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CHEBI:145070 - stemphyloxin I

ChEBI IDCHEBI:145070
ChEBI Namestemphyloxin I
Stars
DefinitionAn octahydronaphthalene that is 2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one which is substituted by hydroxy groups at positions 2 and 7, a (2R)-1-hydroxybutan-2-yl group at position 3, and a (2Z)-3-hydroxyprop-2-enoyl group at position 4 (the 2S,3R,4R,4aS,5R,7R,8aS stereoisomer). Isolated from the endophytic fungus Stemphylium botryosum, it is the causal agent of leaf spot and foliage blight disease in tomatoes. Its phytotoxcity is at least 200 times greater than that of stemphyloxin II. It shows high affinity for Fe3+ (but not Fe2+) ions.
Last Modified22 August 2023
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC21H34O6
Net Charge0
Average Mass382.497
Monoisotopic Mass382.23554
SMILES[H][C@]12[C@H](C)C[C@@](C)(O)C[C@]1([H])C(=O)[C@@](C)(O)[C@H]([C@@H](CC)CO)[C@]2(C)C(=O)/C=C\O
InChIInChI=1S/C21H34O6/c1-6-13(11-23)17-20(4,15(24)7-8-22)16-12(2)9-19(3,26)10-14(16)18(25)21(17,5)27/h7-8,12-14,16-17,22-23,26-27H,6,9-11H2,1-5H3/b8-7-/t12-,13+,14+,16+,17-,19-,20-,21+/m1/s1
InChIKeyYRECHDUAXCBBOZ-HOCCXODSSA-N
Species of MetaboliteComponentSourceComments
Stemphylium botryosum (ncbitaxon:120510) - PubMed (16662165)
Roles Classification
Chemical Role:
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
stemphyloxin I (CHEBI:145070) has role fungal metabolite (CHEBI:76946)
stemphyloxin I (CHEBI:145070) has role iron chelator (CHEBI:38157)
stemphyloxin I (CHEBI:145070) has role phytotoxin (CHEBI:38231)
stemphyloxin I (CHEBI:145070) is a 3-oxo aldehyde (CHEBI:145078)
stemphyloxin I (CHEBI:145070) is a cyclic ketone (CHEBI:3992)
stemphyloxin I (CHEBI:145070) is a enol (CHEBI:33823)
stemphyloxin I (CHEBI:145070) is a octahydronaphthalenes (CHEBI:138397)
stemphyloxin I (CHEBI:145070) is a primary alcohol (CHEBI:15734)
stemphyloxin I (CHEBI:145070) is a tertiary alcohol (CHEBI:26878)
stemphyloxin I (CHEBI:145070) is a tetrol (CHEBI:33573)
stemphyloxin I (CHEBI:145070) is a α-hydroxy ketone (CHEBI:139588)
Incoming Relation(s)
dihydrostemphyloxin I (CHEBI:145071) has functional parent stemphyloxin I (CHEBI:145070)
IUPAC Name 
(2S,3R,4R,4aS,5R,7R,8aS)-2,7-dihydroxy-3-[(2R)-1-hydroxybutan-2-yl]-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one
Synonym  Source
deacyl-FR 225654ChemIDplus
UniProt Name  Source
stemphyloxin IUniProt
Manual XrefsDatabases
C00000534KNApSAcK
Registry NumbersSources
CAS:81210-11-9ChemIDplus
Citations