Molecule ID: 9928315

IUPAC Name: (2S,3S)-3-[[(2S)-1-(4-aminobutylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]oxirane-2-carboxylic acid

Description: The molecule is a dicarboxylic acid monoamide obtained by the formal condensation of the carboxylic group of oxirane-2,3-dicarboxylic acid with the amino group of N-(4-aminobutyl)-L-phenylalaninamide (the 2S,3S stereoisomer). An antibiotic isolated from the fermentation broth of Penicillium citrinum, it acts as a potent inhibitor of cysteine protease. It has a role as an antimicrobial agent, a cysteine protease inhibitor and a Penicillium metabolite. It is a monocarboxylic acid, a primary amino compound, an epoxide and a dicarboxylic acid monoamide.

SMILES: NCCCCN=C(O)[C@H](Cc1ccccc1)N=C(O)[C@H]1O[C@@H]1C(=O)O

SELFIES: [N][C][C][C][C][N][=C][Branch1][C][O][C@H1][Branch1][#Branch2][C][C][=C][C][=C][C][=C][Ring1][=Branch1][N][=C][Branch1][C][O][C@H1][O][C@@H1][Ring1][Ring1][C][=Branch1][C][=O][O]

InChI: InChI=1S/C17H23N3O5/c18-8-4-5-9-19-15(21)12(10-11-6-2-1-3-7-11)20-16(22)13-14(25-13)17(23)24/h1-3,6-7,12-14H,4-5,8-10,18H2,(H,19,21)(H,20,22)(H,23,24)/t12-,13-,14-/m0/s1

Molecular Properties:
- Polar Surface Area: 134.0 Ų
- LogP: -2.3