Myriocin

Myriocin
Names
	IUPAC name 2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
	Other names Antibiotic ISP-1; Thermozymocidin
Identifiers
CAS Number	35891-70-4 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	5113331
ChEBI	CHEBI:582124 ;
ChEMBL	ChEMBL55076 ;
ChemSpider	4942874 (2S,3R,4R,6E) ; 11654743 (6E) ; 266093 () ; 21467337 (3S,4S,6E) ;
ECHA InfoCard	100.164.620
IUPHAR/BPS	6664;
KEGG	C19914 ;
PubChem CID	6438394 (6E); 301119 ();
RTECS number	JX3890000;
UNII	YRM4E8R9ST ;
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) Key: ZZIKIHCNFWXKDY-UHFFFAOYSA-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).
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	Infobox references

Myriocin, also known as antibiotic ISP-1 and thermozymocidin, is a non-proteinogenic amino acid derived from certain thermophilic fungi.

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.

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.

References

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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[pmid7794249-1] 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.