Birinapant

Key facts

CAS number

1260251-31-7

Purity

>98%

Form

Solid

form

Molecular weight

806.9 Da

Molecular formula

C₄₂H₅₆F₂N₈O₆

PubChem

49836020

Nature

Synthetic

Solubility

Soluble in DMSO to 50 mM

Soluble in ethanol to 50 mM

Biochemical name

Birinapant

Biological description

Potent antagonist for cIAP1 (Kd <1 nM) and XIAP (Kd = 45 nM). Not only binds to the isolated BIR3 domains of cIAP1, cIAP2, XIAP but the single BIR domain of ML-IAP with high affinity and degrades TRAF2-bound cIAP1 and cIAP2 rapidly accordingly inhibiting the activation of TNF-mediated NF- kB. SMAC mimetic. Promotes caspase-8 formation.

Canonical smiles

CCC(C(=O)N1CC(CC1CC2=C(NC3=C2C=CC(=C3)F)C4=C(C5=C(N4)C=C(C=C5)F)CC6CC(CN6C(=O)C(CC)NC(=O)C(C)NC)O)O)NC(=O)C(C)NC

Isomeric smiles

CC[C@@H](C(=O)N1C[C@H](C[C@H]1CC2=C(NC3=C2C=CC(=C3)F)C4=C(C5=C(N4)C=C(C=C5)F)C[C@@H]6C[C@@H](CN6C(=O)[C@H](CC)NC(=O)[C@H](C)NC)O)O)NC(=O)[C@H](C)NC

InChi

InChI=1S/C42H56F2N8O6/c1-7-33(49-39(55)21(3)45-5)41(57)51-19-27(53)15-25(51)17-31-29-11-9-23(43)13-35(29)47-37(31)38-32(30-12-10-24(44)14-36(30)48-38)18-26-16-28(54)20-52(26)42(58)34(8-2)50-40(56)22(4)46-6/h9-14,21-22,25-28,33-34,45-48,53-54H,7-8,15-20H2,1-6H3,(H,49,55)(H,50,56)/t21-,22-,25-,26-,27-,28-,33-,34-/m0/s1

InChiKey

PKWRMUKBEYJEIX-DXXQBUJASA-N

IUPAC Name

(2S)-N-[(2S)-1-[(2R,4S)-2-[[6-fluoro-2-[6-fluoro-3-[[(2R,4S)-4-hydroxy-1-[(2S)-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidin-2-yl]methyl]-1H-indol-2-yl]-1H-indol-3-yl]methyl]-4-hydroxypyrrolidin-1-yl]-1-oxobutan-2-yl]-2-(methylamino)propanamide