Enniatin C | CAS#19893-23-3 | ionophore

MedKoo Cat#: 598636 | Name: Enniatin C

Description:

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

Enniatin C is an ionophore that bind ammonium.

Chemical Structure

Enniatin C

CAS#19893-23-3

Theoretical Analysis

MedKoo Cat#: 598636

Name: Enniatin C

CAS#: 19893-23-3

Chemical Formula: C36H63N3O9

Exact Mass: 681.4564

Molecular Weight: 681.91

Elemental Analysis: C, 63.41; H, 9.31; N, 6.16; O, 21.12

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

Enniatin C;

IUPAC/Chemical Name

(3S,6R,9S,12R,15S,18R)-3,9,15-triisobutyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexaone

InChi Key

WICJNWLMJRLFKQ-NHODMIADSA-N

InChi Code

InChI=1S/C36H63N3O9/c1-19(2)16-25-34(43)46-29(23(9)10)32(41)38(14)27(18-21(5)6)36(45)48-30(24(11)12)33(42)39(15)26(17-20(3)4)35(44)47-28(22(7)8)31(40)37(25)13/h19-30H,16-18H2,1-15H3/t25-,26-,27-,28+,29+,30+/m0/s1

SMILES Code

CC(C[C@@H]1N(C([C@@H](C(C)C)OC([C@@H](N(C([C@@H](C(C)C)OC([C@@H](N(C([C@@H](C(C)C)OC1=O)=O)C)CC(C)C)=O)=O)C)CC(C)C)=O)=O)C)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

>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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 681.91 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

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Toxicol In Vitro. 2016 Aug;34:309-20. doi: 10.1016/j.tiv.2016.04.017. Epub 2016 May 6. PubMed PMID: 27163883. 5: Taevernier L, Detroyer S, Veryser L, De Spiegeleer B. Enniatin-containing solutions for oromucosal use: Quality-by-design ex-vivo transmucosal risk assessment of composition variability. Int J Pharm. 2015 Aug 1;491(1-2):144-51. doi: 10.1016/j.ijpharm.2015.06.029. Epub 2015 Jun 23. PubMed PMID: 26116015. 6: Juan-García A, Ruiz MJ, Font G, Manyes L. Enniatin A1, enniatin B1 and beauvericin on HepG2: Evaluation of toxic effects. Food Chem Toxicol. 2015 Oct;84:188-96. doi: 10.1016/j.fct.2015.08.030. Epub 2015 Sep 3. PubMed PMID: 26342765. 7: Zobel S, Kumpfmüller J, Süssmuth RD, Schweder T. Bacillus subtilis as heterologous host for the secretory production of the non-ribosomal cyclodepsipeptide enniatin. Appl Microbiol Biotechnol. 2015 Jan;99(2):681-91. doi: 10.1007/s00253-014-6199-0. Epub 2014 Nov 15. PubMed PMID: 25398283; PubMed Central PMCID: PMC4306738. 8: Fæste CK, Ivanova L, Uhlig S. In vitro metabolism of the mycotoxin enniatin B in different species and cytochrome p450 enzyme phenotyping by chemical inhibitors. Drug Metab Dispos. 2011 Sep;39(9):1768-76. doi: 10.1124/dmd.111.039529. Epub 2011 May 26. PubMed PMID: 21622627. 9: Zaher AM, Makboul MA, Moharram AM, Tekwani BL, Calderón AI. A new enniatin antibiotic from the endophyte Fusarium tricinctum Corda. J Antibiot (Tokyo). 2015 Mar;68(3):197-200. doi: 10.1038/ja.2014.129. Epub 2014 Oct 15. PubMed PMID: 25315756. 10: Wang JP, Debbab A, Hemphill CF, Proksch P. Optimization of enniatin production by solid-phase fermentation of Fusarium tricinctum. Z Naturforsch C. 2013 May-Jun;68(5-6):223-30. PubMed PMID: 23923619. 11: Stępień L, Waśkiewicz A. Sequence divergence of the enniatin synthase gene in relation to production of beauvericin and enniatins in Fusarium species. Toxins (Basel). 2013 Mar 13;5(3):537-55. doi: 10.3390/toxins5030537. PubMed PMID: 23486233; PubMed Central PMCID: PMC3705277. 12: Fraeyman S, Devreese M, Antonissen G, De Baere S, Rychlik M, Croubels S. Comparative Oral Bioavailability, Toxicokinetics, and Biotransformation of Enniatin B1 and Enniatin B in Broiler Chickens. J Agric Food Chem. 2016 Sep 28;64(38):7259-64. doi: 10.1021/acs.jafc.6b02913. Epub 2016 Sep 15. PubMed PMID: 27632250. 13: Herrmann M, Zocher R, Haese A. Effect of disruption of the enniatin synthetase gene on the virulence of Fusarium avenaceum. Mol Plant Microbe Interact. 1996 May;9(4):226-32. PubMed PMID: 8634475. 14: Dornetshuber-Fleiss R, Heilos D, Mohr T, Richter L, Süssmuth RD, Zlesak M, Novicky A, Heffeter P, Lemmens-Gruber R, Berger W. The naturally born fusariotoxin enniatin B and sorafenib exert synergistic activity against cervical cancer in vitro and in vivo. Biochem Pharmacol. 2015 Feb 1;93(3):318-331. doi: 10.1016/j.bcp.2014.12.013. Epub 2014 Dec 31. PubMed PMID: 25557295; PubMed Central PMCID: PMC4379350. 15: Kolf-Clauw M, Sassahara M, Lucioli J, Rubira-Gerez J, Alassane-Kpembi I, Lyazhri F, Borin C, Oswald IP. The emerging mycotoxin, enniatin B1, down-modulates the gastrointestinal toxicity of T-2 toxin in vitro on intestinal epithelial cells and ex vivo on intestinal explants. Arch Toxicol. 2013 Dec;87(12):2233-41. doi: 10.1007/s00204-013-1067-8. Epub 2013 May 7. PubMed PMID: 23649843. 16: Gammelsrud A, Solhaug A, Dendelé B, Sandberg WJ, Ivanova L, Kocbach Bølling A, Lagadic-Gossmann D, Refsnes M, Becher R, Eriksen G, Holme JA. Enniatin B-induced cell death and inflammatory responses in RAW 267.4 murine macrophages. Toxicol Appl Pharmacol. 2012 May 15;261(1):74-87. doi: 10.1016/j.taap.2012.03.014. Epub 2012 Mar 27. PubMed PMID: 22483798. 17: Ficheux AS, Sibiril Y, Le Garrec R, Parent-Massin D. In vitro myelotoxicity assessment of the emerging mycotoxins Beauvericin, Enniatin b and Moniliformin on human hematopoietic progenitors. Toxicon. 2012 Jan;59(1):182-91. doi: 10.1016/j.toxicon.2011.11.006. Epub 2011 Nov 19. PubMed PMID: 22120168. 18: Devreese M, Broekaert N, De Mil T, Fraeyman S, De Backer P, Croubels S. Pilot toxicokinetic study and absolute oral bioavailability of the Fusarium mycotoxin enniatin B1 in pigs. Food Chem Toxicol. 2014 Jan;63:161-5. doi: 10.1016/j.fct.2013.11.005. Epub 2013 Nov 13. PubMed PMID: 24239892. 19: Glinski M, Urbanke C, Hornbogen T, Zocher R. Enniatin synthetase is a monomer with extended structure: evidence for an intramolecular reaction mechanism. Arch Microbiol. 2002 Oct;178(4):267-73. Epub 2002 Jul 12. PubMed PMID: 12209259. 20: Fernández-Blanco C, Font G, Ruiz MJ. Interaction effects of enniatin B, deoxinivalenol and alternariol in Caco-2 cells. Toxicol Lett. 2016 Jan 22;241:38-48. doi: 10.1016/j.toxlet.2015.11.005. Epub 2015 Nov 12. 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