Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C31H38O11 |
| Molecular Weight | 586.6268 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)O[C@@H]1C2=C(C)[C@@H](O)C[C@@](O)([C@@H](OC(=O)C3=CC=CC=C3)[C@@H]4[C@@]5(CO[C@@H]5C[C@H](O)[C@@]4(C)C1=O)OC(C)=O)C2(C)C
InChI
InChIKey=OVMSOCFBDVBLFW-VHLOTGQHSA-N
InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,26-,29+,30-,31+/m0/s1
| Molecular Formula | C31H38O11 |
| Molecular Weight | 586.6268 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Baccatin III is an isolate of the Pacific yew tree (Taxus brevifolia) and related species. Baccatin III is the precursor to paclitaxel/ taxol. Antileukaemic and antitumor agent, Baccatin III, binds to tubules when they are assembled in the cell and stabilizes the polymerized form of tubules so that they remain assembled even under conditions in which microtubules dissociate into tubulin subunits. Baccatin III is also an inducer of apoptosis and shows antitumor properties in vitro. Baccatin III exerts anti-tumor immunomodulatory activity in very low doses (0.05-0.5mg/kg), although it is regarded as an inactive derivative of paclitaxel. Oral administration of Baccatin III significantly reduced the growth of tumors induced by engrafting BALB/c mice with either 4 T1 mammary carcinoma or CT26 colon cancer cells. Baccatin III reduced tumor progression by inhibiting the accumulation and suppressive function of MDSCs. Baccatin III inhibited cell proliferation of a number of cancer cell lines. The cytotoxic activity exhibited by fungal taxol and Baccatin III involves the same mechanism, dependent on caspase-10 and membrane potential loss of mitochondria, with taxol having far greater cytotoxic potential.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: MHC-restricted antigen presentation Sources: https://www.ncbi.nlm.nih.gov/pubmed/21354357 |
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Target ID: GO:0046785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11389612 |
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Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24152585 |
3.0 µM [IC50] | ||
Target ID: CHEMBL614361 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24152585 |
2.0 µM [IC50] | ||
Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24152585 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Changes in gene transcription and taxane production in elicited cell cultures of Taxus × media and Taxus globosa. | 2015-09 |
|
| Bioproduction of baccatin III, an advanced precursor of paclitaxol, with transgenic Flammulina velutipes expressing the 10-deacetylbaccatin III-10-O-acetyl transferase gene. | 2014-09 |
|
| Baccatin III, a precursor for the semisynthesis of paclitaxel, inhibits the accumulation and suppressive activity of myeloid-derived suppressor cells in tumor-bearing mice. | 2014-08 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24957690
Oral administration of baccatin III (0.05-0.5mg/kg) significantly reduced the growth of tumors induced by engrafting BALB/c mice with either 4 T1 mammary carcinoma or CT26 colon cancer cells.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24152585
Baccatin III inhibited cell proliferation of a number of cancer cell lines with IC50 ranging from 2 to 5 uM. JR4-Jurkat and HeLa cells treated with 3.5 and 3 uM of baccatin III showed a considerable increase in the percentage of apoptotic nuclei after 12 h incubation.
| Substance Class |
Chemical
Created
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| Record UNII |
40K5PZ0K67
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C67437
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NCI_THESAURUS |
C1490
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300000053089
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330753
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C1436
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BACCATIN III
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65366
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40K5PZ0K67
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DTXSID301029474
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32898
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PARENT -> IMPURITY |
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