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MedKoo Cat#: 562746 | Name: Myxopyronin A

Description:

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

Myxopyronin A is a bacterial RNA polymerase (RNAP) inhibitor.

Chemical Structure

Myxopyronin A
Myxopyronin A
CAS#88192-98-7

Theoretical Analysis

MedKoo Cat#: 562746

Name: Myxopyronin A

CAS#: 88192-98-7

Chemical Formula: C23H31NO6

Exact Mass: 417.2151

Molecular Weight: 417.50

Elemental Analysis: C, 66.17; H, 7.48; N, 3.35; O, 22.99

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 #
No Data
Synonym
Myxopyronin A; Myxopyronin-A; Myx;
IUPAC/Chemical Name
Methyl N-[(E,5R)-5-[(5E)-5-[(2E,4E)-1-hydroxy-2,5-dimethylocta-2,4-dienylidene]-4,6-dioxopyran-2-yl]hex-1-enyl]carbamate
InChi Key
XIBGXHNKXPLLAN-YDDADCBQSA-N
InChi Code
InChI=1S/C23H31NO6/c1-6-9-15(2)11-12-17(4)21(26)20-18(25)14-19(30-22(20)27)16(3)10-7-8-13-24-23(28)29-5/h8,11-14,16,26H,6-7,9-10H2,1-5H3,(H,24,28)/b13-8+,15-11+,17-12+,21-20+/t16-/m1/s1
SMILES Code
O=C(OC)N/C=C/CC[C@H](C1=CC(/C(C(O1)=O)=C(O)/C(C)=C/C=C(C)/CCC)=O)C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 417.50 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: Molodtsov V, Fleming PR, Eyermann CJ, Ferguson AD, Foulk MA, McKinney DC, Masse CE, Buurman ET, Murakami KS. X-ray crystal structures of Escherichia coli RNA polymerase with switch region binding inhibitors enable rational design of squaramides with an improved fraction unbound to human plasma protein. J Med Chem. 2015 Apr 9;58(7):3156-71. doi: 10.1021/acs.jmedchem.5b00050. Epub 2015 Mar 23. PubMed PMID: 25798859; PubMed Central PMCID: PMC4658208. 2: Fruth M, Plaza A, Hinsberger S, Sahner JH, Haupenthal J, Bischoff M, Jansen R, Müller R, Hartmann RW. Binding mode characterization of novel RNA polymerase inhibitors using a combined biochemical and NMR approach. ACS Chem Biol. 2014 Nov 21;9(11):2656-63. doi: 10.1021/cb5005433. Epub 2014 Sep 26. PubMed PMID: 25207839. 3: Jeong YC, Bikadi Z, Hazai E, Moloney MG. A detailed study of antibacterial 3-acyltetramic acids and 3-acylpiperidine-2,4-diones. ChemMedChem. 2014 Aug;9(8):1826-37. doi: 10.1002/cmdc.201402093. Epub 2014 May 18. PubMed PMID: 24838989. 4: Sucipto H, Wenzel SC, Müller R. Exploring chemical diversity of α-pyrone antibiotics: molecular basis of myxopyronin biosynthesis. Chembiochem. 2013 Sep 2;14(13):1581-9. doi: 10.1002/cbic.201300289. Epub 2013 Aug 26. PubMed PMID: 23983106. 5: Haupenthal J, Hüsecken K, Negri M, Maurer CK, Hartmann RW. Influence of DNA template choice on transcription and inhibition of Escherichia coli RNA polymerase. Antimicrob Agents Chemother. 2012 Aug;56(8):4536-9. doi: 10.1128/AAC.00198-12. Epub 2012 Jun 4. PubMed PMID: 22664971; PubMed Central PMCID: PMC3421607. 6: Srivastava A, Talaue M, Liu S, Degen D, Ebright RY, Sineva E, Chakraborty A, Druzhinin SY, Chatterjee S, Mukhopadhyay J, Ebright YW, Zozula A, Shen J, Sengupta S, Niedfeldt RR, Xin C, Kaneko T, Irschik H, Jansen R, Donadio S, Connell N, Ebright RH. New target for inhibition of bacterial RNA polymerase: 'switch region'. Curr Opin Microbiol. 2011 Oct;14(5):532-43. doi: 10.1016/j.mib.2011.07.030. Epub 2011 Aug 19. Review. PubMed PMID: 21862392; PubMed Central PMCID: PMC3196380. 7: Haebich D, von Nussbaum F. Lost in transcription--inhibition of RNA polymerase. Angew Chem Int Ed Engl. 2009;48(19):3397-400. doi: 10.1002/anie.200900338. PubMed PMID: 19294713. 8: Tupin A, Gualtieri M, Brodolin K, Leonetti JP. Myxopyronin: a punch in the jaws of bacterial RNA polymerase. Future Microbiol. 2009 Mar;4(2):145-9. doi: 10.2217/17460913.4.2.145. PubMed PMID: 19257840. 9: Mukhopadhyay J, Das K, Ismail S, Koppstein D, Jang M, Hudson B, Sarafianos S, Tuske S, Patel J, Jansen R, Irschik H, Arnold E, Ebright RH. The RNA polymerase "switch region" is a target for inhibitors. Cell. 2008 Oct 17;135(2):295-307. doi: 10.1016/j.cell.2008.09.033. PubMed PMID: 18957204; PubMed Central PMCID: PMC2580802. 10: Irschik H, Gerth K, Höfle G, Kohl W, Reichenbach H. The myxopyronins, new inhibitors of bacterial RNA synthesis from Myxococcus fulvus (Myxobacterales). J Antibiot (Tokyo). 1983 Dec;36(12):1651-8. PubMed PMID: 6420386.