Amastatin

Amastatin
Clinical data
ATC code	None;
Identifiers
	IUPAC name (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-Amino-2-hydroxy-5-methylhexanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]butanedioic acid;
CAS Number	67655-94-1;
PubChem CID	439518;
ChemSpider	388612;
KEGG	C01552;
CompTox Dashboard (EPA)	DTXSID10987015 ;
ECHA InfoCard	100.131.532
Chemical and physical data
Formula	C21H38N4O8
Molar mass	474.555 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)CC(C(C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CC(=O)O)C(=O)O)O)N;
	InChI InChI=1S/C21H38N4O8/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33)/t12-,13+,15+,16+,17+/m1/s1; Key:QFAADIRHLBXJJS-ZAZJUGBXSA-N;

Amastatin, also known as 3-amino-2-hydroxy-5-methylhexanoyl-L-valyl-L-valyl-L-aspartic acid, is a naturally occurring, competitive and reversible aminopeptidase inhibitor that was isolated from Streptomyces sp. ME 98-M3.^[1] It specifically inhibits leucyl aminopeptidase, alanyl aminopeptidase (aminopeptidase M/N), bacterial leucyl aminopeptidase (Aeromonas proteolytica aminopeptidase), leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase),^[2] and, to a lesser extent, glutamyl aminopeptidase (aminopeptidase A),^[3] as well as other aminopeptidases.^[4] It does not inhibit arginyl aminopeptidase (aminopeptidase B).^[5]^[6] Amastatin has been found to potentiate the central nervous system effects of oxytocin and vasopressin in vivo.^[7] It also inhibits the degradation of met-enkephalin, dynorphin A, and other endogenous peptides.^[8]