CHEBI:3556 - cercosporin

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ChEBI Name cercosporin
ChEBI ID CHEBI:3556
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H26O10
Net Charge 0
Average Mass 534.517
Monoisotopic Mass 534.15260
InChI InChI=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
InChIKey DGAZLNHJYDOWLG-GHMZBOCLSA-N
SMILES C1=2C3=C4C5=C(C(=O)C(=C4C[C@@H](C)O)OC)C(O)=CC6=C5C1=C(C=C(C2C(=O)C(=C3C[C@@H](C)O)OC)O)OCO6
Metabolite of Species Details
Pseudocercosporella capsellae (NCBI:txid1873268) See: PubMed
Cercospora coffeicola (NCBI:txid225974) See: DOI
Cercospora (NCBI:txid29002) See: DOI
Cercospora kikuchii (NCBI:txid84275) Isolated from dried mycelia. See: DOI
Roles Classification
Chemical Role(s): reactive oxygen species generator
Any entity used to generate reactive oxygen species.
Biological Role(s): 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(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(+)-cercosporin ChEBI
cercosporin KEGG COMPOUND
Manual Xrefs Databases
C00002801 KNApSAcK
C10309 KEGG COMPOUND
View more database links
Registry Number Type Source
35082-49-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
17 July 2020