Compound Information

General Information of the Compound

Compound ID

CP0036082

Compound Name

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

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Synonyms

4-(3'-Chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline

6-(3-morpholinopropoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine

CU-00000000396-1

Gefitini

Gefitinib

Gefitinib (JAN/USAN/INN)

Gefitinib [USAN]

Gefitinib,Iressa, ZD1839

IRE

Iressa

Iressa (TN)

Iressa(TM)

Irressat

N-(3-Chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamide

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine

ZD 1839

ZD-1839

ZD-1839, Iressa, Gefitinib

ZD1839

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Structure

Formula

C22H24ClFN4O3

Molecular Weight

446.91

Canonical SMILES

COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1OCCCN1CCOCC1

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InChI

InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)

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InChIKey

XGALLCVXEZPNRQ-UHFFFAOYSA-N

CAS

184475-35-2

Physicochemical Property

logP	4.2756
Rotatable Bonds	8
Heavy Atom Count	31
Polar Areas	68.74
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Complexity	31

"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: 123631

SID: 14833109

ChEMBL ID

CHEMBL939

DrugBank ID

DB00317

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: PT05334, ATP-binding cassette sub-family C member 4

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 = 4600 nM Bioactivity Info	TI LI LO TS

Protein ID: PT01546, ATP-dependent translocase ABCB1

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000137	K562/A02 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 19970 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 > 1000 nM

Protein ID: PT04542, Bile salt export pump

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 = 10900 nM Bioactivity Info	TI LI LO TS

Protein ID: PT02718, Broad substrate specificity ATP-binding cassette transporter ABCG2

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 = 400 nM Bioactivity Info	TI LI LO TS
CL000756	MCF/MX Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 1100 nM Bioactivity Info	TI LI LO TS
CL000031	MDCK Cell Line Info	Canis lupus familiaris (Dog)	1
1	IC50 = 1260 nM Bioactivity Info	TI LI LO TS
CL000036	MDCK-II Cell Line Info	Canis lupus familiaris (Dog)	1
1	IC50 = 3190 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 300 nM

Protein ID: PT01920, Cyclin-G-associated kinase

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 = 420 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	Kd = 7 nM
2	Kd = 13 nM

Protein ID: PT00922, Epidermal growth factor receptor

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000052	A-431 Cell Line Info	Homo sapiens (Human)	4
1	EC50 = 2162 nM Bioactivity Info	TI LI LO TS
2	IC50 < 15 nM Bioactivity Info	TI LI LO TS
3	IC50 = 23 nM Bioactivity Info	TI LI LO TS
4	IC50 = 1080 nM Bioactivity Info	TI LI LO TS
CL000157	NCI-H1975 Cell Line Info	Homo sapiens (Human)	3
1	EC50 = 10733 nM Bioactivity Info	TI LI LO TS
2	IC50 = 3300 nM Bioactivity Info	TI LI LO TS
3	IC50 = 13980 nM Bioactivity Info	TI LI LO TS
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	10
1	IC50 < 1 nM Bioactivity Info	TI LI LO TS
2	IC50 = 3 nM Bioactivity Info	TI LI LO TS
3	IC50 = 4 nM Bioactivity Info	TI LI LO TS
4	IC50 = 15.5 nM Bioactivity Info	TI LI LO TS
5	IC50 = 20 nM Bioactivity Info	TI LI LO TS
6	IC50 = 33 nM Bioactivity Info	TI LI LO TS
7	IC50 = 390 nM Bioactivity Info	TI LI LO TS
8	IC50 = 823.3 nM Bioactivity Info	TI LI LO TS
9	IC50 = 3170 nM Bioactivity Info	TI LI LO TS
10	IC50 = 4990 nM Bioactivity Info	TI LI LO TS
CL000324	NCI-H3255 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 6.5 nM Bioactivity Info	TI LI LO TS
CL000220	KB Cell Line Info	Homo sapiens (Human)	4
1	IC50 = 11 nM Bioactivity Info	TI LI LO TS
2	IC50 = 25 nM Bioactivity Info	TI LI LO TS
3	IC50 = 54 nM Bioactivity Info	TI LI LO TS
4	IC50 = 80 nM Bioactivity Info	TI LI LO TS
CL000379	PC-9 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 12 nM Bioactivity Info	TI LI LO TS
CL000012	Sf21 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	5
1	IC50 = 12 nM Bioactivity Info	TI LI LO TS
2	IC50 = 129.7 nM Bioactivity Info	TI LI LO TS
3	IC50 = 460 nM Bioactivity Info	TI LI LO TS
4	IC50 = 639 nM Bioactivity Info	TI LI LO TS
5	IC50 > 5000 nM Bioactivity Info	TI LI LO TS
CL000063	Hep-G2 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 12.5 nM Bioactivity Info	TI LI LO TS
CL000035	NIH 3T3 Cell Line Info	Mus musculus (Mouse)	2
1	IC50 = 14 nM Bioactivity Info	TI LI LO TS
2	IC50 = 14.4 nM Bioactivity Info	TI LI LO TS
CL000068	A-549 Cell Line Info	Homo sapiens (Human)	3
1	IC50 = 39.9 nM Bioactivity Info	TI LI LO TS
2	IC50 = 60 nM Bioactivity Info	TI LI LO TS
3	IC50 = 498 nM Bioactivity Info	TI LI LO TS
CL000323	LoVo Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 62 nM Bioactivity Info	TI LI LO TS
CL000145	NCI-H460 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 22800 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 0.1 nM
2	IC50 = 0.32 nM
3	IC50 = 0.45 nM
4	IC50 < 0.5 nM
5	IC50 = 0.6 nM
6	IC50 = 0.769 nM
7	IC50 = 0.9 nM
8	IC50 = 1 nM
9	IC50 < 1 nM
10	IC50 = 1.3 nM
11	IC50 = 1.5 nM
12	IC50 = 1.9 nM
13	IC50 = 2.3 nM
14	IC50 = 2.6 nM
15	IC50 = 3.1 nM
16	IC50 = 3.22 nM
17	IC50 = 3.7 nM
18	IC50 = 3.8 nM
19	IC50 = 4 nM
20	IC50 = 4.2 nM
21	IC50 = 5.4 nM
22	IC50 = 7.3 nM
23	IC50 = 8.43 nM
24	IC50 = 9.6 nM
25	IC50 = 10.6 nM
26	IC50 = 11.8 nM
27	IC50 = 13 nM
28	IC50 = 15.5 nM
29	IC50 = 20 nM
30	IC50 = 21 nM
31	IC50 = 22 nM
32	IC50 = 23 nM
33	IC50 = 26 nM
34	IC50 = 27 nM
35	IC50 = 29 nM
36	IC50 = 29.6 nM
37	IC50 = 31 nM
38	IC50 = 33 nM
39	IC50 = 37 nM
40	IC50 = 39 nM
41	IC50 = 62 nM
42	IC50 = 70 nM
43	IC50 = 72 nM
44	IC50 = 76 nM
45	IC50 = 127.9 nM
46	IC50 = 166 nM
47	IC50 = 380 nM
48	IC50 = 515 nM
49	IC50 = 1740 nM
50	IC50 = 2753 nM
51	IC50 = 2874.7 nM
52	IC50 = 6746 nM
53	IC50 = 15500 nM
54	IC50 > 100 nM
55	IC50 > 1000 nM
56	IC50 > 2000 nM
57	Kd = 0.52 nM
58	Kd = 0.54 nM
59	Kd = 0.57 nM
60	Kd = 0.94 nM
61	Kd = 0.98 nM
62	Kd = 1 nM
63	Kd = 1.1 nM
64	Kd = 1.4 nM
65	Kd = 1.8 nM
66	Kd = 2 nM
67	Kd = 35.3 nM
68	Kd = 40 nM
69	Kd = 140 nM
70	Ki = 0.4 nM

Protein ID: PT06109, Geminin

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000015	SW480 Cell Line Info	Homo sapiens (Human)	1
1	Potency ~ 13335.9 nM Bioactivity Info	TI LI LO TS

Protein ID: PT01233, Receptor tyrosine-protein kinase erbB-2

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000083	MCF-7 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 24 nM Bioactivity Info	TI LI LO TS
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	2
1	IC50 = 97 nM Bioactivity Info	TI LI LO TS
2	IC50 = 343 nM Bioactivity Info	TI LI LO TS
CL000012	Sf21 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	1
1	IC50 = 151 nM Bioactivity Info	TI LI LO TS
CL000203	T24 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 599 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 240 nM
2	IC50 = 280 nM
3	IC50 = 281 nM
4	IC50 = 343 nM
5	IC50 = 1000 nM
6	IC50 = 1830 nM
7	IC50 = 2700 nM
8	Kd = 1100 nM
9	Kd = 3500 nM

Protein ID: PT01159, Receptor tyrosine-protein kinase erbB-4

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 = 476 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	Kd = 410 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 > 1000 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	Kd > 10000 nM

Cell Viability or Cytotoxicity Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000002	K-562 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 14270 nM	TI LI LO TS
CL000004	SH-SY5Y Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 18210 nM	TI LI LO TS
CL000007	HT-29 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 9800 nM	TI LI LO TS
CL000018	HL-60 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 54500 nM	TI LI LO TS
CL000052	A-431 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 3300 nM	TI LI LO TS
CL000068	A-549 Cell Line Info	Homo sapiens (Human)	6
1	IC50 > 10000 nM	TI LI LO TS
2	IC50 = 10070 nM	TI LI LO TS
3	IC50 = 10080 nM	TI LI LO TS
4	IC50 = 11800 nM	TI LI LO TS
5	IC50 = 12080 nM	TI LI LO TS
6	IC50 = 21170 nM	TI LI LO TS
CL000083	MCF-7 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 12050 nM	TI LI LO TS
CL000157	NCI-H1975 Cell Line Info	Homo sapiens (Human)	2
1	IC50 > 10000 nM	TI LI LO TS
2	IC50 = 12700 nM	TI LI LO TS
CL000216	NCI-N87 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 1000 nM	TI LI LO TS
CL000379	PC-9 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 6.1 nM	TI LI LO TS
CL000380	HCC827 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 6 nM	TI LI LO TS

Clinical Information about the Compound

Drug 1 ( Gefitinib )

Drug Name	Gefitinib
Company	AstraZeneca
Indication	Solid tumour/cancer Approved Head and neck cancer Phase 3 Urethral cancer Phase 2
Target(s)	Epidermal growth factor receptor (EGFR) Target Info Inhibitor

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About MolBiC

Correspondence

Prof. Feng ZHU

Prof. Leo, Lianyi Han