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Compound Detail

CHEMBL481245

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COc1cc(/C=C/C(=O)OCCc2ccc(O)cc2)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL481245
Phase Preclinical
Structure Type MOL
InChI Key JMSFLLZUCIXALN-WEVVVXLNSA-N
13
Targets
16
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

314.3
MW (Da)
2.91
ALogP
5
HBA
2
HBD
76.0
PSA (Ų)
0.63
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 C18H18O5
MW 314.34
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.70

Activity Summary

Ki 9 meas. best 6.21
IC50 7 meas. best 4.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 7
CHEMBL2326
 Ki 6.21 6.21 620.0 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 6.17 6.17 670.0 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 6.14 6.14 720.0 1
Carbonic anhydrase 6
CHEMBL3025
 Ki 6.11 6.11 770.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 6.09 6.09 810.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 6.09 6.09 810.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 6.03 6.03 930.0 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 5.07 5.07 8470.0 1
Hepatocyte growth factor receptor
CHEMBL3717
 IC50 4.89 4.89 12900.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 4.36 4.36 44000.0 1
MDA-MB-231
CHEMBL400
 IC50 4.35 4.205 44300.0 2
5-hydroxytryptamine receptor 7
CHEMBL3155
 IC50 4.32 4.32 47600.0 1
MDA-MB-468
CHEMBL614335
 IC50 4.02 4.02 95500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 7 Ki = 620.0 nM 6.21 Inhibition of human carbonic anhydrase 7 preincubated for 15 mins by stopped-flo... 26498394
Carbonic anhydrase 5B, mitochondrial Ki = 670.0 nM 6.17 Inhibition of human carbonic anhydrase 5B preincubated for 15 mins by stopped-fl... 26498394
Carbonic anhydrase 14 Ki = 720.0 nM 6.14 Inhibition of human carbonic anhydrase 14 preincubated for 15 mins by stopped-fl... 26498394
Carbonic anhydrase 6 Ki = 770.0 nM 6.11 Inhibition of human carbonic anhydrase 6 preincubated for 15 mins by stopped-flo... 26498394
Carbonic anhydrase 5A, mitochondrial Ki = 810.0 nM 6.09 Inhibition of human carbonic anhydrase 5A preincubated for 15 mins by stopped-fl... 26498394
Carbonic anhydrase 9 Ki = 810.0 nM 6.09 Inhibition of human catalytic domain of carbonic anhydrase 9 preincubated for 15... 26498394
Carbonic anhydrase 13 Ki = 930.0 nM 6.03 Inhibition of mouse carbonic anhydrase 13 preincubated for 15 mins by stopped-fl... 26498394
Carbonic anhydrase 12 Ki = 8470.0 nM 5.07 Inhibition of human catalytic domain of carbonic anhydrase 12 preincubated for 1... 26498394
Hepatocyte growth factor receptor IC50 = 12900.0 nM 4.89 Inhibition of recombinant human N-terminal His-tagged cytoplasmic c-MET kinase d... 27258622
Carbonic anhydrase 4 Ki = 44000.0 nM 4.36 Inhibition of human carbonic anhydrase 4 preincubated for 15 mins by stopped-flo... 26498394
MDA-MB-231 IC50 = 44300.0 nM 4.35 Antimigratory activity against human MDA-MB-231 cells expressing c-MET assessed ... 27258622
5-hydroxytryptamine receptor 7 IC50 = 47600.0 nM 4.32 Displacement of [3H]LSD from human recombinant 5HT7 receptor expressed in CHO ce... 16643021
MDA-MB-231 IC50 = 87600.0 nM 4.06 Antiproliferative activity against human MDA-MB-231 cells expressing c-MET asses... 27258622
MDA-MB-468 IC50 = 95500.0 nM 4.02 Antiproliferative activity against human MDA-MB-468 cells expressing c-MET asses... 27258622

Literature References

PubMed DOI Target Context # Activities
29631958 10.1016/j.bmcl.2018.03.079 Erythrocyte 2
16643021 10.1021/np050301s 5-hydroxytryptamine receptor 7 2
27258622 10.1016/j.ejmech.2016.04.043 MDA-MB-231 2
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 6 1
27258622 10.1016/j.ejmech.2016.04.043 MDA-MB-468 1
27258622 10.1016/j.ejmech.2016.04.043 Hepatocyte growth factor receptor 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 14 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 13 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 12 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 9 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 7 1
11374950 10.1021/np000607t NON-PROTEIN TARGET 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 5B, mitochondrial 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 5A, mitochondrial 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 4 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 1 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 2 1
26498394 10.1016/j.bmc.2015.10.014 Carbonic anhydrase 3 1
11374950 10.1021/np000607t HT-1080 1

Data from ChEMBL 36 via Core Engine