Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C32H46O8 |
Molecular Weight | 558.7028 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1([C@H](O)C[C@@]2(C)[C@]3([H])CC=C4[C@@]([H])(C[C@H](O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C)[C@@](C)(O)C(=O)\C=C\C(C)(C)OC(C)=O
InChI
InChIKey=IXQKXEUSCPEQRD-DKRGWESNSA-N
InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1
Molecular Formula | C32H46O8 |
Molecular Weight | 558.7028 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 9 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Cucurbitacin B (CuB), an oxygenated tetracyclic triterpenoid compound extracted from Cucurbitaceae plant species, is a long-term anticancer agent by disruption of microtubule polymerization. Cucurbitacin B is a naturally occurring compound that is found abundantly in cucumbers and other vegetables, and it is known to exert anti-cancer activities (primarily via apoptosis-induction) in several human cancers. Cucurbitacin B also protects against cardiac hypertrophy through increasing the autophagy level in cardiomyocytes, which is associated with the inhibition of Akt/mTOR/FoxO3a signal axis. ACLY over-expression abrogated CuB's apoptotic effects in prostate cancer cells, confirming ACLY as a direct target of CuB. Thus, CuB harbors potent chemopreventive activity for prostate cancer, and we revealed a novel anti-tumor mechanism of CuB via inhibition of ACLY signaling in human cancer. It has being suggested that cucurbitacin B exerts an anticancer effect by inhibiting telomerase via down regulating both the hTERT and c-Myc expression in breast cancer cells.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4722 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27418139 |
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Target ID: CHEMBL3720 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24690568 |
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Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20153103 |
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Target ID: CHEMBL2916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21614210 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20153103
Mice: When the BEL-7402 tumor size reached 30–50 mm3, the mice were dosed with cucurbitacin B at 0.1, 0.5, 1.0 and 3.0 mg/kg twice a day through oral administration. Oral administration of cucurbitacin B at 0.5 and
1 mg/kg obviously inhibited tumor growth in more than half of the treated
mice. The tumor weight of the 0.5 mg/kg and 1 mg/kg treated
groups was 0.42 ± 0.19 g and 0.34 ± 0.16 g, respectively. When compared
to the control group (0.69 ± 0.22 g), the inhibition rate was 40.03% at
0.5 mg/kg (P < 0.05) and 50.43% at 1 mg/kg (P < 0.01).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24729020
Cucurbitacin B (CuB) inhibited the growth of various breast cancer cells with an IC50 ranging from 18-50nM after 48 and 72 h of treatment.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:14:32 GMT 2023
by
admin
on
Sat Dec 16 09:14:32 GMT 2023
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Record UNII |
0115W5MABF
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Record Status |
Validated (UNII)
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Record Version |
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