Myriocin
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Names | |
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Systematic IUPAC name (2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid | |
Other names Antibiotic ISP-1; Thermozymocidin | |
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3D model (JSmol) |
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Beilstein Reference | 5113331 |
ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.164.620 ![]() |
IUPHAR/BPS |
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KEGG |
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PubChem CID |
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RTECS number |
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UNII |
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UN number | 2811 |
CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C21H39NO6 |
Molar mass | 401.54 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
Myriocin, also known as antibiotic ISP-1 and thermozymocidin, is a non-proteinogenic amino acid derived from the entomopathogenic fungus, Isaria sinclairii.[1]
Myriocin is a very potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis.[1] Due to this property, it is used in biochemical research as a tool for depleting cells of sphingolipids.
Myriocin was shown to inhibit the proliferation of an IL-2-dependent mouse cytotoxic T cell line.[citation needed]
Myriocin possesses immunosuppressant activity. It is reported to be 10- to 100-fold more potent than ciclosporin.[citation needed]
The multiple sclerosis drug fingolimod was derived from myriocin by using structure–activity relationship studies to determine the parts of the molecule important to its activity.[citation needed]
References
- ^ a b Miyake Y, Kozutsumi Y, Nakamura S, Fujita T, Kawasaki T (1995). "Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressant, ISP-1/myriocin". Biochem. Biophys. Res. Commun. 211 (2): 396–403. doi:10.1006/bbrc.1995.1827. PMID 7794249.
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(ligands)
LPARTooltip Lysophosphatidic acid receptor |
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S1PRTooltip Sphingosine-1-phosphate receptor |
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(inhibitors)
SPTTooltip Serine C-palmitoyltransferase |
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Ceramidase |
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SphKTooltip Sphingosine kinase |
- Precursors: LPA: LPC; S1P: Palmitoyl-CoA
- Serine
- 3-Ketosphinganine (dehydrosphingosine)
- Dihydrosphingosine (sphinganine)
- Dihydroceramide
- Ceramide
- Sphingosine