CHEBI:3556 - cercosporin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name cercosporin
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
Download Molfile XML SDF
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
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)
Synonyms Sources
(+)-cercosporin ChEBI
cercosporin KEGG COMPOUND
Manual Xrefs Databases
C00002801 KNApSAcK
View more database links
Registry Number Type Source
35082-49-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12200262 PubMed citation Europe PMC
18388998 PubMed citation Europe PMC
19095071 PubMed citation Europe PMC
19894744 PubMed citation Europe PMC
20835913 PubMed citation Europe PMC
23517289 PubMed citation Europe PMC
25670706 PubMed citation Europe PMC
25862648 PubMed citation Europe PMC
26474162 PubMed citation Europe PMC
26938470 PubMed citation Europe PMC
28535078 PubMed citation Europe PMC
29844193 PubMed citation Europe PMC
30107033 PubMed citation Europe PMC
30126995 PubMed citation Europe PMC
30184412 PubMed citation Europe PMC
30686233 PubMed citation Europe PMC
31580376 PubMed citation Europe PMC
31642594 PubMed citation Europe PMC
32125700 PubMed citation Europe PMC
32176712 PubMed citation Europe PMC
549738 PubMed citation Europe PMC
IND606512896 Agricola citation Europe PMC
Last Modified
17 July 2020