Taccalonolide A

CAS

108885-68-3

Catalog Number

ACM108885683

Category

Inhibitors

Molecular Weight

702.74

Molecular Formula

C36H46O14

MSDS COA Spec Sheet

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Specification

Description

Taccalonolide A is a microtubule stabilizer, which is a steroid isolated from Tacca chantrieri, with cytotoxic and antimalarial activities. Taccalonolide A causes G2-M accumulation, Bcl-2 phosphorylation and initiation of apoptosis. Taccalonolide A is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug resistance protein 7 (MRP7), with an IC50 of 622 nM for SK-OV-3 cells.

Synonyms

Potato ketolide A

IUPAC Name

[(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-10,14,25-triacetyloxy-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-13-yl] acetate

Canonical SMILES

C[C@@H]1C=C2[C@@]([C@H]3[C@H]1[C@@]4([C@@H]([C@H]3OC(=O)C)[C@H]5[C@H]([C@@H]([C@@H]4OC(=O)C)OC(=O)C)[C@@]6([C@H](C[C@H]7[C@@H]([C@@H]6OC(=O)C)O7)C(=O)[C@@H]5O)C)C)([C@](C(=O)O2)(C)O)C

InChI

InChI=1S/C36H46O14/c1-12-10-19-35(8,36(9,44)32(43)50-19)24-21(12)34(7)22(28(24)45-13(2)37)20-23(29(46-14(3)38)31(34)48-16(5)40)33(6)17(25(41)26(20)42)11-18-27(49-18)30(33)47-15(4)39/h10,12,17-18,20-24,26-31,42,44H,11H2,1-9H3/t12-,17-,18+,20+,21+,22-,23-,24+,26-,27+,28-,29+,30+,31+,33+,34-,35+,36-/m1/s1

InChI Key

PTTJLTMUKRRHAT-VJAKQJMOSA-N

Boiling Point

776.8±60.0 °C

Density

1.41±0.1 g/ml

Appearance

Powder

Storage

4°C, sealed storage, away from moisture and light*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)

pKa

11.56±0.70