6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid

• ChemBase ID: 1708
• Molecular Formular: C24H29NO2
• Molecular Mass: 363.49256
• Monoisotopic Mass: 363.21982917
• SMILES: Cc1cc2c(cc1C1(CC1)c1ccc(cn1)C(=O)O)C(C)(C)CCC2(C)C
• Canonical SMILES: Cc1cc2c(cc1C1(CC1)c1ccc(cn1)C(=O)O)C(C)(C)CCC2(C)C
• InChI: InChI=1S/C24H29NO2/c1-15-12-18-19(23(4,5)9-8-22(18,2)3)13-17(15)24(10-11-24)20-7-6-16(14-25-20)21(26)27/h6-7,12-14H,8-11H2,1-5H3,(H,26,27)
• InChIKey: SLXTWXQUEZSSTJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid
• IUPAC Traditional name: 6-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid
• Synonyms: 6-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)cyclopropyl]-3-Pyridinecarboxylic Acid; AGN 192620; ALRT 268; CD 3127; LG 268; LGD 100268; LGD 1268; LG 100268; 6-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-Tetrahydronaphthalen-2-Yl)Cyclopropyl]Pyridine-3-Carboxylic Acid

Database IDs

• CAS Number: 153559-76-3
• PubChem SID: 46505129; 160965165
• PubChem CID: 3922

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.9288204
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.396279
• LogD (pH = 7.4): 2.867808
• Log P: 5.816521
• Molar Refractivity: 118.8092 cm^3
• Polarizability: 41.678032 Å^3
• Polar Surface Area: 50.19 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.15
• LOG S: -6.08
• Solubility (Water): 3.02e-04 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 275-277°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB01941

Drug information: experimental

Toronto Research Chemicals - L397650

LG 100268 is a potent RXR agonist for evaluation in the treatment of non-insulin-dependent (type II) diabetes mellitus (NIDDM).

REFERENCES

• Clyne, C., et al.: J. Biol. Chem., 277, 20591 (2002)
• Santen, R., et al.: J. Clin. Endocrinol. Metab., 87, 3007 (2002)
• Falender, A., et al.: Endocrinology, 144, 3598 (2002)
• Sablin, E., et al.: Mol. Cell., 11, 1575 (2003)