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Taccalonolide B

Names

[ CAS No. ]:
108885-69-4

[ Name ]:
Taccalonolide B

[Synonym ]:
1H-Oxireno[6',7']naphtho[1',2':7,8]fluoreno[2,1-b]furan-4,8-dione, 11,12,13-tris(acetyloxy)-5,5a,5b,6,6a,6b,7,8a,9,9a,10a,11,11a,11b,12,13,13a,13b-octadecahydro-5,6,7-trihydroxy-1,5,5a,11a,13a-pentamethyl-, (1S,5S,5aS,5bR,6R,6aS,6bS,7R,8aS,9aS,10aS,11R,11aR,11bS,12S,13R,13aR,13bS)-
(1S,5S,5aS,5bR,6R,6aS,6bS,7R,8aS,9aS,10aS,11R,11aR,11bS,12S,13R,13aR,13bS)-5,6,7-Trihydroxy-1,5,5a,11a,13a-pentamethyl-4,8-dioxo-4,5,5a,5b,6,6a,6b,7,8,8a,9,9a,10a,11,11a,11b,12,13,13a,13b-icosahydro-1H-oxireno[6',7']naphtho[1',2':7,8]fluoreno[2,1-b]furan-11,12,13-triyl triacetate

Biological Activity

[Description]:

Taccalonolide B is microtubule stabilizer isolated from Tacca plantaginea, with antitumor activity. Taccalonolide B is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug-resistance protein (MRP7). Taccalonolide B inhibits growth of SK-OV-3 cells with an IC50 of 208 nM[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin
Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[Target]

microtubule[2]


[References]

[1]. LiangChen Zhong, et al. Steroidal bitter principles from tacca plantaginea structures of taccalonolide A and B. Tetrahedron Letters. 1987, 28(15): 1673-1675.

[2]. Risinger AL, et al. The taccalonolides: microtubule stabilizers that circumvent clinically relevant taxane resistance mechanisms. Cancer Res. 2008 Nov 1;68(21):8881-8.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
775.9±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C34H44O13

[ Molecular Weight ]:
660.705

[ Flash Point ]:
242.4±26.4 °C

[ Exact Mass ]:
660.278198

[ PSA ]:
195.49000

[ LogP ]:
1.88

[ Vapour Pressure ]:
0.0±6.0 mmHg at 25°C

[ Index of Refraction ]:
1.604

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds