NPASS drugs

Drug Information

Drug ID:	NPD5878
Drug Name:	Afatinib
Molecular Formula:	C24H25ClFN5O3
Canonical SMILES:	CN(C/C=C/C(=Nc1cc2c(ncnc2cc1O[C@@H]1COCC1)Nc1ccc(c(c1)Cl)F)O)C
Standard InCHI:	InChI=1S/C24H25ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15/h3-6,10-12,14,16H,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29)/b4-3+/t16-/m0/s1
Standard InCHIKey:	ULXXDDBFHOBEHA-CWDCEQMOSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5878

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	544
0.1-0.2	5283
0.2-0.3	7973
0.3-0.4	11353
0.4-0.5	3503
0.5-0.6	1812
0.6-0.7	413
0.7-0.8	8
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
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	0.8803	NPC56271
Intermediate Similarity	0.7352	NPC472067
Intermediate Similarity	0.7352	NPC472031
Intermediate Similarity	0.7352	NPC472066
Intermediate Similarity	0.7339	NPC30540
Intermediate Similarity	0.7306	NPC160666
Intermediate Similarity	0.7273	NPC472068
Intermediate Similarity	0.7042	NPC162530
Intermediate Similarity	0.7037	NPC250178
Remote Similarity	0.6929	NPC471603
Remote Similarity	0.6926	NPC173080
Remote Similarity	0.692	NPC285558
Remote Similarity	0.6901	NPC469592
Remote Similarity	0.6901	NPC471080
Remote Similarity	0.6858	NPC144114
Remote Similarity	0.6855	NPC130570
Remote Similarity	0.684	NPC187145
Remote Similarity	0.6836	NPC471614
Remote Similarity	0.6833	NPC475910
Remote Similarity	0.6822	NPC329747
Remote Similarity	0.6805	NPC469589
Remote Similarity	0.6789	NPC469594
Remote Similarity	0.6761	NPC193267
Remote Similarity	0.6761	NPC213530
Remote Similarity	0.675	NPC476106
Remote Similarity	0.6748	NPC473513
Remote Similarity	0.6723	NPC470586
Remote Similarity	0.6723	NPC232727
Remote Similarity	0.6708	NPC123976
Remote Similarity	0.6708	NPC167860
Remote Similarity	0.6706	NPC473185
Remote Similarity	0.6695	NPC291535
Remote Similarity	0.6695	NPC475085
Remote Similarity	0.6695	NPC475112
Remote Similarity	0.6681	NPC472289
Remote Similarity	0.668	NPC242923
Remote Similarity	0.6667	NPC475774
Remote Similarity	0.6667	NPC72211
Remote Similarity	0.6654	NPC115595
Remote Similarity	0.6652	NPC164664
Remote Similarity	0.664	NPC288349
Remote Similarity	0.6638	NPC477891
Remote Similarity	0.6628	NPC473183
Remote Similarity	0.6627	NPC475253
Remote Similarity	0.6627	NPC300114
Remote Similarity	0.6627	NPC308906
Remote Similarity	0.6627	NPC17565
Remote Similarity	0.6624	NPC70956
Remote Similarity	0.6624	NPC243834
Remote Similarity	0.6615	NPC473184
Remote Similarity	0.6614	NPC66777
Remote Similarity	0.6614	NPC471762
Remote Similarity	0.6611	NPC315957
Remote Similarity	0.6609	NPC110741
Remote Similarity	0.6602	NPC469554
Remote Similarity	0.6593	NPC208060
Remote Similarity	0.6585	NPC316981
Remote Similarity	0.6585	NPC48353
Remote Similarity	0.6585	NPC203168
Remote Similarity	0.6582	NPC70259
Remote Similarity	0.658	NPC84478
Remote Similarity	0.6579	NPC283152
Remote Similarity	0.6573	NPC170114
Remote Similarity	0.6571	NPC11464
Remote Similarity	0.6571	NPC219664
Remote Similarity	0.657	NPC470930
Remote Similarity	0.6565	NPC118776
Remote Similarity	0.656	NPC473179
Remote Similarity	0.6559	NPC266931
Remote Similarity	0.6557	NPC18348
Remote Similarity	0.6549	NPC105758
Remote Similarity	0.6549	NPC476688
Remote Similarity	0.6549	NPC314954
Remote Similarity	0.6549	NPC476686
Remote Similarity	0.6542	NPC121772
Remote Similarity	0.654	NPC205934
Remote Similarity	0.654	NPC43787
Remote Similarity	0.6538	NPC230805
Remote Similarity	0.6535	NPC2497
Remote Similarity	0.6535	NPC132631
Remote Similarity	0.6535	NPC103687
Remote Similarity	0.6534	NPC132642
Remote Similarity	0.6533	NPC278874
Remote Similarity	0.6532	NPC470549
Remote Similarity	0.6531	NPC209769
Remote Similarity	0.6529	NPC162484
Remote Similarity	0.6522	NPC65277
Remote Similarity	0.6519	NPC150447
Remote Similarity	0.6518	NPC26679
Remote Similarity	0.6516	NPC193777
Remote Similarity	0.6512	NPC473182
Remote Similarity	0.6512	NPC323198
Remote Similarity	0.6512	NPC180504
Remote Similarity	0.6509	NPC62069
Remote Similarity	0.6502	NPC477806
Remote Similarity	0.6502	NPC477796
Remote Similarity	0.6502	NPC316756
Remote Similarity	0.6502	NPC477805
Remote Similarity	0.6502	NPC477795
Remote Similarity	0.6498	NPC79293
Remote Similarity	0.6498	NPC279401
Remote Similarity	0.6496	NPC125597
Remote Similarity	0.6496	NPC254762
Remote Similarity	0.649	NPC470931
Remote Similarity	0.6489	NPC99891
Remote Similarity	0.6488	NPC135887
Remote Similarity	0.6488	NPC199277
Remote Similarity	0.6478	NPC208284
Remote Similarity	0.6475	NPC472111
Remote Similarity	0.6473	NPC19872
Remote Similarity	0.6463	NPC201697
Remote Similarity	0.6463	NPC174758
Remote Similarity	0.6461	NPC223427
Remote Similarity	0.6461	NPC476138
Remote Similarity	0.6461	NPC245816
Remote Similarity	0.6454	NPC473041
Remote Similarity	0.6454	NPC197141
Remote Similarity	0.6453	NPC314573
Remote Similarity	0.6452	NPC202605
Remote Similarity	0.6452	NPC94157
Remote Similarity	0.6452	NPC112206
Remote Similarity	0.645	NPC41501
Remote Similarity	0.6446	NPC267423
Remote Similarity	0.6446	NPC476044
Remote Similarity	0.6445	NPC110151
Remote Similarity	0.6444	NPC13880
Remote Similarity	0.6443	NPC60621
Remote Similarity	0.6443	NPC310118
Remote Similarity	0.6441	NPC471593
Remote Similarity	0.644	NPC470799
Remote Similarity	0.644	NPC8022
Remote Similarity	0.6437	NPC184680
Remote Similarity	0.6437	NPC472061
Remote Similarity	0.6434	NPC16452
Remote Similarity	0.6434	NPC21461
Remote Similarity	0.6434	NPC36229
Remote Similarity	0.6434	NPC476581
Remote Similarity	0.6432	NPC128823
Remote Similarity	0.6429	NPC224632
Remote Similarity	0.6429	NPC307963
Remote Similarity	0.6426	NPC476287
Remote Similarity	0.6426	NPC478074
Remote Similarity	0.6423	NPC476465
Remote Similarity	0.642	NPC66815
Remote Similarity	0.6417	NPC280272
Remote Similarity	0.6415	NPC228206
Remote Similarity	0.6412	NPC470785
Remote Similarity	0.641	NPC42591
Remote Similarity	0.6409	NPC101543
Remote Similarity	0.6408	NPC471736
Remote Similarity	0.6405	NPC234197
Remote Similarity	0.6403	NPC128115
Remote Similarity	0.6403	NPC477533
Remote Similarity	0.6398	NPC295228
Remote Similarity	0.6397	NPC185782
Remote Similarity	0.6391	NPC288943
Remote Similarity	0.6387	NPC133140
Remote Similarity	0.6387	NPC195268
Remote Similarity	0.6386	NPC264176
Remote Similarity	0.6386	NPC53069
Remote Similarity	0.6386	NPC202768
Remote Similarity	0.6386	NPC296482
Remote Similarity	0.6383	NPC204385
Remote Similarity	0.6381	NPC257851
Remote Similarity	0.6381	NPC51854
Remote Similarity	0.6378	NPC477532
Remote Similarity	0.6378	NPC473317
Remote Similarity	0.6375	NPC251090
Remote Similarity	0.6375	NPC242209
Remote Similarity	0.6375	NPC194967
Remote Similarity	0.6375	NPC477110
Remote Similarity	0.6374	NPC177056
Remote Similarity	0.6371	NPC199667
Remote Similarity	0.637	NPC314882
Remote Similarity	0.6368	NPC26850
Remote Similarity	0.6364	NPC4071
Remote Similarity	0.6364	NPC476578
Remote Similarity	0.6364	NPC132385
Remote Similarity	0.6364	NPC476582
Remote Similarity	0.6364	NPC96890
Remote Similarity	0.636	NPC63109
Remote Similarity	0.6357	NPC252251
Remote Similarity	0.6356	NPC46580
Remote Similarity	0.6353	NPC208522
Remote Similarity	0.635	NPC470784
Remote Similarity	0.6349	NPC267928
Remote Similarity	0.6349	NPC305984
Remote Similarity	0.6348	NPC312872
Remote Similarity	0.6346	NPC49547
Remote Similarity	0.6345	NPC92111
Remote Similarity	0.6343	NPC270515
Remote Similarity	0.6343	NPC9729
Remote Similarity	0.6342	NPC200888
Remote Similarity	0.6342	NPC470018
Remote Similarity	0.6337	NPC176538
Remote Similarity	0.6337	NPC477019
Remote Similarity	0.6337	NPC11017
Remote Similarity	0.6337	NPC329793
Remote Similarity	0.6333	NPC131017
Remote Similarity	0.6331	NPC174672

Drug Structure

NPD5878 OpenBabel08211708292D 36 39 0 0 1 0 0 0 0 0999 V2000 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 -0.6636 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -0.0055 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 1 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 -1.7321 2.0000 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 1.7321 -1.0000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 -2.5981 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 F 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 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 4.3301 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 0.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 31 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 19 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 31 1 0 0 0 0 9 33 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 20 2 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 13 33 1 0 0 0 0 14 27 2 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 34 1 6 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 22 2 0 0 0 0 21 30 1 0 0 0 0 22 34 1 0 0 0 0 23 30 2 3 0 0 0 23 32 1 0 0 0 0 24 28 2 0 0 0 0 24 29 1 0 0 0 0 29 35 1 0 0 0 0 32 36 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000498
DrugBank	DB08916
ChEMBL	CHEMBL1173655
IUPHAR/BPS	5667
PharmaGKB
KEGG Drug	D09724
PubChem CID	10184653
ChEBI	61390
CAS Number	850140-72-6

Drug Properties

Molecular Weight	485.16
ALogP	0.6891
MLogP	3
XLogP	3.647
HDA	7
HBD	2
Rotatable Bonds	13
TPSA	92.1
RO5 Violation	0