Terminology Service for NFDI4Health
JSON

salinosporamide A

Go to external page http://purl.obolibrary.org/obo/CHEBI_48045

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.

Term info

Label

salinosporamide A

Synonyms
  • (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
database cross reference
Subsets

3_STAR

IUPAC NAME
(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 [ IUPAC ]

INN
marizomib [ WHO_MedNet ]

INN
marizomibum [ WHO_MedNet ]

charge

0

formula

C15H20ClNO4

has obo namespace

chebi_ontology

has related synonym

(-)-salinosporamide A, marizomibum, NPI-0052, marizomib, ML 858, NPI 0052

id

CHEBI:48045

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

inchikey

NGWSFRIPKNWYAO-SHTIJGAHSA-N

mass

313.77634

monoisotopicmass

313.10809

smiles

[H][C@@]1(CCCC=C1)[C@H](O)[C@@]12NC(=O)[C@H](CCCl)[C@]1(C)OC2=O