(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide

• ChemBase ID: 172068
• Molecular Formular: C26H31NO3
• Molecular Mass: 405.52924
• Monoisotopic Mass: 405.23039386
• SMILES: C1CC(=O)C(=C(C1(C)C)/C=C/C(=C/C=C/C(=C/C(=O)Nc1ccc(cc1)O)/C)/C)C
• Canonical SMILES: O=C(Nc1ccc(cc1)O)/C=C(/C=C/C=C(/C=C/C1=C(C)C(=O)CCC1(C)C)\C)\C
• InChI: InChI=1S/C26H31NO3/c1-18(9-14-23-20(3)24(29)15-16-26(23,4)5)7-6-8-19(2)17-25(30)27-21-10-12-22(28)13-11-21/h6-14,17,28H,15-16H2,1-5H3,(H,27,30)/b8-6+,14-9+,18-7+,19-17+
• InChIKey: NZVOGZATHCUFRC-KFJFTADJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• IUPAC Traditional name: (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• Synonyms: 4-Oxo Fenretinide; N-(4-Hydroxyphenyl)-4-oxoretinamide; 4-Keto-4-HPR; 4-Oxo-4-HPR; 4-Oxo-N-(4-hydroxyphenyl)retinamide; 3-Keto Fenretinide

Database IDs

• CAS Number: 865536-65-8
• PubChem SID: 164227978
• PubChem CID: 11258242

CALCULATED PROPERTIES

• Acid pKa: 9.447084
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.477772
• LogD (pH = 7.4): 5.473964
• Log P: 5.477821
• Molar Refractivity: 128.7422 cm^3
• Polarizability: 47.118885 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Solid
• Melting Point: 233-235°C

Safety Information

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

DETAILS

Toronto Research Chemicals - K188800

The active metabolite of Fenretinide (4-HPR) (F250000).

REFERENCES

• Formelli, F., et al.: J. Clin. Oncol., 11, 2036 (1993)
• Villani, M., et al.: Cancer Res., 66, 3238 (1993)
• Villablanca, J., et al.: J. Clin. Oncol., 24, 3423 (1993)