Salinosporamide A

Salinosporamide A
Names
	Preferred 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
	Other names Marizomib; NPI-0052
Identifiers
CAS Number	437742-34-2 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:48045 ;
ChEMBL	ChEMBL371405 ;
ChemSpider	9522473 ;
KEGG	D09640;
PubChem CID	11347535;
UNII	703P9YDP7F ;
CompTox Dashboard (EPA)	DTXSID00904019 ;
	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 Key: NGWSFRIPKNWYAO-SHTIJGAHSA-N ; InChI=1/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 Key: NGWSFRIPKNWYAO-SHTIJGAHBB;
	SMILES O=C1O[C@@]3(C)[C@H](C(=O)N[C@@]13[C@@H](O)[C@@H]2/C=C\CCC2)CCCl; C[C@]13OC(=O)C3(NC(=O)[C@@H]1CCCl)[C@@H](O)C2/C=C\CCC2;
Properties
Chemical formula	C15H20ClNO4
Molar mass	313.781 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Salinosporamide A (Marizomib) is a potent proteasome inhibitor being studied as a potential anticancer agent. It entered phase I human clinical trials for the treatment of multiple myeloma, only three years after its discovery in 2003. This marine natural product is produced by the obligate marine bacteria Salinispora tropica and Salinispora arenicola, which are found in ocean sediment. Salinosporamide A belongs to a family of compounds, known collectively as salinosporamides, which possess a densely functionalized γ-lactam-β-lactone bicyclic core.