Stereochemistry | ABSOLUTE |
Molecular Formula | C29H36O10 |
Molecular Weight | 544.5901 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C4=C(C)[C@@H](O)C[C@@](O)([C@@H](OC(=O)C5=CC=CC=C5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C
InChI
InChIKey=YWLXLRUDGLRYDR-ZHPRIASZSA-N
InChI=1S/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1
Molecular Formula | C29H36O10 |
Molecular Weight | 544.5901 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
10-Deacetylbaccatin III is a natural taxoid, isolated from the leaves of the European yew tree, Taxus baccata. 10-Deacetylbaccatin III is a very useful starting material in the semisynthetic production of the anticancer drug taxol and analogs. The first chemical conversion of 10-deacetylbaccatin III into paclitaxel and 10-deacetylpaclitaxel was achieved through the hydroxyamination of the 13-cinnamoylbaccatin IIΙ derivatives. This strategy led also to the discovery of docetaxel. A more convenient procedure for a large scale production of paclitaxel and docetaxel, based on the direct coupling of O-protected baccatin III derivatives with the acid side chain of paclitaxel or docetaxel, made paclitaxel as well as docetaxel available for clinical use.
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Patents
Sample Use Guides
Cytotoxicity study of human cancer cell lines (A549, SW480, MCF-7, HepG2, A2780, A2780/TAX, HCT-8, HCT-8/VCT, A549/CDDP, MCF-7/DOX, and NIH-3T3) of different tissues was determined using 96-well tissue culture plates. Sulforhodamine B (SRB) assay was performed to evaluate cell viability and to obtain the IC50 values. Cells were plated at 5000 cells/well. The cells were allowed to grow in carbon dioxide incubator (37 C, 5% CO2, 90% RH) for 24 h. Then test compounds (14, 10-Deacetylbaccatin III) in complete growth medium (100 L) were added to the wells in triplicate. The plates were further incubated for 48 h. The cell growth was stopped by gently layering trichloroacetic acid (50%, 50 L) on top of the medium in all the wells. The plates were incubated at 4 C for 1 h to fix the cells attached to the bottom of the wells. The liquid of all the wells was gently pipetted out and discarded. The plates were washed five times with distilled water to remove trichloroacetic acid, growth medium, low molecular weight metabolites, serum proteins etc. and air-dried. The plates were stained with SRB dye (0.4% in 1% acetic acid, 100 L) for 30 min. The plates were washed five times with 1% acetic acid and then air-dried. The adsorbed dye was dissolved in Tris base solution (150 L, 10 mM, pH 10.4) and plates were gently shaken for 1 h on an orbital shaker. The optical density (OD) was recorded on a TECAN infinite M200 pro multimode reader at 515 nm.