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Compound Detail

CHEMBL471655

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COc1cc(/C=C/C(=O)c2ccc(N)cc2)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL471655
Phase Preclinical
Structure Type MOL
InChI Key HORVIDXMQQVQAS-RUDMXATFSA-N
8
Targets
10
Activities
2
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

313.4
MW (Da)
3.19
ALogP
5
HBA
1
HBD
70.8
PSA (Ų)
0.50
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 C18H19NO4
MW 313.35
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.15

Activity Summary

IC50 6 meas. best 5.64
Ki 4 meas. best 8.29

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 1
CHEMBL261
 Ki 8.29 8.14 5.1 2
Carbonic anhydrase 2
CHEMBL205
 Ki 7.93 7.7 11.8 2
CCRF-CEM
CHEMBL382
 IC50 5.64 5.64 2300.0 1
MOLT-4
CHEMBL614177
 IC50 5.25 5.25 5600.0 1
HeLa
CHEMBL399
 IC50 5.16 5.16 6900.0 1
L1210
CHEMBL386
 IC50 5.11 5.11 7800.0 1
FM3A
CHEMBL614297
 IC50 5.06 5.06 8800.0 1
GTPase KRas
CHEMBL2189121
 IC50 5.04 5.04 9170.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 1 Ki = 5.13 nM 8.29 Inhibition of human CA1 32795767
Carbonic anhydrase 1 Ki = 10.17 nM 7.99 Binding affinity to human CA1 assessed as inhibition constant using 4-nitropheny... 33121862
Carbonic anhydrase 2 Ki = 11.77 nM 7.93 Inhibition of human CA2 32795767
Carbonic anhydrase 2 Ki = 33.75 nM 7.47 Binding affinity to human CA2 assessed as inhibition constant using 4-nitropheny... 33121862
CCRF-CEM IC50 = 2300.0 nM 5.64 Antiproliferative activity against human CEM cells after 48 hrs by Coulter count... 19250822
MOLT-4 IC50 = 5600.0 nM 5.25 Antiproliferative activity against human MOLT4 cells after 48 hrs by Coulter cou... 19250822
HeLa IC50 = 6900.0 nM 5.16 Antiproliferative activity against human HeLa cells after 48 hrs by Coulter coun... 19250822
L1210 IC50 = 7800.0 nM 5.11 Antiproliferative activity against mouse L1210 cells after 48 hrs by Coulter cou... 19250822
FM3A IC50 = 8800.0 nM 5.06 Antiproliferative activity against mouse FM3A cells after 48 hrs by Coulter coun... 19250822
GTPase KRas IC50 = 9170.0 nM 5.04 Inhibition of GFP-tagged KRAS G12V mutant (unknown origin) expressed in MDCK cel... 32276831

Literature References

PubMed DOI Target Context # Activities
32276831 10.1016/j.bmcl.2020.127144 GTPase KRas 2
19250822 10.1016/j.bmcl.2009.02.038 L1210 1
19250822 10.1016/j.bmcl.2009.02.038 FM3A 1
19250822 10.1016/j.bmcl.2009.02.038 MOLT-4 1
19250822 10.1016/j.bmcl.2009.02.038 CCRF-CEM 1
19250822 10.1016/j.bmcl.2009.02.038 HeLa 1
33121862 10.1016/j.ejmech.2020.112923 Carbonic anhydrase 1 1
33121862 10.1016/j.ejmech.2020.112923 Carbonic anhydrase 2 1
32795767 10.1016/j.ejmech.2020.112666 Carbonic anhydrase 1 1
32795767 10.1016/j.ejmech.2020.112666 Carbonic anhydrase 2 1

Data from ChEMBL 36 via Core Engine