Myriocin

Myriocin
Names

IUPAC name 2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Other names Antibiotic ISP-1; Thermozymocidin
Identifiers
Beilstein Reference	5113331
CAS Registry Number	35891-70-4^N
ChEBI	CHEBI:582124^Y CHEBI:183131^N
ChEMBL	ChEMBL55076^Y
ChemSpider	4942874 (2S,3R,4R,6E)^Y 11654743 (6E)^N 266093 ()^N 21467337 (3S,4S,6E)^N
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
Jmol-3D images	Image Image
KEGG	C19914^N
PubChem	6438394 (6E) 301119 ()
RTECS number	JX3890000
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
UN number	2811
Properties
Chemical formula	C₂₁H₃₉NO₆
Molar mass	401.54 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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^[1] and Isaria sinclairii.

Myriocin is a very potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis.^[2] 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

↑ Myriocin from Fermentek
↑ 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.