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CHEBI:3556 - cercosporin

Default Structure
ChEBI IDCHEBI:3556
ChEBI Namecercosporin
Stars
DefinitionAn organic heterohexacyclic compound that is perylo[1,12-def][1,3]dioxepine-6,11-dione substituted by hydroxy groups at positions 5 and 12, by methoxy groups at positions 7 and 10, and by 2-hydroxypropyl groups at positions 8 and 9 (the R,R-stereoisomer). It is a phytotoxin which was first isolated from the pathogenic soybean fungus, Cercospora kikuchii and later found in multiple members of the genus Cercospora.
Last Modified17 July 2020
DownloadsMolfile
FormulaC29H26O10
Net Charge0
Average Mass534.517
Monoisotopic Mass534.15260
SMILESCOc1c(C[C@@H](C)O)c2c3c(C[C@@H](C)O)c(OC)c(=O)c4c(O)cc5c(c6c(cc(O)c(c1=O)c62)OCO5)c43
InChIInChI=1S/C29H26O10/c1-10(30)5-12-18-19-13(6-11(2)31)29(37-4)27(35)21-15(33)8-17-23(25(19)21)22-16(38-9-39-17)7-14(32)20(24(18)22)26(34)28(12)36-3/h7-8,10-11,30-33H,5-6,9H2,1-4H3/t10-,11-/m1/s1
InChIKeyDGAZLNHJYDOWLG-GHMZBOCLSA-N
Species of MetaboliteComponentSourceComments
Cercospora (ncbitaxon:29002) - DOI (10.1016/0048-4059(78)90029-2)
Cercospora coffeicola (ncbitaxon:225974) - DOI (10.1111/jph.12802)
Cercospora kikuchii (ncbitaxon:84275) - DOI (10.1021/ja01578a038) Isolated from dried mycelia.
Pseudocercosporella capsellae (ncbitaxon:1873268) - PubMed (30686233)
Roles Classification
Chemical Role:
reactive oxygen species generator  Any entity used to generate reactive oxygen species.
Biological Roles:
phytotoxin  Any toxin produced by a plant.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application:
photosensitizing agent  A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
ChEBI Ontology
Outgoing Relation(s)
cercosporin (CHEBI:3556) has role fungal metabolite (CHEBI:76946)
cercosporin (CHEBI:3556) has role photosensitizing agent (CHEBI:47868)
cercosporin (CHEBI:3556) has role phytotoxin (CHEBI:38231)
cercosporin (CHEBI:3556) has role reactive oxygen species generator (CHEBI:70982)
cercosporin (CHEBI:3556) is a organic heterohexacyclic compound (CHEBI:51914)
cercosporin (CHEBI:3556) is a polyketide (CHEBI:26188)
cercosporin (CHEBI:3556) is a polyphenol (CHEBI:26195)
cercosporin (CHEBI:3556) is conjugate acid of cercosporin(2−) (CHEBI:146017)
Incoming Relation(s)
cercosporin(2−) (CHEBI:146017) is conjugate base of cercosporin (CHEBI:3556)
IUPAC Name 
5,12-dihydroxy-8,9-bis[(2R)-2-hydroxypropyl]-7,10-dimethoxyperylo[1,12-def][1,3]dioxepine-6,11-dione
Synonyms  Source
(+)-cercosporinChEBI
cercosporinKEGG COMPOUND
Manual XrefsDatabases
C00002801KNApSAcK
C10309KEGG COMPOUND
Registry NumbersSources
CAS:35082-49-6ChemIDplus
Citations