SML1155

22-NHC

≥98% (HPLC)

• Synonym(s): (3β,20S)-20-[(3-Methylbutyl)amino]-pregn-5-en-3-ol, 22-Azacholesterol
• Empirical Formula (Hill Notation): C₂₆H₄₅NO
• CAS Number: 3915-24-0
• Molecular Weight: 387.64
• UNSPSC Code: 51111800

Properties

• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 1 mg/mL, clear (warmed)
• storage temp.: 2-8°C
• InChI: 1S/C26H45NO/c1-17(2)12-15-27-18(3)22-8-9-23-21-7-6-19-16-20(28)10-13-25(19,4)24(21)11-14-26(22,23)5/h6,17-18,20-24,27-28H,7-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25-,26+/m0/s1
• InChI key: PCLDERUMTJBTMY-MJHCCXMASA-N

Description

Biochem/physiol Actions

22-NHC (22-Azacholesterol) is the first small molecule inhibitor that inhibits Hedgehog (Hh) signaling by binding the oxysterol-binding site of Smo. Oxysterols are the only known endogenous activators of Hedgehog signaling, with 20(S)-hydroxycholesterol being the most potent, and act at a site distinct from that targeted by current Smo inhibitors such as cyclopamine and SANT1. 22-Azacholesterol (22-NHC) inhibited Sonic Hedgehog (Shh) signaling with an IC₅₀ of 3 μM in NIH-3T3 cells. 22-NHC binds to the same allosteric site as 20(S)-hydroxycholesterol (20-OHC), which is distinct from the cyclopamine site and the itraconazole site, and appears to act by competing with binding of 20-OHC to mSmo.

22-NHC is the first small molecule inhibitor that inhibits Hedgehog (Hh) signaling by binding the oxysterol-binding site of Smo.

Safety Information

• Storage Class: 13 - Non Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable