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MedKoo Cat#: 125843 | Name: Coumermycin sodium

Description:

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

Coumermycin is an antibacterial agent effective against Staphylococcus aureus and Staphylococcus epidermidis.

Chemical Structure

Coumermycin sodium
Coumermycin sodium
CAS#4575-42-2 (sodium)

Theoretical Analysis

MedKoo Cat#: 125843

Name: Coumermycin sodium

CAS#: 4575-42-2 (sodium)

Chemical Formula: C55H58N5NaO20

Exact Mass: 0.0000

Molecular Weight: 1132.07

Elemental Analysis: C, 58.35; H, 5.16; N, 6.19; Na, 2.03; O, 28.26

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.
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Related CAS #
4575-42-2 (sodium) 4434-05-3 (free base)
Synonym
Coumermycin sodium ;Sodium coumermycin A1; Coumermycin sodium; Coumermycin A1, sodium deriv
IUPAC/Chemical Name
sodium 7-(((2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-((5-methyl-1H-pyrrole-2-carbonyl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3-(4-((4-hydroxy-7-(((2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-((5-methyl-1H-pyrrole-2-carbonyl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)carbamoyl)-3-methyl-1H-pyrrole-2-carboxamido)-8-methyl-2-oxo-2H-chromen-4-olate
InChi Key
WTUXHNVTMYDUAM-DHHSFAMCSA-M
InChi Code
InChI=1S/C55H59N5O20.Na/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30;/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66);/q;+1/p-1/t38-,39-,42+,43+,44-,45-,52-,53-;/m1./s1
SMILES Code
[Na+].CO[C@@H]1[C@@H](OC(=O)C2=CC=C(C)N2)[C@@H](O)[C@H](OC3=C(C)C4=C(C=C3)C(O)=C(NC(=O)C5=CNC(C(=O)NC6=C([O-])C7=C(OC6=O)C(C)=C(O[C@@H]8OC(C)(C)[C@H](OC)[C@@H](OC(=O)C9=CC=C(C)N9)[C@H]8O)C=C7)=C5C)C(=O)O4)OC1(C)C
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 1,132.07 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
1: Kincade JM, deHaseth PL. Bacteriophage lambda promoters pL and pR: sequence determinants of in vivo activity and of sensitivity to the DNA gyrase inhibitor, coumermycin. Gene. 1991 Jan 2;97(1):7-12. PubMed PMID: 1847348. 2: Vanden Broeck A, McEwen AG, Chebaro Y, Potier N, Lamour V. Structural Basis for DNA Gyrase Interaction with Coumermycin A1. J Med Chem. 2019 Apr 25;62(8):4225-4231. doi: 10.1021/acs.jmedchem.8b01928. Epub 2019 Apr 3. PubMed PMID: 30920824. 3: Xu H, Wang ZX, Schmidt J, Heide L, Li SM. Genetic analysis of the biosynthesis of the pyrrole and carbamoyl moieties of coumermycin A1 and novobiocin. Mol Genet Genomics. 2002 Nov;268(3):387-96. Epub 2002 Oct 11. PubMed PMID: 12436260. 4: Novotna J, Gust B, Kulik A, Spizek J, Heide L. Five gene products are required for assembly of the central pyrrole moiety of coumermycin A1. J Ind Microbiol Biotechnol. 2013 Aug;40(8):915-25. doi: 10.1007/s10295-013-1266-6. Epub 2013 May 8. PubMed PMID: 23652970. 5: Cele FN, Kumalo H, Soliman ME. Mechanism of Inhibition of Hsp90 Dimerization by Gyrase B Inhibitor Coumermycin A1 (C-A1) Revealed by Molecular Dynamics Simulations and Thermodynamic Calculations. Cell Biochem Biophys. 2016 Sep;74(3):353-63. doi: 10.1007/s12013-016-0743-8. Epub 2016 Jul 4. PubMed PMID: 27376828. 6: Pacholec M, Tao J, Walsh CT. CouO and NovO: C-methyltransferases for tailoring the aminocoumarin scaffold in coumermycin and novobiocin antibiotic biosynthesis. Biochemistry. 2005 Nov 15;44(45):14969-76. PubMed PMID: 16274243. 7: Schmutz E, Steffensky M, Schmidt J, Porzel A, Li SM, Heide L. An unusual amide synthetase (CouL) from the coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis DSM 40489. Eur J Biochem. 2003 Nov;270(22):4413-9. PubMed PMID: 14622269. 8: Garneau-Tsodikova S, Stapon A, Kahne D, Walsh CT. Installation of the pyrrolyl-2-carboxyl pharmacophore by CouN1 and CouN7 in the late biosynthetic steps of the aminocoumarin antibiotics clorobiocin and coumermycin A1. Biochemistry. 2006 Jul 18;45(28):8568-78. PubMed PMID: 16834331. 9: Perronne CM, Malinverni R, Glauser MP. Treatment of Staphylococcus aureus endocarditis in rats with coumermycin A1 and ciprofloxacin, alone or in combination. Antimicrob Agents Chemother. 1987 Apr;31(4):539-43. PubMed PMID: 3606060; PubMed Central PMCID: PMC174774. 10: Neu HC, Chin NX, Labthavikul P. Antibacterial activity of coumermycin alone and in combination with other antibiotics. Antimicrob Agents Chemother. 1984 Jun;25(6):687-9. PubMed PMID: 6331295; PubMed Central PMCID: PMC185623. 11: Garneau S, Dorrestein PC, Kelleher NL, Walsh CT. Characterization of the formation of the pyrrole moiety during clorobiocin and coumermycin A1 biosynthesis. Biochemistry. 2005 Mar 1;44(8):2770-80. PubMed PMID: 15723521. 12: Fedorko J, Katz S, Allnoch H. In vitro activity of coumermycin A1. Appl Microbiol. 1969 Nov;18(5):869-73. PubMed PMID: 4391844; PubMed Central PMCID: PMC378103. 13: Samuels DS, Garon CF. Coumermycin A1 inhibits growth and induces relaxation of supercoiled plasmids in Borrelia burgdorferi, the Lyme disease agent. Antimicrob Agents Chemother. 1993 Jan;37(1):46-50. PubMed PMID: 8381639; PubMed Central PMCID: PMC187602. 14: Li SM, Westrich L, Schmidt J, Kuhnt C, Heide L. Methyltransferase genes in Streptomyces rishiriensis: new coumermycin derivatives from gene-inactivation experiments. Microbiology. 2002 Oct;148(Pt 10):3317-26. PubMed PMID: 12368465. 15: Jovanovich SB, Lebowitz J. Estimation of the effect of coumermycin A1 on Salmonella typhimurium promoters by using random operon fusions. J Bacteriol. 1987 Oct;169(10):4431-5. PubMed PMID: 2820924; PubMed Central PMCID: PMC213804. 16: Sekiguchi J, Stivers JT, Mildvan AS, Shuman S. Mechanism of inhibition of vaccinia DNA topoisomerase by novobiocin and coumermycin. J Biol Chem. 1996 Jan 26;271(4):2313-22. PubMed PMID: 8567695. 17: Farrar MA, Olson SH, Perlmutter RM. Coumermycin-induced dimerization of GyrB-containing fusion proteins. Methods Enzymol. 2000;327:421-9. PubMed PMID: 11045000. 18: Siebenberg S, Burkard N, Knuplesch A, Gust B, Grond S, Heide L. Two pathways for pyrrole formation in coumermycin A(1) biosynthesis: the central pyrrole moiety is formed from L-threonine. Chembiochem. 2011 Nov 25;12(17):2677-85. doi: 10.1002/cbic.201100494. Epub 2011 Sep 27. PubMed PMID: 21953874. 19: KAWAGUCHI H, NAITO T, TSUKIURA H. STUDIES ON COUMERMYCIN. A NEW ANTIBIOTIC. II. STRUCTURE OF COUMERMYCIN A1. J Antibiot (Tokyo). 1965 Jan;18:11-25. PubMed PMID: 14285468. 20: Zhao HF, Boyd J, Jolicoeur N, Shen SH. A coumermycin/novobiocin-regulated gene expression system. Hum Gene Ther. 2003 Nov 20;14(17):1619-29. PubMed PMID: 14633404.