Salinosporamide B

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461724

CAS#: 863126-95-8

Description: Salinosporamide B is a deschloro analog isolated from the marine Actinomycete Salinispora tropica.


Chemical Structure

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Salinosporamide B
CAS# 863126-95-8

Theoretical Analysis

MedKoo Cat#: 461724
Name: Salinosporamide B
CAS#: 863126-95-8
Chemical Formula: C15H21NO4
Exact Mass: 279.1471
Molecular Weight: 279.33
Elemental Analysis: C, 64.50; H, 7.58; N, 5.01; O, 22.91

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Salinosporamide B;

IUPAC/Chemical Name: (1R,4R,5S)-1-(((S)-cyclohex-2-en-1-yl)(hydroxy)methyl)-4-ethyl-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

InChi Key: SCJZQKFFYIGMCI-BOZRLRFCSA-N

InChi Code: InChI=1S/C15H21NO4/c1-3-10-12(18)16-15(13(19)20-14(10,15)2)11(17)9-7-5-4-6-8-9/h5,7,9-11,17H,3-4,6,8H2,1-2H3,(H,16,18)/t9-,10+,11?,14+,15+/m1/s1

SMILES Code: O=C([C@H](CC)[C@]1(C)O2)N[C@@]1(C([C@@H]3C=CCCC3)O)C2=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 279.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Beer LL, Moore BS. Biosynthetic convergence of salinosporamides A and B in the marine actinomycete Salinispora tropica. Org Lett. 2007 Mar 1;9(5):845-8. Epub 2007 Feb 3. PubMed PMID: 17274624.

2: Dineshkumar K, Vasudevan A, Hopper W. Ligand Based-Pharmacophore Modeling and Extended Bi oactivity Prediction for Salinosporamide A, B and C from Marine Actino mycetes Salinispora tropica. Comb Chem High Throughput Screen. 2017;20(1):3-19. doi: 10.2174/1386207319666161215154128. PubMed PMID: 28000560.

3: Manam RR, Macherla VR, Tsueng G, Dring CW, Weiss J, Neuteboom ST, Lam KS, Potts BC. Antiprotealide is a natural product. J Nat Prod. 2009 Feb 27;72(2):295-7. doi: 10.1021/np800578e. PubMed PMID: 19133779.

4: Tsueng G, McArthur KA, Potts BC, Lam KS. Unique butyric acid incorporation patterns for salinosporamides A and B reveal distinct biosynthetic origins. Appl Microbiol Biotechnol. 2007 Jul;75(5):999-1005. Epub 2007 Mar 6. PubMed PMID: 17340108.

5: Williams PG, Buchanan GO, Feling RH, Kauffman CA, Jensen PR, Fenical W. New cytotoxic salinosporamides from the marine Actinomycete Salinispora tropica. J Org Chem. 2005 Aug 5;70(16):6196-203. PubMed PMID: 16050677.

6: Reed KA, Manam RR, Mitchell SS, Xu J, Teisan S, Chao TH, Deyanat-Yazdi G, Neuteboom ST, Lam KS, Potts BC. Salinosporamides D-J from the marine actinomycete Salinispora tropica, bromosalinosporamide, and thioester derivatives are potent inhibitors of the 20S proteasome. J Nat Prod. 2007 Feb;70(2):269-76. Epub 2007 Jan 23. PubMed PMID: 17243724.

7: Tsueng G, Lam KS. A low-sodium-salt formulation for the fermentation of salinosporamides by Salinispora tropica strain NPS21184. Appl Microbiol Biotechnol. 2008 Apr;78(5):821-6. doi: 10.1007/s00253-008-1357-x. Epub 2008 Feb 1. PubMed PMID: 18239916.

8: Eustáquio AS, Moore BS. Mutasynthesis of fluorosalinosporamide, a potent and reversible inhibitor of the proteasome. Angew Chem Int Ed Engl. 2008;47(21):3936-8. doi: 10.1002/anie.200800177. PubMed PMID: 18407559.

9: Tsueng G, Sing Lam K. Effect of cobalt and vitamin B12 on the production of salinosporamides by Salinispora tropica. J Antibiot (Tokyo). 2009 Apr;62(4):213-6. doi: 10.1038/ja.2009.7. Epub 2009 Feb 6. PubMed PMID: 19198638.