CHEBI:145066 - stemphyloxin II

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ChEBI Name stemphyloxin II
ChEBI ID CHEBI:145066
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information ChemicalBook:CB0308124, eMolecules:502935, Selleckchem:deferiprone, ZINC000000006226
Download Molfile XML SDF
Formula C21H34O6
Net Charge 0
Average Mass 382.497
Monoisotopic Mass 382.23554
InChI InChI=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
InChIKey JTFGPTHCAAUOQL-RNPLJHCFSA-N
SMILES [C@]12(C(/C(/[C@]([C@@]3([C@@]1([C@@](C[C@](C3)(O)C)(C)[H])[H])[H])(O)[C@@]([C@@]2([C@@H](CC)CO)[H])(C)O)=C\O)=O)C
Roles Classification
Chemical Role(s): iron chelator

Biological Role(s): phytotoxin
Any toxin produced by a plant.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
Synonyms Sources
(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)-one IUPAC
stemphyloxin II UniProt
Citation Type Source
31553484 PubMed citation SUBMITTER
Last Modified
27 January 2020