6,8,9-tetramethyloctahydro-1,4-ethanonaphthalen-2(1H)-oneIUPAC
UniProt Name  Source
stemphyloxin IIUniProt
Citations