4-{2-[5,5-dimethyl-8-(4-methylphenyl)-5,6-dihydronaphthalen-2-yl]ethynyl}benzoic acid

• ChemBase ID: 159596
• Molecular Formular: C28H24O2
• Molecular Mass: 392.48896
• Monoisotopic Mass: 392.17763001
• SMILES: c12c(cc(cc1)C#Cc1ccc(cc1)C(=O)O)C(=CCC2(C)C)c1ccc(cc1)C
• Canonical SMILES: Cc1ccc(cc1)C1=CCC(c2c1cc(cc2)C#Cc1ccc(cc1)C(=O)O)(C)C
• InChI: InChI=1S/C28H24O2/c1-19-4-11-22(12-5-19)24-16-17-28(2,3)26-15-10-21(18-25(24)26)7-6-20-8-13-23(14-9-20)27(29)30/h4-5,8-16,18H,17H2,1-3H3,(H,29,30)
• InChIKey: NCEQLLNVRRTCKJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[5,5-dimethyl-8-(4-methylphenyl)-5,6-dihydronaphthalen-2-yl]ethynyl}benzoic acid
• IUPAC Traditional name: 4-{2-[5,5-dimethyl-8-(4-methylphenyl)-6H-naphthalen-2-yl]ethynyl}benzoic acid
• Synonyms: 4-[2-[5,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl]ethynyl]benzoic Acid; CD 3106; AGN 193109

Database IDs

• CAS Number: 171746-21-7
• PubChem SID: 162253731
• PubChem CID: 177238

CALCULATED PROPERTIES

• Acid pKa: 4.208285
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.1477695
• LogD (pH = 7.4): 4.4308147
• Log P: 7.4586167
• Molar Refractivity: 127.3672 cm^3
• Polarizability: 46.29104 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 246-255°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A427000

A retinoic acid receptor (RAR) antagonist used for treating chemotherapy and radiation therapy side effects.

REFERENCES

• Johnson, A., et al.: J. Med. Chem., 38, 4764 (1995)
• Agarwal, C., et al.: J. Biol. Chem., 271, 12209 (1995)
• Vicent, D., et al.: Mol. Cell Biol., 20, 2158 (1995)
• Kodaira, Y., et al.: J. Biochem., 132, 327 (1995)