CHEBI:145055 - betaenone A

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ChEBI Name betaenone A
ChEBI ID CHEBI:145055
Definition A carbotricyclic compound that is tricyclo[6.2.2.02,7]dodecan-9-one which is substituted by hydroxy groups at positions 1, 4, and 11; by methyl groups at positions 4, 6, 8, and 11; by a hydroxymethylene group at position 10; and by a (2R)-butan-2-yl group at position 12 (the 1S,2S,4R,6R,7S,8R,10Z,11S,12R stereoisomer). A phytotoxin produced by Pleospora betae, the causal fungus of leaf spot disease on sugar beet.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
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Formula C21H34O5
Net Charge 0
Average Mass 366.498
Monoisotopic Mass 366.24062
InChI InChI=1S/C21H34O5/c1-7-11(2)16-19(5)15-12(3)8-18(4,24)9-13(15)21(26,20(16,6)25)14(10-22)17(19)23/h10-13,15-16,22,24-26H,7-9H2,1-6H3/b14-10+/t11-,12-,13+,15+,16-,18-,19-,20+,21+/m1/s1
InChIKey FHJXKTOXQHRDTL-PSWVRJCXSA-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)C)[H])(C)O)=C\O)=O)C
Roles Classification
Biological Role(s): 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.
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ChEBI Ontology
Outgoing betaenone A (CHEBI:145055) has role fungal metabolite (CHEBI:76946)
betaenone A (CHEBI:145055) has role phytotoxin (CHEBI:38231)
betaenone A (CHEBI:145055) is a 3-oxo aldehyde (CHEBI:145078)
betaenone A (CHEBI:145055) is a bridged compound (CHEBI:35990)
betaenone A (CHEBI:145055) is a carbotricyclic compound (CHEBI:38032)
betaenone A (CHEBI:145055) is a tertiary alcohol (CHEBI:26878)
Incoming stemphyloxin II (CHEBI:145066) has functional parent betaenone A (CHEBI:145055)
IUPAC Name
(1S,2S,4R,6R,7S,8R,10Z,11S,12R)-12-[(2R)-butan-2-yl]-1,4,11-trihydroxy-10-(hydroxymethylene)-4,6,8,11-tetramethyltricyclo[6.2.2.02,7]dodecan-9-one
Synonym Source
betaenone A UniProt
Manual Xref Database
Betaenone_A Wikipedia
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Registry Number Type Source
85269-22-3 CAS Registry Number Wikipedia
Citations Waiting for Citations Types Sources
25530455 PubMed citation SUBMITTER
31553484 PubMed citation SUBMITTER
Last Modified
11 October 2019
General Comment
2019-10-10 For the crystal structure of this compound, see PMID:31553484 (p. S5) reports.