Molecule ID: 11347535

IUPAC Name: (1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

Description: The molecule is a salinosporamide in which the core (1R)-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione skeleton is substituted at positions 1, 4, and 5 by (1S)-cyclohex-2-en-1-yl(hydroxy)methyl, 2-chloroethyl, and methyl groups, respectively (the 1R,4R,5S diastereoisomer). A potent proteasome inhibitor, it has attracted interest for potential use in the treatment of various cancers. It has a role as an antineoplastic agent and a proteasome inhibitor. It is a salinosporamide, an organochlorine compound, an organic heterobicyclic compound, a beta-lactone and a gamma-lactam.

SMILES: C[C@@]12OC(=O)[C@]1([C@@H](O)[C@@H]1C=CCCC1)N=C(O)[C@@H]2CCCl

SELFIES: [C][C@@][O][C][=Branch1][C][=O][C@][Ring1][Branch1][Branch1][=N][C@@H1][Branch1][C][O][C@@H1][C][=C][C][C][C][Ring1][=Branch1][N][=C][Branch1][C][O][C@@H1][Ring1][P][C][C][Cl]

InChI: InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1

Molecular Properties:
- Polar Surface Area: 75.6 Ų
- LogP: 1.8