(-)-Salinosporamide A
(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
Molecular Identity
(-)-Salinosporamide A
(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
PubChem CID: 11347535
Salinosporamide A 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 an organic heterobicyclic compound, an organochlorine compound, a salinosporamide, a beta-lactone and a gamma-lactam.
2D Structure
Properties
C15H20ClNO4
Molecular Formula
313.77
Molecular Weight
g/mol
313.1081
Exact Mass
Da
1.8
XLogP
Drug-like (Lipinski: < 5)
75.6
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
4
H-Bond Acceptors
508
Complexity
SMILES
Canonical SMILES
SMILES: CC12C(C(=O)NC1(C(=O)O2)C(C3CCCC=C3)O)CCClIsomeric SMILES
SMILES: C[C@]12[C@H](C(=O)N[C@]1(C(=O)O2)[C@H]([C@H]3CCCC=C3)O)CCClSynonyms(20)
MARIZOMIBsalinosporamide A437742-34-2(-)-Salinosporamide ANPI-0052marizomibumML 858703P9YDP7FCHEBI:48045DTXSID009040196-OXA-2-AZABICYCLO(3.2.0)HEPTANE-3,7-DIONE, 4-(2-CHLOROETHYL)-1-((S)-(1S)-2-CYCLOHEXEN-1-YLHYDROXYMETHYL)-5-METHYL-, (1R,4R,5S)-(1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione(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-dioneSalinosporin A(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
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to (-)-Salinosporamide A
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