Molecule ID: 21597398

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

Description: The molecule is a carboxamide obtained by the formal condensation of the carboxylic group of oxirane-2,3-dicarboxylic acid with the amino group of N-(4-aminobutyl)-L-tyrosinamide (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 an epoxide, a monocarboxylic acid, a primary amino compound, a member of phenols and a dicarboxylic acid monoamide.

SMILES: NCCCCN=C(O)[C@H](Cc1ccc(O)cc1)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][=N][C][C][=C][C][=C][Branch1][C][O][C][=C][Ring1][#Branch1][N][=C][Branch1][C][O][C@H1][O][C@@H1][Ring1][Ring1][C][=Branch1][C][=O][O]

InChI: InChI=1S/C17H23N3O6/c18-7-1-2-8-19-15(22)12(9-10-3-5-11(21)6-4-10)20-16(23)13-14(26-13)17(24)25/h3-6,12-14,21H,1-2,7-9,18H2,(H,19,22)(H,20,23)(H,24,25)/t12-,13-,14-/m0/s1

Molecular Properties:
- Polar Surface Area: 154.0 Ų
- LogP: -2.7