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CHEBI:65867 - espicufolin

ChEBI IDCHEBI:65867
ChEBI Nameespicufolin
Stars
DefinitionA naphthochromene that is 4H-naphtho[2,3-h]chromene which is substituted at position 2 by a (2R)-butan-2-yl group, at position 5 by a hydroxymethyl group, at position 11 by a hydroxy group, and at positions 4, 7, and 12 by oxogroups. An antibiotic isolated from Streptomyces sp. cu39, it exerts a potent protecting effect on neuronal cells through suppressing L-glutamate toxicity.
Last Modified5 June 2016
DownloadsMolfile
FormulaC22H18O6
Net Charge0
Average Mass378.380
Monoisotopic Mass378.11034
SMILESCC[C@@H](C)c1cc(=O)c2c(CO)cc3c(c2o1)C(=O)c1c(O)cccc1C3=O
InChIInChI=1S/C22H18O6/c1-3-10(2)16-8-15(25)17-11(9-23)7-13-19(22(17)28-16)21(27)18-12(20(13)26)5-4-6-14(18)24/h4-8,10,23-24H,3,9H2,1-2H3/t10-/m1/s1
InChIKeyHXAZTNIVBVVFJS-SNVBAGLBSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) - PubMed (8931733) Strain: cu39
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
espicufolin (CHEBI:65867) has role antimicrobial agent (CHEBI:33281)
espicufolin (CHEBI:65867) has role metabolite (CHEBI:25212)
espicufolin (CHEBI:65867) is a p-quinones (CHEBI:25830)
espicufolin (CHEBI:65867) is a benzyl alcohols (CHEBI:22743)
espicufolin (CHEBI:65867) is a naphthochromene (CHEBI:68504)
espicufolin (CHEBI:65867) is a phenols (CHEBI:33853)
IUPAC Name 
2-[(2R)-butan-2-yl]-11-hydroxy-5-(hydroxymethyl)-4H-naphtho[2,3-h]chromene-4,7,12-trione
Registry NumbersSources
Reaxys:8804787Reaxys
Citations