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^N
Beilstein Reference	5113331
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
IUPHAR/BPS	6664
Jmol interactive 3D	Image Image
KEGG	C19914^N
PubChem	6438394 (6E) 301119 ()
RTECS number	JX3890000
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 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.

Lysophospholipid signaling

Receptor
(ligands)

LPA	Agonists: 1-Oleoyl-LPA 1-Palmitoyl-LPA GRI-977143 LPA OMPT Antagonists: H2L-5186303 H2L-5765834 Ki-16425 TC-LPA5 4 VPC-32183

S1P	Agonists: Amiselimod Ceralifimod CS-2100 CYM-5442 CYM-5520 CYM 5541 CYM-50260 CYM-50308 Dihydro-S1P (sphinganine 1-phosphate) Fingolimod Fingolimod phosphate KRP-203 Phyto-S1P Ponesimod RP-001 RP-002 RPC-1063 SEW-2871 Siponimod S1P SPC TC-G 1006 TC-SP 14 W-061 XAX-162 Antagonists: CS-0777 CYM-50358 JTE-013 TY-52156 VPC-23019 W-146

Enzyme
(inhibitors)

SPT	Myriocin

Ceramidase	Ceranib 1 OEA

SphK	N,N-DMS Safingol SKI II

Others

Precursors: LPA: LPC; S1P: Palmitoyl-CoA
Serine
3-Ketosphinganine (dehydrosphingosine)
Dihydrosphingosine (sphinganine)
Dihydroceramide
Ceramide
Sphingosine

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