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Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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SKU | Size | Availability | Price | Qty |
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M102400-1mg | 1mg | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $73.90 | |
M102400-5mg | 5mg | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $307.90 | |
M102400-25mg | 25mg | In stock | $1,033.90 |
Highly potent serine palmitoyltransferase inhibitor
Synonyms | Myriocin|thermozymocidin|35891-70-4|ISP-1|ISP-I|Myriocin from Mycelia sterilia|(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid|CHEBI:582124|YRM4E8R9ST|(E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic a |
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Specifications & Purity | Moligand™, ≥98% |
Biochemical and Physiological Mechanisms | Fungal metabolite with potent immunosuppressant activity. Inhibits serine palmitoyltransferase at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin and glycosphingolipids. Disrupts substratum adhesion of melanoma cells. |
Storage Temp | Store at -20°C |
Shipped In | Ice chest + Ice pads |
Grade | Moligand™ |
Action Type | INHIBITOR |
Mechanism of action | Inhibitor of serine palmitoyltransferase long chain base subunit 1;Inhibitor of serine palmitoyltransferase long chain base subunit 2;Inhibitor of serine palmitoyltransferase long chain base subunit 3 |
Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
Product Description | Myriocin is an amino fatty acid antibiotic derived from certain thermophylic fungi, in this case Mycelia sterilia. It is a potent immunosuppressant having 10- to 100-fold more activity than cyclosporin A. Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. It disrupts substratum adhesion of melanoma cells. It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis. Myriocin suppresses replication of the hepatitis C virus (HCV) in a murine model. |
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IUPAC Name | (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid |
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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)/b12-9+/t18-,19+,21+/m1/s1 |
InChi Key | ZZIKIHCNFWXKDY-GNTQXERDSA-N |
Canonical SMILES | CCCCCCC(=O)CCCCCCC=CCC(C(C(CO)(C(=O)O)N)O)O |
Isomeric SMILES | CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@@](CO)(C(=O)O)N)O)O |
WGK Germany | 3 |
RTECS | JX3890000 |
PubChem CID | 6438394 |
UN Number | 2811 |
Molecular Weight | 401.54 |
ChEMBL Ligand | CHEMBL55076 |
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PubChem CID | 6438394 |
Wikipedia | Myriocin |
CAS Registry No. | 35891-70-4 |
RCSB PDB Ligand | VRP |
Enter Lot Number to search for COA:
To view the certificate results,please click on a Lot number.For Lot numbers from past orders,please use our order status section
Lot Number | Certificate Type | Date | Item |
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J1925148 | Certificate of Analysis | Aug 07, 2023 | M102400 |
F1822086 | Certificate of Analysis | Apr 26, 2022 | M102400 |
C2427029 | Certificate of Analysis | Nov 18, 2021 | M102400 |
Solubility | Soluble in DMSO (heat briefly in boiling water bath) (25 mg/ml), dilute base (50 mM NaOH) (~5 mg/ml), and methanol (2 mg/ml). Insoluble in water. |
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Sensitivity | light sensitive & Moisture sensitive |
Pictogram(s) | GHS06 |
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Signal | Danger |
Hazard Statements | H301:Toxic if swallowed |
Precautionary Statements | P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P270:Do not eat, drink or smoke when using this product. P330:Rinse mouth. P301+P316:IF SWALLOWED: Get emergency medical help immediately. |
WGK Germany | 3 |
RTECS | JX3890000 |
1. 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). [PMID:7794249] |