Drug Information

Drug ID:  NPD3445
Drug Name:  doxepin
Molecular Formula:  C19H21NO
Canonical SMILES:  CN(CC/C=C1/c2ccccc2OCc2c1cccc2)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/b17-11+
Standard InCHIKey:  ODQWQRRAPPTVAG-GZTJUZNOSA-N
Max Developmental Stage:  Approved
Max Developmental Stage Source:  TTD; IUPHAR/BPS

  Structural Similarity Between NPASS Natural Products and NPD3445

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.


  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

External Identifiers

TTD   DAP000177
DrugBank  
ChEMBL  
IUPHAR/BPS   1225
PharmaGKB  
KEGG Drug  
PubChem CID   667477
ChEBI  
CAS Number  

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