NPASS drugs

Drug Information

Drug ID:	NPD2402
Drug Name:	Eszopiclone
Molecular Formula:	C17H17ClN6O3
Canonical SMILES:	CN1CCN(CC1)C(=O)O[C@H]1c2nccnc2C(=O)N1c1ccc(cn1)Cl
Standard InCHI:	InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3/t16-/m0/s1
Standard InCHIKey:	GBBSUAFBMRNDJC-INIZCTEOSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2402

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	626
0.1-0.2	9731
0.2-0.3	14469
0.3-0.4	2672
0.4-0.5	2013
0.5-0.6	1316
0.6-0.7	63
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	0.6681	NPC147983
Remote Similarity	0.6681	NPC177996
Remote Similarity	0.6635	NPC40530
Remote Similarity	0.6635	NPC314281
Remote Similarity	0.657	NPC178664
Remote Similarity	0.6549	NPC243850
Remote Similarity	0.6535	NPC123839
Remote Similarity	0.652	NPC266249
Remote Similarity	0.6457	NPC313421
Remote Similarity	0.638	NPC198673
Remote Similarity	0.6339	NPC168911
Remote Similarity	0.6316	NPC314930
Remote Similarity	0.6316	NPC214827
Remote Similarity	0.6311	NPC123395
Remote Similarity	0.6303	NPC116961
Remote Similarity	0.629	NPC210123
Remote Similarity	0.6278	NPC135950
Remote Similarity	0.6275	NPC471614
Remote Similarity	0.6275	NPC472260
Remote Similarity	0.6267	NPC239954
Remote Similarity	0.6239	NPC103361
Remote Similarity	0.6234	NPC475024
Remote Similarity	0.6228	NPC182507
Remote Similarity	0.6213	NPC477979
Remote Similarity	0.6197	NPC118940
Remote Similarity	0.6193	NPC270834
Remote Similarity	0.6189	NPC21461
Remote Similarity	0.6184	NPC169586
Remote Similarity	0.6175	NPC73994
Remote Similarity	0.6148	NPC116622
Remote Similarity	0.6132	NPC107160
Remote Similarity	0.6121	NPC316403
Remote Similarity	0.6104	NPC472259
Remote Similarity	0.6101	NPC61011
Remote Similarity	0.6094	NPC116555
Remote Similarity	0.6094	NPC287208
Remote Similarity	0.6087	NPC107287
Remote Similarity	0.6083	NPC28848
Remote Similarity	0.6083	NPC83774
Remote Similarity	0.6083	NPC14325
Remote Similarity	0.6073	NPC141053
Remote Similarity	0.6073	NPC47596
Remote Similarity	0.607	NPC121327
Remote Similarity	0.6067	NPC197141
Remote Similarity	0.6063	NPC311282
Remote Similarity	0.6057	NPC315062
Remote Similarity	0.6053	NPC212213
Remote Similarity	0.6053	NPC474916
Remote Similarity	0.6047	NPC249614
Remote Similarity	0.6047	NPC54214
Remote Similarity	0.6035	NPC472116
Remote Similarity	0.6033	NPC253987
Remote Similarity	0.6027	NPC469489
Remote Similarity	0.6026	NPC81535
Remote Similarity	0.6018	NPC46895
Remote Similarity	0.6017	NPC143977
Remote Similarity	0.6017	NPC57398
Remote Similarity	0.6008	NPC64216
Remote Similarity	0.6	NPC472288
Remote Similarity	0.6	NPC302159
Remote Similarity	0.6	NPC192712
Remote Similarity	0.6	NPC219963
Remote Similarity	0.6	NPC186351
Remote Similarity	0.5992	NPC260434
Remote Similarity	0.5992	NPC267853
Remote Similarity	0.5991	NPC282103
Remote Similarity	0.5991	NPC317701
Remote Similarity	0.5984	NPC316411
Remote Similarity	0.5984	NPC182222
Remote Similarity	0.5983	NPC471192
Remote Similarity	0.5982	NPC12649
Remote Similarity	0.5975	NPC313804
Remote Similarity	0.5975	NPC315804
Remote Similarity	0.5971	NPC112741
Remote Similarity	0.5968	NPC244897
Remote Similarity	0.5967	NPC312942
Remote Similarity	0.5967	NPC327095
Remote Similarity	0.5965	NPC102592
Remote Similarity	0.5965	NPC109922
Remote Similarity	0.5965	NPC79356
Remote Similarity	0.5965	NPC77061
Remote Similarity	0.5964	NPC476527
Remote Similarity	0.5964	NPC17273
Remote Similarity	0.5964	NPC141612
Remote Similarity	0.5964	NPC135601
Remote Similarity	0.5962	NPC478182
Remote Similarity	0.5958	NPC267811
Remote Similarity	0.5957	NPC476525
Remote Similarity	0.5955	NPC24864
Remote Similarity	0.5955	NPC16659
Remote Similarity	0.5949	NPC242923
Remote Similarity	0.5946	NPC284678
Remote Similarity	0.5943	NPC473706
Remote Similarity	0.5943	NPC40455
Remote Similarity	0.5941	NPC50511
Remote Similarity	0.5928	NPC161887
Remote Similarity	0.5928	NPC266551
Remote Similarity	0.5926	NPC476518
Remote Similarity	0.5924	NPC153980
Remote Similarity	0.5924	NPC471194
Remote Similarity	0.5924	NPC6865
Remote Similarity	0.5924	NPC471193
Remote Similarity	0.5919	NPC20249
Remote Similarity	0.5917	NPC317054
Remote Similarity	0.5916	NPC74619
Remote Similarity	0.5909	NPC265710
Remote Similarity	0.5907	NPC56233
Remote Similarity	0.5905	NPC263455
Remote Similarity	0.5901	NPC102755
Remote Similarity	0.59	NPC53534
Remote Similarity	0.5899	NPC121658
Remote Similarity	0.5899	NPC273532
Remote Similarity	0.5899	NPC14651
Remote Similarity	0.5897	NPC327592
Remote Similarity	0.5893	NPC311858
Remote Similarity	0.5892	NPC244425
Remote Similarity	0.5892	NPC471197
Remote Similarity	0.5892	NPC15384
Remote Similarity	0.5888	NPC478184
Remote Similarity	0.5882	NPC72956
Remote Similarity	0.5878	NPC476817
Remote Similarity	0.5873	NPC240384
Remote Similarity	0.5872	NPC317373
Remote Similarity	0.5872	NPC238457
Remote Similarity	0.5871	NPC328029
Remote Similarity	0.587	NPC257851
Remote Similarity	0.5868	NPC469717
Remote Similarity	0.5868	NPC471198
Remote Similarity	0.5865	NPC472070
Remote Similarity	0.5859	NPC138370
Remote Similarity	0.5858	NPC318299
Remote Similarity	0.5857	NPC312860
Remote Similarity	0.5856	NPC191415
Remote Similarity	0.5851	NPC470731
Remote Similarity	0.5847	NPC297862
Remote Similarity	0.5833	NPC282247
Remote Similarity	0.5833	NPC317752
Remote Similarity	0.5833	NPC41717
Remote Similarity	0.5833	NPC114637
Remote Similarity	0.583	NPC132539
Remote Similarity	0.5826	NPC226835
Remote Similarity	0.5826	NPC128244
Remote Similarity	0.5823	NPC69843
Remote Similarity	0.5822	NPC293487
Remote Similarity	0.5818	NPC136441
Remote Similarity	0.5816	NPC54981
Remote Similarity	0.5814	NPC161801
Remote Similarity	0.5813	NPC229893
Remote Similarity	0.5811	NPC317010
Remote Similarity	0.581	NPC104712
Remote Similarity	0.5808	NPC56271
Remote Similarity	0.5808	NPC71236
Remote Similarity	0.5808	NPC226202
Remote Similarity	0.5804	NPC148889
Remote Similarity	0.5804	NPC207851
Remote Similarity	0.5804	NPC284559
Remote Similarity	0.5804	NPC285923
Remote Similarity	0.5801	NPC174281
Remote Similarity	0.5801	NPC475286
Remote Similarity	0.5799	NPC111624
Remote Similarity	0.5798	NPC174672
Remote Similarity	0.5792	NPC240088
Remote Similarity	0.5792	NPC473380
Remote Similarity	0.5789	NPC19170
Remote Similarity	0.5789	NPC129909
Remote Similarity	0.5787	NPC143325
Remote Similarity	0.5779	NPC308906
Remote Similarity	0.5777	NPC196718
Remote Similarity	0.5773	NPC469529
Remote Similarity	0.5771	NPC472289
Remote Similarity	0.5769	NPC26543
Remote Similarity	0.5768	NPC152620
Remote Similarity	0.5763	NPC289086
Remote Similarity	0.576	NPC478183
Remote Similarity	0.5759	NPC143533
Remote Similarity	0.5758	NPC313823
Remote Similarity	0.5756	NPC476524
Remote Similarity	0.5756	NPC82548
Remote Similarity	0.5755	NPC323969
Remote Similarity	0.5755	NPC229055
Remote Similarity	0.5755	NPC33229
Remote Similarity	0.5755	NPC120070
Remote Similarity	0.5753	NPC476421
Remote Similarity	0.5753	NPC28096
Remote Similarity	0.5753	NPC227489
Remote Similarity	0.5752	NPC112489
Remote Similarity	0.5751	NPC19696
Remote Similarity	0.5751	NPC474767
Remote Similarity	0.5751	NPC136957
Remote Similarity	0.5749	NPC230085
Remote Similarity	0.5749	NPC159630
Remote Similarity	0.5749	NPC122436
Remote Similarity	0.5748	NPC477591
Remote Similarity	0.5746	NPC324091
Remote Similarity	0.5745	NPC472069
Remote Similarity	0.5745	NPC472062
Remote Similarity	0.5745	NPC472063
Remote Similarity	0.5743	NPC475258
Remote Similarity	0.5743	NPC476491
Remote Similarity	0.5739	NPC326422

Drug Structure

NPD2402 OpenBabel08211702172D 27 30 0 0 1 0 0 0 0 0999 V2000 -5.3183 3.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7321 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 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6710 2.8681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9582 1.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0019 2.1249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2891 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 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 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 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 -0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6418 0.4307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 3.4641 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6492 2.6601 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3109 1.1738 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 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9508 -0.5204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 5 1 0 0 0 0 4 19 2 0 0 0 0 5 20 2 0 0 0 0 6 8 1 0 0 0 0 6 22 1 0 0 0 0 7 9 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 23 1 0 0 0 0 10 11 2 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 12 21 2 0 0 0 0 12 24 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 15 25 2 0 0 0 0 16 24 1 0 0 0 0 16 27 1 6 0 0 0 17 23 1 0 0 0 0 17 26 2 0 0 0 0 17 27 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000933
DrugBank	DB00402
ChEMBL	CHEMBL1522
IUPHAR/BPS	7429
PharmaGKB	PA162630444
KEGG Drug
PubChem CID	969472
ChEBI	53760
CAS Number	138729-47-2

Drug Properties

Molecular Weight	388.11
ALogP	0.3196
MLogP	2.23
XLogP	0.587
HDA	9
HBD	0
Rotatable Bonds	6
TPSA	91.76
RO5 Violation	0