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Details

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
Structure of 10-DEACETYLBACCATIN III

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

HIDE SMILES / InChI

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

Description

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.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
4K6EWW2Z45
Record Status Validated (UNII)
Record Version