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Compound Detail

CHEMBL36455

E-COMBRETASTATIN A-4
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COc1ccc(/C=C/c2cc(OC)c(OC)c(OC)c2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL36455
Name E-COMBRETASTATIN A-4
Phase Preclinical
Structure Type MOL
InChI Key HVXBOLULGPECHP-AATRIKPKSA-N
7
Targets
10
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

316.4
MW (Da)
3.60
ALogP
5
HBA
1
HBD
57.1
PSA (Ų)
0.83
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H20O5
MW 316.35
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.57

Activity Summary

IC50 10 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 8.85 7.905 1.4 2
P388
CHEMBL389
 IC50 8.59 8.59 2.6 1
KB 3-1
CHEMBL614590
 IC50 7.0 7.0 100.0 1
HEK293
CHEMBL614818
 IC50 6.7 6.7 200.0 1
NCI-H460
CHEMBL396
 IC50 6.6 6.6 250.0 1
Unchecked
CHEMBL612545
 IC50 5.96 5.22 1100.0 2
Tubulin beta-1 chain
CHEMBL1915
 IC50 4.48 4.39 33000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 1.4 nM 8.85 Antiproliferative activity against human MCF7 cells after 48 hrs by sulforhodami... 19135763
P388 IC50 = 2.6 nM 8.59 Concentration required for 50% inhibition of P388 murine leukemia cell growth in... 11140732
KB 3-1 IC50 = 100.0 nM 7.0 Cytotoxicity against human KB3-1 cells after 68 hrs by MTT assay 32243160
MCF7 IC50 = 110.0 nM 6.96 Cytotoxicity against human MCF7 cells after 68 hrs by MTT assay 32243160
HEK293 IC50 = 200.0 nM 6.7 Cytotoxicity against HEK293 cells after 68 hrs by MTT assay 32243160
NCI-H460 IC50 = 250.0 nM 6.6 Cytotoxicity against human NCI-H460 cells after 68 hrs by MTT assay 32243160
Unchecked IC50 = 1100.0 nM 5.96 Inhibition of bovine brain tubulin by spectrophotometry 19135763
Tubulin beta-1 chain IC50 = 33000.0 nM 4.48 Inhibition of tubulin polymerization upon incubation for 20 min at 30 degree C 15943482
Unchecked IC50 = 33000.0 nM 4.48 Inhibition of tubulin polymerization 19709889
Tubulin beta-1 chain IC50 = 50000.0 nM 4.3 Concentration required for 50% inhibition of tubulin polymerization 15658859

Literature References

PubMed DOI Target Context # Activities
21497957 10.1016/j.ejmech.2011.03.049 MCF7 15
21497957 10.1016/j.ejmech.2011.03.049 HepG2 10
20363626 10.1016/j.bmcl.2010.03.066 Saccharomyces cerevisiae 3
19135763 10.1016/j.ejmech.2008.12.018 Unchecked 3
21497957 10.1016/j.ejmech.2011.03.049 HeLa 2
- 10.1007/s00044-012-0212-x Brontispa longissima 2
10924176 10.1021/np0000623 Cryptococcus neoformans 1
19709889 10.1016/j.bmc.2009.07.076 BXPC-3 1
19709889 10.1016/j.bmc.2009.07.076 P388 1
32243160 10.1021/acs.jnatprod.0c00027 MCF7 1
10924176 10.1021/np0000623 Enterobacter cloacae 1
10924176 10.1021/np0000623 Escherichia coli 1
10924176 10.1021/np0000623 Micrococcus luteus 1
10924176 10.1021/np0000623 Candida albicans 1
10924176 10.1021/np0000623 Stenotrophomonas maltophilia 1
10924176 10.1021/np0000623 Streptococcus pneumoniae 1
10924176 10.1021/np0000623 Staphylococcus aureus 1
15658859 10.1021/jm049444m Tubulin beta-1 chain 1
15943482 10.1021/jm0205797 Tubulin beta-1 chain 1
11140732 10.1016/s0960-894x(00)00596-5 P388 1

Data from ChEMBL 36 via Core Engine