Key Documents

View All Documentation

M1177

Myriocin

Name: Myriocin
Brand: SIGMA

from Mycelia sterilia, ≥98% (HPLC), powder, immunosuppressant

Synonym(s):

(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid, ISP-I, Thermozymocidin

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₂₁H₃₉NO₆

CAS Number:

35891-70-4

Molecular Weight:

401.54

UNSPSC Code:

51111800

PubChem Substance ID:

24896622

NACRES:

NA.77

MDL number:

MFCD01632772

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

200

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Product Name

Myriocin from Mycelia sterilia, ≥98% (HPLC), powder

Quality Level

200

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

methanol: 2 mg/mL

storage temp.

2-8°C

SMILES string

CCCCCCC(=O)CCCCCC\C=C\C[C@@H](O)[C@H](O)[C@@](N)(CO)C(O)=O

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

Related Categories

Bioactive Small Molecules

Application

Myriocin from Mycelia sterilia has been used as an inhibitor of sphingolipid or ceramide biosynthesis in various studies.

Biochem/physiol Actions

Myriocin from Mycelia sterilia is a fungal metabolite with potent immunosuppressant activity. It inhibits serine palmitoyltransferase at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin and glycosphingolipids. It disrupts substratum adhesion of melanoma cells. It has been suggested that its immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction.

Preparation Note

The material is readily and completely dissolved in 2 mg/ml methanol after heating at 55°C for several minutes.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

涉药品监管产品

This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

0000520125

0000488206

0000448170

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Inhibition of serine palmitoyl transferase I reduces cardiac ceramide levels and increases glycolysis rates following diet-induced insulin resistance.

John R Ussher et al.

PloS one, 7(5), e37703-e37703 (2012-05-26)

Diet-induced obesity (DIO) leads to an accumulation of intra-myocardial lipid metabolites implicated in causing cardiac insulin resistance and contractile dysfunction. One such metabolite is ceramide, and our aim was to determine the effects of inhibiting de novo ceramide synthesis on

Ceramide mediates vascular dysfunction in diet-induced obesity by PP2A-mediated dephosphorylation of the eNOS-Akt complex.

Quan-Jiang Zhang et al.

Diabetes, 61(7), 1848-1859 (2012-05-16)

Vascular dysfunction that accompanies obesity and insulin resistance may be mediated by lipid metabolites. We sought to determine if vascular ceramide leads to arterial dysfunction and to elucidate the underlying mechanisms. Pharmacological inhibition of de novo ceramide synthesis, using the

Secretion of Tau via an Unconventional Non-vesicular Mechanism

Merezhko M, et al.

Cell Reports, 25(8), 2027-2035 (2018)

Accumulation of long-chain bases in yeast promotes their conversion to a long-chain base vinyl ether.

Fernando Martínez-Montañés et al.

Journal of lipid research, 57(11), 2040-2050 (2016-11-03)

Long-chain bases (LCBs) are the precursors to ceramide and sphingolipids in eukaryotic cells. They are formed by the action of serine palmitoyl-CoA transferase (SPT), a complex of integral membrane proteins located in the endoplasmic reticulum. SPT activity is negatively regulated

Susceptibility of low-density lipoprotein particles to aggregate depends on particle lipidome, is modifiable, and associates with future cardiovascular deaths.

Maija Ruuth et al.

European heart journal, 39(27), 2562-2573 (2018-07-10)

Low-density lipoprotein (LDL) particles cause atherosclerotic cardiovascular disease (ASCVD) through their retention, modification, and accumulation within the arterial intima. High plasma concentrations of LDL drive this disease, but LDL quality may also contribute. Here, we focused on the intrinsic propensity

View All Related Papers

Global Trade Item Number

SKU	GTIN
M1177-5MG	04061834037989
M1177-25MG	04061833272732

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service