(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide

• ChemBase ID: 177444
• Molecular Formular: C20H29NO
• Molecular Mass: 299.45036
• Monoisotopic Mass: 299.22491455
• SMILES: C1CCC(=C(C1(C)C)/C=C/C(=C/C=C/C(=C/C(=O)N)/C)/C)C
• Canonical SMILES: C/C(=C\C=C\C(=C\C(=O)N)\C)/C=C/C1=C(C)CCCC1(C)C
• InChI: InChI=1S/C20H29NO/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H2,21,22)/b9-6+,12-11+,15-8+,16-14+
• InChIKey: NUXWXMZVAHSICO-YCNIQYBTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• IUPAC Traditional name: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• Synonyms: all-trans-Retinamide; Retinoyl Amide; Ro 4-3930; all-trans-Vitamin A Amide; Retinamide

Database IDs

• CAS Number: 20638-84-0
• PubChem SID: 164233354
• PubChem CID: 5370221

CALCULATED PROPERTIES

• Acid pKa: 16.783653
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.207383
• LogD (pH = 7.4): 4.2074246
• Log P: 4.207425
• Molar Refractivity: 99.613 cm^3
• Polarizability: 36.89997 Å^3
• Polar Surface Area: 43.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R243000

A Vitamin A derivative; a potent and selective apoptosis-inducing agent. It can be used in the treatment of cancer and other hyperproliferative disorders.

REFERENCES

• Formelli, F., et al.: J. Clin. Oncol., 11, 2036 (1993)
• Fanjul, A., ET AL.: J. Biol. Chem., 271, 22441 (1993)
• Smith, M., ET AL.: Clin. Cancer Res., 7, 2955 (1993)
• Um, S., et al.: Cancer Lett., 174, 127 (1993)