NPASS drugs

Drug Information

Drug ID:	NPD8108
Drug Name:	Simeprevir
Molecular Formula:	C38H47N5O7S2
Canonical SMILES:	COc1ccc2c(c1C)nc(cc2O[C@@H]1C[C@@H]2[C@@H](C1)C(=O)N(C)CCCC/C=C[C@H]1[C@](N=C2O)(C1)C(=NS(=O)(=O)C1CC1)O)c1scc(n1)C(C)C
Standard InCHI:	InChI=1S/C38H47N5O7S2/c1-21(2)30-20-51-35(40-30)29-18-32(26-13-14-31(49-5)22(3)33(26)39-29)50-24-16-27-28(17-24)36(45)43(4)15-9-7-6-8-10-23-19-38(23,41-34(27)44)37(46)42-52(47,48)25-11-12-25/h8,10,13-14,18,20-21,23-25,27-28H,6-7,9,11-12,15-17,19H2,1-5H3,(H,41,44)(H,42,46)/b10-8-/t23-,24-,27-,28-,38-/m1/s1
Standard InCHIKey:	JTZZSQYMACOLNN-VDWJNHBNSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD8108

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	434
0.1-0.2	2197
0.2-0.3	9877
0.3-0.4	6188
0.4-0.5	9689
0.5-0.6	2075
0.6-0.7	430
0.7-0.8	0
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
Remote Similarity	0.6899	NPC310118
Remote Similarity	0.6897	NPC110151
Remote Similarity	0.6866	NPC99891
Remote Similarity	0.6854	NPC474183
Remote Similarity	0.685	NPC133609
Remote Similarity	0.6848	NPC303658
Remote Similarity	0.6825	NPC189079
Remote Similarity	0.682	NPC21638
Remote Similarity	0.6816	NPC184680
Remote Similarity	0.6791	NPC470784
Remote Similarity	0.6791	NPC470785
Remote Similarity	0.6784	NPC264176
Remote Similarity	0.6767	NPC473105
Remote Similarity	0.6756	NPC473449
Remote Similarity	0.6744	NPC305984
Remote Similarity	0.6732	NPC469589
Remote Similarity	0.6732	NPC174672
Remote Similarity	0.6731	NPC128115
Remote Similarity	0.6724	NPC315061
Remote Similarity	0.6719	NPC251036
Remote Similarity	0.6713	NPC471303
Remote Similarity	0.6712	NPC315411
Remote Similarity	0.6705	NPC148183
Remote Similarity	0.6705	NPC60621
Remote Similarity	0.6705	NPC152768
Remote Similarity	0.6692	NPC97746
Remote Similarity	0.6679	NPC194740
Remote Similarity	0.6667	NPC174758
Remote Similarity	0.6667	NPC131486
Remote Similarity	0.6667	NPC145178
Remote Similarity	0.6667	NPC153467
Remote Similarity	0.6667	NPC475350
Remote Similarity	0.6667	NPC14877
Remote Similarity	0.6654	NPC469594
Remote Similarity	0.6645	NPC470900
Remote Similarity	0.6643	NPC472436
Remote Similarity	0.6642	NPC475816
Remote Similarity	0.6628	NPC298436
Remote Similarity	0.6604	NPC321592
Remote Similarity	0.6604	NPC54803
Remote Similarity	0.6595	NPC472435
Remote Similarity	0.6589	NPC472098
Remote Similarity	0.6585	NPC315634
Remote Similarity	0.6585	NPC100734
Remote Similarity	0.6585	NPC88923
Remote Similarity	0.6584	NPC284685
Remote Similarity	0.6571	NPC216507
Remote Similarity	0.6564	NPC469592
Remote Similarity	0.6564	NPC471080
Remote Similarity	0.6562	NPC470931
Remote Similarity	0.6559	NPC244543
Remote Similarity	0.6552	NPC79386
Remote Similarity	0.6551	NPC115282
Remote Similarity	0.6549	NPC472111
Remote Similarity	0.6547	NPC316110
Remote Similarity	0.6547	NPC313587
Remote Similarity	0.6547	NPC315893
Remote Similarity	0.6545	NPC81939
Remote Similarity	0.6545	NPC472434
Remote Similarity	0.6545	NPC78609
Remote Similarity	0.6543	NPC474192
Remote Similarity	0.6543	NPC475196
Remote Similarity	0.6543	NPC475720
Remote Similarity	0.6541	NPC319232
Remote Similarity	0.6541	NPC24370
Remote Similarity	0.654	NPC477533
Remote Similarity	0.653	NPC223409
Remote Similarity	0.653	NPC95240
Remote Similarity	0.6522	NPC475666
Remote Similarity	0.6519	NPC260909
Remote Similarity	0.6519	NPC284888
Remote Similarity	0.6517	NPC118559
Remote Similarity	0.6517	NPC34580
Remote Similarity	0.6517	NPC304307
Remote Similarity	0.6517	NPC124920
Remote Similarity	0.6515	NPC477532
Remote Similarity	0.6514	NPC140284
Remote Similarity	0.6514	NPC75609
Remote Similarity	0.6513	NPC274982
Remote Similarity	0.6509	NPC188400
Remote Similarity	0.6508	NPC197881
Remote Similarity	0.6496	NPC295898
Remote Similarity	0.6493	NPC100547
Remote Similarity	0.6493	NPC66777
Remote Similarity	0.6484	NPC476106
Remote Similarity	0.6468	NPC322135
Remote Similarity	0.6467	NPC470901
Remote Similarity	0.6464	NPC153400
Remote Similarity	0.6457	NPC476044
Remote Similarity	0.6455	NPC261251
Remote Similarity	0.6449	NPC75179
Remote Similarity	0.6445	NPC257511
Remote Similarity	0.6444	NPC191489
Remote Similarity	0.6444	NPC14288
Remote Similarity	0.644	NPC79293
Remote Similarity	0.644	NPC279401
Remote Similarity	0.6438	NPC237901
Remote Similarity	0.6438	NPC195788
Remote Similarity	0.6434	NPC475910
Remote Similarity	0.6431	NPC471762
Remote Similarity	0.6429	NPC67401
Remote Similarity	0.6418	NPC214142
Remote Similarity	0.6417	NPC11017
Remote Similarity	0.641	NPC473187
Remote Similarity	0.6406	NPC200836
Remote Similarity	0.6404	NPC122436
Remote Similarity	0.6404	NPC314176
Remote Similarity	0.6402	NPC473041
Remote Similarity	0.6401	NPC478013
Remote Similarity	0.6397	NPC323752
Remote Similarity	0.6397	NPC323198
Remote Similarity	0.6392	NPC232727
Remote Similarity	0.6392	NPC313966
Remote Similarity	0.6392	NPC314254
Remote Similarity	0.6389	NPC227824
Remote Similarity	0.6384	NPC217176
Remote Similarity	0.6382	NPC62069
Remote Similarity	0.638	NPC1608
Remote Similarity	0.6377	NPC213530
Remote Similarity	0.6377	NPC37957
Remote Similarity	0.6377	NPC193267
Remote Similarity	0.6374	NPC245055
Remote Similarity	0.6374	NPC33064
Remote Similarity	0.6371	NPC82548
Remote Similarity	0.6371	NPC287208
Remote Similarity	0.637	NPC478011
Remote Similarity	0.637	NPC478012
Remote Similarity	0.6367	NPC475112
Remote Similarity	0.6367	NPC475085
Remote Similarity	0.6367	NPC291535
Remote Similarity	0.6364	NPC70956
Remote Similarity	0.6364	NPC82472
Remote Similarity	0.6364	NPC243834
Remote Similarity	0.6353	NPC323969
Remote Similarity	0.6353	NPC150239
Remote Similarity	0.6353	NPC472099
Remote Similarity	0.6347	NPC326363
Remote Similarity	0.6344	NPC58209
Remote Similarity	0.6342	NPC53144
Remote Similarity	0.6342	NPC223427
Remote Similarity	0.6339	NPC72211
Remote Similarity	0.6337	NPC220852
Remote Similarity	0.6337	NPC470889
Remote Similarity	0.633	NPC198503
Remote Similarity	0.6327	NPC168486
Remote Similarity	0.6327	NPC222592
Remote Similarity	0.6326	NPC170114
Remote Similarity	0.6324	NPC260434
Remote Similarity	0.6324	NPC475253
Remote Similarity	0.6324	NPC477531
Remote Similarity	0.6322	NPC269367
Remote Similarity	0.6314	NPC325976
Remote Similarity	0.631	NPC252251
Remote Similarity	0.631	NPC311906
Remote Similarity	0.6306	NPC478141
Remote Similarity	0.6304	NPC101350
Remote Similarity	0.63	NPC477516
Remote Similarity	0.6299	NPC91868
Remote Similarity	0.6299	NPC63971
Remote Similarity	0.6298	NPC314056
Remote Similarity	0.6295	NPC124300
Remote Similarity	0.6295	NPC166712
Remote Similarity	0.6289	NPC329747
Remote Similarity	0.6288	NPC470549
Remote Similarity	0.6287	NPC209174
Remote Similarity	0.6286	NPC469734
Remote Similarity	0.6282	NPC168922
Remote Similarity	0.6279	NPC75498
Remote Similarity	0.6279	NPC162484
Remote Similarity	0.6278	NPC247803
Remote Similarity	0.6277	NPC203373
Remote Similarity	0.6277	NPC165964
Remote Similarity	0.6277	NPC329631
Remote Similarity	0.6274	NPC26679
Remote Similarity	0.6273	NPC473185
Remote Similarity	0.6272	NPC291609
Remote Similarity	0.6269	NPC53344
Remote Similarity	0.6268	NPC235685
Remote Similarity	0.6268	NPC285343
Remote Similarity	0.6268	NPC329982
Remote Similarity	0.6265	NPC470586
Remote Similarity	0.6264	NPC74969
Remote Similarity	0.626	NPC11464
Remote Similarity	0.626	NPC167860
Remote Similarity	0.626	NPC123976
Remote Similarity	0.626	NPC249662
Remote Similarity	0.626	NPC471304
Remote Similarity	0.626	NPC219664
Remote Similarity	0.626	NPC70259
Remote Similarity	0.6259	NPC258048
Remote Similarity	0.6255	NPC14339
Remote Similarity	0.6255	NPC153923
Remote Similarity	0.6255	NPC253675
Remote Similarity	0.6255	NPC277351
Remote Similarity	0.625	NPC279589
Remote Similarity	0.6246	NPC478080
Remote Similarity	0.6246	NPC303374
Remote Similarity	0.6245	NPC205926
Remote Similarity	0.6241	NPC469554
Remote Similarity	0.6236	NPC87413

Drug Structure

NPD8108 OpenBabel08211713002D 54 60 0 0 1 0 0 0 0 0999 V2000 7.7159 -1.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0710 0.0203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6290 -5.8779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7313 0.3053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5642 -7.6087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0950 2.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0957 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9791 1.8871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8209 1.9918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5729 1.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6311 -5.7657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0983 -6.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4732 1.2339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2393 -2.9717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6699 -2.2157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2279 -3.1882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4659 -0.6072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1545 -0.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9294 -0.9696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6297 -5.8405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7588 0.0999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2293 -3.1134 0.0000 C 0 0 2 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 3.1631 -4.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0682 -1.9865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9523 -1.5192 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2272 -3.2256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0013 -1.3419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0976 -6.6872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6958 -4.0349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1624 -4.9564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9312 -2.0239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7592 -2.3788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5461 -0.7146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6944 -4.1097 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7569 -2.3116 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8477 -1.6240 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7320 0.2679 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1171 -3.0065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4626 -1.1145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5649 -7.5713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6965 -3.9975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3869 -1.4507 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.3591 -3.6587 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 43 1 0 0 0 0 5 49 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 15 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 25 1 0 0 0 0 13 14 2 0 0 0 0 13 26 1 0 0 0 0 14 31 1 0 0 0 0 15 43 1 0 0 0 0 16 24 1 0 0 0 0 17 24 1 0 0 0 0 18 29 2 0 0 0 0 18 32 1 0 0 0 0 19 23 1 0 0 0 0 19 38 1 0 0 0 0 20 30 2 0 0 0 0 20 51 1 0 0 0 0 21 30 1 0 0 0 0 22 31 2 0 0 0 0 22 33 1 0 0 0 0 23 38 1 1 0 0 0 24 50 1 6 0 0 0 25 52 1 0 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 27 16 1 1 0 0 0 27 28 1 0 0 0 0 27 34 1 0 0 0 0 28 17 1 6 0 0 0 28 36 1 0 0 0 0 29 35 1 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 31 49 1 0 0 0 0 32 50 1 0 0 0 0 33 39 2 0 0 0 0 34 41 2 3 0 0 0 34 44 1 0 0 0 0 35 40 2 0 0 0 0 35 51 1 0 0 0 0 36 43 1 0 0 0 0 36 45 2 0 0 0 0 37 42 2 3 0 0 0 37 46 1 0 0 0 0 38 37 1 1 0 0 0 38 41 1 0 0 0 0 42 52 1 0 0 0 0 44 53 1 0 0 0 0 46 54 1 0 0 0 0 47 52 2 0 0 0 0 48 52 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DNCL003637; DCL001247
DrugBank	DB06290
ChEMBL	CHEMBL501849
IUPHAR/BPS	7367
PharmaGKB
KEGG Drug	D10081
PubChem CID	24873435
ChEBI	134743
CAS Number	923604-59-5

Drug Properties

Molecular Weight	749.29
ALogP	-0.9921
MLogP	4.1
XLogP	4.84
HDA	10
HBD	2
Rotatable Bonds	15
TPSA	200.49
RO5 Violation	0