TAPI-1, TNF alpha processing inhibitor

Key facts

CAS number

171235-71-5

Purity

>95%

Form

Solid

form

Molecular weight

499.6 Da

Molecular formula

C₂₆H₃₇N₅O₅

PubChem

9827273

Nature

Synthetic

Solubility

Soluble in DMSO to 10 mM

Biochemical name

TNF-alpha Protease Inhibitor-1

Biological description

Stable, selective inhibitor of TNF-α processing (IC₅₀ = ~100 nM). Inhibits TACE (P< 0.01) and other metalloproteases in vivo. Blocks release of TNF-α (IC₅₀ = 50-100 μM), APP (IC₅₀ = 1-8 μM), ACE (IC₅₀ = 10 μM), IL6R (IC₅₀ = 5-10 μM), TNFRI (IC₅₀ = 5-10 μM), TNFRII (IC₅₀ = 25-50 μM), and ObRa (leptin receptor), but not CSF-1 in vivo. Structural analog of TAPI-0.

Canonical smiles

CC(C)CC(CC(=O)NO)C(=O)NC(CC1=CC2=CC=CC=C2C=C1)C(=O)NC(C)C(=O)NCCN

Isomeric smiles

C[C@@H](C(=O)NCCN)NC(=O)[C@H](CC1=CC2=CC=CC=C2C=C1)NC(=O)C(CC(C)C)CC(=O)NO

InChi

InChI=1S/C26H37N5O5/c1-16(2)12-21(15-23(32)31-36)25(34)30-22(26(35)29-17(3)24(33)28-11-10-27)14-18-8-9-19-6-4-5-7-20(19)13-18/h4-9,13,16-17,21-22,36H,10-12,14-15,27H2,1-3H3,(H,28,33)(H,29,35)(H,30,34)(H,31,32)/t17-,21?,22-/m0/s1

InChiKey

AWNBSWDIOCXWJW-OWHMDLSXSA-N

IUPAC Name

N-[(2S)-1-[[(2S)-1-(2-aminoethylamino)-1-oxopropan-2-yl]amino]-3-naphthalen-2-yl-1-oxopropan-2-yl]-N'-hydroxy-2-(2-methylpropyl)butanediamide