TAPI-2, MMP and ADAM inhibitor

Key facts

CAS number

689284-12-6

Purity

>95%

Form

Solid

form

Molecular weight

415.5 Da

Molecular formula

C₁₉H₃₇N₅O₅

PubChem

10093303

Nature

Synthetic

Solubility

Soluble in water to 50 mM

Biochemical name

N-(R)-[2-(Hydroxyaminocarbonyl)methyl]-4-methylpentanoyl-L-t-butyl-alanyl-L-alanine, 2-aminoethyl Amide

Biological description

Broad spectrum inhibitor of TACE (TNF-α convertase/ADAM17/α-secre​tase), MMPs and other ADAMs. Blocks phorbol-​12-​myristate-​13-​acetate-​induced (PMA) shedding of cell surface proteins such as TGF-​α and β-amyloid precursor protein (IC₅₀ = 10 μM). Inhibits TNF-α release.

Canonical smiles

CC(C)CC(CC(=O)NO)C(=O)NC(C(=O)NC(C)C(=O)NCCN)C(C)(C)C

Isomeric smiles

C[C@@H](C(=O)NCCN)NC(=O)[C@H](C(C)(C)C)NC(=O)C(CC(C)C)CC(=O)NO

InChi

InChI=1S/C19H37N5O5/c1-11(2)9-13(10-14(25)24-29)17(27)23-15(19(4,5)6)18(28)22-12(3)16(26)21-8-7-20/h11-13,15,29H,7-10,20H2,1-6H3,(H,21,26)(H,22,28)(H,23,27)(H,24,25)/t12-,13?,15+/m0/s1

InChiKey

LMIQCBIEAHJAMZ-RMTCENKZSA-N

IUPAC Name

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