SML1155
22-NHC
≥98% (HPLC)
Synonym(s):
(3β,20S)-20-[(3-Methylbutyl)amino]-pregn-5-en-3-ol, 22-Azacholesterol
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About This Item
Empirical Formula (Hill Notation):
C26H45NO
CAS Number:
Molecular Weight:
387.64
UNSPSC Code:
51111800
InChI key
PCLDERUMTJBTMY-MJHCCXMASA-N
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
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 1 mg/mL, clear (warmed)
storage temp.
2-8°C
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.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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