NPASS drugs

Drug Information

Drug ID:	NPD8116
Drug Name:	Grazoprevir Hydrate
Molecular Formula:	C38H50N6O9S.H2O
Canonical SMILES:	C=C[C@@H]1C[C@]1(N=C([C@@H]1C[C@@H]2CN1C(=O)[C@@H](N=C(O)O[C@@H]1C[C@H]1CCCCCc1c(O2)nc2cc(OC)ccc2n1)C(C)(C)C)O)C(=NS(=O)(=O)C1CC1)O.O
Standard InCHI:	InChI=1S/C38H50N6O9S.H2O/c1-6-22-19-38(22,35(47)43-54(49,50)25-13-14-25)42-32(45)29-18-24-20-44(29)34(46)31(37(2,3)4)41-36(48)53-30-16-21(30)10-8-7-9-11-27-33(52-24)40-28-17-23(51-5)12-15-26(28)39-27;/h6,12,15,17,21-22,24-25,29-31H,1,7-11,13-14,16,18-20H2,2-5H3,(H,41,48)(H,42,45)(H,43,47);1H2/t21-,22-,24-,29+,30-,31-,38-;/m1./s1
Standard InCHIKey:	RXSARIJMSJWJLZ-CIAYNJNFSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD8116

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	311
0.1-0.2	1989
0.2-0.3	10489
0.3-0.4	9999
0.4-0.5	5428
0.5-0.6	2162
0.6-0.7	506
0.7-0.8	6
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	0.7117	NPC110741
Intermediate Similarity	0.71	NPC471736
Intermediate Similarity	0.7078	NPC118776
Intermediate Similarity	0.7039	NPC308392
Intermediate Similarity	0.7	NPC470586
Intermediate Similarity	0.7	NPC128115
Remote Similarity	0.6984	NPC472434
Remote Similarity	0.6965	NPC472435
Remote Similarity	0.696	NPC477590
Remote Similarity	0.696	NPC477585
Remote Similarity	0.696	NPC477588
Remote Similarity	0.696	NPC477586
Remote Similarity	0.6958	NPC315804
Remote Similarity	0.6958	NPC313804
Remote Similarity	0.695	NPC472436
Remote Similarity	0.6948	NPC184680
Remote Similarity	0.6936	NPC469589
Remote Similarity	0.692	NPC474183
Remote Similarity	0.692	NPC470785
Remote Similarity	0.6917	NPC303658
Remote Similarity	0.688	NPC477589
Remote Similarity	0.688	NPC477587
Remote Similarity	0.688	NPC472111
Remote Similarity	0.6865	NPC99891
Remote Similarity	0.6853	NPC470784
Remote Similarity	0.6851	NPC316403
Remote Similarity	0.6838	NPC124300
Remote Similarity	0.6824	NPC310618
Remote Similarity	0.6822	NPC287208
Remote Similarity	0.6811	NPC291609
Remote Similarity	0.6783	NPC316110
Remote Similarity	0.6783	NPC315893
Remote Similarity	0.6783	NPC133609
Remote Similarity	0.6783	NPC313587
Remote Similarity	0.6778	NPC472098
Remote Similarity	0.6763	NPC148183
Remote Similarity	0.6763	NPC152768
Remote Similarity	0.675	NPC469592
Remote Similarity	0.675	NPC471080
Remote Similarity	0.6743	NPC1527
Remote Similarity	0.6736	NPC305984
Remote Similarity	0.6734	NPC194740
Remote Similarity	0.6723	NPC174672
Remote Similarity	0.6711	NPC320394
Remote Similarity	0.6708	NPC469594
Remote Similarity	0.6708	NPC264176
Remote Similarity	0.6694	NPC186351
Remote Similarity	0.6693	NPC475816
Remote Similarity	0.6692	NPC189079
Remote Similarity	0.6681	NPC267928
Remote Similarity	0.6681	NPC295898
Remote Similarity	0.6667	NPC475841
Remote Similarity	0.6667	NPC478141
Remote Similarity	0.6667	NPC285635
Remote Similarity	0.6667	NPC474145
Remote Similarity	0.6653	NPC24370
Remote Similarity	0.6653	NPC174758
Remote Similarity	0.6653	NPC319232
Remote Similarity	0.664	NPC95240
Remote Similarity	0.6627	NPC304307
Remote Similarity	0.6627	NPC141053
Remote Similarity	0.6627	NPC118559
Remote Similarity	0.6627	NPC34580
Remote Similarity	0.6627	NPC124920
Remote Similarity	0.6627	NPC244536
Remote Similarity	0.6625	NPC219664
Remote Similarity	0.6623	NPC279401
Remote Similarity	0.6623	NPC79293
Remote Similarity	0.6622	NPC219963
Remote Similarity	0.6615	NPC316224
Remote Similarity	0.6612	NPC151781
Remote Similarity	0.6612	NPC316181
Remote Similarity	0.6612	NPC74562
Remote Similarity	0.6611	NPC82548
Remote Similarity	0.6604	NPC227824
Remote Similarity	0.66	NPC100547
Remote Similarity	0.66	NPC311906
Remote Similarity	0.6587	NPC475720
Remote Similarity	0.6587	NPC474192
Remote Similarity	0.6587	NPC321592
Remote Similarity	0.6587	NPC54803
Remote Similarity	0.6585	NPC472099
Remote Similarity	0.6574	NPC322135
Remote Similarity	0.6574	NPC223409
Remote Similarity	0.657	NPC203168
Remote Similarity	0.6561	NPC473105
Remote Similarity	0.6561	NPC323198
Remote Similarity	0.6561	NPC323752
Remote Similarity	0.656	NPC261251
Remote Similarity	0.6559	NPC60621
Remote Similarity	0.6553	NPC18487
Remote Similarity	0.6553	NPC313421
Remote Similarity	0.6552	NPC226202
Remote Similarity	0.6549	NPC266551
Remote Similarity	0.6549	NPC161887
Remote Similarity	0.6548	NPC14288
Remote Similarity	0.6546	NPC21638
Remote Similarity	0.6543	NPC476287
Remote Similarity	0.6542	NPC475910
Remote Similarity	0.6542	NPC475024
Remote Similarity	0.6532	NPC258773
Remote Similarity	0.6525	NPC19872
Remote Similarity	0.6525	NPC315957
Remote Similarity	0.6523	NPC131486
Remote Similarity	0.652	NPC214142
Remote Similarity	0.6504	NPC473041
Remote Similarity	0.6504	NPC197141
Remote Similarity	0.6504	NPC96321
Remote Similarity	0.6502	NPC26679
Remote Similarity	0.6496	NPC284888
Remote Similarity	0.6494	NPC110151
Remote Similarity	0.6494	NPC478013
Remote Similarity	0.6492	NPC310118
Remote Similarity	0.649	NPC274982
Remote Similarity	0.649	NPC288349
Remote Similarity	0.6489	NPC283152
Remote Similarity	0.6486	NPC75179
Remote Similarity	0.6471	NPC245055
Remote Similarity	0.6471	NPC311357
Remote Similarity	0.6471	NPC33064
Remote Similarity	0.6468	NPC314954
Remote Similarity	0.6463	NPC20249
Remote Similarity	0.6459	NPC82472
Remote Similarity	0.6445	NPC272549
Remote Similarity	0.6444	NPC223427
Remote Similarity	0.6439	NPC260909
Remote Similarity	0.6437	NPC314270
Remote Similarity	0.6435	NPC314573
Remote Similarity	0.6432	NPC53344
Remote Similarity	0.6431	NPC220852
Remote Similarity	0.6426	NPC26543
Remote Similarity	0.6425	NPC254700
Remote Similarity	0.6423	NPC316756
Remote Similarity	0.6423	NPC8022
Remote Similarity	0.6423	NPC470799
Remote Similarity	0.642	NPC471304
Remote Similarity	0.6417	NPC214827
Remote Similarity	0.6417	NPC314930
Remote Similarity	0.6417	NPC260434
Remote Similarity	0.6416	NPC211997
Remote Similarity	0.6415	NPC244543
Remote Similarity	0.6407	NPC66083
Remote Similarity	0.6393	NPC146418
Remote Similarity	0.6392	NPC469554
Remote Similarity	0.6392	NPC477516
Remote Similarity	0.6391	NPC42591
Remote Similarity	0.6387	NPC329747
Remote Similarity	0.6384	NPC314056
Remote Similarity	0.6379	NPC185782
Remote Similarity	0.6377	NPC314176
Remote Similarity	0.6375	NPC476138
Remote Similarity	0.6375	NPC200836
Remote Similarity	0.6375	NPC245816
Remote Similarity	0.6375	NPC473460
Remote Similarity	0.6372	NPC134586
Remote Similarity	0.6367	NPC329631
Remote Similarity	0.6364	NPC165964
Remote Similarity	0.636	NPC232727
Remote Similarity	0.6357	NPC285343
Remote Similarity	0.6354	NPC195788
Remote Similarity	0.6354	NPC237901
Remote Similarity	0.6349	NPC165349
Remote Similarity	0.6349	NPC47059
Remote Similarity	0.6349	NPC329708
Remote Similarity	0.6349	NPC264166
Remote Similarity	0.6349	NPC274291
Remote Similarity	0.6349	NPC118832
Remote Similarity	0.6349	NPC97746
Remote Similarity	0.6348	NPC62069
Remote Similarity	0.6348	NPC315411
Remote Similarity	0.6345	NPC193267
Remote Similarity	0.6345	NPC213530
Remote Similarity	0.6345	NPC17565
Remote Similarity	0.6341	NPC478012
Remote Similarity	0.6341	NPC478011
Remote Similarity	0.634	NPC473800
Remote Similarity	0.6337	NPC470931
Remote Similarity	0.6335	NPC79911
Remote Similarity	0.6335	NPC177404
Remote Similarity	0.6322	NPC472287
Remote Similarity	0.6322	NPC472286
Remote Similarity	0.6318	NPC249040
Remote Similarity	0.6318	NPC176538
Remote Similarity	0.6318	NPC329793
Remote Similarity	0.6316	NPC16066
Remote Similarity	0.6314	NPC326363
Remote Similarity	0.6312	NPC58209
Remote Similarity	0.6311	NPC14651
Remote Similarity	0.6311	NPC121658
Remote Similarity	0.631	NPC205372
Remote Similarity	0.631	NPC65277
Remote Similarity	0.6307	NPC476098
Remote Similarity	0.6307	NPC475774
Remote Similarity	0.6307	NPC317572
Remote Similarity	0.6307	NPC53144
Remote Similarity	0.6305	NPC131885
Remote Similarity	0.6303	NPC315061
Remote Similarity	0.6303	NPC239954
Remote Similarity	0.6303	NPC477527
Remote Similarity	0.63	NPC315467

Drug Structure

NPD8116 OpenBabel08211713002D 60 65 0 0 1 0 0 0 0 0999 V2000 0.4051 -3.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7035 -5.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5806 -4.7518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0618 -5.8972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1336 -0.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0905 -3.8165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3212 -1.0730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7978 -1.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8624 -1.1086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3489 -1.5192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3627 -1.3180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4048 -0.7565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9937 -6.7242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9937 -7.6934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8625 -0.7507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4926 -2.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3948 -1.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1995 -2.7598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7120 -2.8803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8772 -4.1741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0231 -1.9528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0267 -3.5656 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6709 -1.2290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0521 -3.2208 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8330 -7.2088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5863 -1.2175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7679 -1.6785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8525 -1.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4977 -3.4282 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8557 -2.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8489 -4.2320 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5444 -3.2533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0340 -2.1510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3768 -4.3562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9629 -5.7549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0496 -3.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4747 -5.1261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9629 -3.8165 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0440 -1.2117 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.5763 -2.1568 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3899 -3.9431 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9162 -3.9914 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8023 -6.2396 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9165 -4.3023 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2192 -2.3402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3132 -5.3234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1235 -6.2396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3607 -4.4722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7715 -7.2088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8023 -8.1780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6401 -1.2393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1323 -2.6844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8649 -3.0109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8023 -7.2088 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 11.6456 -0.8103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8474 -1.6021 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2841 -5.7549 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3504 -5.4413 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3473 -0.4051 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9439 -0.4051 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 37 1 0 0 0 0 3 37 1 0 0 0 0 4 37 1 0 0 0 0 5 51 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 11 27 1 0 0 0 0 12 15 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 19 38 1 0 0 0 0 20 24 1 0 0 0 0 20 44 1 0 0 0 0 21 10 1 1 0 0 0 21 30 1 0 0 0 0 22 38 1 6 0 0 0 23 51 1 0 0 0 0 24 18 1 6 0 0 0 24 52 1 0 0 0 0 25 54 1 0 0 0 0 26 28 1 0 0 0 0 26 39 2 0 0 0 0 27 33 2 0 0 0 0 27 39 1 0 0 0 0 28 40 2 0 0 0 0 29 32 1 6 0 0 0 29 44 1 0 0 0 0 30 16 1 6 0 0 0 30 53 1 0 0 0 0 31 34 1 0 0 0 0 31 37 1 6 0 0 0 31 41 1 0 0 0 0 32 42 2 3 0 0 0 32 45 1 0 0 0 0 33 40 1 0 0 0 0 33 52 1 0 0 0 0 34 44 1 0 0 0 0 34 46 2 0 0 0 0 35 43 2 3 0 0 0 35 47 1 0 0 0 0 36 41 2 3 0 0 0 36 48 1 0 0 0 0 36 53 1 0 0 0 0 38 35 1 6 0 0 0 38 42 1 0 0 0 0 43 54 1 0 0 0 0 45 56 1 0 0 0 0 47 57 1 0 0 0 0 48 58 1 0 0 0 0 49 54 2 0 0 0 0 50 54 2 0 0 0 0 55 59 1 0 0 0 0 55 60 1 0 0 0 0 M END $$$$

External Identifiers

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

Drug Properties

Molecular Weight	766.34
ALogP	-1.5921
MLogP	3.88
XLogP	5.153
HDA	13
HBD	3
Rotatable Bonds	15
TPSA	214.07
RO5 Violation	2