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

• ChemBase ID: 153227
• Molecular Formular: C29H24O2
• Molecular Mass: 404.49966
• Monoisotopic Mass: 404.17763001
• SMILES: CC1(CC=C(c2c1ccc(c2)/C=C/c1ccc(cc1)C(=O)O)C#Cc1ccccc1)C
• Canonical SMILES: OC(=O)c1ccc(cc1)/C=C/c1ccc2c(c1)C(=CCC2(C)C)C#Cc1ccccc1
• InChI: InChI=1S/C29H24O2/c1-29(2)19-18-24(14-10-21-6-4-3-5-7-21)26-20-23(13-17-27(26)29)9-8-22-11-15-25(16-12-22)28(30)31/h3-9,11-13,15-18,20H,19H2,1-2H3,(H,30,31)
• InChIKey: YCADIXLLWMXYKW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[5,5-dimethyl-8-(2-phenylethynyl)-5,6-dihydronaphthalen-2-yl]ethenyl}benzoic acid
• IUPAC Traditional name: 4-{2-[5,5-dimethyl-8-(2-phenylethynyl)-6H-naphthalen-2-yl]ethenyl}benzoic acid
• Synonyms: (E)-4-[2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)naphthalen-2-yl]ethen-1-yl]benzoic acid; 4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(phenylethynyl)-2-naphthalenyl]ethenyl]-benzoic acid; BMS204, 493; BMS 493

Database IDs

• CAS Number: 215030-90-3
• MDL Number: MFCD17215944
• PubChem SID: 162247366
• PubChem CID: 9909190

CALCULATED PROPERTIES

• Acid pKa: 4.122646
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.245662
• LogD (pH = 7.4): 4.553244
• Log P: 7.637811
• Molar Refractivity: 126.4004 cm^3
• Polarizability: 48.150867 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: light yellow to yellow powder

Safety Information

• German water hazard class: 2
• GHS Hazard statements: H413
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C29H24O2

DETAILS

Sigma Aldrich - B6688

Biochem/physiol Actions
BMS 493 is an inverse pan-RAR agonist. Retinoic acid receptors (RARs) are ligand-dependent transcription factors that control a number of physiological processes. RARs exert their functions by regulating gene networks controlling cell growth, differentiation, survival, and death.