(3S)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro(6,6,7,8,8-2H5)-1H-2-benzoxacyclotetradecin-1-one

• ChemBase ID: 179630
• Molecular Formular: C18H24O5
• Molecular Mass: 320.38016
• Monoisotopic Mass: 320.16237387
• SMILES: c1c(cc2c(c1O)C(=O)O[C@H](CCCC(CCC/C=C/2)O)C)O
• Canonical SMILES: OC1CCC/C=C/c2cc(O)cc(c2C(=O)O[C@H](CCC1)C)O
• InChI: InChI=1S/C18H24O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/b7-3+/t12-,14?/m0/s1
• InChIKey: FPQFYIAXQDXNOR-FLBVUZLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro(6,6,7,8,8-^2H₅)-1H-2-benzoxacyclotetradecin-1-one
• IUPAC Traditional name: (3S)-7,14,16-trihydroxy-3-methyl-4,5,9,10-tetrahydro(6,6,7,8,8-^2H₅)-3H-2-benzoxacyclotetradecin-1-one
• Synonyms: (3S,11E)-3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one; (-)-β-Zearalenol; β-trans-Zearalenol; α/β-Zearalenol-d5(Mixture of Diastereomers)Discontinued. See Z270472 and Z270477

Database IDs

• PubChem SID: 164235540
• PubChem CID: 71753015

CALCULATED PROPERTIES

• Acid pKa: 8.537725
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.16627
• LogD (pH = 7.4): 4.136334
• Log P: 4.1666646
• Molar Refractivity: 89.3676 cm^3
• Polarizability: 34.10992 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Z270462

The major labelled metabolites of Zearalenone (Z270500) .

REFERENCES

• Olsen, M., et al.: Acta Pharmacol. Toxicol., 48, 15 (1981)
• Chang, W., et al.: Food Chem. Toxicol., 22, 887 (1981)
• El Golli, E., et al.: Toxicol Lett., 166, 122 (1981)
• Hassen, W., et al.: Toxicology, 232, 294 (1981)
• Benzoni, E., et al.: Reprod. Toxicol