Synonym
Albamycin, Novobiocin calcium
IUPAC/Chemical Name
calcium 7-(((2R,3R,4S,5R)-4-(carbamoyloxy)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido)-8-methyl-2-oxo-2H-chromen-4-olate
InChi Key
HEJBMFPJLCJWER-CWPVBXIBSA-L
InChi Code
1S/2C31H36N2O11.Ca/c2*1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29;/h2*7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q;;+2/p-2/t2*23-,25+,26-,29-;/m11./s1
SMILES Code
[Ca+2].CO[C@@H]1[C@@H](OC(=O)N)[C@@H](O)[C@H](Oc2ccc3C(=C(NC(=O)c4ccc(O)c(CC=C(C)C)c4)C(=O)Oc3c2C)[O-])OC1(C)C.CO[C@@H]5[C@@H](OC(=O)N)[C@@H](O)[C@H](Oc6ccc7C(=C(NC(=O)c8ccc(O)c(CC=C(C)C)c8)C(=O)Oc7c6C)[O-])OC5(C)C
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
2934.99.9001
|
Solvent |
mg/mL |
mM |
| Solubility |
| Soluble in DMSO |
0.0 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,263.33
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.
| 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 |
1: Mandler MD, Baidin V, Lee J, Pahil KS, Owens TW, Kahne D. Novobiocin Enhances Polymyxin Activity by Stimulating Lipopolysaccharide Transport. J Am Chem Soc. 2018 Jun 6;140(22):6749-6753. doi: 10.1021/jacs.8b02283. Epub 2018 May 16. PubMed PMID: 29746111; PubMed Central PMCID: PMC5990483.
2: May JM, Owens TW, Mandler MD, Simpson BW, Lazarus MB, Sherman DJ, Davis RM, Okuda S, Massefski W, Ruiz N, Kahne D. The Antibiotic Novobiocin Binds and Activates the ATPase That Powers Lipopolysaccharide Transport. J Am Chem Soc. 2017 Dec 6;139(48):17221-17224. doi: 10.1021/jacs.7b07736. Epub 2017 Nov 22. PubMed PMID: 29135241; PubMed Central PMCID: PMC5735422.
3: Dlugosz A, Janecka A. Novobiocin Analogs as Potential Anticancer Agents. Mini Rev Med Chem. 2017;17(9):728-733. doi: 10.2174/1389557516666161223155525. Review. PubMed PMID: 28019639.
4: Chen W, Wang D, Zhou W, Sang H, Liu X, Ge Z, Zhang J, Lan L, Yang CG, Chen H. Novobiocin binding to NalD induces the expression of the MexAB-OprM pump in Pseudomonas aeruginosa. Mol Microbiol. 2016 Jun;100(5):749-58. doi: 10.1111/mmi.13346. Epub 2016 Mar 16. PubMed PMID: 26844397.
5: Audisio D, Methy-Gonnot D, Radanyi C, Renoir JM, Denis S, Sauvage F, Vergnaud-Gauduchon J, Brion JD, Messaoudi S, Alami M. Synthesis and antiproliferative activity of novobiocin analogues as potential hsp90 inhibitors. Eur J Med Chem. 2014 Aug 18;83:498-507. doi: 10.1016/j.ejmech.2014.06.067. Epub 2014 Jun 28. PubMed PMID: 24992077.
