3-chloro-N-{[3-(pyridin-4-yl)phenyl]methyl}-N-[(1s,4s)-4-(methylamino)cyclohexyl]-1-benzothiophene-2-carboxamide

• ChemBase ID: 177674
• Molecular Formular: C28H28ClN3OS
• Molecular Mass: 490.05942
• Monoisotopic Mass: 489.16416121
• SMILES: c1ccc2c(c1)sc(c2Cl)C(=O)N(Cc1cccc(c1)c1ccncc1)[C@H]1CC[C@H](CC1)NC
• Canonical SMILES: CN[C@@H]1CC[C@@H](CC1)N(C(=O)c1sc2c(c1Cl)cccc2)Cc1cccc(c1)c1ccncc1
• InChI: InChI=1S/C28H28ClN3OS/c1-30-22-9-11-23(12-10-22)32(28(33)27-26(29)24-7-2-3-8-25(24)34-27)18-19-5-4-6-21(17-19)20-13-15-31-16-14-20/h2-8,13-17,22-23,30H,9-12,18H2,1H3/t22-,23+
• InChIKey: VFSUUTYAEQOIMW-ZRZAMGCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-chloro-N-{[3-(pyridin-4-yl)phenyl]methyl}-N-[(1s,4s)-4-(methylamino)cyclohexyl]-1-benzothiophene-2-carboxamide
• IUPAC Traditional name: 3-chloro-N-{[3-(pyridin-4-yl)phenyl]methyl}-N-[(1s,4s)-4-(methylamino)cyclohexyl]-1-benzothiophene-2-carboxamide
• Synonyms: 3-Chloro-N-[trans-4-(methylamino)cyclohexyl]-N-[[3-(4-pyridinyl)phenyl]methyl]- benzo[b]thiophene-2-carboxamide; SAG

Database IDs

• CAS Number: 912545-86-9
• PubChem SID: 164233584
• PubChem CID: 5284330

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.4241936
• LogD (pH = 7.4): 2.9723134
• Log P: 5.776024
• Molar Refractivity: 139.5665 cm^3
• Polarizability: 56.455242 Å^3
• Polar Surface Area: 45.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Orange to Red Oil

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Light Sensitive

DETAILS

Toronto Research Chemicals - S083600

A potent agonist of Hedgehog (Hh) signalling by activating the Smoothened (Smo) protein function. Studies identify novel properties of molecules displaying potential interest in the treatment of various cancers and brain diseases, and demonstrate that Smo

REFERENCES

• DeCamp, D., et al.: J. Biol. Chem., 275, 26322 (2000)
• Ahn, S., et al.: Nature, 437, 894 (2000)
• Huangfu, D., et al.: Development, 133, 3 (2000)
• Loulier, K., et al.: J. Neurochem., 98, 530 (2000)