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Compound Detail

CHEMBL589354

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O=C(Cc1ccc(O)c(Cl)c1)NCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL589354
Phase Preclinical
Structure Type MOL
InChI Key DEUPTZFEFNDUTO-UHFFFAOYSA-N
7
Targets
7
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

275.7
MW (Da)
2.90
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.90
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H14ClNO2
MW 275.74
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.96

Activity Summary

Ki 6 meas. best 6.14
IC50 1 meas. best 5.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 2
CHEMBL1697676
 Ki 6.14 6.14 720.0 1
Carbonic anhydrase
CHEMBL5337
 Ki 6.11 6.11 780.0 1
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)
CHEMBL5767
 Ki 6.01 6.01 980.0 1
17-beta-hydroxysteroid dehydrogenase type 2
CHEMBL2789
 IC50 5.47 5.47 3420.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 4.98 4.98 10500.0 1
Carbonic anhydrase 2
CHEMBL205
 Ki 4.94 4.94 11400.0 1
Beta-carbonic anhydrase 1
CHEMBL5631
 Ki 4.91 4.91 12200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 2 Ki = 720.0 nM 6.14 Inhibition of Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase a... 21332115
Carbonic anhydrase Ki = 780.0 nM 6.11 Inhibition of Candida albicans recombinant Nce103 beta-carbonic anhydrase after ... 21332115
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) Ki = 980.0 nM 6.01 Inhibition of Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydr... 21332115
17-beta-hydroxysteroid dehydrogenase type 2 IC50 = 3420.0 nM 5.47 Inhibition of human 17beta-HSD2 expressed in HEK293 cell lysates incubated for 1... 28319389
Carbonic anhydrase 1 Ki = 10500.0 nM 4.98 Inhibition of human recombinant alpha-carbonic anhydrase 1 after 15 mins by stop... 21332115
Carbonic anhydrase 2 Ki = 11400.0 nM 4.94 Inhibition of human recombinant alpha-carbonic anhydrase 2 after 15 mins by stop... 21332115
Beta-carbonic anhydrase 1 Ki = 12200.0 nM 4.91 Inhibition of Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydr... 21332115

Literature References

PubMed DOI Target Context # Activities
21332115 10.1021/jm1013242 Unchecked 8
19962903 10.1016/j.bmc.2009.11.021 Unchecked 4
21332115 10.1021/jm1013242 Carbonic anhydrase 2 2
28319389 10.1021/acs.jnatprod.6b00950 Unchecked 1
28319389 10.1021/acs.jnatprod.6b00950 17-beta-hydroxysteroid dehydrogenase type 1 1
28319389 10.1021/acs.jnatprod.6b00950 17-beta-hydroxysteroid dehydrogenase type 2 1
25803573 10.1021/np500856u Trypanosoma brucei brucei 1
25803573 10.1021/np500856u Plasmodium falciparum 1
25803573 10.1021/np500856u LNCaP 1
21332115 10.1021/jm1013242 Carbonic anhydrase 1 1
21332115 10.1021/jm1013242 Carbonic anhydrase 1
21332115 10.1021/jm1013242 Beta-carbonic anhydrase 1 1
21332115 10.1021/jm1013242 PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) 1
19962903 10.1016/j.bmc.2009.11.021 Carbonic anhydrase 1 1
19962903 10.1016/j.bmc.2009.11.021 Carbonic anhydrase 2 1
19962903 10.1016/j.bmc.2009.11.021 Carbonic anhydrase 5A, mitochondrial 1
19962903 10.1016/j.bmc.2009.11.021 Carbonic anhydrase 5B, mitochondrial 1

Data from ChEMBL 36 via Core Engine