Novobiocin Free Base | CAS# 303-81-1 (free base) | antibiotic

MedKoo Cat#: 413360 | Name: Novobiocin Free Base

Description:

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

Novobiocin Free Base is an antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity.

Chemical Structure

Novobiocin Free Base

CAS#303-81-1 (free base)

Theoretical Analysis

MedKoo Cat#: 413360

Name: Novobiocin Free Base

CAS#: 303-81-1 (free base)

Chemical Formula: C31H36N2O11

Exact Mass: 612.2319

Molecular Weight: 612.63

Elemental Analysis: C, 60.78; H, 5.92; N, 4.57; O, 28.73

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

303-81-1 (free base) 1476-53-5 (Na) 4309-70-0 (Ca)

Synonym

Novobiocin Free Base; HSDB7443; HSDB-7443; HSDB 7443

IUPAC/Chemical Name

(3R,4S,5R,6R)-5-hydroxy-6-((4-hydroxy-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido)-8-methyl-2-oxo-2H-chromen-7-yl)oxy)-3-methoxy-2,2-dimethyltetrahydro-2H-pyran-4-yl carbamate

InChi Key

YJQPYGGHQPGBLI-KGSXXDOSSA-N

InChi Code

InChI=1S/C31H36N2O11/c1-14(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/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37)/t23-,25+,26-,29-/m1/s1

SMILES Code

CO[C@@H]1[C@H]([C@H]([C@@H](OC1(C)C)Oc2c(C)c3c(C(O)=C(C(O3)=O)NC(c4cc(C/C=C(C)\C)c(O)cc4)=O)cc2)O)OC(N)=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

>2 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

More Info

Instruction

View handling instruction

	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 612.63 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: Dlugosz A, Janecka A. Novobiocin Analogs as Potential Anticancer Agents. Mini Rev Med Chem. 2017;17(9):728-733. doi: 10.2174/1389557516666161223155525. PMID: 28019639. 2: 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. PMID: 29746111; PMCID: PMC5990483. 3: Riley HD Jr. Vancomycin and novobiocin. Med Clin North Am. 1970 Sep;54(5):1277-89. PMID: 4248512. 4: Suzuki K, Taniyama K, Aoyama T, Watanabe Y. Usefulness of novobiocin as a selective inhibitor of intestinal breast cancer resistance protein (Bcrp) in rats. Xenobiotica. 2020 Sep;50(9):1121-1127. doi: 10.1080/00498254.2019.1708514. Epub 2020 Jan 3. PMID: 31868552. 5: Sun G, de Resende PE, Stapleton P, Kuta M, Wang X, Haider S, Yang M. Regioselective glycosylation of novobiocin alters activity. Carbohydr Res. 2017 Nov 27;452:116-121. doi: 10.1016/j.carres.2017.10.011. Epub 2017 Oct 22. PMID: 29096184. 6: 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. PMID: 29135241; PMCID: PMC5735422. 7: Idowu T, Ammeter D, Rossong H, Zhanel GG, Schweizer F. Homodimeric Tobramycin Adjuvant Repurposes Novobiocin as an Effective Antibacterial Agent against Gram- Negative Bacteria. J Med Chem. 2019 Oct 24;62(20):9103-9115. doi: 10.1021/acs.jmedchem.9b00876. Epub 2019 Oct 9. PMID: 31557020. 8: Donnelly A, Blagg BS. Novobiocin and additional inhibitors of the Hsp90 C-terminal nucleotide-binding pocket. Curr Med Chem. 2008;15(26):2702-17. doi: 10.2174/092986708786242895. PMID: 18991631; PMCID: PMC2729083. 9: Hall JA, Seedarala S, Zhao H, Garg G, Ghosh S, Blagg BS. Novobiocin Analogues That Inhibit the MAPK Pathway. J Med Chem. 2016 Feb 11;59(3):925-33. doi: 10.1021/acs.jmedchem.5b01354. Epub 2016 Jan 27. PMID: 26745854; PMCID: PMC5444390. 10: HOEKSEMA H, SMITH CG. Novobiocin. Prog Ind Microbiol. 1961;3:91-139. PMID: 13714897.