9,19-dihydroxy-5,21-bis(2-hydroxypropyl)-6,20-dimethoxy-12,14-dioxahexacyclo[13.8.0.02,11.03,8.04,22.018,23]tricosa-1(23),2,4(22),5,8,10,15,18,20-nonaene-7,17-dione

• ChemBase ID: 132679
• Molecular Formular: C29H26O10
• Molecular Mass: 534.51074
• Monoisotopic Mass: 534.15259703
• SMILES: CC(Cc1c2c3C(=C(C(=O)c4c3c3c(cc4O)OCOC4=CC(=O)c(c2c34)c(c1OC)O)OC)CC(C)O)O
• Canonical SMILES: COC1=C(CC(O)C)c2c3c(C1=O)c(O)cc1c3c3c4c2c(CC(O)C)c(OC)c(c4C(=O)C=C3OCO1)O
• 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/h7-8,10-11,30-32,35H,5-6,9H2,1-4H3
• InChIKey: JWFLIMIGORGZMQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9,19-dihydroxy-5,21-bis(2-hydroxypropyl)-6,20-dimethoxy-12,14-dioxahexacyclo[13.8.0.0^2,^1^1.0^3,^8.0^4,^2^2.0^1^8,^2^3]tricosa-1(23),2,4(22),5,8,10,15,18,20-nonaene-7,17-dione
• IUPAC Traditional name: 9,19-dihydroxy-5,21-bis(2-hydroxypropyl)-6,20-dimethoxy-12,14-dioxahexacyclo[13.8.0.0^2,^1^1.0^3,^8.0^4,^2^2.0^1^8,^2^3]tricosa-1(23),2,4(22),5,8,10,15,18,20-nonaene-7,17-dione
• Synonyms: Cercosporin from Cercospora hayii

Database IDs

• CAS Number: 35082-49-6
• MDL Number: MFCD00212919
• PubChem SID: 24892884; 162226956
• PubChem CID: 2674

CALCULATED PROPERTIES

• Acid pKa: 7.8695245
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 3.0369003
• LogD (pH = 7.4): 2.913416
• Log P: 3.0429993
• Molar Refractivity: 142.7914 cm^3
• Polarizability: 55.66673 Å^3
• Polar Surface Area: 151.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - C6696

Biochem/physiol Actions
A light-induced polyketide phytotoxin reported to produce singlet oxygen when photoactivated.
Cercosporin, a polyketide phytotoxin, is activated by light and in the activated state, reacts with oxygen to produce toxic oxygen species such as singlet oxygen (O2) and superoxide (O2-). Production of reactive oxygen species leads to peroxidation of lipids in the plant cell membranes.
Application
Cercosporin (C29H26O10) is a red pigment that has been isolated from cultures of a banana pathogen 1. It has been used to study toxin biodegredation in species such as Bacterium Xanthomonas campestris pv. Zinniae 2.