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.


  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

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