Myriocin

Myriocin
IUPAC name 2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Identifiers
CAS number	35891-70-4
PubChem	6438394 (6E) Y, 301119 () Y
ChemSpider	4942874 (2S,3R,4R,6E) Y, 11654743 (6E) Y, 266093 () Y, 21467337 (3S,4S,6E) Y
UN number	2811
ChEBI	CHEBI:183131
ChEMBL	CHEMBL55076
RTECS number	JX3890000
Beilstein Reference	5113331
Jmol-3D images	Image 1 Image 2
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
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
Properties
Molecular formula	C21H39NO6
Molar mass	401.54 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

See also

• Fingolimod

References

1. ^ Myriocin from Fermentek
2. ^ 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.