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salinosporamide A (CHEBI:48045)

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ChEBI Name salinosporamide A
ChEBI ID CHEBI:48045
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula Source
C15H20ClNO4 ChEBI
Net Charge 0
Average Mass 313.77634
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
SMILES
[H][C@@]1(CCCC=C1)[C@H](O)[C@@]12NC(=O)[C@H](CCCl)[C@]1(C)OC2=O
Metabolite of Species Source
Isolated from Salinispora tropica (NCBI:168695) of strain CNB-392 PubMed
Roles Classification
Biological Role(s): marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
(via salinosporamide )
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via salinosporamide )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
proteasome inhibitor
A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-lactone (CHEBI:49043)
salinosporamide A (CHEBI:48045) is a γ-lactam (CHEBI:74222)
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)
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 Sources
marizomib WHO MedNet
marizomib WHO MedNet
marizomib WHO MedNet
marizomibum WHO MedNet
Synonyms Sources
(−)-salinosporamide A ChemIDplus
ML 858 ChemIDplus
NPI 0052 ChemIDplus
NPI-0052 ChemIDplus
Database Links Databases
C00040190 KNApSAcK
CPD-12674 MetaCyc
D09640 KEGG DRUG
Salinosporamide_A Wikipedia
View more database links
Registry Numbers Types Sources
437742-34-2 CAS Registry Number ChemIDplus
9349224 Beilstein Registry Number Beilstein
9349224 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12548698 PubMed citation CiteXplore
15916417 PubMed citation CiteXplore
17121896 PubMed citation CiteXplore
17497868 PubMed citation CiteXplore
17609425 PubMed citation CiteXplore
18939815 PubMed citation CiteXplore
19022674 PubMed citation CiteXplore
19133779 PubMed citation CiteXplore
20479958 PubMed citation CiteXplore
21058386 PubMed citation CiteXplore
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21303921 PubMed citation CiteXplore
21591679 PubMed citation CiteXplore
21824108 PubMed citation CiteXplore
22195555 PubMed citation CiteXplore
22500807 PubMed citation CiteXplore
24737138 PubMed citation CiteXplore
25068416 PubMed citation CiteXplore
Last Modified
08 agosto 2014

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