Compounds
| ID | Spectrum Quality | Annotated Name |
|---|---|---|
| CCMSLIB00005721043 | Gold | 3 |
COMPOUND NPA011013
PROPERTIES
| NPAID | NPA011013 |
|---|---|
| CLUSTER ID | 841 |
| NODE ID | 730 |
| NAME | Salinosporamide A |
| FORMULA | C15H20ClNO4 |
| MOLECULAR WEIGHT (Da) | 313.7810 |
| ACCURATE MASS (Da) | 313.1081 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Salinispora |
| ORIGIN SPECIES | sp. strain CNB-392 |
| InChIKey | NGWSFRIPKNWYAO-SHTIJGAHSA-N |
| 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 |
| SMILES | C[C@]12[C@H](C(=O)N[C@]1(C(=O)O2)[C@H]([C@H]3CCCC=C3)O)CCCl |
ORIGINAL ISOLATION REFERENCE
| CITATION | Feling, Robert H; Buchanan, Greg O; Mincer, Tracy J; Kauffman, Christopher A; Jensen, Paul R; Fenical, William Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora Angewandte Chemie International Edition 2003 42 (3) 355-357. | ||
|---|---|---|---|
| DOI | 10.1002/anie.200390115 | PMID | 12548698 |
SYNTHESES
| CITATION 1 | Ma G; Nguyen H; Romo D Concise total synthesis of (+/-)-salinosporamide A, (+/-)-cinnabaramide A, and derivatives via a bis-cyclization process: implications for a biosynthetic pathway? Organic Letters 2007 9 (11) 2143-2146. DOI: 10.1021/ol070616u PMID: 17477539 | ||
|---|---|---|---|
| CITATION 2 | Endo A; Danishefsky SJ Total synthesis of salinosporamide A. Journal of the American Chemical Society 2005 127 (23) 8298-9. DOI: 10.1021/ja0522783 PMID: 15941259 | ||
| CITATION 3 | Reddy LR; Fournier JF; Reddy BV; Corey EJ New synthetic route for the enantioselective total synthesis of salinosporamide A and biologically active analogues. Organic Letters 2005 7 (13) 2699-701. DOI: 10.1021/ol0508734 PMID: 15957925 | ||
| CITATION 4 | Mulholland NP; Pattenden G; Walters IA A concise total synthesis of salinosporamide A. Organic & Biomolecular Chemistry 2006 4 (15) 2845-6. DOI: 10.1039/b607109k PMID: 16855730 | ||
| CITATION 5 | Shibasaki M; Kanai M; Fukuda N Total synthesis of lactacystin and salinosporamide A. Chemistry - An Asian Journal 2007 2 (1) 20-38. DOI: 10.1002/asia.200600310 PMID: 17441136 | ||
| CITATION 6 | Ling T; Macherla VR; Manam RR; McArthur KA; Potts BC Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052). Organic Letters 2007 9 (12) 2289-92. DOI: 10.1021/ol0706051 PMID: 17497868 | ||
| CITATION 7 | Mulholland NP; Pattenden G; Walters IA A concise and straightforward total synthesis of (+/-)-salinosporamide A, based on a biosynthesis model. Organic & Biomolecular Chemistry 2008 6 (15) 2782-9. DOI: 10.1039/b803818j PMID: 18633536 | ||
| CITATION 8 | Fukuda T; Sugiyama K; Arima S; Harigaya Y; Nagamitsu T; Omura S Total synthesis of salinosporamide A. Organic Letters 2008 10 (19) 4239-42. DOI: 10.1021/ol8016066 PMID: 18763797 | ||
| CITATION 9 | Nguyen H; Ma G; Romo D A(1,3)-strain enabled retention of chirality during bis-cyclization of beta-ketoamides: total synthesis of (-)-salinosporamide A and (-)-homosalinosporamide A. Chemical Communications 2010 46 (26) 4803-5. DOI: 10.1039/c0cc00607f PMID: 20498903 | ||
| CITATION 10 | Kaiya Y; Hasegawa J; Momose T; Sato T; Chida N Total synthesis of (-)-salinosporamide A. Chemistry - An Asian Journal 2011 6 (1) 209-19. DOI: 10.1002/asia.201000602 PMID: 21058386 | ||
| CITATION 11 | Satoh N; Yokoshima S; Fukuyama T Total synthesis of (-)-salinosporamide A. Organic Letters 2011 13 (12) 3028-31. DOI: 10.1021/ol200886j PMID: 21591679 | ||
