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.

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Formula

C15H20ClNO4

Net Charge

Average Mass

313.77634

Monoisotopic Mass

313.10809

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	Details
Salinispora tropica (NCBI:txid168695)	of strain CNB-392 See: 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.

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

Last Modified

08 August 2014