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Compound Detail

CHEMBL55285

BENZYL ISOTHIOCYANATE
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S=C=NCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL55285
Name BENZYL ISOTHIOCYANATE
Phase Preclinical
Structure Type MOL
InChI Key MDKCFLQDBWCQCV-UHFFFAOYSA-N
13
Targets
31
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

149.2
MW (Da)
2.29
ALogP
2
HBA
0
HBD
12.4
PSA (Ų)
0.46
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 C8H7NS
MW 149.22
Aromatic Rings 1
Heavy Atoms 10

Activity Summary

IC50 18 meas. best 6.28
EC50 10 meas. best 6.6
Ki 2 meas. best 5.37
Kd 1 meas. best 5.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transient receptor potential cation channel subfamily A member 1
CHEMBL6007
 EC50 6.6 5.3417 250.0 6
Macrophage migration inhibitory factor
CHEMBL2085
 IC50 6.28 6.2167 530.0 3
Macrophage migration inhibitory factor
CHEMBL2085
 Kd 5.54 5.54 2900.0 1
Unchecked
CHEMBL612545
 IC50 5.43 4.9433 3700.0 3
Macrophage migration inhibitory factor
CHEMBL2085
 Ki 5.37 5.37 4300.0 1
Cytochrome P450 2B1
CHEMBL3335
 Ki 5.24 5.24 5800.0 1
T47D
CHEMBL614361
 IC50 5.13 5.13 7400.0 1
LoVo
CHEMBL614721
 IC50 4.98 4.882 10500.0 5
UACC-903
CHEMBL612446
 IC50 4.82 4.82 15000.0 1
Caco-2
CHEMBL614058
 IC50 4.82 4.82 15000.0 1
MCF7
CHEMBL387
 IC50 4.72 4.72 18900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.7 4.7 19800.0 1
A549
CHEMBL392
 IC50 4.69 4.69 20500.0 1
MDA-MB-231
CHEMBL400
 IC50 4.38 4.38 42000.0 1
Sclerotinia sclerotiorum
CHEMBL613280
 EC50 4.22 4.17 60100.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Transient receptor potential cation channel subfamily A member 1 EC50 = 250.0 nM 6.6 Activation of human TRPA1 expressed in TREx-HEK cells by Fluo-4 AM dye-based Ca2... 26263397
Transient receptor potential cation channel subfamily A member 1 EC50 = 319.0 nM 6.5 Activation of TRPA1 channel 20356305
Macrophage migration inhibitory factor IC50 = 530.0 nM 6.28 Inhibition of human recombinant macrophage migration inhibitory factor tautomera... 25743213
Macrophage migration inhibitory factor IC50 = 540.0 nM 6.27 Inhibition of macrophage migration inhibitory factor tautomerase activity in hum... 25743213
Macrophage migration inhibitory factor IC50 = 790.0 nM 6.1 Inhibition of recombinant human MIF expressed in Escherichia coli BL21(DE3) usin... 29812929
Macrophage migration inhibitory factor Kd = 2900.0 nM 5.54 Displacement of 4'-(7-Hydroxy-2-oxo-2H-chromen-3-yl)-[1,1'-biphenyl]-4-carboxyli... 32940040
Unchecked IC50 = 3700.0 nM 5.43 Inhibition of Escherichia coli MurA using UNAG and PEP as substrate preincubated... 30321804
Macrophage migration inhibitory factor Ki = 4300.0 nM 5.37 Inhibition of C-terminal His-tagged recombinant human MIF expressed in Escherich... 32940040
Cytochrome P450 2B1 Ki = 5800.0 nM 5.24 Mechanism based inhibition of rat cytochrome P450 CYP2B1 measured by 7-EFC O-dee... 16248836
T47D IC50 = 7400.0 nM 5.13 Antiproliferative activity against human T47D cells after 72 hrs by SRB assay 21704523
LoVo IC50 = 10500.0 nM 4.98 Antiproliferative activity against doxorubicin-resistant human LoVo cells after ... 21704523
Transient receptor potential cation channel subfamily A member 1 EC50 = 10964.78 nM 4.96 Agonist activity at human TRPA1 expressed in T-REx-HEK293 cells assessed as time... 20806939
LoVo IC50 = 12300.0 nM 4.91 Antiproliferative activity against human LoVo cells after 72 hrs by SRB assay 21704523
LoVo IC50 = 14500.0 nM 4.84 Antiproliferative activity against human LoVo cells assessed as reduction in cel... 26639764
LoVo IC50 = 14500.0 nM 4.84 Cytotoxicity against human LoVo cells after 72 hrs by sulforhodamine B assay 28342398
LoVo IC50 = 14500.0 nM 4.84 Antiproliferative activity against human LoVo cells after 72 hrs by SRB assay 29945793
UACC-903 IC50 = 15000.0 nM 4.82 Cytotoxicity against human UACC-903 cells after 72 hrs by MTS assay 19053750
Caco-2 IC50 = 15000.0 nM 4.82 Cytotoxicity against human Caco-2 cells after 72 hrs by MTS assay 19053750
Transient receptor potential cation channel subfamily A member 1 EC50 = 15488.17 nM 4.81 Agonist activity at human TRPA1 expressed in T-REx-HEK293 cells at -30 mV holdin... 20806939
MCF7 IC50 = 18900.0 nM 4.72 Antiproliferative activity against human MCF7 cells after 72 hrs by SRB assay 21704523

Literature References

PubMed DOI Target Context # Activities
21370393 10.1002/ps.2126 Sclerotinia sclerotiorum 29
28342398 10.1016/j.ejmech.2017.03.028 Mus musculus 15
19053750 10.1021/jm800993r UACC-903 7
28342398 10.1016/j.ejmech.2017.03.028 LoVo 7
1732527 10.1021/jm00079a025 Glutathione S-transferase Mu 1 6
21241062 10.1021/jm101199t Cellular tumor antigen p53 6
1732527 10.1021/jm00079a025 Glutathione S-transferase kappa 1 6
30321804 10.1016/j.ejmech.2018.10.010 Unchecked 5
26263397 10.1021/acs.jnatprod.5b00272 Transient receptor potential cation channel subfamily A member 1 4
20806939 10.1021/jm100477n Transient receptor potential cation channel subfamily A member 1 4
26263397 10.1021/acs.jnatprod.5b00272 Transient receptor potential cation channel subfamily V member 1 4
28342398 10.1016/j.ejmech.2017.03.028 Unchecked 4
- 10.1016/j.cropro.2010.09.004 Meloidogyne javanica 4
28342398 10.1016/j.ejmech.2017.03.028 4T1 3
16248836 10.2174/138920005774330639 Cytochrome P450 2B1 3
26338358 10.1016/j.bmcl.2015.08.065 Tyrosine-protein phosphatase non-receptor type 1 2
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 2
21704523 10.1016/j.bmcl.2011.05.113 LoVo 2
15176077 10.1002/jps.20101 ATP-dependent translocase ABCB1 2
26263397 10.1021/acs.jnatprod.5b00272 ADMET 2

Data from ChEMBL 36 via Core Engine