CUCURBITACIN E

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H44O8
Molecular Weight	556.687
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1([C@H](O)C[C@@]2(C)[C@]3([H])CC=C4[C@@]([H])(C=C(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=NDYMQXYDSVBNLL-MUYMLXPFSA-N

InChI=1S/C32H44O8/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/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27653525 | https://www.ncbi.nlm.nih.gov/pubmed/21871542 | https://www.ncbi.nlm.nih.gov/pubmed/25915611 | https://www.ncbi.nlm.nih.gov/pubmed/28274497

Cucurbitacin E (CuE), a potent member of triterpenoid family isolated from plants, has been confirmed as an antitumor agent by inhibiting proliferation, migration, and metastasis in diverse cancer. Cucurbitacin E nhibits OS tumor growth and invasion through inhibiting the PI3K/Akt/mTOR signaling pathway. CuE can be considered to be a promising anticancer agent for OS. Cucurbitacin E exerts anti-inflammatory actions. It inhibited both COX enzymes with more selectivity toward COX-2. CuE has been reported to possess anti-inflammatory and anti-tumorigenic properties mediated by its action on the cellular cytoskeleton, on mitotic pathways as well as on cellular autophagy.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20110807 \| https://www.ncbi.nlm.nih.gov/pubmed/22272214 \| https://www.ncbi.nlm.nih.gov/pubmed/27106530	Activator 1430
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21871542	Inhibitor 8297	90.0 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21871542	Inhibitor 8297	69.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteosarcoma 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27653525	Primary	Preclinical	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25915611 https://www.ncbi.nlm.nih.gov/pubmed/21871542	Primary	Preclinical	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28599494	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The cucurbitacins E, D and I: investigation of their cytotoxicity toward human chondrosarcoma SW 1353 cell line and their biotransformation in man liver.	2013 Feb 4	23194827

Patents

Sample Use Guides

In Vivo Use Guide

Cucurbitacin E was intra-peritoneally administered to mice at the dose of 30 and 60 mg/kg.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Cucurbitacin E at low concentrations (3-50 nmol/l) inhibited the growth of HL-60 cells, which was associated with G2/M cell-cycle arrest, decrease in the levels of cyclin-dependent kinase1, and increase in the levels of p21. Cucurbitacin E at high concentrations (1-10 mol/l) induced apoptosis of HL-60 cells and activation of caspase-3, caspase-8, and caspase-9

Name

Type

Language

CUCURBITACIN E

Common Name

English

(-)-CUCURBITACIN E

Common Name

English

.ALPHA.-ELATERIN

Common Name

English

ALPHA-ELATERIN

Common Name

English

CUCURBITACIN E [MI]

Common Name

English

(9.BETA.,10.ALPHA.,16.ALPHA.,23E)-25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-19-NORLANOSTA-1,5,23-TRIENE-3,11,22-TRIONE

Systematic Name

English

.ALPHA.-ELATERINE

Common Name

English

NSC-106399

Code

English

NSC-521775

Code

English

19-NORLANOSTA-1,5,23-TRIENE-3,11,22-TRIONE, 25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-, (9.BETA.,10.ALPHA.,16.ALPHA.,23E)-

Common Name

English

CUCURBITACINE E

Common Name

English

Code System Code Type Description

FDA UNII

V8A45XYI21