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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
Structure of CUCURBITACIN B

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

HIDE SMILES / InChI

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

PubMed

PubMed

TitleDatePubMed
Cucurbitacin B and cucurbitacin I suppress adipocyte differentiation through inhibition of STAT3 signaling.
2014 Feb
Patents

Sample Use Guides

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
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 Sat Dec 16 09:14:32 GMT 2023
Edited
by admin
on Sat Dec 16 09:14:32 GMT 2023
Record UNII
0115W5MABF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CUCURBITACIN B
INCI   MI  
INCI  
Official Name English
CUCURBITACIN B [MI]
Common Name English
(+)-CUCURBITACIN B
Common Name English
NSC-144154
Code English
DATISCACIN
Common Name English
AMARINE
Common Name English
1,2-DIHYDRO-.ALPHA.-ELATERIN
Common Name English
CUCURBITACIN B [INCI]
Common Name English
19-NORLANOSTA-5,23-DIENE-3,11,22-TRIONE, 25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-, (2.BETA.,9.BETA.,10.ALPHA.,16.ALPHA.,23E)-
Systematic Name English
NSC-49451
Code English
(2.BETA.,9.BETA.,10.ALPHA.,16.ALPHA.,23E)-25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-19-NORLANOSTA-5,23-DIENE-3,11,22-TRIONE
Systematic Name English
Code System Code Type Description
PUBCHEM
5281316
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
NSC
49451
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
FDA UNII
0115W5MABF
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
CHEBI
3941
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
MERCK INDEX
m3874
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY Merck Index
NSC
144154
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID501316196
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
CAS
6199-67-3
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
HSDB
3476
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
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