Myxopyronin A

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

MedKoo CAT#: 562746

CAS#: 88192-98-7

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


Chemical Structure

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Myxopyronin A
CAS# 88192-98-7

Theoretical Analysis

MedKoo Cat#: 562746
Name: Myxopyronin A
CAS#: 88192-98-7
Chemical Formula: C23H31NO6
Exact Mass: 417.22
Molecular Weight: 417.500
Elemental Analysis: C, 66.17; H, 7.48; N, 3.35; O, 22.99

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.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.