EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:142135 - equisetin

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member of the class of tetramic acids that is trichosetin in which the hydrogen attached to the lactam nitrogen has been replaced by a methyl group.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:
quorum sensing inhibitor  Any compound that interferes with bacterial communication (quorum sensing, QS).
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.
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.
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