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Myriocin

Myriocin
Myriocin
Names
IUPAC name
2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Other names
Antibiotic ISP-1; Thermozymocidin
Identifiers
35891-70-4 N
3D model (Jmol) Interactive image
Interactive image
5113331
ChEBI CHEBI:582124 YesY
ChEMBL ChEMBL55076 YesY
ChemSpider 4942874 (2S,3R,4R,6E) YesY
11654743 (6E) YesY
266093 () YesY
21467337 (3S,4S,6E) YesY
ECHA InfoCard 100.164.620
6664
KEGG C19914 N
PubChem 6438394 (6E)
301119 ()
RTECS number JX3890000
UN number 2811
Properties
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).
N  (what is YesYN ?)
Infobox references

Myriocin, also known as antibiotic ISP-1 and thermozymocidin, is an atypical amino acid and an antibiotic derived from certain thermophilic fungi. Among the producing strains are Mycelia sterilia.

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.

Myriocin was shown to inhibit the proliferation of an IL-2-dependent mouse cytotoxic T cell line.

Myriocin possesses immunosuppressant activity. It is reported to be 10- to 100-fold more potent than ciclosporin.

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.


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