4-{1-[5,5,8,8-tetrakis(13C)methyl-3-methyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethenyl}benzoic acid

• ChemBase ID: 162026
• Molecular Formular: C24H28O2
• Molecular Mass: 352.44853935
• Monoisotopic Mass: 352.22234949
• SMILES: C1(CCC(c2c1cc(c(c2)C)C(=C)c1ccc(cc1)C(=O)O)([13CH3])[13CH3])([13CH3])[13CH3]
• Canonical SMILES: Cc1cc2c(cc1C(=C)c1ccc(cc1)C(=O)O)C([13CH3])([13CH3])CCC2([13CH3])[13CH3]
• InChI: InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)/i3+1,4+1,5+1,6+1
• InChIKey: NAVMQTYZDKMPEU-PQVJJBODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{1-[5,5,8,8-tetrakis(^1^3C)methyl-3-methyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethenyl}benzoic acid
• IUPAC Traditional name: 4-{1-[5,5,8,8-tetrakis(^1^3C)methyl-3-methyl-6,7-dihydronaphthalen-2-yl]ethenyl}benzoic acid
• Synonyms: 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic Acid-13C4; LG 100069-13C4; LG 1069-13C4; LG 69-13C4; LGD 1069-13C4; RO 26-4455-13C4; SR 11247-13C4; Targret-13C4; Targretin-13C4; Targretyn-13C4; Targrexin-13C4; Bexarotene-13C4

Database IDs

• CAS Number: 1185030-01-6
• PubChem SID: 162256161
• PubChem CID: 45038331

CALCULATED PROPERTIES

• Acid pKa: 4.0707927
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.4988923
• LogD (pH = 7.4): 3.8234684
• Log P: 6.9405375
• Molar Refractivity: 117.124 cm^3
• Polarizability: 41.398285 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 216-219°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B336752

Labelled Bexarotene (B336750). Used as an antineoplastic. A selective retinoid X receptor (RXR) agonist.

REFERENCES

• Boehm, M.F., et al.: J. Med. Che., 37,2930 (1994)
• Gottardis, M.M., et al.: Cancer Res., 56, 5566 (1994)
• Mukherjee, R., et al.: Nature, 386, 407 (1994)
• Miller, V.A., et al.: J. Clin. Oncol., 15, 790 (1997)