U-18666A, cholesterol transport inhibitor

Key facts

CAS number

3039-71-2

Form

Solid

form

Molecular weight

424.1 Da

Molecular formula

C₂₅H₄₂ClNO₂

PubChem

9954082

Nature

Synthetic

Solubility

Soluble in DMSO to 50 mM

Soluble in water to 50 mM

Biochemical name

3beta-(2-Diethylaminoethoxy)androst-5-en-17-one hydrochloride

Biological description

Inhibitor of cholesterol synthesis and cellular transport. Impairs intracellular transport of LDL-derived cholesterol in CHO cells. Blocks the ability of LDL-derived cholesterol to suppress HMG-CoA reductase and LDL receptor activity. Weak inhibitor of Hedgehog signaling. Modulates APP cleavage in cultured cells. Tool compound for studying Niemann-Pick disease.

Canonical smiles

CCN(CC)CCOC1CCC2(C3CCC4(C(C3CC=C2C1)CCC4=O)C)C.Cl

Isomeric smiles

CCN(CC)CCO[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CCC4=O)C)C.Cl

InChi

InChI=1S/C25H41NO2.ClH/c1-5-26(6-2)15-16-28-19-11-13-24(3)18(17-19)7-8-20-21-9-10-23(27)25(21,4)14-12-22(20)24;/h7,19-22H,5-6,8-17H2,1-4H3;1H/t19-,20-,21-,22-,24-,25-;/m0./s1

InChiKey

GZFYZYBWLCYBMI-MYZJJQSMSA-N

IUPAC Name

(3S,8R,9S,10R,13S,14S)-3-[2-(diethylamino)ethoxy]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one;hydrochloride