Compound Detail

CHEMBL151649

PHENETHYLISOTHIOCYANATE

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S=C=NCCc1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL151649
Name	PHENETHYLISOTHIOCYANATE
Phase	Preclinical
Structure Type	MOL
InChI Key	IZJDOKYDEWTZSO-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

163.2

MW (Da)

2.33

ALogP

HBA

HBD

12.4

PSA (Å²)

0.49

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C9H9NS
MW	163.24
Aromatic Rings	1
Heavy Atoms	11
NP-Likeness	0.17

Activity Summary

IC50 22 meas. best 5.8

EC50 6 meas. best 6.43

Ki 4 meas. best 5.77

Kd 2 meas. best 6.37

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	EC50	6.43	5.715	370.0	2
Cytochrome P450 2A13 CHEMBL3542436	Kd	6.37	6.37	430.0	1
Macrophage migration inhibitory factor CHEMBL2085	IC50	5.8	5.3	1600.0	2
Cytochrome P450 2A6 CHEMBL5282	Ki	5.77	5.77	1700.0	1
Cytochrome P450 2A13 CHEMBL3542436	Ki	5.42	5.42	3800.0	1
MEF CHEMBL614342	IC50	5.33	5.215	4700.0	2
Cytochrome P450 2A6 CHEMBL5282	Kd	5.21	5.21	6200.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.16	4.9567	7000.0	3
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha CHEMBL2221345	IC50	5.12	5.12	7500.0	1
T47D CHEMBL614361	IC50	5.01	5.01	9700.0	1
LoVo CHEMBL614721	IC50	5.01	4.9167	9800.0	3
Cytochrome P450 2E1 CHEMBL5281	Ki	5.0	4.98	9980.0	2
UACC-903 CHEMBL612446	IC50	4.92	4.92	12000.0	1
Caco-2 CHEMBL614058	IC50	4.85	4.85	14000.0	1
HT-1080 CHEMBL614580	IC50	4.82	4.82	15000.0	1
MCF7 CHEMBL387	IC50	4.79	4.79	16300.0	1
A549 CHEMBL392	IC50	4.78	4.78	16800.0	1
OVCAR-3 CHEMBL614213	IC50	4.63	4.63	23200.0	1
PC-3 CHEMBL390	IC50	4.62	4.62	24000.0	1
SW480 CHEMBL612544	IC50	4.45	4.45	35550.0	1
MDA-MB-231 CHEMBL400	IC50	4.42	4.42	38000.0	1
DLD-1 CHEMBL614285	IC50	4.26	4.26	54590.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	0.05	hr	Homo sapiens

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	=	370.0	nM	6.43	Activation of human TRPA1 expressed in TREx-HEK cells by Fluo-4 AM dye-based Ca2...	26263397
Cytochrome P450 2A13	Kd	=	430.0	nM	6.37	Binding affinity to CYP2A13 (unknown origin) assessed as type 1 interaction as i...	22696418
Macrophage migration inhibitory factor	IC50	=	1600.0	nM	5.8	Inhibition of macrophage migration inhibitory factor tautomerase activity in hum...	25743213
Cytochrome P450 2A6	Ki	=	1700.0	nM	5.77	Mixed inhibition of CYP2A6 (unknown origin)	22696418
Cytochrome P450 2A13	Ki	=	3800.0	nM	5.42	Mixed inhibition of CYP2A13 (unknown origin)	22696418
MEF	IC50	=	4700.0	nM	5.33	Inhibition of growth in wild type MEF cells after 6 days	22607231
Cytochrome P450 2A6	Kd	=	6200.0	nM	5.21	Binding affinity to CYP2A6 (unknown origin) assessed as type 1 interaction as in...	22696418
NON-PROTEIN TARGET	IC50	=	7000.0	nM	5.16	Antiproliferative activity against human LS 174T cells	18855447
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	=	7500.0	nM	5.12	Inhibition of Serine/threonine-protein kinase mTOR complex 1-mediated HIF1alpha ...	22607231
MEF	IC50	=	8000.0	nM	5.1	Inhibition of growth in TSC2-deficient MEF cells after 6 days	22607231
T47D	IC50	=	9700.0	nM	5.01	Antiproliferative activity against human T47D cells after 72 hrs by SRB assay	21704523
LoVo	IC50	=	9800.0	nM	5.01	Antiproliferative activity against doxorubicin-resistant human LoVo cells after ...	21704523
NON-PROTEIN TARGET	IC50	=	9800.0	nM	5.01	Antiproliferative activity against human LoVo/DX cells assessed as reduction in ...	26639764
Transient receptor potential cation channel subfamily A member 1	EC50	=	10000.0	nM	5.0	Activation of TRPA1 channel	20356305
Cytochrome P450 2E1	Ki	=	9980.0	nM	5.0	Mechanism based inhibition of human cytochrome P450 2E1	16248836
Cytochrome P450 2E1	Ki	=	11000.0	nM	4.96	Inhibition of human CYP2E1 expressed in Escherichia coli MV1304 assessed as redu...	23371965
UACC-903	IC50	=	12000.0	nM	4.92	Cytotoxicity against human UACC-903 cells after 72 hrs by MTS assay	19053750
LoVo	IC50	=	13500.0	nM	4.87	Antiproliferative activity against human LoVo cells assessed as reduction in cel...	26639764
LoVo	IC50	=	13500.0	nM	4.87	Antiproliferative activity against human LoVo cells after 72 hrs by SRB assay	21704523
Caco-2	IC50	=	14000.0	nM	4.85	Cytotoxicity against human Caco-2 cells after 72 hrs by MTS assay	19053750

Literature References

PubMed	DOI	Target Context	# Activities
21370393	10.1002/ps.2126	Sclerotinia sclerotiorum	28
23371965	10.1124/dmd.112.050609	Cytochrome P450 2E1	23
21704523	10.1016/j.bmcl.2011.05.113	A549	17
21241062	10.1021/jm101199t	Cellular tumor antigen p53	14
22607231	10.1021/np300049b	Unchecked	13
19053750	10.1021/jm800993r	UACC-903	7
21241062	10.1021/jm101199t	NCI-H596	6
18855447	10.1021/np800233q	NON-PROTEIN TARGET	5
21241062	10.1021/jm101199t	Unchecked	5
26263397	10.1021/acs.jnatprod.5b00272	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
-	10.1016/j.cropro.2010.09.004	Meloidogyne javanica	4
33961435	10.1021/acs.jmedchem.0c01971	MCF7	3
33961435	10.1021/acs.jmedchem.0c01971	MDA-MB-231	3
22607231	10.1021/np300049b	mTORC1	3
33961435	10.1021/acs.jmedchem.0c01971	Unchecked	3
22696418	10.1124/dmd.112.045161	Cytochrome P450 2A6	2
16248836	10.2174/138920005774330639	Cytochrome P450 2E1	2
22696418	10.1124/dmd.112.045161	ADMET	2
22696418	10.1124/dmd.112.045161	Cytochrome P450 2A13	2

Data from ChEMBL 36 via Core Engine