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SML1192

Sigma-Aldrich

SB290157 trifluoroacetate salt

≥97% (HPLC)

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Synonym(s):
N2-[2-(2,2-Diphenylethoxy)acetyl]-L-arginine trifluoroacetate salt, SB 290157 trifluoroacetate salt
Empirical Formula (Hill Notation):
C22H28N4O4 · CF3CO2H
CAS Number:
1140525-25-2
Molecular Weight:
526.51
UNSPSC Code:
12352200
PubChem Substance ID:
329825711
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

optical activity

[α]/D +1.5 to +5°, c = 1.0 in DMSO

storage condition

desiccated

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

NC(NCCC[C@@H](C(O)=O)NC(COCC(C1=CC=CC=C1)C2=CC=CC=C2)=O)=N.FC(F)(C(O)=O)F

InChI

1S/C22H28N4O4.C2HF3O2/c23-22(24)25-13-7-12-19(21(28)29)26-20(27)15-30-14-18(16-8-3-1-4-9-16)17-10-5-2-6-11-17;3-2(4,5)1(6)7/h1-6,8-11,18-19H,7,12-15H2,(H,26,27)(H,28,29)(H4,23,24,25);(H,6,7)/t19-;/m0./s1

InChI key

ZJRMPPVJAQWGEG-FYZYNONXSA-N

Biochem/physiol Actions

SB290157 is a selective antagonist of complement anaphylatoxin C3a receptor, a 74 amino acid proinflammatory peptide that is a potent chemotaxin for eosinophils, macrophages and mast cells, and has recently been found to be involved in nonimmunological roles in osteoblast differentiation, angiogenesis, and lipid metabolism. SB290157 is selective for C3aR over C5aR or other chemotactic GPCRs with an IC50 of 200 nM. It effectively blocks C3aR in humans, rat, guinea pig, and mouse.SB290157 was found to inhibit diet-induced obesity, metabolic dysfunction, and adipocyte signaling, in addition to inhibiting macrophage signaling.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Y Zhang et al.
Clinical and experimental immunology, 189(1), 60-70 (2017-03-16)
Complement activation has a deep pathogenic influence in immunoglobulin (Ig)A nephropathy (IgAN). C3a and C5a, small cleavage fragments generated by complement activation, are key mediators of inflammation. The fragments exert broad proinflammatory effects by binding to specific receptors (C3aR and

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