Myriocin

Myriocin
Names

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
Identifiers
CAS Number	35891-70-4^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	5113331
ChEBI	CHEBI:582124^Y
ChEMBL	ChEMBL55076^Y
ChemSpider	4942874 (2S,3R,4R,6E)^Y 11654743 (6E)^Y 266093 ()^Y 21467337 (3S,4S,6E)^Y
ECHA InfoCard	100.164.620
IUPHAR/BPS	6664
KEGG	C19914^N
PubChem CID	6438394 (6E) 301119 ()
RTECS number	JX3890000
UNII	YRM4E8R9ST^Y
UN number	2811
CompTox Dashboard (EPA)	DTXSID9046360
InChI 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)^N Key: ZZIKIHCNFWXKDY-UHFFFAOYSA-N^N 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 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 Key: ZZIKIHCNFWXKDY-GNTQXERDSA-N
SMILES CCCCCCC(=O)CCCCCCC=CCC(O)C(O)C(N)(CO)C(O)=O O=C(O)[C@@](N)([C@@H](O)[C@H](O)C/C=C/CCCCCCC(=O)CCCCCC)CO
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). N verify (what is ^YN ?) 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]}

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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.