| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H39NO6 |
| Molecular Weight | 401.5375 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCC(=O)CCCCCC\C=C\C[C@@H](O)[C@H](O)[C@@](N)(CO)C(O)=O
InChI
InChIKey=ZZIKIHCNFWXKDY-GNTQXERDSA-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
| Molecular Formula | C21H39NO6 |
| Molecular Weight | 401.5375 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Myriocin ((2S,3R,4R,6E)-2-amino-3,4- dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid, ISP-1, thermozymocidin) is a small-molecule immunosuppressant, isolated from the Mycelia sterilia thermophilic fungus. Myriocin inhibits serine palmitoyltransferase (SPT) at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin (SM) and glycosphingolipids. Inhibition of hepatic serine palmitoyl transferase reduces plasma sphingomyelin levels in the absence of changes in cholesterol or triglyceride (TG) concentration and this leads to a reduction of atherosclerosis. In preclinical studies, Myriocin treated mice shows significant reductions in both plasma SM and Glycosphingolipids (GSL) concentration. Moreover, SM and GSL concentrations were significantly correlated, indicating that SPT inhibition suppresses the synthesis of both these sphingolipids concomitantly. The inhibition of atherosclerosis induced by myriocin was not associated with changes in plasma cholesterol or TG concentrations or lipoprotein profiles.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Mice were treated with 0.3 mg/kg every 48 h.
Route of Administration:
Intraperitoneal
Human oligodendroglioma cells were used for activity evaluation. Cells were grown to 70–80% confluent state and divided into four groups [Group # 1: untreated cells or control; Group # 2: cells treated with TNFα (100 ng/ml); Group # 3: cells treated with myriocin (5 µM), along with TNFα stimulation; and Group # 4: cells treated with TNFα, IFNγ, and combination of both cytokines (100 ng/ ml each) in presence and absence of myriocin(5 µM),]. After 24 h of incubation, cells were trypsinized, collected in cold PBS, and washed once with PBS. Lipids were extracted and ceramide purification was carried out. The protein content was measured by BCA (Pierce, Rockford, IL, USA) method.