L-685,458, gamma-secretase inhibitor

Key facts

CAS number

292632-98-5

Purity

>98%

Form

Liquid

form

Molecular weight

672.9 Da

Molecular formula

C₃₉H₅₂N₄O₆

PubChem

456313

Nature

Synthetic

Biochemical name

tert-butyl N-[(2S,3R,5S)-6-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate

Biological description

Potent, selective and non-competitive γ-secretase inhibitor (IC₅₀ = 17 nM). Shows 50-fold selectivity over a range of aspartyl, serine and cysteine proteases. Inhibits Aβ40 and Aβ42 peptides (IC₅₀ values are 48 and 67 nM respectively). Active in vivo. Orally active.

Canonical smiles

CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)N)NC(=O)C(CC2=CC=CC=C2)CC(C(CC3=CC=CC=C3)NC(=O)OC(C)(C)C)O

Isomeric smiles

CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N)NC(=O)[C@@H](CC2=CC=CC=C2)C[C@H]([C@H](CC3=CC=CC=C3)NC(=O)OC(C)(C)C)O

InChi

InChI=1S/C39H52N4O6/c1-26(2)21-33(37(47)41-32(35(40)45)24-29-19-13-8-14-20-29)42-36(46)30(22-27-15-9-6-10-16-27)25-34(44)31(23-28-17-11-7-12-18-28)43-38(48)49-39(3,4)5/h6-20,26,30-34,44H,21-25H2,1-5H3,(H2,40,45)(H,41,47)(H,42,46)(H,43,48)/t30-,31-,32-,33-,34+/m0/s1

InChiKey

MURCDOXDAHPNRQ-PJRHAEEISA-N

IUPAC Name

tert-butyl N-[(2S,3R,5S)-6-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate