NPASS drugs

Drug Information

Drug ID:	NPD6485
Drug Name:	lirequinil
Molecular Formula:	C26H25ClN2O3
Canonical SMILES:	CCO[C@H]1CCN(C1)C(=O)c1cc(c2ccccc2)c(=O)n2c1c1cc(Cl)ccc1CC2
Standard InCHI:	InChI=1S/C26H25ClN2O3/c1-2-32-20-11-12-28(16-20)25(30)23-15-22(17-6-4-3-5-7-17)26(31)29-13-10-18-8-9-19(27)14-21(18)24(23)29/h3-9,14-15,20H,2,10-13,16H2,1H3/t20-/m0/s1
Standard InCHIKey:	CBSWRAUYCIIUEI-FQEVSTJZSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD6485

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	133
0.1-0.2	1074
0.2-0.3	5089
0.3-0.4	13861
0.4-0.5	9301
0.5-0.6	1301
0.6-0.7	131
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	0.6842	NPC179224
Remote Similarity	0.6757	NPC314192
Remote Similarity	0.6752	NPC316906
Remote Similarity	0.6714	NPC55529
Remote Similarity	0.6667	NPC313352
Remote Similarity	0.6645	NPC473962
Remote Similarity	0.6579	NPC79698
Remote Similarity	0.6571	NPC473418
Remote Similarity	0.6491	NPC73644
Remote Similarity	0.6454	NPC167336
Remote Similarity	0.6443	NPC220698
Remote Similarity	0.6429	NPC136453
Remote Similarity	0.6424	NPC324445
Remote Similarity	0.6397	NPC256452
Remote Similarity	0.6395	NPC113099
Remote Similarity	0.6387	NPC105114
Remote Similarity	0.6387	NPC239990
Remote Similarity	0.6387	NPC152850
Remote Similarity	0.6387	NPC89923
Remote Similarity	0.6387	NPC71933
Remote Similarity	0.6369	NPC126458
Remote Similarity	0.634	NPC175726
Remote Similarity	0.634	NPC474082
Remote Similarity	0.6325	NPC246412
Remote Similarity	0.6316	NPC257490
Remote Similarity	0.6313	NPC475427
Remote Similarity	0.6279	NPC477887
Remote Similarity	0.6266	NPC157311
Remote Similarity	0.6258	NPC130251
Remote Similarity	0.6243	NPC475094
Remote Similarity	0.6226	NPC44805
Remote Similarity	0.6226	NPC8761
Remote Similarity	0.6221	NPC29285
Remote Similarity	0.6204	NPC474974
Remote Similarity	0.6196	NPC469560
Remote Similarity	0.6193	NPC472106
Remote Similarity	0.6185	NPC113946
Remote Similarity	0.6184	NPC177684
Remote Similarity	0.6184	NPC291962
Remote Similarity	0.6176	NPC243756
Remote Similarity	0.6171	NPC472117
Remote Similarity	0.6169	NPC26285
Remote Similarity	0.6169	NPC291027
Remote Similarity	0.6169	NPC317474
Remote Similarity	0.6169	NPC213126
Remote Similarity	0.6169	NPC84281
Remote Similarity	0.6169	NPC169485
Remote Similarity	0.6158	NPC214960
Remote Similarity	0.6158	NPC279527
Remote Similarity	0.6154	NPC474847
Remote Similarity	0.6145	NPC209509
Remote Similarity	0.6144	NPC316582
Remote Similarity	0.6144	NPC112373
Remote Similarity	0.6144	NPC258531
Remote Similarity	0.6144	NPC161956
Remote Similarity	0.614	NPC117032
Remote Similarity	0.6136	NPC138293
Remote Similarity	0.6136	NPC113056
Remote Similarity	0.6125	NPC207428
Remote Similarity	0.6124	NPC63047
Remote Similarity	0.6124	NPC475248
Remote Similarity	0.6121	NPC161069
Remote Similarity	0.6121	NPC471164
Remote Similarity	0.6121	NPC470301
Remote Similarity	0.6121	NPC22082
Remote Similarity	0.6121	NPC186284
Remote Similarity	0.6111	NPC475598
Remote Similarity	0.6111	NPC273907
Remote Similarity	0.6111	NPC475318
Remote Similarity	0.6111	NPC49577
Remote Similarity	0.6111	NPC474855
Remote Similarity	0.6111	NPC151706
Remote Similarity	0.6111	NPC9687
Remote Similarity	0.6111	NPC293377
Remote Similarity	0.6111	NPC118099
Remote Similarity	0.6111	NPC260045
Remote Similarity	0.6111	NPC76785
Remote Similarity	0.6111	NPC79465
Remote Similarity	0.6111	NPC96901
Remote Similarity	0.6111	NPC476102
Remote Similarity	0.6111	NPC474787
Remote Similarity	0.6111	NPC90194
Remote Similarity	0.6111	NPC474811
Remote Similarity	0.6101	NPC69496
Remote Similarity	0.6093	NPC315276
Remote Similarity	0.6093	NPC285926
Remote Similarity	0.6093	NPC14672
Remote Similarity	0.6092	NPC104345
Remote Similarity	0.609	NPC285394
Remote Similarity	0.6089	NPC116961
Remote Similarity	0.6087	NPC233910
Remote Similarity	0.6087	NPC245836
Remote Similarity	0.6082	NPC66936
Remote Similarity	0.608	NPC472120
Remote Similarity	0.608	NPC472101
Remote Similarity	0.6078	NPC226143
Remote Similarity	0.6074	NPC325599
Remote Similarity	0.6071	NPC472258
Remote Similarity	0.6069	NPC473498
Remote Similarity	0.6067	NPC471318
Remote Similarity	0.6067	NPC33742
Remote Similarity	0.6061	NPC207554
Remote Similarity	0.6058	NPC470926
Remote Similarity	0.6049	NPC266425
Remote Similarity	0.6043	NPC473615
Remote Similarity	0.6039	NPC302169
Remote Similarity	0.6039	NPC27833
Remote Similarity	0.6038	NPC103605
Remote Similarity	0.6038	NPC81092
Remote Similarity	0.6037	NPC178662
Remote Similarity	0.6037	NPC98424
Remote Similarity	0.6037	NPC92784
Remote Similarity	0.6037	NPC476133
Remote Similarity	0.6037	NPC77992
Remote Similarity	0.6037	NPC470884
Remote Similarity	0.6034	NPC36836
Remote Similarity	0.6034	NPC63370
Remote Similarity	0.6033	NPC286994
Remote Similarity	0.6026	NPC473573
Remote Similarity	0.6024	NPC301760
Remote Similarity	0.6024	NPC471574
Remote Similarity	0.6022	NPC139085
Remote Similarity	0.6022	NPC214626
Remote Similarity	0.6022	NPC177261
Remote Similarity	0.6022	NPC251212
Remote Similarity	0.6013	NPC320656
Remote Similarity	0.6012	NPC300299
Remote Similarity	0.6012	NPC262077
Remote Similarity	0.6011	NPC229484
Remote Similarity	0.6	NPC305602
Remote Similarity	0.6	NPC17497
Remote Similarity	0.5989	NPC470548
Remote Similarity	0.5989	NPC176983
Remote Similarity	0.5989	NPC259626
Remote Similarity	0.5988	NPC154602
Remote Similarity	0.5987	NPC192533
Remote Similarity	0.5979	NPC292675
Remote Similarity	0.5976	NPC471123
Remote Similarity	0.5976	NPC138775
Remote Similarity	0.5964	NPC315051
Remote Similarity	0.5964	NPC263493
Remote Similarity	0.5964	NPC269398
Remote Similarity	0.596	NPC246904
Remote Similarity	0.5959	NPC45033
Remote Similarity	0.5957	NPC116007
Remote Similarity	0.5954	NPC122106
Remote Similarity	0.5952	NPC471680
Remote Similarity	0.5952	NPC469537
Remote Similarity	0.5952	NPC308197
Remote Similarity	0.5951	NPC316104
Remote Similarity	0.5951	NPC162417
Remote Similarity	0.5949	NPC472165
Remote Similarity	0.5939	NPC122553
Remote Similarity	0.5938	NPC473322
Remote Similarity	0.5938	NPC213969
Remote Similarity	0.5938	NPC165726
Remote Similarity	0.5936	NPC2933
Remote Similarity	0.5934	NPC285622
Remote Similarity	0.5932	NPC472102
Remote Similarity	0.5932	NPC309531
Remote Similarity	0.593	NPC473329
Remote Similarity	0.5917	NPC136002
Remote Similarity	0.5912	NPC65310
Remote Similarity	0.5909	NPC228515
Remote Similarity	0.5901	NPC187231
Remote Similarity	0.59	NPC477999
Remote Similarity	0.5882	NPC256288
Remote Similarity	0.5879	NPC471264
Remote Similarity	0.5879	NPC471265
Remote Similarity	0.5876	NPC472539
Remote Similarity	0.5876	NPC472540
Remote Similarity	0.5876	NPC470787
Remote Similarity	0.5868	NPC469426
Remote Similarity	0.5868	NPC469427
Remote Similarity	0.5864	NPC255447
Remote Similarity	0.586	NPC11149
Remote Similarity	0.586	NPC39818
Remote Similarity	0.5856	NPC471651
Remote Similarity	0.5855	NPC472164
Remote Similarity	0.5854	NPC248283
Remote Similarity	0.5852	NPC469536
Remote Similarity	0.5846	NPC472542
Remote Similarity	0.5846	NPC472541
Remote Similarity	0.5843	NPC225319
Remote Similarity	0.5843	NPC281104
Remote Similarity	0.5839	NPC158854
Remote Similarity	0.5839	NPC209389
Remote Similarity	0.5833	NPC179605
Remote Similarity	0.5833	NPC200964
Remote Similarity	0.5833	NPC279385
Remote Similarity	0.5829	NPC295021
Remote Similarity	0.5828	NPC325479
Remote Similarity	0.582	NPC322621
Remote Similarity	0.5819	NPC222029
Remote Similarity	0.5813	NPC119326
Remote Similarity	0.5813	NPC322433
Remote Similarity	0.581	NPC286871
Remote Similarity	0.5808	NPC83214
Remote Similarity	0.5802	NPC200589
Remote Similarity	0.5799	NPC476978

Drug Structure

NPD6485 OpenBabel08211710072D 32 36 0 0 1 0 0 0 0 0999 V2000 -5.8916 3.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8970 4.0409 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 -4.3301 -0.5000 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 -3.4641 0.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 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 -2.8147 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 3.9945 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 0.8660 2.5000 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 -2.6456 2.5933 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 1.7321 1.0000 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 -3.3147 3.3364 0.0000 C 0 0 1 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 -1.7321 0.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 1.7321 4.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3092 3.2319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 19 27 1 0 0 0 0 20 32 1 1 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 24 29 1 0 0 0 0 25 28 1 0 0 0 0 25 30 2 0 0 0 0 26 29 1 0 0 0 0 26 31 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB004410
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	448.16
ALogP	-0.2771
MLogP	3.66
XLogP	5.543
HDA	5
HBD	0
Rotatable Bonds	7
TPSA	49.85
RO5 Violation	1