NPASS drugs

Drug Information

Drug ID:	NPD4532
Drug Name:	Tianeptine
Molecular Formula:	C21H25ClN2O4S
Canonical SMILES:	OC(=O)CCCCCCNC1c2ccccc2N(S(=O)(=O)c2c1ccc(c2)Cl)C
Standard InCHI:	InChI=1S/C21H25ClN2O4S/c1-24-18-9-6-5-8-16(18)21(23-13-7-3-2-4-10-20(25)26)17-12-11-15(22)14-19(17)29(24,27)28/h5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26)
Standard InCHIKey:	JICJBGPOMZQUBB-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; DrugBank; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4532

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	148
0.1-0.2	1305
0.2-0.3	8507
0.3-0.4	15005
0.4-0.5	4678
0.5-0.6	1196
0.6-0.7	51
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	0.6509	NPC287358
Remote Similarity	0.65	NPC36495
Remote Similarity	0.6429	NPC253476
Remote Similarity	0.6429	NPC313352
Remote Similarity	0.6395	NPC43477
Remote Similarity	0.6352	NPC476440
Remote Similarity	0.6323	NPC313981
Remote Similarity	0.6284	NPC474058
Remote Similarity	0.6284	NPC472102
Remote Similarity	0.6284	NPC309531
Remote Similarity	0.6264	NPC61013
Remote Similarity	0.6264	NPC123241
Remote Similarity	0.625	NPC99632
Remote Similarity	0.625	NPC282339
Remote Similarity	0.6235	NPC316104
Remote Similarity	0.6235	NPC162417
Remote Similarity	0.623	NPC193410
Remote Similarity	0.6228	NPC328590
Remote Similarity	0.6196	NPC248117
Remote Similarity	0.6171	NPC472241
Remote Similarity	0.6168	NPC72473
Remote Similarity	0.6168	NPC58827
Remote Similarity	0.6168	NPC307437
Remote Similarity	0.6163	NPC325599
Remote Similarity	0.6162	NPC293458
Remote Similarity	0.6158	NPC472242
Remote Similarity	0.6129	NPC189116
Remote Similarity	0.6105	NPC173295
Remote Similarity	0.6075	NPC286871
Remote Similarity	0.6071	NPC316141
Remote Similarity	0.6062	NPC218594
Remote Similarity	0.6062	NPC213468
Remote Similarity	0.6062	NPC99043
Remote Similarity	0.6062	NPC471318
Remote Similarity	0.6057	NPC315051
Remote Similarity	0.6045	NPC478040
Remote Similarity	0.6037	NPC179605
Remote Similarity	0.6037	NPC279385
Remote Similarity	0.6034	NPC264589
Remote Similarity	0.6032	NPC223595
Remote Similarity	0.6032	NPC167724
Remote Similarity	0.6032	NPC224970
Remote Similarity	0.6022	NPC225319
Remote Similarity	0.6022	NPC473329
Remote Similarity	0.602	NPC97584
Remote Similarity	0.6013	NPC319579
Remote Similarity	0.601	NPC272483
Remote Similarity	0.6	NPC67043
Remote Similarity	0.6	NPC472118
Remote Similarity	0.6	NPC477432
Remote Similarity	0.6	NPC103292
Remote Similarity	0.599	NPC52262
Remote Similarity	0.5989	NPC176983
Remote Similarity	0.5979	NPC219336
Remote Similarity	0.5976	NPC226143
Remote Similarity	0.5969	NPC292265
Remote Similarity	0.5969	NPC477159
Remote Similarity	0.5969	NPC470317
Remote Similarity	0.5967	NPC300596
Remote Similarity	0.5967	NPC237649
Remote Similarity	0.5966	NPC472243
Remote Similarity	0.5964	NPC268534
Remote Similarity	0.596	NPC235684
Remote Similarity	0.5959	NPC267885
Remote Similarity	0.5952	NPC472244
Remote Similarity	0.5952	NPC470343
Remote Similarity	0.595	NPC329858
Remote Similarity	0.5946	NPC63370
Remote Similarity	0.5946	NPC36836
Remote Similarity	0.5944	NPC478039
Remote Similarity	0.5941	NPC209389
Remote Similarity	0.5938	NPC285622
Remote Similarity	0.5936	NPC68650
Remote Similarity	0.593	NPC476687
Remote Similarity	0.593	NPC476689
Remote Similarity	0.593	NPC476685
Remote Similarity	0.5928	NPC186669
Remote Similarity	0.5928	NPC15573
Remote Similarity	0.5928	NPC217372
Remote Similarity	0.5928	NPC183662
Remote Similarity	0.5924	NPC478076
Remote Similarity	0.5922	NPC311330
Remote Similarity	0.5917	NPC322433
Remote Similarity	0.5917	NPC477937
Remote Similarity	0.5907	NPC149155
Remote Similarity	0.5907	NPC110500
Remote Similarity	0.5907	NPC203468
Remote Similarity	0.5906	NPC314431
Remote Similarity	0.5906	NPC194562
Remote Similarity	0.5904	NPC257490
Remote Similarity	0.5902	NPC314223
Remote Similarity	0.59	NPC321708
Remote Similarity	0.59	NPC284706
Remote Similarity	0.5897	NPC283219
Remote Similarity	0.5897	NPC248041
Remote Similarity	0.5897	NPC126709
Remote Similarity	0.5897	NPC6974
Remote Similarity	0.5895	NPC279527
Remote Similarity	0.5895	NPC472115
Remote Similarity	0.5895	NPC472114
Remote Similarity	0.5895	NPC278887
Remote Similarity	0.5895	NPC214960
Remote Similarity	0.5885	NPC355
Remote Similarity	0.5885	NPC318183
Remote Similarity	0.5879	NPC177684
Remote Similarity	0.5879	NPC291962
Remote Similarity	0.5876	NPC264482
Remote Similarity	0.5876	NPC203202
Remote Similarity	0.5876	NPC242933
Remote Similarity	0.5872	NPC314098
Remote Similarity	0.5871	NPC474059
Remote Similarity	0.5871	NPC313293
Remote Similarity	0.5871	NPC314333
Remote Similarity	0.5864	NPC78020
Remote Similarity	0.5858	NPC474926
Remote Similarity	0.5851	NPC201424
Remote Similarity	0.5848	NPC321053
Remote Similarity	0.5843	NPC161956
Remote Similarity	0.5843	NPC316202
Remote Similarity	0.5843	NPC317564
Remote Similarity	0.5843	NPC258531
Remote Similarity	0.5843	NPC112373
Remote Similarity	0.5839	NPC474584
Remote Similarity	0.5833	NPC190945
Remote Similarity	0.5829	NPC211525
Remote Similarity	0.5829	NPC153694
Remote Similarity	0.5825	NPC469726
Remote Similarity	0.5825	NPC329338
Remote Similarity	0.5821	NPC175474
Remote Similarity	0.582	NPC476231
Remote Similarity	0.582	NPC472101
Remote Similarity	0.582	NPC472117
Remote Similarity	0.582	NPC472121
Remote Similarity	0.582	NPC472120
Remote Similarity	0.5815	NPC475763
Remote Similarity	0.5814	NPC472245
Remote Similarity	0.5808	NPC475915
Remote Similarity	0.5806	NPC291610
Remote Similarity	0.5799	NPC192533
Remote Similarity	0.5798	NPC310403
Remote Similarity	0.5798	NPC243673
Remote Similarity	0.5798	NPC97380
Remote Similarity	0.5798	NPC263709
Remote Similarity	0.5798	NPC276085
Remote Similarity	0.5798	NPC148468
Remote Similarity	0.5798	NPC63210
Remote Similarity	0.5793	NPC313673
Remote Similarity	0.5792	NPC109787
Remote Similarity	0.5792	NPC5630
Remote Similarity	0.5787	NPC11149
Remote Similarity	0.5787	NPC469896
Remote Similarity	0.5782	NPC477173
Remote Similarity	0.5779	NPC471742
Remote Similarity	0.5775	NPC476464
Remote Similarity	0.5775	NPC29285
Remote Similarity	0.5774	NPC39818
Remote Similarity	0.5765	NPC14849
Remote Similarity	0.5765	NPC84827
Remote Similarity	0.5765	NPC145885
Remote Similarity	0.5765	NPC14113
Remote Similarity	0.5764	NPC203628
Remote Similarity	0.5763	NPC316906
Remote Similarity	0.5759	NPC472106
Remote Similarity	0.5755	NPC470488
Remote Similarity	0.5754	NPC470301
Remote Similarity	0.5754	NPC2823
Remote Similarity	0.5752	NPC122493
Remote Similarity	0.5752	NPC10781
Remote Similarity	0.5752	NPC293628
Remote Similarity	0.5751	NPC471778
Remote Similarity	0.575	NPC307396
Remote Similarity	0.5745	NPC222029
Remote Similarity	0.5744	NPC328611
Remote Similarity	0.5744	NPC248862
Remote Similarity	0.5744	NPC469938
Remote Similarity	0.5741	NPC471663
Remote Similarity	0.5741	NPC471741
Remote Similarity	0.574	NPC35996
Remote Similarity	0.5738	NPC254798
Remote Similarity	0.5729	NPC182131
Remote Similarity	0.5729	NPC159963
Remote Similarity	0.5723	NPC228515
Remote Similarity	0.5722	NPC473297
Remote Similarity	0.5714	NPC471743
Remote Similarity	0.5714	NPC471122
Remote Similarity	0.5714	NPC476874
Remote Similarity	0.5714	NPC476441
Remote Similarity	0.5706	NPC317758
Remote Similarity	0.57	NPC90967
Remote Similarity	0.5698	NPC476950
Remote Similarity	0.5693	NPC14994
Remote Similarity	0.5691	NPC314287
Remote Similarity	0.5686	NPC276430
Remote Similarity	0.5685	NPC111275
Remote Similarity	0.5684	NPC27904
Remote Similarity	0.5682	NPC474473
Remote Similarity	0.5679	NPC329011
Remote Similarity	0.5678	NPC113626
Remote Similarity	0.5677	NPC470069
Remote Similarity	0.5677	NPC52059

Drug Structure

NPD4532 OpenBabel08211705262D 31 33 0 0 1 0 0 0 0 0999 V2000 1.1974 -1.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5536 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3311 4.5638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5092 5.8335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3755 4.2691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7317 6.8084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1530 3.2941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9944 1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6873 7.1032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 2.0245 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.9916 1.5777 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 2.9994 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.4204 6.4230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9098 8.0781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9309 -0.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1490 -0.9888 0.0000 O 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 0.4644 3.6796 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8654 8.3729 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 13 1 0 0 0 0 8 16 2 0 0 0 0 9 18 2 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 24 1 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 26 31 1 0 0 0 0 27 29 2 0 0 0 0 28 29 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001528
DrugBank	DB09289
ChEMBL	CHEMBL1289110
IUPHAR/BPS	7558
PharmaGKB
KEGG Drug	D02575
PubChem CID	68870
ChEBI	91749
CAS Number	72797-41-2

Drug Properties

Molecular Weight	436.12
ALogP	-1.9061
MLogP	2.89
XLogP	4.15
HDA	6
HBD	2
Rotatable Bonds	11
TPSA	95.09
RO5 Violation	0