CHEBI:142133 - trichosetin

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ChEBI Name trichosetin ChEBI ID CHEBI:142133 Definition A member of the class of octahydronaphthalenes that is (2R,4aS,5R,6R,8aS)-2,5-dimethyl-6-[(1E)-prop-1-en-1-yl]-1,2,3,4,4a,5,6,8a-octahydronaphthalene in which the hydrogen at position 5 has been replaced by a (Z)-hydroxy[(5S)-5-(hydroxymethyl)-2,4-dioxopyrrolidin-3-ylidene]methyl group. Produced by the dual culture of Trichoderma harzianum and Catharanthus roseus callus, it exhibits significant antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus and Bacillus subtilis. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C21H29NO4 Net Charge 0 Average Mass 359.460 Monoisotopic Mass 359.20966 InChI InChI=1S/C21H29NO4/c1-4-5-14-8-7-13-10-12(2)6-9-15(13)21(14,3)19(25)17-18(24)16(11-23)22-20(17)26/h4-5,7-8,12-16,23,25H,6,9-11H2,1-3H3,(H,22,26)/b5-4+,19-17-/t12-,13-,14-,15-,16+,21-/m1/s1 InChIKey TYCWBBBQIATAJE-GEZPOGBYSA-N SMILES C1C[C@H](C[C@@]2([C@@]1([C@@]([C@@](C=C2)(/C=C/C)[H])(\C(\O)=C/3\C(N[C@H](C3=O)CO)=O)C)[H])[H])C Roles Classification Biological Role(s): phytotoxin Any toxin produced by a plant. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. View more via ChEBI Ontology ChEBI Ontology Outgoing trichosetin (CHEBI:142133) has role antibacterial agent (CHEBI:33282) trichosetin (CHEBI:142133) has role phytotoxin (CHEBI:38231) trichosetin (CHEBI:142133) is a enol (CHEBI:33823) trichosetin (CHEBI:142133) is a octahydronaphthalenes (CHEBI:138397) trichosetin (CHEBI:142133) is a primary alcohol (CHEBI:15734) trichosetin (CHEBI:142133) is a tetramic acids (CHEBI:140155) trichosetin (CHEBI:142133) is conjugate acid of trichosetin(1−) (CHEBI:142061) Incoming equisetin (CHEBI:142135) has functional parent trichosetin (CHEBI:142133) trichosetin(1−) (CHEBI:142061) is conjugate base of trichosetin (CHEBI:142133) IUPAC Name (3Z,5S)-3-[{(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}(hydroxy)methylidene]-5-(hydroxymethyl)pyrrolidine-2,4-dione Synonym Source N-desmethylequisetin ChEBI Manual Xref Database CPD-17993 MetaCyc View more database links Registry Number Type Source 25498311 Reaxys Registry Number Reaxys Citations Types Sources 12132686 PubMed citation Europe PMC 12620323 PubMed citation Europe PMC 15724180 PubMed citation Europe PMC 28379186 PubMed citation Europe PMC Last Modified 07 September 2018