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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H38O11
Molecular Weight 586.628
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BACCATIN III

SMILES

CC1=C2[C@]([H])(C(=O)[C@]3(C)[C@]([H])(C[C@]4([H])[C@@](CO4)([C@@]3([H])[C@@]([H])([C@](C[C@]1([H])O)(C2(C)C)O)OC(=O)c5ccccc5)OC(=O)C)O)OC(=O)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

HIDE SMILES / InChI

Molecular Formula C31H38O11
Molecular Weight 586.628
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: MHC-restricted antigen presentation
3 µM [IC50]
Target ID: CHEMBL614361
2 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
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 Aug
Bioproduction of baccatin III, an advanced precursor of paclitaxol, with transgenic Flammulina velutipes expressing the 10-deacetylbaccatin III-10-O-acetyl transferase gene.
2014 Sep
Changes in gene transcription and taxane production in elicited cell cultures of Taxus × media and Taxus globosa.
2015 Sep
Patents

Sample Use Guides

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
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
by admin
on Sat Jun 26 06:16:55 UTC 2021
Edited
by admin
on Sat Jun 26 06:16:55 UTC 2021
Record UNII
40K5PZ0K67
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BACCATIN III
WHO-DD  
Common Name English
7,11-METHANO-5H-CYCLODECA(3,4)BENZ(1,2-B)OXET-5-ONE, 6,12B-BIS(ACETYLOXY)-12-(BENZOYLOXY)-1,2A,3,4,4A,6,9,10,11,12,12A,12B-DODECAHYDRO-4,9,11-TRIHYDROXY-4A,8,13,13-TETRAMETHYL-, (2AR,4S,4AS,6R,9S,11S,12S,12AR,12BS)-
Common Name English
NSC-330753
Code English
BACCATIN III [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67437
Created by admin on Sat Jun 26 06:16:55 UTC 2021 , Edited by admin on Sat Jun 26 06:16:55 UTC 2021
NCI_THESAURUS C1490
Created by admin on Sat Jun 26 06:16:55 UTC 2021 , Edited by admin on Sat Jun 26 06:16:55 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C1436
Created by admin on Sat Jun 26 06:16:55 UTC 2021 , Edited by admin on Sat Jun 26 06:16:55 UTC 2021
PRIMARY
WIKIPEDIA
BACCATIN III
Created by admin on Sat Jun 26 06:16:55 UTC 2021 , Edited by admin on Sat Jun 26 06:16:55 UTC 2021
PRIMARY
PUBCHEM
65366
Created by admin on Sat Jun 26 06:16:55 UTC 2021 , Edited by admin on Sat Jun 26 06:16:55 UTC 2021
PRIMARY
CAS
27548-93-2
Created by admin on Sat Jun 26 06:16:55 UTC 2021 , Edited by admin on Sat Jun 26 06:16:55 UTC 2021
PRIMARY
FDA UNII
40K5PZ0K67
Created by admin on Sat Jun 26 06:16:55 UTC 2021 , Edited by admin on Sat Jun 26 06:16:55 UTC 2021
PRIMARY
Related Record Type Details
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