methyl (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carboxylate

• ChemBase ID: 163866
• Molecular Formular: C32H43NO4
• Molecular Mass: 505.68812
• Monoisotopic Mass: 505.31920886
• SMILES: C1(=C[C@]2([C@H](C(C1=O)(C)C)CC[C@@]1(C2=CC(=O)[C@H]2[C@]1(CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)OC)C)C)C)C#N
• Canonical SMILES: N#CC1=C[C@@]2(C)[C@H](C(C1=O)(C)C)CC[C@@]1(C2=CC(=O)[C@H]2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)OC)C
• InChI: InChI=1S/C32H43NO4/c1-27(2)11-13-32(26(36)37-8)14-12-31(7)24(20(32)17-27)21(34)15-23-29(5)16-19(18-33)25(35)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3/t20-,22-,24-,29-,30+,31+,32-/m0/s1
• InChIKey: WPTTVJLTNAWYAO-KPOXMGGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carboxylate
• IUPAC Traditional name: bardoxolone methyl
• Synonyms: 2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic Acid Methyl Ester; Bardoxolone Methyl; CDDO-Me; Methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate; NSC 713200; RTA 402; CDDO Methyl Ester; TP-155; CDDO Methyl Ester; Bardoxolone Methyl

Database IDs

• CAS Number: 218600-53-4
• PubChem SID: 162258001
• PubChem CID: 400769

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 6.5504317
• LogD (pH = 7.4): 6.5504317
• Log P: 6.5504317
• Molar Refractivity: 144.3622 cm^3
• Polarizability: 56.290703 Å^3
• Polar Surface Area: 84.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 215-219°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: IKK; IκB

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - C228100

CDDO Methyl Ester is a synthetic triterpenoid that inhibits IκBα kinase and enhances apoptosis induced by TNF and chemotherapeutic agents through down-regulation of expression of nuclear factor κB-regulated gene products in human leukemic cells. CDDO Meth

REFERENCES

• Shishodia, S. et al.: Clin. Cancer Res., 12, 1828 (2006)
• Konopleva, M. et al.: Leukemia, 19, 1350 (2006)
• Deeb, D. et al.: Cancers, 2, 1779 (2006)
• Gao, X. et al.: J. Exp. Therap. Oncol., 9, 119 (2006)