14,16-dihydroxy-3-(2H3)methyl-3,4,5,6,7,8,9,10-octahydro(3,4,4-2H3)-1H-2-benzoxacyclotetradecine-1,7-dione

• ChemBase ID: 179634
• Molecular Formular: C18H22O5
• Molecular Mass: 318.36428
• Monoisotopic Mass: 318.1467238
• SMILES: c1c(cc2c(c1O)C(=O)OC(CCCC(=O)CCC/C=C/2)C)O
• Canonical SMILES: CC1CCCC(=O)CCC/C=C/c2c(C(=O)O1)c(O)cc(c2)O
• InChI: InChI=1S/C18H22O5/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/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+
• InChIKey: MBMQEIFVQACCCH-XVNBXDOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14,16-dihydroxy-3-(^2H₃)methyl-3,4,5,6,7,8,9,10-octahydro(3,4,4-^2H₃)-1H-2-benzoxacyclotetradecine-1,7-dione
• IUPAC Traditional name: 14,16-dihydroxy-3-(^2H₃)methyl-6,8,9,10-tetrahydro(3,4,4-^2H₃)-5H-2-benzoxacyclotetradecine-1,7-dione
• Synonyms: (+/-)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione-d6; (+/-)-Zearalenone-d6; (+/-)-Mycotoxin F2-d6; (+/-)-Toxin F2-d6; trans-Zearalenone-d6; FES-d6; ZON-d6; rac Zearalenone-d6

Database IDs

• CAS Number: 1185236-04-7
• PubChem SID: 164235544
• PubChem CID: 46783266

CALCULATED PROPERTIES

• Acid pKa: 8.5377245
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.3737707
• LogD (pH = 7.4): 4.3438344
• Log P: 4.3741655
• Molar Refractivity: 88.3395 cm^3
• Polarizability: 33.566277 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 186-188°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - Z270502

Estrogenic mycotoxin produced by Fusarium fungi commonly found in grains. One of a group of compounds known as resorcylic acid lactones.

REFERENCES

• Tanaka, T., et al.: J. Agric. Food Chem., 36, 979 (1988)
• Hamilton, S., et al.: Anticancer Res., 16, 3597 (1988)
• Hecht, S., et al.: Cancer Lett., 150, 49 (1988)
• Hussein, H., et al.: Toxicology, 167, 101 (1988)
• Lim, H., et al.: J. Immunol., 175, 4180 (2