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

MedKoo CAT#: 561301

CAS#: 35891-70-4

Description: Myriocin, also known as antibiotic ISP-1 and thermozymocidin, is an atypical amino acid and an antibiotic derived from certain thermophilic fungi. Myriocin is a very potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Due to this property, it is used in biochemical research as a tool for depleting cells of sphingolipids.


Chemical Structure

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Myriocin
CAS# 35891-70-4

Theoretical Analysis

MedKoo Cat#: 561301
Name: Myriocin
CAS#: 35891-70-4
Chemical Formula: C21H39NO6
Exact Mass: 401.2777
Molecular Weight: 401.54
Elemental Analysis: C, 62.82; H, 9.79; N, 3.49; O, 23.91

Price and Availability

Size Price Availability Quantity
5.0mg USD 205.0 2 Weeks
10.0mg USD 340.0 2 Weeks
25.0mg USD 610.0 2 Weeks
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Synonym: Thermozymocidin; ISP-I; ISP-1; Myriocin;

IUPAC/Chemical Name: (2R,3R,4S,E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid

InChi Key: ZZIKIHCNFWXKDY-ANSFIGKPSA-N

InChi Code: InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19-,21+/m0/s1

SMILES Code: CCCCCCC(CCCCCC/C=C/C[C@H](O)[C@H](O)[C@@](CO)(N)C(O)=O)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 401.54 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

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1: Aburasayn H, Al Batran R, Ussher JR. Targeting ceramide metabolism in obesity. Am J Physiol Endocrinol Metab. 2016 Aug 1;311(2):E423-35. doi: 10.1152/ajpendo.00133.2016. Epub 2016 Jul 5. Review. PubMed PMID: 27382035.

2: Zécri FJ. From Natural Product to the First Oral Treatment for Multiple Sclerosis: The Discovery of FTY720 (Gilenya™)? Curr Opin Chem Biol. 2016 Jun;32:60-6. doi: 10.1016/j.cbpa.2016.04.014. Epub 2016 May 31. Review. PubMed PMID: 27258401.

3: Huang X, Withers BR, Dickson RC. Sphingolipids and lifespan regulation. Biochim Biophys Acta. 2014 May;1841(5):657-64. doi: 10.1016/j.bbalip.2013.08.006. Epub 2013 Aug 15. Review. PubMed PMID: 23954556; PubMed Central PMCID: PMC3925463.

4: Lo HC, Hsieh C, Lin FY, Hsu TH. A Systematic Review of the Mysterious Caterpillar Fungus Ophiocordyceps sinensis in Dong-ChongXiaCao ( Dōng Chóng Xià Cǎo) and Related Bioactive Ingredients. J Tradit Complement Med. 2013 Jan;3(1):16-32. doi: 10.4103/2225-4110.106538. Review. PubMed PMID: 24716152; PubMed Central PMCID: PMC3924981.

5: Chiba K, Adachi K. Discovery of fingolimod, the sphingosine 1-phosphate receptor modulator and its application for the therapy of multiple sclerosis. Future Med Chem. 2012 Apr;4(6):771-81. doi: 10.4155/fmc.12.25. Review. PubMed PMID: 22530640.

6: Podbielska M, Krotkiewski H, Hogan EL. Signaling and regulatory functions of bioactive sphingolipids as therapeutic targets in multiple sclerosis. Neurochem Res. 2012 Jun;37(6):1154-69. doi: 10.1007/s11064-012-0728-y. Epub 2012 Mar 27. Review. PubMed PMID: 22451227.

7: Jiang XC, Goldberg IJ, Park TS. Sphingolipids and cardiovascular diseases: lipoprotein metabolism, atherosclerosis and cardiomyopathy. Adv Exp Med Biol. 2011;721:19-39. doi: 10.1007/978-1-4614-0650-1_2. Review. PubMed PMID: 21910080.

8: Yeung BK. Natural product drug discovery: the successful optimization of ISP-1 and halichondrin B. Curr Opin Chem Biol. 2011 Aug;15(4):523-8. doi: 10.1016/j.cbpa.2011.05.019. Epub 2011 Jun 22. Review. PubMed PMID: 21684798.

9: Strader CR, Pearce CJ, Oberlies NH. Fingolimod (FTY720): a recently approved multiple sclerosis drug based on a fungal secondary metabolite. J Nat Prod. 2011 Apr 25;74(4):900-7. doi: 10.1021/np2000528. Epub 2011 Apr 1. Review. PubMed PMID: 21456524.

10: Friedrich FW, Eschenhagen T. [Fingolimod - a new immunomodulator]. Dtsch Med Wochenschr. 2009 Oct;134(42):2127-31. doi: 10.1055/s-0029-1241903. Epub 2009 Oct 6. Review. German. PubMed PMID: 19809964.

11: Chiba K. [New therapeutic approach for autoimmune diseases by the sphingosine 1-phosphate receptor modulator, fingolimod (FTY720)]. Yakugaku Zasshi. 2009 Jun;129(6):655-65. Review. Japanese. PubMed PMID: 19483408.

12: Chiba K. [A new therapeutic approach for autoimmune diseases by the sphingosine 1-phosphate receptor modulator, fingolimod (FTY720)]. Nihon Rinsho Meneki Gakkai Kaishi. 2009 Apr;32(2):92-101. Review. Japanese. PubMed PMID: 19404007.

13: Hiestand PC, Rausch M, Meier DP, Foster CA. Ascomycete derivative to MS therapeutic: S1P receptor modulator FTY720. Prog Drug Res. 2008;66:361, 363-81. Review. PubMed PMID: 18416311.

14: Bismuth J, Lin P, Yao Q, Chen C. Ceramide: a common pathway for atherosclerosis? Atherosclerosis. 2008 Feb;196(2):497-504. Epub 2007 Oct 25. Review. PubMed PMID: 17963772; PubMed Central PMCID: PMC2924671.

15: Baumruker T, Billich A, Brinkmann V. FTY720, an immunomodulatory sphingolipid mimetic: translation of a novel mechanism into clinical benefit in multiple sclerosis. Expert Opin Investig Drugs. 2007 Mar;16(3):283-9. Review. PubMed PMID: 17302523.

16: Chiba K, Matsuyuki H, Maeda Y, Sugahara K. Role of sphingosine 1-phosphate receptor type 1 in lymphocyte egress from secondary lymphoid tissues and thymus. Cell Mol Immunol. 2006 Feb;3(1):11-9. Review. PubMed PMID: 16549044.

17: Nishikido M, Kanekake H, Harada T. [Molecular action mechanisms of the therapeutic agents for kidney diseases: Immunosuppressants]. Nihon Rinsho. 2006 Feb;64 Suppl 2:634-8. Review. Japanese. PubMed PMID: 16523968.

18: Chiba K. FTY720, a new class of immunomodulator, inhibits lymphocyte egress from secondary lymphoid tissues and thymus by agonistic activity at sphingosine 1-phosphate receptors. Pharmacol Ther. 2005 Dec;108(3):308-19. Epub 2005 Jun 13. Review. PubMed PMID: 15951022.

19: Kahan BD. FTY720: from bench to bedside. Transplant Proc. 2004 Mar;36(2 Suppl):531S-543S. Review. PubMed PMID: 15041402.

20: Aki FT, Kahan BD. FTY720: A new kid on the block for transplant immunosuppression. Expert Opin Biol Ther. 2003 Jul;3(4):665-81. Review. PubMed PMID: 12831371.