Neoseptin-3

SIGMA/SML1686 - ≥98% (HPLC)

Synonym: (αS)-α-[[4-Amino-3-[2-(4-hydroxyphenyl)ethyl]benzoyl]amino]-benzenebutanoic acid 1,1-dimethylethyl ester

CAS Number: 1622863-21-1
Empirical Formula (Hill Notation): C₂₉H₃₄N₂O₄
Molecular Weight: 474.59
Linear Formula: C₂₉H₃₄N₂O₄
Product Type: Chemical

assay	≥98% (HPLC)
color	white to beige
form	powder
InChI	1S/C29H34N2O4/c1-29(2,3)35-28(34)26(18-12-20-7-5-4-6-8-20)31-27(33)23-14-17-25(30)22(19-23)13-9-21-10-15-24(32)16-11-21/h4-8,10-11,14-17,19,26,32H,9,12-13,18,30H2,1-3H3,(H,31,33)/t26-/m0/s1
InChI key	OACODUCFPHHCIH-SANMLTNESA-N
optical activity	[α]/D 37 to 45°, c = 0.1 in chloroform
Quality Level	100
SMILES string	NC1=CC=C(C(N[C@@H](CCC2=CC=CC=C2)C(OC(C)(C)C)=O)=O)C=C1CCC3=CC=C(O)C=C3
solubility	DMSO: 15 mg/mL, clear
storage temp.	−20°C

Biochem/physiol Actions:	Highly efficacious and specific agonist of mouse TLR4/MD-2
Biochem/physiol Actions:	Neoseptin-3 is a highly efficacious and specific agonist of the mouse TLR4 (mTLR4)/myeloid differentiation factor 2 (MD-2) complex. Neoseptin-3 binds to MD2, changes the conformation of MD-2 and facilitates active TLR4/MD-2 dimer formation. Neoseptin-3 exhibits no structural similarity to lipid A.
Biochem/physiol Actions:	Neoseptin-3 stimulates the activity of mouse TLR4 (mTLR4)/myeloid differentiation factor 2 (mTLR) independently of CD14 (cluster of differentiation 14). This activated mTLR4/ mTLR promotes canonical myeloid differentiation primary response gene 88 (MyD88) and toll-interleukin(IL) 1 receptor (TIR) domain-containing adaptor inducing interferon (IFN)-β (TRIF)-dependent signaling. In addition, neoseptin-3 also stimulates tumor necrosis factor α (TNF-α), IL-6 and IFNβ production in a dose-dependent manner.
Packaging:	5, 25 mg in glass bottle

Hazard statements	H413
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable