Structure Database (LMSD)
Common Name
Cucurbitacin E
Systematic Name
Synonyms
LM ID
LMST01010107
Formula
Exact Mass
Calculate m/z
556.30362
Sum Composition
Status
Curated
3D model of Cucurbitacin E
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Cucurbitacin E is a plant-derived triterpene that has diverse biological activities. At a concentration of 10 pM, it reduces MPP+-induced death of neuronal PC12 cells through inhibition of autophagy in vitro.1 Cucurbitacin E inhibits growth of T24 bladder, MDA-MB-468 and MCF-7 breast, PC3 prostate, and colorectal cancer cell lines (IC50s = 50-1,000 nM) through induction of G2/M arrest and apoptosis.2,3,4 It increases bilirubin binding to human serum albumin (HSA) in human plasma in a dose-dependent manner.5 Cucurbitacin E also inhibits depolymerization of actin filaments isolated from rabbit skeletal muscle actin and in HeLa cells.6
This information has been provided by Cayman Chemical
References
1. Hsu, Y.-C., Huang, T.-Y., and Chen, M.-J. Therapeutic ROS targeting of GADD45γ in the induction of G2/M arrest in primary human colorectal cancer cell lines by cucurbitacin E. Cell Death Dis. 5(4), e1198 (2014).
3. Huang, W.-W., Yang, Y.-S., Lin, M.-W., et al. Cucurbitacin E induces G2/M phase arrest through STAT3/p53/p21 signaling and provokes apoptosis via Fas/CD95 and mitochondria-dependent pathways in human bladder cancer T24 cells. Evid. Based Complement. Altnernat. Med. 952762 (2012).
4. Greige-Gerges, H., Abou Khalil, R., Chahine, R., et al. Effect of cucurbitacins on bilirubin-albumin binding in human plasma. Life Sci. 80(6), 579-585 (2007).
5. Sörensen, P.M., Iacob, R.E., Fritzsche, M., et al. The natural product cucurbitacin E inhibits depolymerization of actin filaments. ACS Chem Biol. 7(9), 1502-1508 (2012).
6. Arel-Dubeau, A.-M., Longpré, F., Bournival, J., et al. Cucurbitacin E has neuroprotective properties and autophagic modulating activities on dopaminergic neurons. Oxid. Med. Cell. Longev. 425496 (2014).
String Representations
InChiKey (Click to copy)
NDYMQXYDSVBNLL-MUYMLXPFSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@@]12(C)C[C@H]([C@]([H])([C@](O)(C)C(=O)/C=C/C(C)(C)OC(=O)C)[C@@]1(C)CC([C@@]1(C)[C@]3([H])C=C(C(=O)C(C)(C)C3=CC[C@@]21[H])O)=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
40
Rings
4
Aromatic Rings
0
Rotatable Bonds
6
Van der Waals Molecular Volume
564.56
Topological Polar Surface Area
138.20
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
8
logP
5.05
Molar Refractivity
149.39
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Updated at
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