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stemphyloxin I |
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CHEBI:145070 |
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An 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. |
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This entity has been manually annotated by the ChEBI Team.
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Kristian Axelsen
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Molfile
XML
SDF
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InChI=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 |
YRECHDUAXCBBOZ-HOCCXODSSA-N |
[C@]1([C@H]([C@](C([C@@]2([C@@]1([C@@H](C[C@](C2)(O)C)C)[H])[H])=O)(C)O)[C@@H](CC)CO)(C(=O)/C=C\O)C |
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Stemphylium botryosum
(NCBI:txid120510)
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See:
PubMed
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iron chelator
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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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View more via ChEBI Ontology
(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
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deacyl-FR 225654
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ChemIDplus
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stemphyloxin I
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UniProt
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81210-11-9
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CAS Registry Number
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ChemIDplus
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16662165
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PubMed citation
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Europe PMC
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17754554
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PubMed citation
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Europe PMC
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31553484
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PubMed citation
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SUBMITTER
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