(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(3S)-16-hydroxy-3-methyl-1,7-dioxo-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-14-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 179635
• Molecular Formular: C24H30O11
• Molecular Mass: 494.4884
• Monoisotopic Mass: 494.17881178
• SMILES: c1c(cc2c(c1O)C(=O)O[C@H](CCCC(=O)CCC/C=C/2)C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: O=C1CCC/C=C/c2cc(O[C@@H]3O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]3O)O)O)cc(c2C(=O)O[C@H](CCC1)C)O
• InChI: InChI=1S/C24H30O11/c1-12-6-5-9-14(25)8-4-2-3-7-13-10-15(11-16(26)17(13)23(32)33-12)34-24-20(29)18(27)19(28)21(35-24)22(30)31/h3,7,10-12,18-21,24,26-29H,2,4-6,8-9H2,1H3,(H,30,31)/b7-3+/t12-,18-,19-,20+,21-,24+/m0/s1
• InChIKey: FZLJLIKPCMZUSJ-YUTAZWDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(3S)-16-hydroxy-3-methyl-1,7-dioxo-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-14-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(3S)-16-hydroxy-3-methyl-1,7-dioxo-4,5,6,8,9,10-hexahydro-3H-2-benzoxacyclotetradecin-14-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (3S,11E)-3,4,5,6,7,8,9,10-Octahydro-16-hydroxy-3-methyl-1,7-dioxo-1H-2-benzoxacyclotetradecin-14-yl β-D-Glucopyranosiduronic Acid; Zearalenone β-D-GlucuronideDiscontinued

Database IDs

• CAS Number: 1032558-19-2
• PubChem SID: 164235545
• PubChem CID: 71753018

CALCULATED PROPERTIES

• Acid pKa: 2.917293
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.11099626
• LogD (pH = 7.4): -1.0603539
• Log P: 2.426372
• Molar Refractivity: 120.3513 cm^3
• Polarizability: 47.237774 Å^3
• Polar Surface Area: 180.05 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: N/A

DETAILS

Toronto Research Chemicals - Z270510

A metabolite of Zearalenone.

REFERENCES

• Bories, G., et al.: Drug Metab. Dispos., 19, 140 (1991)
• Biehl, M., et al.: Toxicol. Appl. Pharmacol., 121, 152 (1991)
• Erasmuson, A., et al.: J. Agric. Food Chem., 42, 2721 (1991)
• Chichila, T., et al.: J. Anal. Toxicol., 12, 310 (1991)