(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoyloxy}oxane-2-carboxylic acid

• ChemBase ID: 162027
• Molecular Formular: C30H36O8
• Molecular Mass: 524.60204
• Monoisotopic Mass: 524.24101811
• SMILES: C1(CCC(c2c1cc(c(c2)C)C(=C)c1ccc(cc1)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)(C)C)(C)C
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)c2ccc(cc2)C(=C)c2cc3c(cc2C)C(C)(C)CCC3(C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C30H36O8/c1-15-13-20-21(30(5,6)12-11-29(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)27(36)38-28-24(33)22(31)23(32)25(37-28)26(34)35/h7-10,13-14,22-25,28,31-33H,2,11-12H2,1,3-6H3,(H,34,35)/t22-,23-,24+,25-,28-/m0/s1
• InChIKey: VINSDXGLDYSZBG-SLIMJBHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoyloxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoyloxy}oxane-2-carboxylic acid
• Synonyms: 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-benzoic Acid Methyl Ester-13C4; Methyl 4-(1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-1-ethenyl]benzoate-13C4; Bexarotene-13C4 Methyl Ester

Database IDs

• PubChem SID: 162256162
• PubChem CID: 71313961

CALCULATED PROPERTIES

• Acid pKa: 3.0585227
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.7837884
• LogD (pH = 7.4): 1.7255182
• Log P: 5.192744
• Molar Refractivity: 149.4226 cm^3
• Polarizability: 55.031235 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate
• Apperance: White Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B336757

Protected Bexarotene (B336750). Used as an antineoplastic. Also used in the preparation of bexarotene analogs as RXR selective agonists.

REFERENCES

• Wagner, C. et al.; J. Med. Chem. 52, 5950 (2009)
• Boehm, M.F., et al.: J. Med. Che., 37,2930 (2009)
• Gottardis, M.M., et al.: Cancer Res., 56, 5566 (2009)
• Mukherjee, R., et al.: Nature, 386, 407 (2009)
• Miller, V.A., et al.: J. Clin. Oncol., 15, 790 (199