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476300

Myriocin, Mycelia sterilia

A potent immunosuppressant.

Synonym(s):

Myriocin, Mycelia sterilia, ISP-1, Thermozymocidin, [2S,3R,4R]-(E)-2-Amino-3,4-dihydroxy-2-[hydroxymethyl]-14-oxo-6-eicosenoic Acid

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About This Item

Empirical Formula (Hill Notation):
C21H39NO6
CAS Number:
35891-70-4
Molecular Weight:
401.54
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD01632772
Assay:
≥95% (TLC)
Form:
solid
Storage condition:
OK to freeze
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Quality Segment

100

description

RTECS - JX3890000

assay

≥95% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

DMSO: 25 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

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

General description

A potent immunosuppressant. Displays 10- to 100-fold more potent immunosuppressant activity than cyclosporin A. Potently inhibits serine palmitoyltransferase (SPT; Ki = 280 pM) thereby blocking the synthesis of ceramide. Disrupts substratum adhesion of melanoma cells. Inhibits cell proliferation and induces apoptosis in IL-2 dependent murine cytotoxic T lymphocyte cell line CTLL-2.

Biochem/physiol Actions

Cell permeable: no
Primary Target
Serine palmitoyltransferase
Product does not compete with ATP.
Reversible: no
Target Ki: 280 pM against serine palmitoyltransferase

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Hanada, K., et al. 2000. Biochem. Pharmacol.59, 1211.
Chen, J.K., et al. 1999. Chem. Biol. 6, 221.
Hidari, K.I.P.J., et al. 1996. J. Biol. Chem. 271, 14636.
Nakamura, S., et al. 1996. J. Biol. Chem. 271, 1255.
Mikaye, Y., et al. 1995. Biochem. Biophys. Res. Commun. 211, 396.
Fujita, T., et al. 1994. J. Antibiot. 47, 208.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful (C)

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

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

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