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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
Structure of BACCATIN III

SMILES

[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=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=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 586.6268
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
3.0 µM [IC50]
Target ID: CHEMBL614361
2.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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 Fri Dec 15 16:00:42 UTC 2023
Edited
by admin
on Fri Dec 15 16:00:42 UTC 2023
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
PACLITAXEL IMPURITY N [EP IMPURITY]
Common Name English
4,10β-bis(acetyloxy)-1,7β,13α-trihydroxy-9-oxo-5β,20-epoxytax-11-en-2α-yl benzoate (13-O-de[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]paclitaxel
Systematic Name English
Baccatin iii [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67437
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
NCI_THESAURUS C1490
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
Code System Code Type Description
NSC
330753
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
PRIMARY
NCI_THESAURUS
C1436
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
PRIMARY
WIKIPEDIA
BACCATIN III
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
PRIMARY
PUBCHEM
65366
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
PRIMARY
CAS
27548-93-2
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
PRIMARY
FDA UNII
40K5PZ0K67
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID301029474
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
PRIMARY
CHEBI
32898
Created by admin on Fri Dec 15 16:00:42 UTC 2023 , Edited by admin on Fri Dec 15 16:00:42 UTC 2023
PRIMARY
Related Record Type Details
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