14,16-dihydroxy-3-(2H3)methyl-3,4,5,6,7,8,9,10,11,12-decahydro(3,4,4-2H3)-1H-2-benzoxacyclotetradecine-1,7-dione

• ChemBase ID: 179629
• Molecular Formular: C18H24O5
• Molecular Mass: 320.38016
• Monoisotopic Mass: 320.16237387
• SMILES: c1c(cc2c(c1O)C(=O)OC(CCCC(=O)CCCCC2)C)O
• Canonical SMILES: CC1CCCC(=O)CCCCCc2c(C(=O)O1)c(O)cc(c2)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/h10-12,20-21H,2-9H2,1H3
• InChIKey: APJDQUGPCJRQRJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14,16-dihydroxy-3-(^2H₃)methyl-3,4,5,6,7,8,9,10,11,12-decahydro(3,4,4-^2H₃)-1H-2-benzoxacyclotetradecine-1,7-dione
• IUPAC Traditional name: 14,16-dihydroxy-3-(^2H₃)methyl-6,8,9,10,11,12-hexahydro(3,4,4-^2H₃)-5H-2-benzoxacyclotetradecine-1,7-dione
• Synonyms: 3,4,5,6,9,10,11,12-Octahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione-d6; (RS)-Zearalanone-d6; (±)-Zearalanone-d6; DL-Zearalanone-d6; (±)-3,4,5,6,9,10,11,12-Octahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione-d6; rac Zearalanone-d6

Database IDs

• PubChem SID: 164235539
• PubChem CID: 71753014

CALCULATED PROPERTIES

• Acid pKa: 8.677321
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.6531005
• LogD (pH = 7.4): 4.6311846
• Log P: 4.653387
• Molar Refractivity: 87.2229 cm^3
• Polarizability: 33.66443 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 202-204°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - Z270442

Labelled Zearalanone, a secondary metabolite of Zearalenone (ZON). The macrocyclic lactone Zearalanone used in the synthesis of d,l-Zearalanol.

REFERENCES

• Hurd, R.N. et al.: J. Med. Chem., 16, 543 (1973)