trichosetin (CHEBI:142133)

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CHEBI:142133 - trichosetin

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ChEBI ID	CHEBI:142133
ChEBI Name	trichosetin
Stars
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in which the hydrogen at position 5 has been replaced by a (Z)-hydroxy[(5S)-5-(hydroxymethyl)-2,4-dioxopyrrolidin-3-ylidene]methyl group.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.
Last Modified	7 September 2018
Submitter	Gareth Owen
Downloads	Molfile

Formula	C21H29NO4
Net Charge	0
Average Mass	359.466
Monoisotopic Mass	359.20966
SMILES	[H][C@@]12CC[C@@H](C)C[C@@]1([H])C=C[C@@]([H])(/C=C/C)[C@@]2(C)/C(O)=C1/C(=O)N[C@@H](CO)C1=O
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

Roles Classification

Biological Roles:

phytotoxin Any toxin produced by a plant.

antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria.

ChEBI Ontology

Outgoing Relation(s)
	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 Relation(s)
	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 Xrefs	Databases
CPD-17993	MetaCyc

Registry Numbers	Sources
Reaxys:25498311	Reaxys

Citations