4-[(1R,2S,6R,7S)-3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl]-N-(quinolin-8-yl)benzamide

• ChemBase ID: 155536
• Molecular Formular: C25H19N3O3
• Molecular Mass: 409.43666
• Monoisotopic Mass: 409.14264148
• SMILES: c1cc2cccnc2c(c1)NC(=O)c1ccc(cc1)N1C(=O)[C@H]2[C@@H]3C[C@H]([C@H]2C1=O)C=C3
• Canonical SMILES: O=C1N(c2ccc(cc2)C(=O)Nc2cccc3c2nccc3)C(=O)[C@@H]2[C@H]1[C@@H]1C=C[C@H]2C1
• InChI: InChI=1S/C25H19N3O3/c29-23(27-19-5-1-3-14-4-2-12-26-22(14)19)15-8-10-18(11-9-15)28-24(30)20-16-6-7-17(13-16)21(20)25(28)31/h1-12,16-17,20-21H,13H2,(H,27,29)/t16-,17+,20-,21+
• InChIKey: ZGSXEXBYLJIOGF-ALFLXDJESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R,2S,6R,7S)-3,5-dioxo-4-azatricyclo[5.2.1.0^2,^6]dec-8-en-4-yl]-N-(quinolin-8-yl)benzamide
• IUPAC Traditional name: iwr-1-endo
• Synonyms: 4-(1,3,3a,4,7,7a-Hexahydro-1,3-dioxo-4,7-methano-2H-isoindol-2-yl)-N-8-quinolinyl-Benzamide; IWR1; IWR-1; rel-4-[(3aR,4S,7R,7aS)-1,3,3a,4,7,7a-Hexahydro-1,3-dioxo-4,7-methano-2H-isoindol-2-yl]-N-8-quinolinylbenzamide; IWR-1

Database IDs

• CAS Number: 1127442-82-3
• PubChem SID: 162249674
• PubChem CID: 44483163

CALCULATED PROPERTIES

• Acid pKa: 10.268023
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.9495554
• LogD (pH = 7.4): 2.9523058
• Log P: 2.9529083
• Molar Refractivity: 116.7699 cm^3
• Polarizability: 44.96253 Å^3
• Polar Surface Area: 79.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: tan

Safety Information

• German water hazard class: 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C25H19N3O3

DETAILS

Sigma Aldrich - I0161

Biochem/physiol Actions
The Wnt/b-catenin (‘canonical’) pathway maintains transcriptional programs that enable stem cells to remain multipotent. Hyperactivation of the Wnt/b-catenin pathway leads to disease stage. IWR-3 act as inhibitors of Wnt response. It appear that IWR compounds induce stabilization of Axin proteins via a direct interaction, which is a part of the b-catenin destruction complex (consists of Apc, Axin, Ck1 and Gsk3b).

Toronto Research Chemicals - I941800

IWR-3 act as inhibitors of Wnt response. It appear that IWR compounds induce stabilization of Axin proteins via a direct interaction, which is a part of the b-catenin destruction complex (consists of Apc, Axin, Ck1 and Gsk3b).Such compounds may be used in

REFERENCES

• Lepourcelet, M., et al.: Cancer Cell., 5, 91 (2004)
• Clevers, H., et al.: Cell, 127, 469 (2004)
• Jin, G., et al.: Bioorg. Med. Chem. Lett., 19, 606 (2004)