SM-164

Key facts

Purity

>98%

Form

Solid

form

Molecular weight

1121.4 Da

Molecular formula

C₆₂H₈₄N₁₄O₆

PubChem

122172970

Nature

Synthetic

Solubility

Soluble in DMSO to >25 mM

Biochemical name

(3S,6S,10aS)-N-[(S)-[1-[4-[4-[4-[4-[(R)-[[(3S,6R,10aR)-6-[[(2S)-2-(methylamino)propanoyl]amino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carbonyl]amino]-phenylmethyl]triazol-1-yl]butyl]phenyl]butyl]triazol-4-yl]-phenylmethyl]-6-[[(2S)-2-(methylamino)propanoyl]amino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxamide

Biological description

SM-164 is a potent cell-permeable and bivalent Smac mimetic which binds to a XIAP protein with a Ki value of 0.56 nM, and binds to cIAP-1 and cIAP-2 proteins with Ki values of 0.31 and 1.1 nM, respectively. It displays antitumor properties through inducing degradation of cellular inhibitor of apoptosis protein (cIAP)-1/2, antagonizing X-linked inhibitor of apoptosis protein (XIAP) and inducing TNFα–dependent apoptosis in tumor cells.

Canonical smiles

CC(C(=O)NC1CCCCC2CCC(N2C1=O)C(=O)NC(C3=CC=CC=C3)C4=CN(N=N4)CCCCC5=CC=C(C=C5)CCCCN6C=C(N=N6)C(C7=CC=CC=C7)NC(=O)C8CCC9N8C(=O)C(CCCC9)NC(=O)C(C)NC)NC

Isomeric smiles

C[C@@H](C(=O)N[C@@H]1CCCC[C@@H]2CC[C@H](N2C1=O)C(=O)N[C@H](C3=CC=CC=C3)C4=CN(N=N4)CCCCC5=CC=C(C=C5)CCCCN6C=C(N=N6)[C@H](C7=CC=CC=C7)NC(=O)[C@@H]8CC[C@H]9N8C(=O)[C@H](CCCC9)NC(=O)[C@H](C)NC)NC

InChi

InChI=1S/C62H84N14O6/c1-41(63-3)57(77)65-49-27-13-11-25-47-33-35-53(75(47)61(49)81)59(79)67-55(45-21-7-5-8-22-45)51-39-73(71-69-51)37-17-15-19-43-29-31-44(32-30-43)20-16-18-38-74-40-52(70-72-74)56(46-23-9-6-10-24-46)68-60(80)54-36-34-48-26-12-14-28-50(62(82)76(48)54)66-58(78)42(2)64-4/h5-10,21-24,29-32,39-42,47-50,53-56,63-64H,11-20,25-28,33-38H2,1-4H3,(H,65,77)(H,66,78)(H,67,79)(H,68,80)/t41-,42-,47-,48+,49-,50+,53-,54-,55-,56+/m0/s1

InChiKey

LGYDZXNSSLRFJS-YVGVMFSSSA-N

IUPAC Name

(3S,6S,10aS)-N-[(S)-[1-[4-[4-[4-[4-[(R)-[[(3S,6R,10aR)-6-[[(2S)-2-(methylamino)propanoyl]amino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carbonyl]amino]-phenylmethyl]triazol-1-yl]butyl]phenyl]butyl]triazol-4-yl]-phenylmethyl]-6-[[(2S)-2-(methylamino)propanoyl]amino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxamide