NPASS drugs

Drug Information

Drug ID:	NPD6186
Drug Name:	Ibrutinib
Molecular Formula:	C25H24N6O2
Canonical SMILES:	C=CC(=O)N1CCC[C@H](C1)n1nc(c2c1ncnc2N)c1ccc(cc1)Oc1ccccc1
Standard InCHI:	InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1
Standard InCHIKey:	XYFPWWZEPKGCCK-GOSISDBHSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6186

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	614
0.1-0.2	4410
0.2-0.3	8480
0.3-0.4	10397
0.4-0.5	4629
0.5-0.6	1991
0.6-0.7	360
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
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
Intermediate Similarity	0.7554	NPC115595
Intermediate Similarity	0.73	NPC160666
Intermediate Similarity	0.7215	NPC315822
Intermediate Similarity	0.7162	NPC242923
Intermediate Similarity	0.713	NPC471603
Intermediate Similarity	0.7112	NPC62995
Intermediate Similarity	0.7101	NPC187145
Intermediate Similarity	0.7021	NPC308906
Intermediate Similarity	0.7	NPC471762
Remote Similarity	0.6975	NPC130570
Remote Similarity	0.6972	NPC56271
Remote Similarity	0.6951	NPC280638
Remote Similarity	0.6949	NPC250178
Remote Similarity	0.6929	NPC66777
Remote Similarity	0.6926	NPC174758
Remote Similarity	0.6888	NPC157931
Remote Similarity	0.6824	NPC167860
Remote Similarity	0.6824	NPC123976
Remote Similarity	0.6816	NPC180504
Remote Similarity	0.681	NPC82548
Remote Similarity	0.6781	NPC174672
Remote Similarity	0.6774	NPC30540
Remote Similarity	0.6758	NPC144114
Remote Similarity	0.6753	NPC285558
Remote Similarity	0.6751	NPC274982
Remote Similarity	0.6732	NPC51854
Remote Similarity	0.6726	NPC472289
Remote Similarity	0.6723	NPC305984
Remote Similarity	0.6708	NPC2497
Remote Similarity	0.6695	NPC264176
Remote Similarity	0.6693	NPC9729
Remote Similarity	0.6681	NPC287437
Remote Similarity	0.668	NPC257851
Remote Similarity	0.6667	NPC287208
Remote Similarity	0.6667	NPC193267
Remote Similarity	0.6667	NPC213530
Remote Similarity	0.6667	NPC48317
Remote Similarity	0.6653	NPC99891
Remote Similarity	0.6653	NPC314954
Remote Similarity	0.6639	NPC50511
Remote Similarity	0.6625	NPC467439
Remote Similarity	0.661	NPC290689
Remote Similarity	0.6602	NPC472067
Remote Similarity	0.6602	NPC472066
Remote Similarity	0.6602	NPC472031
Remote Similarity	0.6598	NPC471615
Remote Similarity	0.6596	NPC476465
Remote Similarity	0.6581	NPC470164
Remote Similarity	0.6581	NPC323345
Remote Similarity	0.6575	NPC228206
Remote Similarity	0.657	NPC472099
Remote Similarity	0.657	NPC323969
Remote Similarity	0.6552	NPC31930
Remote Similarity	0.6552	NPC232727
Remote Similarity	0.6548	NPC471614
Remote Similarity	0.6543	NPC17305
Remote Similarity	0.6537	NPC4071
Remote Similarity	0.6537	NPC476582
Remote Similarity	0.6537	NPC476578
Remote Similarity	0.6532	NPC477891
Remote Similarity	0.6527	NPC476287
Remote Similarity	0.6524	NPC295898
Remote Similarity	0.6516	NPC220851
Remote Similarity	0.6513	NPC63109
Remote Similarity	0.6511	NPC472111
Remote Similarity	0.6509	NPC329747
Remote Similarity	0.6504	NPC103687
Remote Similarity	0.6504	NPC132631
Remote Similarity	0.6496	NPC53144
Remote Similarity	0.6494	NPC295228
Remote Similarity	0.6484	NPC208060
Remote Similarity	0.6483	NPC313189
Remote Similarity	0.648	NPC329631
Remote Similarity	0.648	NPC141053
Remote Similarity	0.6478	NPC194967
Remote Similarity	0.6473	NPC152768
Remote Similarity	0.6473	NPC148183
Remote Similarity	0.6468	NPC476581
Remote Similarity	0.6468	NPC36229
Remote Similarity	0.6468	NPC16452
Remote Similarity	0.6463	NPC35761
Remote Similarity	0.6463	NPC21638
Remote Similarity	0.6461	NPC136924
Remote Similarity	0.646	NPC254762
Remote Similarity	0.6459	NPC472068
Remote Similarity	0.6456	NPC475910
Remote Similarity	0.6446	NPC12100
Remote Similarity	0.6438	NPC329793
Remote Similarity	0.6438	NPC176538
Remote Similarity	0.6437	NPC303374
Remote Similarity	0.6434	NPC128115
Remote Similarity	0.6431	NPC171393
Remote Similarity	0.6431	NPC295452
Remote Similarity	0.6429	NPC469589
Remote Similarity	0.6426	NPC223427
Remote Similarity	0.6426	NPC150447
Remote Similarity	0.6417	NPC202768
Remote Similarity	0.6417	NPC472098
Remote Similarity	0.6417	NPC53069
Remote Similarity	0.6417	NPC296482
Remote Similarity	0.6414	NPC135549
Remote Similarity	0.6414	NPC243850
Remote Similarity	0.6409	NPC26543
Remote Similarity	0.6407	NPC472193
Remote Similarity	0.6406	NPC75179
Remote Similarity	0.6393	NPC164664
Remote Similarity	0.6393	NPC17565
Remote Similarity	0.639	NPC469592
Remote Similarity	0.639	NPC471080
Remote Similarity	0.6386	NPC237978
Remote Similarity	0.6383	NPC211813
Remote Similarity	0.6382	NPC46970
Remote Similarity	0.6382	NPC280272
Remote Similarity	0.6378	NPC101350
Remote Similarity	0.6375	NPC208284
Remote Similarity	0.6375	NPC469554
Remote Similarity	0.6375	NPC101543
Remote Similarity	0.6356	NPC322482
Remote Similarity	0.6356	NPC476138
Remote Similarity	0.6356	NPC200836
Remote Similarity	0.6356	NPC245816
Remote Similarity	0.6352	NPC303658
Remote Similarity	0.6349	NPC96405
Remote Similarity	0.6349	NPC171409
Remote Similarity	0.6349	NPC26679
Remote Similarity	0.6348	NPC195268
Remote Similarity	0.6348	NPC133140
Remote Similarity	0.6348	NPC324149
Remote Similarity	0.6342	NPC477805
Remote Similarity	0.6342	NPC477795
Remote Similarity	0.6342	NPC477806
Remote Similarity	0.6342	NPC477796
Remote Similarity	0.6339	NPC235685
Remote Similarity	0.6337	NPC170114
Remote Similarity	0.6335	NPC21461
Remote Similarity	0.6333	NPC471304
Remote Similarity	0.6333	NPC85273
Remote Similarity	0.6333	NPC470020
Remote Similarity	0.6329	NPC475070
Remote Similarity	0.6327	NPC168209
Remote Similarity	0.6322	NPC271215
Remote Similarity	0.6322	NPC149471
Remote Similarity	0.632	NPC198673
Remote Similarity	0.6318	NPC472434
Remote Similarity	0.6309	NPC267928
Remote Similarity	0.6306	NPC317054
Remote Similarity	0.6304	NPC39092
Remote Similarity	0.6301	NPC477533
Remote Similarity	0.6298	NPC234197
Remote Similarity	0.6298	NPC19872
Remote Similarity	0.6298	NPC11017
Remote Similarity	0.6298	NPC477019
Remote Similarity	0.6296	NPC470549
Remote Similarity	0.6292	NPC185782
Remote Similarity	0.629	NPC476688
Remote Similarity	0.629	NPC122436
Remote Similarity	0.629	NPC65277
Remote Similarity	0.629	NPC476686
Remote Similarity	0.629	NPC105758
Remote Similarity	0.6287	NPC475774
Remote Similarity	0.6286	NPC473041
Remote Similarity	0.6286	NPC469594
Remote Similarity	0.6282	NPC72211
Remote Similarity	0.6282	NPC168911
Remote Similarity	0.6281	NPC202605
Remote Similarity	0.6281	NPC112206
Remote Similarity	0.6275	NPC60621
Remote Similarity	0.6275	NPC184680
Remote Similarity	0.6273	NPC278874
Remote Similarity	0.6266	NPC11464
Remote Similarity	0.6266	NPC70259
Remote Similarity	0.6266	NPC188420
Remote Similarity	0.6261	NPC471593
Remote Similarity	0.626	NPC253675
Remote Similarity	0.626	NPC208898
Remote Similarity	0.6259	NPC478009
Remote Similarity	0.6255	NPC311906
Remote Similarity	0.625	NPC26850
Remote Similarity	0.625	NPC470785
Remote Similarity	0.625	NPC175150
Remote Similarity	0.625	NPC216612
Remote Similarity	0.625	NPC329541
Remote Similarity	0.625	NPC243633
Remote Similarity	0.625	NPC475190
Remote Similarity	0.625	NPC470784
Remote Similarity	0.625	NPC470931
Remote Similarity	0.6245	NPC476041
Remote Similarity	0.6245	NPC304926
Remote Similarity	0.624	NPC319232
Remote Similarity	0.624	NPC24370
Remote Similarity	0.6239	NPC177404
Remote Similarity	0.6235	NPC477549
Remote Similarity	0.6234	NPC92111
Remote Similarity	0.6233	NPC312872
Remote Similarity	0.6229	NPC121772
Remote Similarity	0.6223	NPC43787
Remote Similarity	0.6223	NPC205934
Remote Similarity	0.6222	NPC315467
Remote Similarity	0.622	NPC23614
Remote Similarity	0.622	NPC100079

Drug Structure

NPD6186 OpenBabel08211709092D 35 39 0 0 1 0 0 0 0 0999 V2000 -1.0392 -4.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0446 -4.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 -1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 -2.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3621 -3.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 2.5602 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 0.5292 3.3034 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 2.7681 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 1.0739 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2257 -2.6361 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 1.3566 -3.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5074 3.0955 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2202 4.2544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 20 2 0 0 0 0 13 20 1 0 0 0 0 14 30 1 0 0 0 0 15 18 1 0 0 0 0 15 30 1 0 0 0 0 16 27 2 0 0 0 0 16 28 1 0 0 0 0 17 23 1 0 0 0 0 18 7 1 1 0 0 0 18 31 1 0 0 0 0 19 33 1 0 0 0 0 20 33 1 0 0 0 0 21 30 1 0 0 0 0 21 32 2 0 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 23 29 2 0 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 25 28 2 0 0 0 0 25 31 1 0 0 0 0 26 34 1 0 0 0 0 26 35 1 0 0 0 0 29 31 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNCL002550
DrugBank	DB09053
ChEMBL	CHEMBL1873475
IUPHAR/BPS	6912
PharmaGKB
KEGG Drug	D10223
PubChem CID	24821094
ChEBI	76612
CAS Number	936563-96-1

Drug Properties

Molecular Weight	440.20
ALogP	-1.528
MLogP	3.33
XLogP	4.182
HDA	7
HBD	1
Rotatable Bonds	7
TPSA	99.16
RO5 Violation	0