4-[1-(7-hydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid

• ChemBase ID: 170150
• Molecular Formular: C24H28O3
• Molecular Mass: 364.47732
• Monoisotopic Mass: 364.20384476
• SMILES: C1(C(CC(c2c1cc(c(c2)C)C(=C)c1ccc(cc1)C(=O)O)(C)C)O)(C)C
• Canonical SMILES: OC1CC(C)(C)c2c(C1(C)C)cc(c(c2)C)C(=C)c1ccc(cc1)C(=O)O
• InChI: InChI=1S/C24H28O3/c1-14-11-19-20(24(5,6)21(25)13-23(19,3)4)12-18(14)15(2)16-7-9-17(10-8-16)22(26)27/h7-12,21,25H,2,13H2,1,3-6H3,(H,26,27)
• InChIKey: ZXOXDVMWISJVGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[1-(7-hydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid
• IUPAC Traditional name: 4-[1-(7-hydroxy-3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid
• Synonyms: 4-[1-(5,6,7,8-Tetrahydro-7-hydroxy-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic Acid; 7-Hydroxy Bexarotene

Database IDs

• CAS Number: 368451-10-9
• PubChem SID: 164226060
• PubChem CID: 71748830

CALCULATED PROPERTIES

• Acid pKa: 4.0707855
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.268075
• LogD (pH = 7.4): 2.592653
• Log P: 5.7097263
• Molar Refractivity: 118.6395 cm^3
• Polarizability: 41.989216 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H817505

A metabolite of Bexarotene (B336750).

REFERENCES

• Hashimoto, S., et al.: Xenobiotica, 24, 1177 ( 1994), Boehm, M., et al.: J. Med. Chem., 38, 3146 (1995)
• Shirley, M.A., et al.: Drug Metab. Dispos., 25, 1144 (1995)