Epothilone A

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Names

[ CAS No. ]:
152044-53-6

[ Name ]:
Epothilone A

[Synonym ]:
UNII-51E07YBX96
Epothilone A
(-)-Epothilone A
Epo A
4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (1S,3S,7S,10R,11S,12S,16R)-
[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
Epothilon A
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (1R,3R,7R,10S,11R,12R,16S)-
(1R,3R,7R,10S,11R,12R,16S)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
epithilone A
Epothilones
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
683.3±55.0 °C at 760 mmHg

[ Melting Point ]:
95ºC

[ Molecular Formula ]:
C₂₆H₃₉NO₆S

[ Molecular Weight ]:
493.656

[ Flash Point ]:
367.1±31.5 °C

[ Exact Mass ]:
493.249817

[ PSA ]:
137.49000

[ LogP ]:
2.54

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.532

[ Storage condition ]:
-20°C

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

EPOTHILONE C
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate
(2E)-2-Methyl-3-(2-methyl-1,3-thiazol-4-yl)acrylaldehyde
4-Formyl-2-methylthiazole
Ethyl 2-methylthiazole-4-carboxylate
(3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-ol
(-)-(3S)-3-(tert-butyldimethylsilyl)oxy-4,4-dimethyl-5-oxoheptanoic acid

DownStream

Articles

Identifying off-target effects and hidden phenotypes of drugs in human cells.

Nat. Chem. Biol. 2 , 329-37, (2006)

We present a strategy for identifying off-target effects and hidden phenotypes of drugs by directly probing biochemical pathways that underlie therapeutic or toxic mechanisms in intact, living cells. ...

Neuronal transcriptional repressor REST suppresses an Atoh7-independent program for initiating retinal ganglion cell development.

Dev. Biol. 349 , 90-9, (2011)

As neuronal progenitors differentiate into neurons, they acquire a unique set of transcription factors. The transcriptional repressor REST prevents progenitors from undergoing differentiation. Notably...

Conformational preferences of natural and C3-modified epothilones in aqueous solution.

J. Med. Chem. 51 , 1469-73, (2008)

The conformational properties of the microtubule-stabilizing agent epothilone A ( 1a) and its 3-deoxy and 3-deoxy-2,3-didehydro derivatives 2 and 3 have been investigated in aqueous solution by a comb...