NPASS drugs

Drug Information

Drug ID:	NPD5008
Drug Name:	Gefitinib
Molecular Formula:	C22H24ClFN4O3
Canonical SMILES:	COc1cc2ncnc(c2cc1OCCCN1CCOCC1)Nc1ccc(c(c1)Cl)F
Standard 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)
Standard InCHIKey:	XGALLCVXEZPNRQ-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5008

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	665
0.1-0.2	7354
0.2-0.3	6119
0.3-0.4	10551
0.4-0.5	3841
0.5-0.6	1929
0.6-0.7	409
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC56271
Intermediate Similarity	0.7331	NPC162530
Intermediate Similarity	0.7283	NPC472067
Intermediate Similarity	0.7283	NPC472066
Intermediate Similarity	0.7283	NPC472031
Intermediate Similarity	0.721	NPC476581
Intermediate Similarity	0.721	NPC36229
Intermediate Similarity	0.721	NPC16452
Intermediate Similarity	0.7205	NPC472068
Intermediate Similarity	0.7143	NPC476582
Intermediate Similarity	0.7143	NPC476578
Intermediate Similarity	0.7143	NPC4071
Intermediate Similarity	0.7131	NPC30540
Intermediate Similarity	0.7082	NPC31930
Intermediate Similarity	0.7059	NPC290689
Intermediate Similarity	0.7028	NPC160666
Intermediate Similarity	0.7025	NPC473513
Intermediate Similarity	0.7	NPC296482
Intermediate Similarity	0.7	NPC112206
Intermediate Similarity	0.7	NPC53069
Intermediate Similarity	0.7	NPC202768
Intermediate Similarity	0.7	NPC202605
Remote Similarity	0.6996	NPC173080
Remote Similarity	0.6957	NPC133140
Remote Similarity	0.6957	NPC195268
Remote Similarity	0.6951	NPC280272
Remote Similarity	0.6933	NPC313189
Remote Similarity	0.6929	NPC316981
Remote Similarity	0.6923	NPC130570
Remote Similarity	0.692	NPC285558
Remote Similarity	0.6917	NPC295228
Remote Similarity	0.6901	NPC266931
Remote Similarity	0.6894	NPC315957
Remote Similarity	0.6861	NPC312872
Remote Similarity	0.686	NPC171409
Remote Similarity	0.686	NPC96405
Remote Similarity	0.6846	NPC167860
Remote Similarity	0.6846	NPC123976
Remote Similarity	0.6836	NPC471614
Remote Similarity	0.6835	NPC135887
Remote Similarity	0.6835	NPC199277
Remote Similarity	0.6831	NPC469592
Remote Similarity	0.6831	NPC471080
Remote Similarity	0.6829	NPC308906
Remote Similarity	0.6822	NPC234197
Remote Similarity	0.6807	NPC162484
Remote Similarity	0.6792	NPC135549
Remote Similarity	0.678	NPC303374
Remote Similarity	0.6763	NPC475910
Remote Similarity	0.6761	NPC193267
Remote Similarity	0.6761	NPC213530
Remote Similarity	0.6758	NPC473183
Remote Similarity	0.6757	NPC477795
Remote Similarity	0.6757	NPC477806
Remote Similarity	0.6757	NPC477805
Remote Similarity	0.6757	NPC477796
Remote Similarity	0.6751	NPC329747
Remote Similarity	0.6751	NPC329793
Remote Similarity	0.6751	NPC477019
Remote Similarity	0.6739	NPC204385
Remote Similarity	0.6736	NPC469589
Remote Similarity	0.6732	NPC469554
Remote Similarity	0.6721	NPC469594
Remote Similarity	0.6708	NPC274291
Remote Similarity	0.6708	NPC329708
Remote Similarity	0.6708	NPC47059
Remote Similarity	0.6708	NPC165349
Remote Similarity	0.6708	NPC264166
Remote Similarity	0.6708	NPC118832
Remote Similarity	0.6706	NPC187145
Remote Similarity	0.6694	NPC476465
Remote Similarity	0.6694	NPC250178
Remote Similarity	0.6693	NPC201508
Remote Similarity	0.6693	NPC475253
Remote Similarity	0.6692	NPC316756
Remote Similarity	0.668	NPC314954
Remote Similarity	0.668	NPC473184
Remote Similarity	0.668	NPC472111
Remote Similarity	0.6667	NPC103687
Remote Similarity	0.6667	NPC201697
Remote Similarity	0.6667	NPC132631
Remote Similarity	0.6653	NPC232727
Remote Similarity	0.6653	NPC100079
Remote Similarity	0.6653	NPC23614
Remote Similarity	0.6641	NPC255800
Remote Similarity	0.6641	NPC96584
Remote Similarity	0.6639	NPC287437
Remote Similarity	0.6638	NPC144114
Remote Similarity	0.6626	NPC149471
Remote Similarity	0.6626	NPC271215
Remote Similarity	0.6624	NPC92111
Remote Similarity	0.6614	NPC471762
Remote Similarity	0.6612	NPC208284
Remote Similarity	0.6611	NPC176538
Remote Similarity	0.661	NPC131017
Remote Similarity	0.6602	NPC101543
Remote Similarity	0.66	NPC472099
Remote Similarity	0.6599	NPC235076
Remote Similarity	0.6597	NPC72211
Remote Similarity	0.6591	NPC270515
Remote Similarity	0.6586	NPC473822
Remote Similarity	0.6585	NPC251160
Remote Similarity	0.6585	NPC471603
Remote Similarity	0.6581	NPC76748
Remote Similarity	0.658	NPC284559
Remote Similarity	0.6577	NPC41501
Remote Similarity	0.6575	NPC473185
Remote Similarity	0.6575	NPC157931
Remote Similarity	0.6573	NPC170114
Remote Similarity	0.6573	NPC477110
Remote Similarity	0.6571	NPC188420
Remote Similarity	0.6571	NPC219664
Remote Similarity	0.6568	NPC307963
Remote Similarity	0.6566	NPC51854
Remote Similarity	0.6565	NPC206201
Remote Similarity	0.656	NPC17565
Remote Similarity	0.656	NPC46451
Remote Similarity	0.6557	NPC18348
Remote Similarity	0.6557	NPC477111
Remote Similarity	0.6549	NPC66777
Remote Similarity	0.6549	NPC476997
Remote Similarity	0.6543	NPC470164
Remote Similarity	0.6543	NPC323345
Remote Similarity	0.6538	NPC296527
Remote Similarity	0.6535	NPC214980
Remote Similarity	0.6532	NPC470549
Remote Similarity	0.6529	NPC223427
Remote Similarity	0.6528	NPC9729
Remote Similarity	0.6523	NPC476998
Remote Similarity	0.6523	NPC476996
Remote Similarity	0.6523	NPC115595
Remote Similarity	0.6522	NPC65277
Remote Similarity	0.6518	NPC48353
Remote Similarity	0.6518	NPC94157
Remote Similarity	0.6518	NPC203168
Remote Similarity	0.6518	NPC26679
Remote Similarity	0.6518	NPC264176
Remote Similarity	0.6515	NPC267423
Remote Similarity	0.6513	NPC70259
Remote Similarity	0.6513	NPC251090
Remote Similarity	0.6512	NPC180504
Remote Similarity	0.6511	NPC471593
Remote Similarity	0.6509	NPC84478
Remote Similarity	0.6504	NPC471304
Remote Similarity	0.6502	NPC470930
Remote Similarity	0.6498	NPC476999
Remote Similarity	0.6488	NPC66815
Remote Similarity	0.6484	NPC132385
Remote Similarity	0.6484	NPC476994
Remote Similarity	0.6476	NPC258773
Remote Similarity	0.6473	NPC121772
Remote Similarity	0.6473	NPC11017
Remote Similarity	0.6471	NPC2497
Remote Similarity	0.6471	NPC205934
Remote Similarity	0.6471	NPC43787
Remote Similarity	0.6468	NPC230805
Remote Similarity	0.6468	NPC477533
Remote Similarity	0.6468	NPC472289
Remote Similarity	0.6466	NPC176127
Remote Similarity	0.6458	NPC284685
Remote Similarity	0.6452	NPC472098
Remote Similarity	0.6449	NPC193777
Remote Similarity	0.6448	NPC473182
Remote Similarity	0.6446	NPC470586
Remote Similarity	0.6443	NPC17305
Remote Similarity	0.6437	NPC184680
Remote Similarity	0.6432	NPC164664
Remote Similarity	0.6426	NPC478074
Remote Similarity	0.6426	NPC236668
Remote Similarity	0.6426	NPC66083
Remote Similarity	0.6423	NPC470931
Remote Similarity	0.6422	NPC118776
Remote Similarity	0.6422	NPC477891
Remote Similarity	0.642	NPC475085
Remote Similarity	0.642	NPC475112
Remote Similarity	0.642	NPC291535
Remote Similarity	0.6417	NPC118121
Remote Similarity	0.6414	NPC305984
Remote Similarity	0.6412	NPC470785
Remote Similarity	0.6408	NPC476106
Remote Similarity	0.6408	NPC477113
Remote Similarity	0.6405	NPC249040
Remote Similarity	0.6405	NPC19872
Remote Similarity	0.6403	NPC132642
Remote Similarity	0.6402	NPC295452
Remote Similarity	0.6402	NPC326634
Remote Similarity	0.6402	NPC171393
Remote Similarity	0.64	NPC146976
Remote Similarity	0.6397	NPC174758
Remote Similarity	0.6397	NPC185782
Remote Similarity	0.6393	NPC475774
Remote Similarity	0.6393	NPC245816
Remote Similarity	0.6393	NPC476138
Remote Similarity	0.6389	NPC204446
Remote Similarity	0.6389	NPC96321
Remote Similarity	0.6389	NPC473041
Remote Similarity	0.6381	NPC257851
Remote Similarity	0.6379	NPC476044
Remote Similarity	0.6376	NPC208060
Remote Similarity	0.6375	NPC148183

Drug Structure

NPD5008 OpenBabel08211706322D 32 35 0 0 0 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 5 1 0 0 0 0 2 8 1 0 0 0 0 3 4 2 0 0 0 0 3 15 1 0 0 0 0 4 18 1 0 0 0 0 5 28 1 0 0 0 0 6 9 1 0 0 0 0 6 28 1 0 0 0 0 7 10 1 0 0 0 0 7 28 1 0 0 0 0 8 31 1 0 0 0 0 9 30 1 0 0 0 0 10 30 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 25 2 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 21 2 0 0 0 0 20 29 1 0 0 0 0 21 31 1 0 0 0 0 22 26 2 0 0 0 0 22 27 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000657
DrugBank	DB00317
ChEMBL	CHEMBL939
IUPHAR/BPS	4941
PharmaGKB	PA131301952
KEGG Drug	D01977
PubChem CID	123631
ChEBI	49668
CAS Number	184475-35-2

Drug Properties

Molecular Weight	446.15
ALogP	0.2384
MLogP	2.89
XLogP	3.056
HDA	5
HBD	1
Rotatable Bonds	11
TPSA	68.74
RO5 Violation	0