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Compound Detail

CHEMBL18981

THIOCOLCHICINE
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COc1cc2c(c(OC)c1OC)-c1ccc(SC)c(=O)cc1[C@@H](NC(C)=O)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL18981
Name THIOCOLCHICINE
Phase Preclinical
Structure Type MOL
InChI Key CMEGANPVAXDBPL-INIZCTEOSA-N
27
Targets
66
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

415.5
MW (Da)
3.58
ALogP
6
HBA
1
HBD
73.9
PSA (Ų)
0.75
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H25NO5S
MW 415.51
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 0.62

Activity Summary

IC50 64 meas. best 10.62
EC50 1 meas. best 8.74
Ki 1 meas. best 6.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
TE-671
CHEMBL615012
 IC50 10.62 10.62 0.0 1
RPMI-7951
CHEMBL612447
 IC50 10.62 10.62 0.0 1
KB
CHEMBL398
 IC50 10.4 10.4 0.0 1
MDA-MB-231
CHEMBL400
 IC50 9.22 7.77 0.6 3
A549
CHEMBL392
 IC50 9.05 7.332 0.9 5
LoVo
CHEMBL614721
 IC50 9.0 8.1833 1.0 3
MCF7
CHEMBL387
 IC50 8.96 7.528 1.1 5
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.77 8.77 1.7 1
H9
CHEMBL614806
 EC50 8.74 8.74 1.8 1
Unchecked
CHEMBL612545
 IC50 8.51 6.3888 3.1 8
DLD-1
CHEMBL614285
 IC50 8.38 8.38 4.2 1
P388
CHEMBL389
 IC50 8.3 8.3 5.0 1
L1210
CHEMBL386
 IC50 8.1 8.1 8.0 1
BALB/3T3
CHEMBL613876
 IC50 8.02 7.44 9.6 2
IGROV-1
CHEMBL613984
 IC50 7.92 7.92 12.0 1
HCT-8
CHEMBL613510
 IC50 7.82 7.82 15.0 1
MDA-MB-468
CHEMBL614335
 IC50 6.7 6.7 200.0 1
HepG2
CHEMBL395
 IC50 6.3 6.3 500.0 1
Caco-2
CHEMBL614058
 IC50 6.3 6.3 500.0 1
Tubulin
CHEMBL2095182
 IC50 6.19 6.088 650.0 5
Tubulin alpha chain
CHEMBL3658
 IC50 6.19 6.19 645.6 1
Tubulin
CHEMBL2094134
 IC50 6.19 5.776 640.0 5
Tubulin alpha chain
CHEMBL3658
 Ki 6.16 6.16 700.0 1
Tubulin beta chain
CHEMBL3394
 IC50 5.89 5.89 1300.0 1
Tubulin
CHEMBL2111464
 IC50 5.85 5.85 1400.0 1
T47D
CHEMBL614361
 IC50 5.39 5.39 4100.0 1
CA46
CHEMBL612566
 IC50 5.35 5.35 4500.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.0 5.0 10000.0 11

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
RPMI-7951 IC50 = 0.024 nM 10.62 Antiproliferative activity against human RPMI-7951 cells incubated for 36 hrs 32432867
TE-671 IC50 = 0.024 nM 10.62 Antiproliferative activity against human TE-671 cells incubated for 36 hrs 32432867
KB IC50 = 0.04 nM 10.4 Antiproliferative activity against human KB cells incubated for 36 hrs 32432867
MDA-MB-231 IC50 = 0.6 nM 9.22 Anti tumor activity on human breast cancer cell line MDR-negative MDA-MB 231 aft... 10602712
A549 IC50 = 0.9 nM 9.05 Antiproliferative activity against human A549 cells assessed as inhibition of ce... 34592435
LoVo IC50 = 1.0 nM 9.0 Antiproliferative activity against human LoVo cells assessed as inhibition of ce... 34592435
MCF7 IC50 = 1.1 nM 8.96 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 34592435
Human immunodeficiency virus 1 IC50 = 1.7 nM 8.77 Antiviral activity against HIV1 HTLV-3B in human H9 cells after 3 days by p24 an... 1919593
H9 EC50 = 1.8 nM 8.74 Cytotoxicity against human H9 cells 1919593
Unchecked IC50 = 3.1 nM 8.51 Antiproliferative activity against human ALL5 cells incubated for 120 hrs follow... 33465696
DLD-1 IC50 = 4.2 nM 8.38 Antiproliferative activity against human DLD1 cells assessed as reduction in cel... 31655432
P388 IC50 = 5.0 nM 8.3 Antiproliferative activity against mouse P388 cells incubated for 36 hrs 32432867
L1210 IC50 = 8.0 nM 8.1 In vitro cytotoxicity against L1210 (murine leukemia) cells. 2299625
MCF7 IC50 = 9.6 nM 8.02 Antiproliferative activity against human MCF-7 cells incubated for 72 hrs by SRB... 33465696
BALB/3T3 IC50 = 9.6 nM 8.02 Cytotoxicity against mouse BALB/3T3 cells assessed as reduction in cell viabilit... 34592435
A549 IC50 = 11.3 nM 7.95 Antiproliferative activity against human A549 cells incubated for 72 hrs by SRB ... 33465696
IGROV-1 IC50 = 12.0 nM 7.92 Antiproliferative activity against human IGROV1 cells assessed as growth inhibit... 19833515
LoVo IC50 = 13.6 nM 7.87 Antiproliferative activity against human LoVo cells assessed as reduction in cel... 31655432
HCT-8 IC50 = 15.0 nM 7.82 Antiproliferative activity against human HCT-8 cells incubated for 36 hrs 32432867
LoVo IC50 = 21.0 nM 7.68 Antiproliferative activity against human LoVo cells incubated for 72 hrs by SRB ... 33465696

Literature References

PubMed DOI Target Context # Activities
19880222 10.1016/j.ejmech.2009.09.047 NON-PROTEIN TARGET 11
19833515 10.1016/j.bmcl.2009.09.075 IGROV-1 5
33465696 10.1016/j.bmc.2021.116014 Unchecked 5
1552500 10.1021/jm00084a011 Tubulin 4
4032423 10.1021/jm00147a014 Mus musculus 4
8496935 10.1021/jm00057a004 Tubulin 3
4032423 10.1021/jm00147a014 Unchecked 3
20542428 10.1016/j.bmcl.2010.05.081 Unchecked 3
19880222 10.1016/j.ejmech.2009.09.047 Unchecked 3
7241524 10.1021/jm00137a031 Mus musculus 3
33465696 10.1016/j.bmc.2021.116014 MCF7 2
1875350 10.1021/jm00112a036 Tubulin 2
32432867 10.1021/acs.jmedchem.0c00222 Tubulin 2
18468444 10.1016/j.bmc.2008.04.025 Tubulin 2
3560165 10.1021/jm00387a028 Mus musculus 2
20187635 10.1021/np900821e Unchecked 2
32432867 10.1021/acs.jmedchem.0c00222 Unchecked 2
4032423 10.1021/jm00147a014 Tubulin 2
9083485 10.1021/jm960663k CA46 1
34592435 10.1016/j.bmcl.2021.128382 BALB/3T3 1

Data from ChEMBL 36 via Core Engine