Chemistry: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
IUPHAR/BPS	6664
KEGG	C19914 N
PubChem CID	6438394 (6E) 301119 ()
RTECS number	JX3890000
UNII	YRM4E8R9ST Y
UN number	2811
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 certain thermophilic fungi.

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.