Manumycin A

Names

[ Name ]:
Manumycin A

[Synonym ]:
Manumycin A
(2E,4E,6R)-N-[(1S,5S,6R)-5-Hydroxy-5-{(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrien-1-yl}-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyl-2,4-decadienamide
(2E,4E,6R)-N-[(1S,5S,6R)-5-hydroxy-5-{(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)amino]-7-oxohepta-1,3,5-trien-1-yl}-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide
MFCD00920782
2,4-Decadienamide, N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyl-, (2E,4E,6R)-

Biological Activity

[Description]:

Manumycin A is an antibiotic. Manumycin A acts as a selective, competitive inhibitor of protein farnesyltransferase (FTase) with respect to farnesylpyrophosphate (Ki =1.2 μM), and as a noncompetitive inhibitor with respect to the Ras protein. Manumycin A induces apoptosis and exerts antitumor activity[1] [2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> GPCR/G Protein >> Ras

Signaling Pathways >> Metabolic Enzyme/Protease >> Farnesyl Transferase

[Target]

Farnesyltransferase, Ras[1]

[References]

[1]. Hara M, et al. Identification of Ras farnesyltransferase inhibitors by microbial screening. Proc Natl Acad Sci U S A. 1993 Mar 15;90(6):2281-5.

[2]. Bernier M, et al. Binding of manumycin A inhibits IkappaB kinase beta activity. J Biol Chem. 2006 Feb 3;281(5):2551-61.

[3]. Kim KH, et al. Manumycin A induces apoptosis in malignant pleural mesothelioma through regulation of Sp1 and activation of the mitochondria-related apoptotic pathway. Oncol Rep. 2016 Jul;36(1):117-24.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
863.6±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₁H₃₈N₂O₇

[ Molecular Weight ]:
550.643

[ Flash Point ]:
476.1±34.3 °C

[ Exact Mass ]:
550.267883

[ PSA ]:
145.33000

[ LogP ]:
3.04

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.605

[ Storage condition ]:
2-8°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Articles

Statins inhibit protein lipidation and induce the unfolded protein response in the non-sterol producing nematode Caenorhabditis elegans.

Proc. Natl. Acad. Sci. U. S. A. 106(43) , 18285-90, (2009)

Statins are compounds prescribed to lower blood cholesterol in millions of patients worldwide. They act by inhibiting HMG-CoA reductase, the rate-limiting enzyme in the mevalonate pathway that leads t...

[Effects of manumycin combined with methoxyamine on apoptosis in myeloid leukemia U937 cells].

Chin. J. Cancer 27(8) , 835-9, (2008)

Repair of DNA damage is important to cell survival. Our previous study showed DNA damage response induced by manumycin in cancer cells. We hypothesized that methoxyamine, an inhibitor of base-excision...

Polygonatum cyrtonema lectin induces murine fibrosarcoma L929 cell apoptosis and autophagy via blocking Ras-Raf and PI3K-Akt signaling pathways.

Biochimie 92(12) , 1934-8, (2010)

Polygonatum cyrtonema lectin (PCL), a mannose/sialic acid-binding lectin, has been reported to display remarkable anti-proliferative and apoptosis-inducing activities toward a variety of cancer cells;...

Related Compounds

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