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Structure Database (LMSD)

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Common Name

myriocin

Systematic Name

(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid

Synonyms

(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid
ISP-I
Thermozymocidin

LM ID

LMFA01060203

Formula

C₂₁H₃₉NO₆

Exact Mass

Calculate m/z

401.277739

Status

Curated

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Classification

Biological Context

Myriocin is an amino fatty acid antibiotic derived from certain thermophylic fungi, in this case Mycelia sterilia. It is a potent immunosuppressant having 10- to 100-fold more activity than cyclosporin A.¹ Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. 2 It disrupts substratum adhesion of melanoma cells.³ It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis.^2,4 Myriocin suppresses replication of the hepatitis C virus in a murine model.⁵

This information has been provided by Cayman Chemical

References

1. Nakamura, S., Kozutsumi, Y., Sun, Y., et al. Dual roles of sphingolipids in signaling of the escape from and onset of apoptosis in a mouse cytotoxic T-cell line, CTLL-2. The Journal of Biological Chemisty 271(3), 1255-1257 (1996).

3. Umehara, T., Sudoh, M., Yasui, F., et al. Serine palmitoyltransferase inhibitor suppresses HCV replication in a mouse model. Biochem. Biophys. Res. Commun. 346(1), 67-73 (2006).

5. Miyake, Y., Kozutsumi, Y., Nakamura, S., et al. Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressant, ISP-1/myriocin. Biochem. Biophys. Res. Commun. 211(2), 396-403 (1995).

2. Fujita, T., Inoue, K., Yamamoto, S., et al. Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite. J. Antibiot. (Tokyo) 47 (2), 208-215 (1994).

4. Hidari, K.I.P.J., Ichikawa, S., Fujita, T., et al. Complete removal of sphingolipids from the plasma membrane disrupts cell to substratum adhesion of mouse melanoma cells. The Journal of Biological Chemisty 271(24), 14636-14641 (1996).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Melanocarpus albomyces (#204285)

Sordariomycetes (#147550)

Elucidation of structure and stereochemistry of myriocin. A novel antifungal antibiotic.,
J Org Chem, 1973

Pubmed ID: 4694226

String Representations

InChiKey (Click to copy)

ZZIKIHCNFWXKDY-GNTQXERDSA-N

InChi (Click to copy)

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+/m1/s1

SMILES (Click to copy)

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