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 N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:48045 N
ChEMBL	ChEMBL371405 N
ChemSpider	9522473 N
KEGG	D09640
PubChem CID	11347535
UNII	703P9YDP7F Y
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 N Key: NGWSFRIPKNWYAO-SHTIJGAHSA-N 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). N verify (what is YN ?) 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.^[1][2] 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.