NPASS drugs

Drug Information

Drug ID:	NPD6216
Drug Name:	Simotinib
Molecular Formula:	C25H26ClFN4O4
Canonical SMILES:	COc1cc2ncnc(c2cc1OCCN1CC2(C3(C1)CC3)OCCO2)Nc1ccc(c(c1)Cl)F
Standard InCHI:	InChI=1S/C25H26ClFN4O4/c1-32-21-12-20-17(23(29-15-28-20)30-16-2-3-19(27)18(26)10-16)11-22(21)33-7-6-31-13-24(4-5-24)25(14-31)34-8-9-35-25/h2-3,10-12,15H,4-9,13-14H2,1H3,(H,28,29,30)
Standard InCHIKey:	OXWUWXCJDBRCCG-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6216

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	659
0.1-0.2	5516
0.2-0.3	7871
0.3-0.4	10631
0.4-0.5	3905
0.5-0.6	1901
0.6-0.7	393
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

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	0.9274	NPC56271
Intermediate Similarity	0.7198	NPC471614
Intermediate Similarity	0.7176	NPC472031
Intermediate Similarity	0.7176	NPC472067
Intermediate Similarity	0.7176	NPC472066
Intermediate Similarity	0.7165	NPC472068
Intermediate Similarity	0.7126	NPC160666
Intermediate Similarity	0.7115	NPC477806
Intermediate Similarity	0.7115	NPC477805
Intermediate Similarity	0.7115	NPC477796
Intermediate Similarity	0.7115	NPC477795
Intermediate Similarity	0.7068	NPC303374
Intermediate Similarity	0.7027	NPC30540
Intermediate Similarity	0.7004	NPC162530
Remote Similarity	0.6964	NPC296482
Remote Similarity	0.6964	NPC53069
Remote Similarity	0.6964	NPC171409
Remote Similarity	0.6964	NPC96405
Remote Similarity	0.6964	NPC202768
Remote Similarity	0.6957	NPC130570
Remote Similarity	0.6929	NPC234197
Remote Similarity	0.6898	NPC313189
Remote Similarity	0.6898	NPC135549
Remote Similarity	0.6867	NPC266931
Remote Similarity	0.6865	NPC308906
Remote Similarity	0.686	NPC477019
Remote Similarity	0.6851	NPC204385
Remote Similarity	0.6827	NPC316981
Remote Similarity	0.6798	NPC46451
Remote Similarity	0.6798	NPC250178
Remote Similarity	0.6786	NPC473513
Remote Similarity	0.676	NPC251160
Remote Similarity	0.6759	NPC23614
Remote Similarity	0.6759	NPC100079
Remote Similarity	0.6748	NPC36229
Remote Similarity	0.6748	NPC285558
Remote Similarity	0.6748	NPC476581
Remote Similarity	0.6748	NPC16452
Remote Similarity	0.6745	NPC17305
Remote Similarity	0.6735	NPC135887
Remote Similarity	0.6735	NPC199277
Remote Similarity	0.6733	NPC271215
Remote Similarity	0.6733	NPC469592
Remote Similarity	0.6733	NPC149471
Remote Similarity	0.6733	NPC471080
Remote Similarity	0.673	NPC473183
Remote Similarity	0.6708	NPC133140
Remote Similarity	0.6708	NPC195268
Remote Similarity	0.6707	NPC162484
Remote Similarity	0.6706	NPC235076
Remote Similarity	0.6693	NPC173080
Remote Similarity	0.6693	NPC469594
Remote Similarity	0.6681	NPC206201
Remote Similarity	0.668	NPC476582
Remote Similarity	0.668	NPC476578
Remote Similarity	0.668	NPC187145
Remote Similarity	0.668	NPC188420
Remote Similarity	0.668	NPC4071
Remote Similarity	0.6667	NPC475253
Remote Similarity	0.6667	NPC316756
Remote Similarity	0.6654	NPC12100
Remote Similarity	0.6654	NPC280272
Remote Similarity	0.6654	NPC473184
Remote Similarity	0.6653	NPC329747
Remote Similarity	0.6642	NPC228206
Remote Similarity	0.664	NPC469589
Remote Similarity	0.6629	NPC295228
Remote Similarity	0.6627	NPC467439
Remote Similarity	0.6626	NPC31930
Remote Similarity	0.6614	NPC170114
Remote Similarity	0.6614	NPC290689
Remote Similarity	0.66	NPC476465
Remote Similarity	0.6585	NPC315957
Remote Similarity	0.6578	NPC469554
Remote Similarity	0.6575	NPC470549
Remote Similarity	0.6561	NPC112206
Remote Similarity	0.6561	NPC202605
Remote Similarity	0.6559	NPC232727
Remote Similarity	0.6553	NPC180504
Remote Similarity	0.6552	NPC473185
Remote Similarity	0.6548	NPC167860
Remote Similarity	0.6548	NPC123976
Remote Similarity	0.6544	NPC51854
Remote Similarity	0.6538	NPC312872
Remote Similarity	0.6534	NPC475910
Remote Similarity	0.6529	NPC92111
Remote Similarity	0.6527	NPC314954
Remote Similarity	0.6525	NPC118121
Remote Similarity	0.6522	NPC208284
Remote Similarity	0.6518	NPC176538
Remote Similarity	0.6518	NPC329793
Remote Similarity	0.6516	NPC131017
Remote Similarity	0.6512	NPC477533
Remote Similarity	0.6508	NPC201697
Remote Similarity	0.6507	NPC9729
Remote Similarity	0.6506	NPC171393
Remote Similarity	0.6506	NPC295452
Remote Similarity	0.6504	NPC72211
Remote Similarity	0.6498	NPC96321
Remote Similarity	0.6498	NPC473041
Remote Similarity	0.6498	NPC204446
Remote Similarity	0.6496	NPC471603
Remote Similarity	0.6496	NPC94157
Remote Similarity	0.6488	NPC76748
Remote Similarity	0.6484	NPC288349
Remote Similarity	0.6482	NPC219664
Remote Similarity	0.6475	NPC307963
Remote Similarity	0.6473	NPC213530
Remote Similarity	0.6473	NPC193267
Remote Similarity	0.6466	NPC253675
Remote Similarity	0.6464	NPC471762
Remote Similarity	0.6453	NPC101543
Remote Similarity	0.6446	NPC296527
Remote Similarity	0.644	NPC223427
Remote Similarity	0.644	NPC475774
Remote Similarity	0.6439	NPC115595
Remote Similarity	0.6431	NPC203168
Remote Similarity	0.6431	NPC26679
Remote Similarity	0.6431	NPC48353
Remote Similarity	0.6431	NPC472098
Remote Similarity	0.6429	NPC473182
Remote Similarity	0.6426	NPC157931
Remote Similarity	0.6423	NPC70259
Remote Similarity	0.6423	NPC251090
Remote Similarity	0.642	NPC471593
Remote Similarity	0.6418	NPC184680
Remote Similarity	0.6417	NPC84478
Remote Similarity	0.6417	NPC471304
Remote Similarity	0.6415	NPC300114
Remote Similarity	0.6415	NPC476999
Remote Similarity	0.6414	NPC470930
Remote Similarity	0.6407	NPC99891
Remote Similarity	0.6406	NPC478074
Remote Similarity	0.6404	NPC277351
Remote Similarity	0.6402	NPC66777
Remote Similarity	0.6402	NPC476997
Remote Similarity	0.6402	NPC252251
Remote Similarity	0.6394	NPC470785
Remote Similarity	0.6392	NPC242923
Remote Similarity	0.6389	NPC472111
Remote Similarity	0.6388	NPC103687
Remote Similarity	0.6388	NPC132631
Remote Similarity	0.6386	NPC121772
Remote Similarity	0.6385	NPC472099
Remote Similarity	0.6385	NPC132642
Remote Similarity	0.6384	NPC39092
Remote Similarity	0.6382	NPC43787
Remote Similarity	0.6382	NPC205934
Remote Similarity	0.638	NPC150447
Remote Similarity	0.6377	NPC476996
Remote Similarity	0.6377	NPC476998
Remote Similarity	0.6375	NPC176127
Remote Similarity	0.6371	NPC473822
Remote Similarity	0.6364	NPC193777
Remote Similarity	0.6364	NPC110151
Remote Similarity	0.636	NPC267423
Remote Similarity	0.636	NPC476044
Remote Similarity	0.636	NPC315467
Remote Similarity	0.6353	NPC477531
Remote Similarity	0.6349	NPC284559
Remote Similarity	0.6346	NPC473179
Remote Similarity	0.6342	NPC476287
Remote Similarity	0.634	NPC476994
Remote Similarity	0.6338	NPC478009
Remote Similarity	0.6337	NPC284141
Remote Similarity	0.6337	NPC81939
Remote Similarity	0.6335	NPC475112
Remote Similarity	0.6335	NPC475085
Remote Similarity	0.6335	NPC291535
Remote Similarity	0.6333	NPC144114
Remote Similarity	0.6332	NPC305984
Remote Similarity	0.633	NPC475720
Remote Similarity	0.633	NPC474192
Remote Similarity	0.6327	NPC270515
Remote Similarity	0.6326	NPC2497
Remote Similarity	0.6326	NPC214980
Remote Similarity	0.6324	NPC476106
Remote Similarity	0.6324	NPC473540
Remote Similarity	0.6321	NPC284685
Remote Similarity	0.632	NPC19872
Remote Similarity	0.6316	NPC209174
Remote Similarity	0.6316	NPC326634
Remote Similarity	0.6314	NPC475666
Remote Similarity	0.6314	NPC185782
Remote Similarity	0.6314	NPC174758
Remote Similarity	0.631	NPC245816
Remote Similarity	0.631	NPC476138
Remote Similarity	0.631	NPC168922
Remote Similarity	0.6306	NPC323198
Remote Similarity	0.6298	NPC237901
Remote Similarity	0.6298	NPC477532
Remote Similarity	0.6298	NPC195788
Remote Similarity	0.6298	NPC310118
Remote Similarity	0.6298	NPC60621
Remote Similarity	0.6295	NPC470586
Remote Similarity	0.6295	NPC314882
Remote Similarity	0.6293	NPC148183
Remote Similarity	0.6293	NPC152768
Remote Similarity	0.6292	NPC201508
Remote Similarity	0.629	NPC13880

Drug Structure

NPD6216 OpenBabel08211709092D 36 41 0 0 0 0 0 0 0 0999 V2000 -5.7788 4.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1808 -2.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1808 -3.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 2.3198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9135 1.3253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4487 2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3147 2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9128 -2.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0468 1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7788 2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3309 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6449 -0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0468 -1.9315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9128 0.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9128 -3.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0468 -3.9315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7788 1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9128 2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0468 2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9128 -0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7788 -3.9315 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.0468 -4.9315 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -6.6449 0.5685 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7788 -0.9315 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0468 -0.9315 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5827 2.0685 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9128 3.5685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1808 2.5685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1808 -0.4315 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 3 2 0 0 0 0 2 16 1 0 0 0 0 3 19 1 0 0 0 0 4 5 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 7 1 0 0 0 0 6 31 1 0 0 0 0 7 33 1 0 0 0 0 8 9 1 0 0 0 0 8 34 1 0 0 0 0 9 35 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 17 2 0 0 0 0 11 22 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 24 1 0 0 0 0 13 31 1 0 0 0 0 14 25 1 0 0 0 0 14 31 1 0 0 0 0 15 28 2 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 22 2 0 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 23 29 2 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 25 34 1 0 0 0 0 25 35 1 0 0 0 0 30 36 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB002255
DrugBank
ChEMBL
IUPHAR/BPS	7640
PharmaGKB
KEGG Drug
PubChem CID	16735117
ChEBI
CAS Number

Drug Properties

Molecular Weight	500.16
ALogP	0.1473
MLogP	3.11
XLogP	3.176
HDA	6
HBD	1
Rotatable Bonds	10
TPSA	77.97
RO5 Violation	0