CHEBI:142135 - equisetin

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ChEBI Name equisetin
ChEBI ID CHEBI:142135
Definition A member of the class of tetramic acids that is trichosetin in which the hydrogen attached to the lactam nitrogen has been replaced by a methyl group. It is produced by the filamentous fungus Fusarium heterosporum.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H31NO4
Net Charge 0
Average Mass 373.487
Monoisotopic Mass 373.22531
InChI InChI=1S/C22H31NO4/c1-5-6-15-9-8-14-11-13(2)7-10-16(14)22(15,3)20(26)18-19(25)17(12-24)23(4)21(18)27/h5-6,8-9,13-17,24,26H,7,10-12H2,1-4H3/b6-5+,20-18-/t13-,14-,15-,16-,17+,22-/m1/s1
InChIKey QNQBPPQLRODXET-HMHJLHGTSA-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)C)=O)C)[H])[H])C
Metabolite of Species Details
Fusarium equiseti (NCBI:txid61235) See: PubMed
Roles Classification
Biological Role(s): antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
quorum sensing inhibitor
Any compound that interferes with bacterial communication (quorum sensing, QS).
HIV-1 integrase inhibitor
An inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing equisetin (CHEBI:142135) has functional parent trichosetin (CHEBI:142133)
equisetin (CHEBI:142135) has role antibacterial agent (CHEBI:33282)
equisetin (CHEBI:142135) has role fungal metabolite (CHEBI:76946)
equisetin (CHEBI:142135) has role HIV-1 integrase inhibitor (CHEBI:67268)
equisetin (CHEBI:142135) has role quorum sensing inhibitor (CHEBI:138977)
equisetin (CHEBI:142135) is a enol (CHEBI:33823)
equisetin (CHEBI:142135) is a octahydronaphthalenes (CHEBI:138397)
equisetin (CHEBI:142135) is a primary alcohol (CHEBI:15734)
equisetin (CHEBI:142135) is a tetramic acids (CHEBI:140155)
equisetin (CHEBI:142135) is conjugate acid of equisetin(1−) (CHEBI:142060)
Incoming equisetin(1−) (CHEBI:142060) is conjugate base of equisetin (CHEBI:142135)
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)-1-methylpyrrolidine-2,4-dione
Synonyms Sources
(−)-equisetin ChemIDplus
N-methyltrichosetin ChEBI
Manual Xrefs Databases
CPD-17992 MetaCyc
US3959468 Patent
View more database links
Registry Numbers Types Sources
5773365 Reaxys Registry Number Reaxys
57749-43-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11073657 PubMed citation Europe PMC
15632969 PubMed citation Europe PMC
15724180 PubMed citation Europe PMC
24038394 PubMed citation Europe PMC
2536535 PubMed citation Europe PMC
25770422 PubMed citation Europe PMC
26075378 PubMed citation Europe PMC
26431450 PubMed citation Europe PMC
28379186 PubMed citation Europe PMC
28401214 PubMed citation Europe PMC
29502217 PubMed citation Europe PMC
541270 PubMed citation Europe PMC
IND605932073 Agricola citation Europe PMC
Last Modified
07 September 2018