NPASS drugs

Drug Information

Drug ID:	NPD3444
Drug Name:	Doxepin
Molecular Formula:	C19H21NO
Canonical SMILES:	CN(CCC=C1c2ccccc2OCc2c1cccc2)C
Standard InCHI:	InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3
Standard InCHIKey:	ODQWQRRAPPTVAG-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD3444

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	142
0.1-0.2	1176
0.2-0.3	2942
0.3-0.4	9820
0.4-0.5	3257
0.5-0.6	7791
0.6-0.7	5254
0.7-0.8	502
0.8-0.85	6
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	0.8333	NPC326801
Intermediate Similarity	0.816	NPC255253
Intermediate Similarity	0.813	NPC321133
Intermediate Similarity	0.8045	NPC318591
Intermediate Similarity	0.8045	NPC231163
Intermediate Similarity	0.8016	NPC328267
Intermediate Similarity	0.792	NPC212559
Intermediate Similarity	0.7876	NPC95755
Intermediate Similarity	0.7869	NPC283169
Intermediate Similarity	0.7845	NPC241224
Intermediate Similarity	0.784	NPC263835
Intermediate Similarity	0.7826	NPC300166
Intermediate Similarity	0.7778	NPC475269
Intermediate Similarity	0.776	NPC256369
Intermediate Similarity	0.7759	NPC24327
Intermediate Similarity	0.7759	NPC12870
Intermediate Similarity	0.7742	NPC25648
Intermediate Similarity	0.7739	NPC316797
Intermediate Similarity	0.7719	NPC470161
Intermediate Similarity	0.7719	NPC313918
Intermediate Similarity	0.7714	NPC473934
Intermediate Similarity	0.771	NPC283079
Intermediate Similarity	0.7705	NPC26524
Intermediate Similarity	0.7705	NPC35344
Intermediate Similarity	0.7705	NPC141003
Intermediate Similarity	0.7686	NPC470723
Intermediate Similarity	0.7669	NPC474200
Intermediate Similarity	0.7661	NPC312105
Intermediate Similarity	0.7656	NPC150026
Intermediate Similarity	0.7656	NPC188997
Intermediate Similarity	0.7652	NPC471576
Intermediate Similarity	0.7647	NPC186469
Intermediate Similarity	0.7627	NPC470393
Intermediate Similarity	0.7619	NPC59561
Intermediate Similarity	0.7619	NPC172253
Intermediate Similarity	0.7615	NPC136112
Intermediate Similarity	0.7615	NPC141739
Intermediate Similarity	0.7612	NPC325568
Intermediate Similarity	0.7597	NPC261992
Intermediate Similarity	0.7583	NPC201959
Intermediate Similarity	0.7578	NPC475839
Intermediate Similarity	0.7563	NPC113457
Intermediate Similarity	0.7542	NPC108875
Intermediate Similarity	0.7542	NPC38079
Intermediate Similarity	0.7538	NPC61685
Intermediate Similarity	0.7538	NPC256015
Intermediate Similarity	0.7538	NPC294156
Intermediate Similarity	0.7521	NPC474272
Intermediate Similarity	0.7519	NPC471315
Intermediate Similarity	0.7519	NPC473464
Intermediate Similarity	0.7519	NPC476332
Intermediate Similarity	0.7519	NPC471314
Intermediate Similarity	0.75	NPC129176
Intermediate Similarity	0.75	NPC470837
Intermediate Similarity	0.7481	NPC81641
Intermediate Similarity	0.748	NPC43275
Intermediate Similarity	0.748	NPC280760
Intermediate Similarity	0.7479	NPC473855
Intermediate Similarity	0.7459	NPC95977
Intermediate Similarity	0.7459	NPC475852
Intermediate Similarity	0.7459	NPC2682
Intermediate Similarity	0.7458	NPC192596
Intermediate Similarity	0.744	NPC303370
Intermediate Similarity	0.7438	NPC75440
Intermediate Similarity	0.7434	NPC321956
Intermediate Similarity	0.7432	NPC129603
Intermediate Similarity	0.7424	NPC26879
Intermediate Similarity	0.7424	NPC283049
Intermediate Similarity	0.7424	NPC50315
Intermediate Similarity	0.7424	NPC230479
Intermediate Similarity	0.7419	NPC165106
Intermediate Similarity	0.7417	NPC30416
Intermediate Similarity	0.741	NPC314682
Intermediate Similarity	0.7407	NPC118419
Intermediate Similarity	0.7402	NPC63010
Intermediate Similarity	0.7402	NPC283616
Intermediate Similarity	0.7398	NPC166837
Intermediate Similarity	0.7394	NPC145304
Intermediate Similarity	0.7385	NPC36016
Intermediate Similarity	0.7385	NPC152946
Intermediate Similarity	0.7385	NPC100099
Intermediate Similarity	0.7381	NPC9341
Intermediate Similarity	0.7381	NPC81067
Intermediate Similarity	0.7381	NPC33900
Intermediate Similarity	0.7373	NPC51633
Intermediate Similarity	0.7368	NPC98745
Intermediate Similarity	0.7368	NPC172403
Intermediate Similarity	0.7364	NPC102639
Intermediate Similarity	0.7364	NPC45663
Intermediate Similarity	0.7364	NPC322569
Intermediate Similarity	0.7364	NPC131868
Intermediate Similarity	0.7357	NPC213206
Intermediate Similarity	0.7357	NPC328750
Intermediate Similarity	0.7357	NPC470925
Intermediate Similarity	0.7357	NPC188163
Intermediate Similarity	0.7357	NPC474915
Intermediate Similarity	0.7355	NPC194034
Intermediate Similarity	0.7348	NPC320242
Intermediate Similarity	0.7347	NPC475557
Intermediate Similarity	0.7345	NPC71853
Intermediate Similarity	0.7344	NPC234956
Intermediate Similarity	0.7344	NPC471449
Intermediate Similarity	0.7344	NPC32152
Intermediate Similarity	0.7344	NPC51341
Intermediate Similarity	0.7344	NPC98748
Intermediate Similarity	0.7339	NPC474920
Intermediate Similarity	0.7333	NPC42383
Intermediate Similarity	0.7328	NPC211218
Intermediate Similarity	0.7328	NPC38761
Intermediate Similarity	0.7328	NPC76465
Intermediate Similarity	0.7328	NPC217277
Intermediate Similarity	0.7323	NPC33270
Intermediate Similarity	0.7323	NPC69261
Intermediate Similarity	0.7319	NPC167944
Intermediate Similarity	0.7319	NPC42793
Intermediate Similarity	0.7319	NPC231884
Intermediate Similarity	0.7317	NPC303521
Intermediate Similarity	0.7315	NPC40389
Intermediate Similarity	0.7315	NPC78359
Intermediate Similarity	0.7315	NPC65490
Intermediate Similarity	0.7315	NPC148014
Intermediate Similarity	0.7315	NPC315707
Intermediate Similarity	0.7313	NPC38664
Intermediate Similarity	0.7313	NPC53986
Intermediate Similarity	0.7308	NPC193364
Intermediate Similarity	0.7308	NPC54972
Intermediate Similarity	0.7308	NPC48623
Intermediate Similarity	0.7308	NPC251259
Intermediate Similarity	0.7308	NPC168707
Intermediate Similarity	0.7304	NPC471581
Intermediate Similarity	0.7302	NPC475815
Intermediate Similarity	0.7302	NPC301321
Intermediate Similarity	0.7302	NPC47194
Intermediate Similarity	0.7302	NPC808
Intermediate Similarity	0.7302	NPC473264
Intermediate Similarity	0.7302	NPC473718
Intermediate Similarity	0.7295	NPC97811
Intermediate Similarity	0.7293	NPC218323
Intermediate Similarity	0.7292	NPC16107
Intermediate Similarity	0.7292	NPC476151
Intermediate Similarity	0.7292	NPC210437
Intermediate Similarity	0.7292	NPC51957
Intermediate Similarity	0.7292	NPC106295
Intermediate Similarity	0.7292	NPC476144
Intermediate Similarity	0.7287	NPC103916
Intermediate Similarity	0.7287	NPC474131
Intermediate Similarity	0.7287	NPC232295
Intermediate Similarity	0.7286	NPC83289
Intermediate Similarity	0.7286	NPC212850
Intermediate Similarity	0.7286	NPC189724
Intermediate Similarity	0.728	NPC90903
Intermediate Similarity	0.7273	NPC134195
Intermediate Similarity	0.7273	NPC95733
Intermediate Similarity	0.7273	NPC62101
Intermediate Similarity	0.7273	NPC197351
Intermediate Similarity	0.7273	NPC86502
Intermediate Similarity	0.7273	NPC246648
Intermediate Similarity	0.7273	NPC248557
Intermediate Similarity	0.7273	NPC106914
Intermediate Similarity	0.7266	NPC474040
Intermediate Similarity	0.7266	NPC329980
Intermediate Similarity	0.7266	NPC190514
Intermediate Similarity	0.7259	NPC93962
Intermediate Similarity	0.7259	NPC16577
Intermediate Similarity	0.7259	NPC160193
Intermediate Similarity	0.7258	NPC21890
Intermediate Similarity	0.7258	NPC275627
Intermediate Similarity	0.7257	NPC99886
Intermediate Similarity	0.7257	NPC177844
Intermediate Similarity	0.7257	NPC259134
Intermediate Similarity	0.7257	NPC8002
Intermediate Similarity	0.7252	NPC74137
Intermediate Similarity	0.7248	NPC323443
Intermediate Similarity	0.7248	NPC180756
Intermediate Similarity	0.7246	NPC11147
Intermediate Similarity	0.7246	NPC473107
Intermediate Similarity	0.7244	NPC229147
Intermediate Similarity	0.7244	NPC150624
Intermediate Similarity	0.7244	NPC54507
Intermediate Similarity	0.7244	NPC85292
Intermediate Similarity	0.7244	NPC69539
Intermediate Similarity	0.7241	NPC7467
Intermediate Similarity	0.7236	NPC149545
Intermediate Similarity	0.7231	NPC316896
Intermediate Similarity	0.7231	NPC100108
Intermediate Similarity	0.7231	NPC277798
Intermediate Similarity	0.7227	NPC84325
Intermediate Similarity	0.7226	NPC189482
Intermediate Similarity	0.7226	NPC475856
Intermediate Similarity	0.7222	NPC161696
Intermediate Similarity	0.7219	NPC18402
Intermediate Similarity	0.7218	NPC29477
Intermediate Similarity	0.7218	NPC232387
Intermediate Similarity	0.7218	NPC102540
Intermediate Similarity	0.7218	NPC4286
Intermediate Similarity	0.7218	NPC103420
Intermediate Similarity	0.7218	NPC76119
Intermediate Similarity	0.7218	NPC105031
Intermediate Similarity	0.7218	NPC113495
Intermediate Similarity	0.7218	NPC17809

Drug Structure

NPD3444 OpenBabel08211703112D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.0017 -5.0399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1764 -6.3096 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 3.4888 -1.4010 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 -1.9944 -1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4644 -3.6796 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 2.6228 -1.9010 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 1.1974 -2.9994 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 0.6869 -4.6545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 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 1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 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 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0461 -5.3347 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 18 2 0 0 0 0 11 17 2 3 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000177
DrugBank	DB01142
ChEMBL	CHEMBL101740
IUPHAR/BPS
PharmaGKB	PA449409
KEGG Drug	D07875
PubChem CID
ChEBI	36691
CAS Number	1668-19-5

Drug Properties

Molecular Weight	279.16
ALogP	0.0711
MLogP	3.33
XLogP	5.105
HDA	1
HBD	0
Rotatable Bonds	5
TPSA	12.47
RO5 Violation	1