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Compound Detail

CHEMBL455056

CUCURBITACIN E
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CC(=O)OC(C)(C)/C=C/C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL455056
Name CUCURBITACIN E
Phase Preclinical
Structure Type MOL
InChI Key NDYMQXYDSVBNLL-MUYMLXPFSA-N
9
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

556.7
MW (Da)
4.19
ALogP
8
HBA
3
HBD
138.2
PSA (Ų)
0.26
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C32H44O8
MW 556.70
Aromatic Rings 0
Heavy Atoms 40
NP-Likeness 3.15

Activity Summary

IC50 9 meas. best 8.15
EC50 2 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.15 8.15 7.0 1
U-937
CHEMBL612794
 IC50 7.8 7.8 16.0 1
HL-60
CHEMBL383
 IC50 7.75 7.75 18.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.4 7.4 40.0 1
HT-1080
CHEMBL614580
 IC50 7.4 7.4 40.0 1
MCF7
CHEMBL387
 IC50 7.26 7.26 55.0 1
HeLa
CHEMBL399
 IC50 7.0 7.0 100.0 1
Integrin alpha-L
CHEMBL1803
 IC50 6.75 6.75 180.0 1
ADMET
CHEMBL612558
 IC50 5.69 5.69 2030.0 1
HepG2
CHEMBL395
 EC50 5.5 5.5 3200.0 1
HepG2
CHEMBL395
 IC50 4.82 4.82 15250.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 7.0 nM 8.15 Growth inhibition of human prostate cancer cells 15332833
U-937 IC50 = 16.0 nM 7.8 Cytotoxicity against human U937 cells after 72 hrs by WST-8 assay 20347305
HL-60 IC50 = 18.0 nM 7.75 Cytotoxicity against human HL60 cells after 72 hrs by WST-8 assay 20347305
NON-PROTEIN TARGET EC50 = 40.0 nM 7.4 Antiproliferative activity against serum-stimulated rat HSC-T6 cells after 24 hr... 21459003
HT-1080 IC50 = 40.0 nM 7.4 Cytotoxicity against human HT1080 cells after 72 hrs by WST-8 assay 20347305
MCF7 IC50 = 55.0 nM 7.26 Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs... 25756299
HeLa IC50 = 100.0 nM 7.0 Cytotoxicity against human HeLa cells after 24 hrs by MTT assay 21459003
Integrin alpha-L IC50 = 180.0 nM 6.75 Inhibition of LFA1 expressed in human JY cells interaction with ICAM1-IG express... 7852999
ADMET IC50 = 2030.0 nM 5.69 Cytotoxicity against rat HSC-T6 cell after 24 hrs by MTT assay 21459003
HepG2 EC50 = 3200.0 nM 5.5 Hepatoprotective activity in human HepG2 cells assessed as inhibition of CCl4-in... 21459003
HepG2 IC50 = 15250.0 nM 4.82 Cytotoxicity against human HepG2 cells after 24 hrs assessed as inhibition of ce... 21459003

Literature References

PubMed DOI Target Context # Activities
7852999 10.1021/np50113a004 JY 7
25756299 10.1021/acs.jnatprod.5b00054 Heat shock protein HSP90 7
21459003 10.1016/j.bmc.2011.01.037 HepG2 6
15332833 10.1021/np049953r NON-PROTEIN TARGET 5
7807128 10.1021/np50112a015 NON-PROTEIN TARGET 4
20347305 10.1016/j.bmcl.2010.02.062 U-937 4
20347305 10.1016/j.bmcl.2010.02.062 Signal transducer and activator of transcription 3 3
7852999 10.1021/np50113a004 Unchecked 3
7807128 10.1021/np50112a015 SK-MEL-28 2
7807128 10.1021/np50112a015 OVCAR-8 2
7807128 10.1021/np50112a015 OVCAR-5 2
7807128 10.1021/np50112a015 UACC-62 2
7807128 10.1021/np50112a015 UACC-257 2
7807128 10.1021/np50112a015 SK-MEL-5 2
7807128 10.1021/np50112a015 M14 2
7807128 10.1021/np50112a015 Malme-3M 2
7807128 10.1021/np50112a015 U-251 2
7807128 10.1021/np50112a015 SNB-75 2
7807128 10.1021/np50112a015 SF-539 2
7807128 10.1021/np50112a015 SF-295 2

Data from ChEMBL 36 via Core Engine