Compound Information

General Information of the Compound

Compound ID

CP0031719

Compound Name

(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine

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Synonyms

Crizotinib

Xalkori (TN)

novel ALK inhibitors

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Structure

Formula

C21H22Cl2FN5O

Molecular Weight

450.345

Canonical SMILES

C[C@@H](Oc1cc(cnc1N)-c1cnn(c1)C1CCNCC1)c1c(Cl)ccc(F)c1Cl

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InChI

InChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1

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InChIKey

KTEIFNKAUNYNJU-GFCCVEGCSA-N

CAS

877399-52-5

Physicochemical Property

logP	5.0377
Rotatable Bonds	5
Heavy Atom Count	30
Polar Areas	77.99
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Complexity	30

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID

CID: 11626560

SID: 16729581

ChEMBL ID

CHEMBL601719

DrugBank ID

DB08865

Map of Molecular Bioactivity Related to the Compound

Map of Molecular Bioactivity Related to the Compound Compound Cell Line Protein Bioactivity Value: <= 0.1 μM > 0.1 μM and <= 10 μM > 10 μM Imprecise Activity

Table of Molecular Bioactivities Related to the Compound

Protein ID: PT01203, ALK tyrosine kinase receptor

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000077	Ba/F3 Cell Line Info	Mus musculus (Mouse)	6
1	GI50 = 150 nM Bioactivity Info	TI LI LO TS
2	GI50 = 320 nM Bioactivity Info	TI LI LO TS
3	GI50 = 430 nM Bioactivity Info	TI LI LO TS
4	GI50 = 590 nM Bioactivity Info	TI LI LO TS
5	IC50 = 150.8 nM Bioactivity Info	TI LI LO TS
6	IC50 = 260 nM Bioactivity Info	TI LI LO TS
CL000300	Karpas-299 Cell Line Info	Homo sapiens (Human)	3
1	IC50 = 20 nM Bioactivity Info	TI LI LO TS
2	IC50 = 62 nM Bioactivity Info	TI LI LO TS
3	IC50 = 110 nM Bioactivity Info	TI LI LO TS
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	4
1	IC50 = 34.5 nM Bioactivity Info	TI LI LO TS
2	IC50 = 1035 nM Bioactivity Info	TI LI LO TS
3	IC50 = 1066 nM Bioactivity Info	TI LI LO TS
4	IC50 = 1540 nM Bioactivity Info	TI LI LO TS
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 37 nM Bioactivity Info	TI LI LO TS
CL000035	NIH 3T3 Cell Line Info	Mus musculus (Mouse)	9
1	IC50 = 80 nM Bioactivity Info	TI LI LO TS
2	IC50 = 165 nM Bioactivity Info	TI LI LO TS
3	IC50 = 478 nM Bioactivity Info	TI LI LO TS
4	IC50 = 605 nM Bioactivity Info	TI LI LO TS
5	IC50 = 626 nM Bioactivity Info	TI LI LO TS
6	IC50 = 843 nM Bioactivity Info	TI LI LO TS
7	IC50 = 1026 nM Bioactivity Info	TI LI LO TS
8	IC50 = 1148 nM Bioactivity Info	TI LI LO TS
9	IC50 = 3039 nM Bioactivity Info	TI LI LO TS
CL000320	NCI-H3122 Cell Line Info	Homo sapiens (Human)	4
1	IC50 = 108 nM Bioactivity Info	TI LI LO TS
2	IC50 = 261 nM Bioactivity Info	TI LI LO TS
3	IC50 = 623 nM Bioactivity Info	TI LI LO TS
4	IC50 = 838 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 0.47 nM
2	IC50 = 0.64 nM
3	IC50 < 1 nM
4	IC50 = 2.47 nM
5	IC50 = 2.6 nM
6	IC50 = 3.33 nM
7	IC50 = 4.5 nM
8	IC50 = 4.66 nM
9	IC50 = 5.012 nM
10	IC50 = 7 nM
11	IC50 = 10.5 nM
12	IC50 = 12 nM
13	IC50 = 13 nM
14	IC50 = 13.7 nM
15	IC50 = 16 nM
16	IC50 = 20 nM
17	IC50 = 23.6 nM
18	IC50 = 24 nM
19	IC50 = 25 nM
20	IC50 = 28 nM
21	IC50 = 30 nM
22	IC50 = 32 nM
23	IC50 = 52 nM
24	IC50 = 71.6 nM
25	IC50 = 73.6 nM
26	IC50 = 77.8 nM
27	IC50 = 122 nM
28	IC50 = 148 nM
29	IC50 = 200 nM
30	IC50 = 353 nM
31	IC50 = 355 nM
32	IC50 = 600 nM
33	IC50 = 891 nM
34	IC50 = 972 nM
35	IC50 > 9000 nM
36	Kd = 3.3 nM
37	Kd = 4.4 nM
38	Ki = 0.74 nM
39	Ki = 8.2 nM

Protein ID: PT01201, Hepatocyte growth factor receptor

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000068	A-549 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 8 nM Bioactivity Info	TI LI LO TS
CL000413	MKN45 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 20 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 0.51 nM
2	IC50 = 0.78 nM
3	IC50 = 0.9 nM
4	IC50 < 1 nM
5	IC50 = 1.053 nM
6	IC50 = 1.1 nM
7	IC50 = 1.4 nM
8	IC50 = 1.5 nM
9	IC50 = 1.6 nM
10	IC50 = 2 nM
11	IC50 = 2.4 nM
12	IC50 = 2.93 nM
13	IC50 = 3 nM
14	IC50 = 3.2 nM
15	IC50 = 4 nM
16	IC50 = 7.1 nM
17	IC50 = 8 nM
18	IC50 = 8.29 nM
19	IC50 = 11 nM
20	IC50 = 16 nM
21	Kd = 0.2 nM
22	Kd = 0.55 nM
23	Kd = 1.5 nM
24	Kd = 2 nM
25	Kd = 2.1 nM
26	Ki = 2 nM
27	Ki = 4 nM

Protein ID: PT01101, Insulin receptor

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000077	Ba/F3 Cell Line Info	Mus musculus (Mouse)	1
1	IC50 = 1643 nM Bioactivity Info	TI LI LO TS
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 2887 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 102 nM
2	IC50 = 201 nM
3	IC50 = 650 nM
4	Kd = 340 nM

Protein ID: PT06925, Macrophage-stimulating protein receptor

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000035	NIH 3T3 Cell Line Info	Mus musculus (Mouse)	1
1	IC50 = 80 nM Bioactivity Info	TI LI LO TS

Protein ID: PT02328, Mitogen-activated protein kinase kinase kinase kinase 3

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000025	HEK-293T Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 1700 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 49 nM
2	Kd = 75 nM

Protein ID: PT03338, Tyrosine-protein kinase ABL1

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000769	BaF3-BCL Cell Line Info	Mus musculus (Mouse)	1
1	IC50 = 1159 nM Bioactivity Info	TI LI LO TS

Protein ID: PT01659, Tyrosine-protein kinase JAK1

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	1
1	IC50 = 563 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	Kd = 330 nM
2	Kd > 10000 nM

Protein ID: PT01214, Tyrosine-protein kinase JAK2

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	2
1	IC50 = 27 nM Bioactivity Info	TI LI LO TS
2	Kd = 10.99 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	Kd = 290 nM

Protein ID: PT00892, Tyrosine-protein kinase JAK3

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	1
1	IC50 = 1360 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	Kd = 200 nM

Protein ID: PT00876, Tyrosine-protein kinase Lck

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000001	Jurkat Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 2741 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 < 1 nM
2	IC50 = 2741 nM
3	Kd = 30 nM

Protein ID: PT01128, Tyrosine-protein kinase receptor UFO

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 294 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 < 1 nM
2	IC50 = 294 nM
3	IC50 = 300 nM
4	IC50 > 100 nM
5	Kd = 7.8 nM

Cell Viability or Cytotoxicity Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000011	CHO Cell Line Info	Cricetulus griseus (Chinese hamster)	1
1	GI50 = 3200 nM	TI LI LO TS
CL000469	NCI-H2228 Cell Line Info	Homo sapiens (Human)	1
1	GI50 = 73 nM	TI LI LO TS

Clinical Information about the Compound

Drug 1 ( Crizotinib )

Drug Name	Crizotinib
Company	Pfizer New York, NY
Indication	Non-small-cell lung cancer Approved
Target(s)	Proto-oncogene c-Met (MET) Target Info Modulator Proto-oncogene c-Ros (ROS1) Target Info Modulator ALK tyrosine kinase receptor (ALK) Target Info Modulator

Cite

About MolBiC

Correspondence

Prof. Feng ZHU

Prof. Leo, Lianyi Han