NPASS drugs

Drug Information

Drug ID:	NPD8255
Drug Name:	Ciluprevir
Molecular Formula:	C40H50N6O8S
Canonical SMILES:	COc1ccc2c(c1)nc(cc2O[C@@H]1C[C@@H]2N(C1)C(=O)[C@H](CCCCC/C=C[C@H]1[C@](N=C2O)(C1)C(=O)O)N=C(OC1CCCC1)O)c1csc(=NC(C)C)[nH]1
Standard InCHI:	InChI=1S/C40H50N6O8S/c1-23(2)41-38-43-32(22-55-38)31-19-34(28-16-15-26(52-3)17-30(28)42-31)53-27-18-33-35(47)45-40(37(49)50)20-24(40)11-7-5-4-6-8-14-29(36(48)46(33)21-27)44-39(51)54-25-12-9-10-13-25/h7,11,15-17,19,22-25,27,29,33H,4-6,8-10,12-14,18,20-21H2,1-3H3,(H,41,43)(H,44,51)(H,45,47)(H,49,50)/b11-7-/t24-,27-,29+,33+,40-/m1/s1
Standard InCHIKey:	PJZPDFUUXKKDNB-KNINVFKUSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD8255

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	306
0.1-0.2	1822
0.2-0.3	8862
0.3-0.4	5977
0.4-0.5	10425
0.5-0.6	2447
0.6-0.7	977
0.7-0.8	74
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	0.7602	NPC184680
Intermediate Similarity	0.7595	NPC303658
Intermediate Similarity	0.7571	NPC470785
Intermediate Similarity	0.75	NPC470784
Intermediate Similarity	0.7479	NPC21638
Intermediate Similarity	0.7439	NPC54803
Intermediate Similarity	0.7439	NPC321592
Intermediate Similarity	0.7406	NPC305984
Intermediate Similarity	0.7406	NPC314176
Intermediate Similarity	0.7388	NPC194740
Intermediate Similarity	0.7377	NPC319232
Intermediate Similarity	0.7377	NPC24370
Intermediate Similarity	0.7368	NPC478011
Intermediate Similarity	0.7364	NPC148183
Intermediate Similarity	0.7364	NPC152768
Intermediate Similarity	0.736	NPC474183
Intermediate Similarity	0.7358	NPC95240
Intermediate Similarity	0.7358	NPC223409
Intermediate Similarity	0.7347	NPC304307
Intermediate Similarity	0.7347	NPC118559
Intermediate Similarity	0.7347	NPC124920
Intermediate Similarity	0.7347	NPC34580
Intermediate Similarity	0.7339	NPC473105
Intermediate Similarity	0.7317	NPC100547
Intermediate Similarity	0.7305	NPC477635
Intermediate Similarity	0.7305	NPC477630
Intermediate Similarity	0.7303	NPC469594
Intermediate Similarity	0.73	NPC314056
Intermediate Similarity	0.7287	NPC322135
Intermediate Similarity	0.7276	NPC261251
Intermediate Similarity	0.7276	NPC133609
Intermediate Similarity	0.7273	NPC315467
Intermediate Similarity	0.7269	NPC220852
Intermediate Similarity	0.7269	NPC323198
Intermediate Similarity	0.7269	NPC323752
Intermediate Similarity	0.7258	NPC14288
Intermediate Similarity	0.7239	NPC478012
Intermediate Similarity	0.7236	NPC214142
Intermediate Similarity	0.722	NPC314882
Intermediate Similarity	0.7218	NPC478013
Intermediate Similarity	0.7208	NPC469592
Intermediate Similarity	0.7208	NPC471080
Intermediate Similarity	0.72	NPC284888
Intermediate Similarity	0.7194	NPC475816
Intermediate Similarity	0.7185	NPC469589
Intermediate Similarity	0.7184	NPC478141
Intermediate Similarity	0.7183	NPC285343
Intermediate Similarity	0.7181	NPC189079
Intermediate Similarity	0.7177	NPC471762
Intermediate Similarity	0.7172	NPC128115
Intermediate Similarity	0.7171	NPC33064
Intermediate Similarity	0.7171	NPC245055
Intermediate Similarity	0.7154	NPC82472
Intermediate Similarity	0.7143	NPC313587
Intermediate Similarity	0.7143	NPC315893
Intermediate Similarity	0.7143	NPC316110
Intermediate Similarity	0.7116	NPC478009
Intermediate Similarity	0.7115	NPC28945
Intermediate Similarity	0.711	NPC284685
Intermediate Similarity	0.7108	NPC66777
Intermediate Similarity	0.7095	NPC264176
Intermediate Similarity	0.7095	NPC472098
Intermediate Similarity	0.7092	NPC474192
Intermediate Similarity	0.7092	NPC475720
Intermediate Similarity	0.709	NPC473041
Intermediate Similarity	0.7073	NPC60621
Intermediate Similarity	0.705	NPC153400
Intermediate Similarity	0.7045	NPC478006
Intermediate Similarity	0.7045	NPC472436
Intermediate Similarity	0.7033	NPC472099
Intermediate Similarity	0.7031	NPC99891
Intermediate Similarity	0.702	NPC131486
Intermediate Similarity	0.7018	NPC260909
Intermediate Similarity	0.7012	NPC326363
Remote Similarity	0.6996	NPC303374
Remote Similarity	0.6996	NPC472435
Remote Similarity	0.6992	NPC313804
Remote Similarity	0.6992	NPC315804
Remote Similarity	0.6989	NPC478010
Remote Similarity	0.6985	NPC471303
Remote Similarity	0.6978	NPC100734
Remote Similarity	0.6978	NPC88923
Remote Similarity	0.6978	NPC315634
Remote Similarity	0.6969	NPC325976
Remote Similarity	0.6941	NPC272549
Remote Similarity	0.6939	NPC74969
Remote Similarity	0.6934	NPC237901
Remote Similarity	0.6934	NPC195788
Remote Similarity	0.6933	NPC311357
Remote Similarity	0.6929	NPC475910
Remote Similarity	0.6926	NPC477586
Remote Similarity	0.6926	NPC477585
Remote Similarity	0.6926	NPC477588
Remote Similarity	0.6926	NPC477590
Remote Similarity	0.6923	NPC59827
Remote Similarity	0.6923	NPC184933
Remote Similarity	0.692	NPC125597
Remote Similarity	0.6917	NPC472111
Remote Similarity	0.6905	NPC311906
Remote Similarity	0.6898	NPC477634
Remote Similarity	0.6894	NPC244543
Remote Similarity	0.6885	NPC78609
Remote Similarity	0.6885	NPC81939
Remote Similarity	0.6885	NPC472434
Remote Similarity	0.688	NPC64216
Remote Similarity	0.688	NPC475271
Remote Similarity	0.6873	NPC124300
Remote Similarity	0.687	NPC330009
Remote Similarity	0.6867	NPC477526
Remote Similarity	0.6865	NPC157931
Remote Similarity	0.6862	NPC295898
Remote Similarity	0.6858	NPC310618
Remote Similarity	0.6858	NPC475666
Remote Similarity	0.6853	NPC97746
Remote Similarity	0.685	NPC260434
Remote Similarity	0.6848	NPC477587
Remote Similarity	0.6848	NPC477589
Remote Similarity	0.6846	NPC291609
Remote Similarity	0.6844	NPC146418
Remote Similarity	0.6842	NPC79386
Remote Similarity	0.6835	NPC306376
Remote Similarity	0.6835	NPC477527
Remote Similarity	0.683	NPC329982
Remote Similarity	0.6828	NPC191489
Remote Similarity	0.6824	NPC89987
Remote Similarity	0.6821	NPC477633
Remote Similarity	0.6818	NPC67401
Remote Similarity	0.6815	NPC96321
Remote Similarity	0.6815	NPC82070
Remote Similarity	0.6815	NPC281049
Remote Similarity	0.681	NPC4910
Remote Similarity	0.6809	NPC79293
Remote Similarity	0.6809	NPC279401
Remote Similarity	0.6802	NPC288349
Remote Similarity	0.68	NPC473317
Remote Similarity	0.68	NPC310118
Remote Similarity	0.6798	NPC110151
Remote Similarity	0.6789	NPC54744
Remote Similarity	0.6787	NPC298436
Remote Similarity	0.6787	NPC52254
Remote Similarity	0.6786	NPC473449
Remote Similarity	0.6782	NPC316224
Remote Similarity	0.6778	NPC329747
Remote Similarity	0.6773	NPC220851
Remote Similarity	0.6766	NPC204970
Remote Similarity	0.6763	NPC473460
Remote Similarity	0.6763	NPC476098
Remote Similarity	0.6763	NPC472789
Remote Similarity	0.6762	NPC14877
Remote Similarity	0.6762	NPC145178
Remote Similarity	0.6762	NPC475350
Remote Similarity	0.6758	NPC475196
Remote Similarity	0.6758	NPC477516
Remote Similarity	0.6755	NPC181081
Remote Similarity	0.6753	NPC62069
Remote Similarity	0.675	NPC470586
Remote Similarity	0.6748	NPC251036
Remote Similarity	0.6739	NPC321939
Remote Similarity	0.6738	NPC329731
Remote Similarity	0.6735	NPC471304
Remote Similarity	0.6735	NPC219664
Remote Similarity	0.6732	NPC257851
Remote Similarity	0.6732	NPC186351
Remote Similarity	0.673	NPC469734
Remote Similarity	0.6717	NPC165964
Remote Similarity	0.6708	NPC277350
Remote Similarity	0.6707	NPC87413
Remote Similarity	0.6706	NPC33949
Remote Similarity	0.6706	NPC148124
Remote Similarity	0.6694	NPC478158
Remote Similarity	0.6694	NPC478157
Remote Similarity	0.6692	NPC473800
Remote Similarity	0.668	NPC203168
Remote Similarity	0.668	NPC174788
Remote Similarity	0.6667	NPC244536
Remote Similarity	0.6667	NPC14339
Remote Similarity	0.6667	NPC248903
Remote Similarity	0.6667	NPC476114
Remote Similarity	0.6667	NPC99724
Remote Similarity	0.6654	NPC188400
Remote Similarity	0.6654	NPC300114
Remote Similarity	0.6653	NPC151781
Remote Similarity	0.6653	NPC316181
Remote Similarity	0.6653	NPC74562
Remote Similarity	0.664	NPC250960
Remote Similarity	0.664	NPC71539
Remote Similarity	0.6639	NPC312870
Remote Similarity	0.6639	NPC128265
Remote Similarity	0.6639	NPC475841
Remote Similarity	0.6639	NPC474145
Remote Similarity	0.6639	NPC476106
Remote Similarity	0.6639	NPC199851
Remote Similarity	0.6639	NPC294909
Remote Similarity	0.6639	NPC254240
Remote Similarity	0.6627	NPC266994
Remote Similarity	0.6627	NPC477533
Remote Similarity	0.6627	NPC26928
Remote Similarity	0.6626	NPC477160
Remote Similarity	0.6626	NPC174758
Remote Similarity	0.6617	NPC478080

Drug Structure

NPD8255 OpenBabel08211713002D 59 65 0 0 1 0 0 0 0 0999 V2000 1.4251 -8.7996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9251 -7.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0904 -5.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3504 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 -0.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 -3.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6601 -6.0686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0723 -6.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 0.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0723 -5.2596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1213 -6.5686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2634 -4.6232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3498 -4.2164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5589 -6.2055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8182 -4.9853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -3.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1137 -7.5676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9251 -7.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1213 -5.5686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3679 -5.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.9962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5408 -4.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -3.8052 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6453 -5.7987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9228 -5.9798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1137 -6.5676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -1.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6272 -4.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -3.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1849 -0.1606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4251 -7.0676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3987 -5.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4251 -7.0676 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8363 -6.3865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1627 -6.2586 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5897 -4.7998 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 0.0000 -2.8271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -0.7056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2431 -4.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8127 -0.0920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6243 -1.0588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2942 -6.3821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2814 -6.0244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5227 -3.4030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3122 -4.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1627 -7.8766 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.1463 -5.3075 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0540 -1.4488 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6220 -1.1274 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1032 -6.9699 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 52 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 11 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 16 2 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 26 2 0 0 0 0 17 30 1 0 0 0 0 18 27 1 0 0 0 0 19 31 1 0 0 0 0 19 34 2 0 0 0 0 20 24 1 0 0 0 0 20 40 1 0 0 0 0 21 27 1 0 0 0 0 21 46 1 0 0 0 0 22 32 2 0 0 0 0 22 55 1 0 0 0 0 23 41 1 0 0 0 0 24 40 1 1 0 0 0 25 54 1 0 0 0 0 26 52 1 0 0 0 0 27 53 1 6 0 0 0 28 30 2 0 0 0 0 28 34 1 0 0 0 0 29 36 1 0 0 0 0 29 44 1 6 0 0 0 30 42 1 0 0 0 0 31 32 1 0 0 0 0 31 42 2 0 0 0 0 32 43 1 0 0 0 0 33 18 1 1 0 0 0 33 35 1 0 0 0 0 33 46 1 0 0 0 0 34 53 1 0 0 0 0 35 45 2 3 0 0 0 35 47 1 0 0 0 0 36 46 1 0 0 0 0 36 48 2 0 0 0 0 37 49 2 0 0 0 0 37 50 1 0 0 0 0 38 41 2 3 0 0 0 38 43 1 0 0 0 0 38 55 1 0 0 0 0 39 44 2 3 0 0 0 39 51 1 0 0 0 0 39 54 1 0 0 0 0 40 37 1 1 0 0 0 40 45 1 0 0 0 0 43 56 1 0 0 0 0 47 57 1 0 0 0 0 50 58 1 0 0 0 0 51 59 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB05868
ChEMBL	CHEMBL297884
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number	300832-84-2

Drug Properties

Molecular Weight	774.34
ALogP	-3.421
MLogP	4.21
XLogP	6.608
HDA	12
HBD	4
Rotatable Bonds	15
TPSA	213.06
RO5 Violation	2