SML3452

CDDO-Im

≥98% (HPLC)

• Synonym(s): (4aR,6aS,6aR,6bR,8aS,12aS,14bS)-8a-(imidazole-1-carbonyl)-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-4a,5,6,6a,7,8,9,10,12,12a-decahydropicene-2-carbonitrile, 1-(2-Cyano-3,12-dioxooleana-1,9-dien-28-oyl) imidazole, CDDO-Imidazole, CDDO-imidazolide, NSC727038
• Empirical Formula (Hill Notation): C₃₄H₄₃N₃O₃
• CAS Number: 443104-02-7
• Molecular Weight: 541.72
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD12756341
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear (Warmed)
• storage temp.: -10 to -25°C
• SMILES string: [n]6(cncc6)C(=O)[C@]21[C@H]([C@@H]3[C@]([C@@]4(CC[C@@H]5[C@@](C4=CC3=O)(C=C(C(=O)C5(C)C)C#N)C)C)(CC2)C)CC(CC1)(C)C
• InChI: 1S/C34H43N3O3/c1-29(2)10-12-34(28(40)37-15-14-36-20-37)13-11-33(7)26(22(34)18-29)23(38)16-25-31(5)17-21(19-35)27(39)30(3,4)24(31)8-9-32(25,33)6/h14-17,20,22,24,26H,8-13,18H2,1-7H3/t22-,24-,26-,31-,32+,33+,34-/m0/s1
• InChI key: ITFBYYCNYVFPKD-FMIDTUQUSA-N

Description

Biochem/physiol Actions

Bifunctional CDDO analog that enhances NRF2-mediated antioxidant and anti-inflammatory activity by forming KEAP1 and GSTP covalent adducts.

CDDO-Im is a bifunctional CDDO analog that enhances NRF2-mediated antioxidant and anti-inflammatory activity by forming not only KEAP1 covalent adducts (Michael adducts via cysteines, acyl adducts via lysines and tyrosines) in the same manner as CDDO and CDDO-Me, but also by covalently transacylating arginine and serine residues in GSTP and cross-linking them to adjacent cysteine residues. CDDO-Im is typically used in the range of 1-40 nM in cultures, 2-5.5 mg/kg via i.p. and 2.5 mg/kg via i.v. in vivo (mice and rats).

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable