4-{14,14,17,17-tetramethyl-2-thia-9-azatetracyclo[9.8.0.03,8.013,18]nonadeca-1(19),3(8),4,6,9,11,13(18)-heptaen-10-yl}benzoic acid

• ChemBase ID: 170021
• Molecular Formular: C28H27NO2S
• Molecular Mass: 441.58448
• Monoisotopic Mass: 441.17625011
• SMILES: c12c(C(CCC1(C)C)(C)C)cc1c(c2)C(=Nc2c(S1)cccc2)c1ccc(cc1)C(=O)O
• Canonical SMILES: OC(=O)c1ccc(cc1)C1=Nc2ccccc2Sc2c1cc1c(c2)C(C)(C)CCC1(C)C
• InChI: InChI=1S/C28H27NO2S/c1-27(2)13-14-28(3,4)21-16-24-19(15-20(21)27)25(17-9-11-18(12-10-17)26(30)31)29-22-7-5-6-8-23(22)32-24/h5-12,15-16H,13-14H2,1-4H3,(H,30,31)
• InChIKey: PFGCWQPTOKPRRK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{14,14,17,17-tetramethyl-2-thia-9-azatetracyclo[9.8.0.0^3,^8.0^1^3,^1^8]nonadeca-1(19),3(8),4,6,9,11,13(18)-heptaen-10-yl}benzoic acid
• IUPAC Traditional name: 4-{14,14,17,17-tetramethyl-2-thia-9-azatetracyclo[9.8.0.0^3,^8.0^1^3,^1^8]nonadeca-1(19),3(8),4,6,9,11,13(18)-heptaen-10-yl}benzoic acid
• Synonyms: 4-(7,8,9,10-tetrahydro-7,7,10,10-tetramethylbenzo[b]naphtho[2,3-f][1,4]thiazepin-12-yl)benzoic Acid; HX 630

Database IDs

• CAS Number: 188844-52-2
• PubChem SID: 164225931
• PubChem CID: 9889522

CALCULATED PROPERTIES

• Acid pKa: 3.9290662
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 6.5158544
• LogD (pH = 7.4): 4.895345
• Log P: 8.093831
• Molar Refractivity: 134.791 cm^3
• Polarizability: 50.540535 Å^3
• Polar Surface Area: 49.66 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H674250

A nuclear receptor retinoid X receptor (RXR) agonist that exerts antiproliferative effects in vascular smooth muscle cells (VSMCs) in vivo and in vitro. A potential therapeutic target for vascular injury and intimal thickening. It efficiently enhanced ABC

REFERENCES

• Haraguchi, G. et al.: J. Mol. Cell. Cardiol., 41, 885 (2006)
• Nishimaki-M. et al.: Biochem. Pharmacol., 76, 1006 (2006)