CHEBI:145070 - stemphyloxin I

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ChEBI Name stemphyloxin I
ChEBI ID CHEBI:145070
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
Download Molfile XML SDF
Formula C21H34O6
Net Charge 0
Average Mass 382.497
Monoisotopic Mass 382.23554
InChI 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
InChIKey YRECHDUAXCBBOZ-HOCCXODSSA-N
SMILES [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
Metabolite of Species Details
Stemphylium botryosum (NCBI:txid120510) See: PubMed
Roles Classification
Chemical Role(s): iron chelator

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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 α-hydroxy ketone (CHEBI:139588)
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)
Incoming 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
Synonyms Sources
deacyl-FR 225654 ChemIDplus
stemphyloxin I UniProt
Manual Xref Database
C00000534 KNApSAcK
View more database links
Registry Number Type Source
81210-11-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16662165 PubMed citation Europe PMC
17754554 PubMed citation Europe PMC
31553484 PubMed citation SUBMITTER
Last Modified
22 August 2023