Molecule ID: 70678756

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

Description: The molecule is an epoxide which is a carboxamide obtained by the formal condensation of one of the carboxy groups of oxirane-2,3-dicarboxylic acid with N-{3-[(4-aminobutyl)amino]propyl}-L-tyrosinamide. It is a natural product, isolated from Gliocladium sp. F-2665. TMC-52A acts as an inhibitor of cysteine proteinases, particularly cathepsin B (EC 3.4.22.1), cathepsin L (EC 3.4.22.15), and papain (EC 3.4.22.2); IC50 values are 320 nM, 13 nM, and 44 nM, respectively. The epoxide group has trans configuration but its exact stereochemistry is uncertain: it is either (2R,3R) or (2S,3S). It has a role as an antimicrobial agent, a cathepsin L (EC 3.4.22.15) inhibitor, an EC 3.4.22.2 (papain) inhibitor, a cathepsin B inhibitor and a fungal metabolite. It is an epoxide, a monocarboxylic acid, a member of phenols, a primary amino compound, a secondary amino compound and a dicarboxylic acid monoamide.

SMILES: NCCCCNCCCN=C(O)[C@H](Cc1ccc(O)cc1)N=C(O)C1OC1C(=O)O

SELFIES: [N][C][C][C][C][N][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][O][C][Ring1][Ring1][C][=Branch1][C][=O][O]

InChI: InChI=1S/C20H30N4O6/c21-8-1-2-9-22-10-3-11-23-18(26)15(12-13-4-6-14(25)7-5-13)24-19(27)16-17(30-16)20(28)29/h4-7,15-17,22,25H,1-3,8-12,21H2,(H,23,26)(H,24,27)(H,28,29)/t15-,16?,17?/m0/s1

Molecular Properties:
- Polar Surface Area: 166.0 Ų
- LogP: -2.7