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Compound Detail

CHEMBL560175

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COc1cc(O)c(/C=C\C(=O)O)cc1[C@@H](O)CC(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL560175
Phase Preclinical
Structure Type MOL
InChI Key KXEZMFMTEVLUPQ-ZFDPJTLLSA-N
12
Targets
12
Activities
1
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

280.3
MW (Da)
2.58
ALogP
4
HBA
3
HBD
87.0
PSA (Ų)
0.70
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H20O5
MW 280.32
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness 0.88

Activity Summary

IC50 12 meas. best 7.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 2
CHEMBL205
 IC50 7.23 7.23 59.0 1
Carbonic anhydrase 1
CHEMBL261
 IC50 7.11 7.11 78.0 1
Carbonic anhydrase 4
CHEMBL3729
 IC50 6.42 6.42 380.0 1
Carbonic anhydrase 14
CHEMBL3510
 IC50 6.11 6.11 780.0 1
Carbonic anhydrase 13
CHEMBL2186
 IC50 6.1 6.1 790.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 IC50 5.02 5.02 9600.0 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 IC50 4.75 4.75 17700.0 1
Carbonic anhydrase 7
CHEMBL2326
 IC50 4.55 4.55 27900.0 1
Carbonic anhydrase 6
CHEMBL3025
 IC50 4.45 4.45 35700.0 1
Carbonic anhydrase 12
CHEMBL3242
 IC50 4.31 4.31 48600.0 1
Carbonic anhydrase 9
CHEMBL3594
 IC50 4.26 4.26 54500.0 1
Carbonic anhydrase 15
CHEMBL5973
 IC50 4.03 4.03 93100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 2 IC50 = 59.0 nM 7.23 Inhibition of human carbonic anhydrase 2 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 1 IC50 = 78.0 nM 7.11 Inhibition of human carbonic anhydrase 1 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 4 IC50 = 380.0 nM 6.42 Inhibition of human carbonic anhydrase 4 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 14 IC50 = 780.0 nM 6.11 Inhibition of human carbonic anhydrase 14 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 13 IC50 = 790.0 nM 6.1 Inhibition of mouse carbonic anhydrase 13 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 5A, mitochondrial IC50 = 9600.0 nM 5.02 Inhibition of human carbonic anhydrase 5A by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 5B, mitochondrial IC50 = 17700.0 nM 4.75 Inhibition of human carbonic anhydrase 5B by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 7 IC50 = 27900.0 nM 4.55 Inhibition of human carbonic anhydrase 7 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 6 IC50 = 35700.0 nM 4.45 Inhibition of human carbonic anhydrase 6 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 12 IC50 = 48600.0 nM 4.31 Inhibition of human carbonic anhydrase 12 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 9 IC50 = 54500.0 nM 4.26 Inhibition of human carbonic anhydrase 9 by stopped flow CO2 hydration assay 19527930
Carbonic anhydrase 15 IC50 = 93100.0 nM 4.03 Inhibition of mouse carbonic anhydrase 15 by stopped flow CO2 hydration assay 19527930

Literature References

PubMed DOI Target Context # Activities
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 1 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 2 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 3 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 4 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 5A, mitochondrial 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 5B, mitochondrial 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 6 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 7 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 9 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 12 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 13 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 14 1
19527930 10.1016/j.bmcl.2009.06.002 Carbonic anhydrase 15 1

Data from ChEMBL 36 via Core Engine