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Compound Detail

CHEMBL226034

TAMARIXETIN
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COc1ccc(-c2oc3cc(O)cc(O)c3c(=O)c2O)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL226034
Name TAMARIXETIN
Phase Preclinical
Structure Type MOL
InChI Key FPLMIPQZHHQWHN-UHFFFAOYSA-N
17
Targets
27
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

316.3
MW (Da)
2.29
ALogP
7
HBA
4
HBD
120.4
PSA (Ų)
0.57
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H12O7
MW 316.27
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness 1.54

Activity Summary

IC50 26 meas. best 7.7
Kd 1 meas. best 5.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 1B1
CHEMBL4878
 IC50 7.7 7.7 20.0 1
Cytochrome P450 1A1
CHEMBL2231
 IC50 6.92 6.92 120.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 5.92 5.92 1215.0 1
HeLa
CHEMBL399
 IC50 5.74 5.74 1810.0 1
Unchecked
CHEMBL612545
 Kd 5.6 5.6 2520.0 1
A549
CHEMBL392
 IC50 5.58 5.58 2630.0 1
NCI-H157
CHEMBL614783
 IC50 5.52 5.52 3040.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.41 4.98 3860.0 8
NCI-H1792
CHEMBL1075525
 IC50 5.39 5.39 4060.0 1
Monocyte
CHEMBL614076
 IC50 5.34 5.34 4600.0 1
HOP-62
CHEMBL614643
 IC50 5.0 5.0 9930.0 1
M14
CHEMBL614317
 IC50 4.83 4.83 14850.0 1
Unchecked
CHEMBL612545
 IC50 4.79 4.545 16400.0 2
Trypanosoma cruzi
CHEMBL368
 IC50 4.69 4.69 20250.0 1
Peritoneal macrophage
CHEMBL5314330
 IC50 4.6 4.6 25000.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.33 4.33 46830.0 1
Leishmania donovani
CHEMBL367
 IC50 4.27 4.27 53150.0 1
Dihydroorotate dehydrogenase (fumarate)
CHEMBL4295843
 IC50 4.03 4.015 93700.0 2

Pharmacokinetic Data

Parameter Value Units Species
Ka 1.69 10^3/M/s Staphylococcus aureus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 1B1 IC50 = 20.0 nM 7.7 Inhibition of human CYP1B1 by EROD assay 20696580
Cytochrome P450 1A1 IC50 = 120.0 nM 6.92 Inhibition of human CYP1A1 by EROD assay 20696580
Cytochrome P450 1A2 IC50 = 1215.0 nM 5.92 Inhibition of human CYP1A2 by EROD assay 20696580
HeLa IC50 = 1810.0 nM 5.74 Anticancer activity against human HeLa cells by HTS assay 25139569
Unchecked Kd = 2520.0 nM 5.6 Binding affinity to methicillin-resistant Staphylococcus aureus USA300 ClpP asse... 35833867
A549 IC50 = 2630.0 nM 5.58 Anticancer activity against human A549 cells by HTS assay 25139569
NCI-H157 IC50 = 3040.0 nM 5.52 Anticancer activity against human NCI-H157 cells by HTS assay 25139569
NON-PROTEIN TARGET IC50 = 3860.0 nM 5.41 Anticancer activity against human NCI-H1944 cells by HTS assay 25139569
NCI-H1792 IC50 = 4060.0 nM 5.39 Anticancer activity against human NCI-H1792 cells by HTS assay 25139569
NON-PROTEIN TARGET IC50 = 4450.0 nM 5.35 Anticancer activity against human H460 cells by HTS assay 25139569
Monocyte IC50 = 4600.0 nM 5.34 Inhibition of procoagulant activity in monocyte from human blood assessed as cou... 8882428
NON-PROTEIN TARGET IC50 = 7570.0 nM 5.12 Anticancer activity against human H266 cells by HTS assay 25139569
NON-PROTEIN TARGET IC50 = 7970.0 nM 5.1 Anticancer activity against human SKBR cells by HTS assay 25139569
HOP-62 IC50 = 9930.0 nM 5.0 Anticancer activity against human HOP62 cells by HTS assay 25139569
NON-PROTEIN TARGET IC50 = 12540.0 nM 4.9 Anticancer activity against human 292G cells by HTS assay 25139569
M14 IC50 = 14850.0 nM 4.83 Anticancer activity against human M14 cells by HTS assay 25139569
Unchecked IC50 = 16400.0 nM 4.79 Inhibition of CAMK2 assessed as level of ATP utilized by luciferase-based biolum... 19296652
NON-PROTEIN TARGET IC50 = 19910.0 nM 4.7 Anticancer activity against human M4E cells by HTS assay 25139569
Trypanosoma cruzi IC50 = 20250.0 nM 4.69 Antitrypanosomal activity against Trypanosoma cruzi Tulahuen C2C4 trypomastigote... 30145372
NON-PROTEIN TARGET IC50 = 21970.0 nM 4.66 Anticancer activity against human H1299 cells by HTS assay 25139569

Literature References

PubMed DOI Target Context # Activities
29851490 10.1021/acs.jnatprod.8b00155 BMDC 32
29851490 10.1021/acs.jnatprod.8b00155 Mus musculus 27
35833867 10.1021/acs.jnatprod.2c00138 Unchecked 25
35833867 10.1021/acs.jnatprod.2c00138 Staphylococcus aureus 18
26517554 10.1021/acs.jnatprod.5b00075 ADMET 10
25139569 10.1016/j.bmcl.2014.08.006 NON-PROTEIN TARGET 9
24853321 10.1016/j.bmc.2014.04.053 B16-F0 6
29851490 10.1021/acs.jnatprod.8b00155 Toll-like receptor 4 6
26974691 10.1021/acs.jnatprod.5b01033 Mycobacterium tuberculosis 5
18855442 10.1021/np800333r Plasmodium falciparum 4
26517554 10.1021/acs.jnatprod.5b00075 Unchecked 4
22647223 10.1016/j.ejmech.2012.04.044 Thrombin 4
24853321 10.1016/j.bmc.2014.04.053 ADMET 3
30145372 10.1016/j.ejmech.2018.08.033 Dihydroorotate dehydrogenase (fumarate) 3
25190466 10.1016/j.bmcl.2014.07.093 Nuclear factor NF-kappa-B complex 3
19296652 10.1021/jm801445c Unchecked 2
21821414 10.1016/j.bmcl.2011.07.008 Radical scavenging activity 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
35833867 10.1021/acs.jnatprod.2c00138 HEK-293T 1
19296652 10.1021/jm801445c Heat shock protein beta-1 1

Data from ChEMBL 36 via Core Engine