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CHEBI:48045 - salinosporamide A

ChEBI IDCHEBI:48045
ChEBI Namesalinosporamide A
Stars
DefinitionA 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.
Last Modified8 August 2014
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC15H20ClNO4
Net Charge0
Average Mass313.781
Monoisotopic Mass313.10809
SMILES[H][C@@]1([C@H](O)[C@@]23NC(=O)[C@H](CCCl)[C@]2(C)OC3=O)C=CCCC1
InChIInChI=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
InChIKeyNGWSFRIPKNWYAO-SHTIJGAHSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Salinispora tropica (ncbitaxon:168695) - PubMed (12548698) Strain: CNB-392
Roles Classification
Biological Roles:
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Applications:
proteasome inhibitor  A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
salinosporamide A (CHEBI:48045) has role antineoplastic agent (CHEBI:35610)
salinosporamide A (CHEBI:48045) has role proteasome inhibitor (CHEBI:52726)
salinosporamide A (CHEBI:48045) is a organic heterobicyclic compound (CHEBI:27171)
salinosporamide A (CHEBI:48045) is a organochlorine compound (CHEBI:36683)
salinosporamide A (CHEBI:48045) is a salinosporamide (CHEBI:48046)
salinosporamide A (CHEBI:48045) is a β-lactone (CHEBI:49043)
salinosporamide A (CHEBI:48045) is a γ-lactam (CHEBI:74222)
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
INNs  Source
marizomibWHO MedNet
marizomibWHO MedNet
marizomibWHO MedNet
marizomibumWHO MedNet
Synonyms  Source
ML 858ChemIDplus
NPI 0052ChemIDplus
NPI-0052ChemIDplus
(−)-salinosporamide AChemIDplus
Manual XrefsDatabases
C00040190KNApSAcK
CPD-12674MetaCyc
D09640KEGG DRUG
Salinosporamide_AWikipedia
Registry NumbersSources
Reaxys:9349224Reaxys
CAS:437742-34-2ChemIDplus
Citations