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CHEBI:142135 - equisetin

Default Structure
ChEBI IDCHEBI:142135
ChEBI Nameequisetin
Stars
DefinitionA member of the class of tetramic acids that is trichosetin in which the hydrogen attached to the lactam nitrogen has been replaced by a methyl group.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.
Last Modified7 September 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H31NO4
Net Charge0
Average Mass373.493
Monoisotopic Mass373.22531
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)[C@H](CO)N(C)C1=O
InChIInChI=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
InChIKeyQNQBPPQLRODXET-HMHJLHGTSA-N
Species of MetaboliteComponentSourceComments
Fusarium equiseti (ncbitaxon:61235) - PubMed (8132493)
Roles Classification
Biological Roles:
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.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
quorum sensing inhibitor  Any compound that interferes with bacterial communication (quorum sensing, QS).
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
N-methyltrichosetinChEBI
(−)-equisetinChemIDplus
Manual XrefsDatabases
CPD-17992MetaCyc
US3959468Patent
Registry NumbersSources
Reaxys:5773365Reaxys
CAS:57749-43-6ChemIDplus
Citations