NPASS drugs

Drug Information

Drug ID:	NPD3981
Drug Name:	Amitriptyline
Molecular Formula:	C20H23N
Canonical SMILES:	CN(CCC=C1c2ccccc2CCc2c1cccc2)C
Standard InCHI:	InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
Standard InCHIKey:	KRMDCWKBEZIMAB-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3981

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	232
0.1-0.2	1782
0.2-0.3	7370
0.3-0.4	13279
0.4-0.5	6767
0.5-0.6	1178
0.6-0.7	184
0.7-0.8	96
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
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
High Similarity	0.9241	NPC133162
Intermediate Similarity	0.8276	NPC470926
Intermediate Similarity	0.7976	NPC104070
Intermediate Similarity	0.7952	NPC231986
Intermediate Similarity	0.7922	NPC246822
Intermediate Similarity	0.7922	NPC213570
Intermediate Similarity	0.7922	NPC139416
Intermediate Similarity	0.7867	NPC155172
Intermediate Similarity	0.7867	NPC291066
Intermediate Similarity	0.7848	NPC54269
Intermediate Similarity	0.7838	NPC22786
Intermediate Similarity	0.7838	NPC71009
Intermediate Similarity	0.7778	NPC271642
Intermediate Similarity	0.7733	NPC113670
Intermediate Similarity	0.7722	NPC87099
Intermediate Similarity	0.7722	NPC1008
Intermediate Similarity	0.7722	NPC158028
Intermediate Similarity	0.7722	NPC280135
Intermediate Similarity	0.7722	NPC135433
Intermediate Similarity	0.7722	NPC226999
Intermediate Similarity	0.7722	NPC193578
Intermediate Similarity	0.7722	NPC39799
Intermediate Similarity	0.7703	NPC246588
Intermediate Similarity	0.7703	NPC210849
Intermediate Similarity	0.7703	NPC310758
Intermediate Similarity	0.7703	NPC238023
Intermediate Similarity	0.7662	NPC267443
Intermediate Similarity	0.7654	NPC98976
Intermediate Similarity	0.7614	NPC60408
Intermediate Similarity	0.7609	NPC329430
Intermediate Similarity	0.7595	NPC263385
Intermediate Similarity	0.7595	NPC251490
Intermediate Similarity	0.7595	NPC72670
Intermediate Similarity	0.7561	NPC139658
Intermediate Similarity	0.75	NPC239854
Intermediate Similarity	0.75	NPC159661
Intermediate Similarity	0.7471	NPC169016
Intermediate Similarity	0.747	NPC3190
Intermediate Similarity	0.747	NPC249018
Intermediate Similarity	0.7468	NPC200936
Intermediate Similarity	0.7467	NPC135924
Intermediate Similarity	0.7439	NPC307195
Intermediate Similarity	0.7436	NPC6107
Intermediate Similarity	0.7432	NPC36357
Intermediate Similarity	0.7432	NPC114327
Intermediate Similarity	0.7412	NPC315216
Intermediate Similarity	0.7407	NPC1901
Intermediate Similarity	0.7403	NPC32312
Intermediate Similarity	0.7403	NPC198023
Intermediate Similarity	0.7368	NPC29680
Intermediate Similarity	0.7368	NPC66517
Intermediate Similarity	0.7349	NPC110264
Intermediate Similarity	0.7342	NPC22760
Intermediate Similarity	0.7317	NPC96835
Intermediate Similarity	0.7317	NPC258492
Intermediate Similarity	0.7308	NPC113837
Intermediate Similarity	0.7308	NPC289915
Intermediate Similarity	0.7308	NPC178527
Intermediate Similarity	0.7303	NPC258046
Intermediate Similarity	0.7297	NPC65873
Intermediate Similarity	0.7297	NPC120441
Intermediate Similarity	0.7297	NPC300345
Intermediate Similarity	0.7297	NPC212114
Intermediate Similarity	0.7273	NPC21211
Intermediate Similarity	0.7273	NPC45756
Intermediate Similarity	0.7273	NPC88566
Intermediate Similarity	0.725	NPC297358
Intermediate Similarity	0.725	NPC473206
Intermediate Similarity	0.7237	NPC150196
Intermediate Similarity	0.7237	NPC54368
Intermediate Similarity	0.7237	NPC248705
Intermediate Similarity	0.7229	NPC276699
Intermediate Similarity	0.7216	NPC474582
Intermediate Similarity	0.7195	NPC244738
Intermediate Similarity	0.7179	NPC264470
Intermediate Similarity	0.7176	NPC255345
Intermediate Similarity	0.7176	NPC66270
Intermediate Similarity	0.7176	NPC12857
Intermediate Similarity	0.7176	NPC245896
Intermediate Similarity	0.7162	NPC269586
Intermediate Similarity	0.7162	NPC198841
Intermediate Similarity	0.716	NPC229235
Intermediate Similarity	0.7159	NPC119677
Intermediate Similarity	0.7159	NPC474088
Intermediate Similarity	0.7143	NPC200745
Intermediate Similarity	0.7111	NPC203076
Intermediate Similarity	0.7108	NPC122327
Intermediate Similarity	0.7108	NPC113000
Intermediate Similarity	0.7108	NPC112609
Intermediate Similarity	0.7105	NPC147062
Intermediate Similarity	0.7059	NPC290638
Intermediate Similarity	0.7051	NPC50266
Intermediate Similarity	0.7045	NPC14326
Intermediate Similarity	0.7027	NPC149436
Intermediate Similarity	0.7027	NPC277704
Intermediate Similarity	0.7011	NPC475289
Intermediate Similarity	0.7011	NPC50063
Intermediate Similarity	0.7011	NPC475573
Remote Similarity	0.6974	NPC64270
Remote Similarity	0.6974	NPC8235
Remote Similarity	0.6947	NPC322040
Remote Similarity	0.6931	NPC474695
Remote Similarity	0.6883	NPC169110
Remote Similarity	0.6875	NPC36440
Remote Similarity	0.6869	NPC316797
Remote Similarity	0.686	NPC9796
Remote Similarity	0.686	NPC98269
Remote Similarity	0.686	NPC325662
Remote Similarity	0.6848	NPC305602
Remote Similarity	0.6848	NPC17497
Remote Similarity	0.6813	NPC3210
Remote Similarity	0.6809	NPC172128
Remote Similarity	0.6765	NPC167336
Remote Similarity	0.6747	NPC219246
Remote Similarity	0.6742	NPC242628
Remote Similarity	0.6706	NPC299134
Remote Similarity	0.6705	NPC272260
Remote Similarity	0.6703	NPC95429
Remote Similarity	0.6667	NPC473031
Remote Similarity	0.6667	NPC473661
Remote Similarity	0.6634	NPC291610
Remote Similarity	0.6629	NPC184030
Remote Similarity	0.6629	NPC164449
Remote Similarity	0.6627	NPC5324
Remote Similarity	0.6602	NPC473418
Remote Similarity	0.6602	NPC474559
Remote Similarity	0.6596	NPC12429
Remote Similarity	0.6588	NPC212463
Remote Similarity	0.6538	NPC45033
Remote Similarity	0.6531	NPC108339
Remote Similarity	0.6526	NPC298115
Remote Similarity	0.6526	NPC470877
Remote Similarity	0.6522	NPC267704
Remote Similarity	0.6517	NPC139901
Remote Similarity	0.6517	NPC151405
Remote Similarity	0.6509	NPC65855
Remote Similarity	0.6509	NPC292758
Remote Similarity	0.6489	NPC53492
Remote Similarity	0.6484	NPC73637
Remote Similarity	0.6484	NPC121478
Remote Similarity	0.6477	NPC179726
Remote Similarity	0.6471	NPC125144
Remote Similarity	0.6471	NPC121708
Remote Similarity	0.6465	NPC471320
Remote Similarity	0.6465	NPC471319
Remote Similarity	0.6458	NPC159178
Remote Similarity	0.6458	NPC74936
Remote Similarity	0.6458	NPC471307
Remote Similarity	0.6458	NPC209764
Remote Similarity	0.6458	NPC78041
Remote Similarity	0.6458	NPC26224
Remote Similarity	0.6458	NPC141139
Remote Similarity	0.6458	NPC121872
Remote Similarity	0.6452	NPC475710
Remote Similarity	0.6429	NPC474974
Remote Similarity	0.6404	NPC103488
Remote Similarity	0.64	NPC311242
Remote Similarity	0.64	NPC472258
Remote Similarity	0.6392	NPC220596
Remote Similarity	0.6392	NPC125226
Remote Similarity	0.6386	NPC52330
Remote Similarity	0.6375	NPC45255
Remote Similarity	0.6364	NPC246904
Remote Similarity	0.6364	NPC256452
Remote Similarity	0.6354	NPC176858
Remote Similarity	0.6337	NPC322598
Remote Similarity	0.6327	NPC59677
Remote Similarity	0.6327	NPC108800
Remote Similarity	0.6316	NPC69057
Remote Similarity	0.6316	NPC471638
Remote Similarity	0.631	NPC311343
Remote Similarity	0.6306	NPC473573
Remote Similarity	0.6304	NPC283012
Remote Similarity	0.6304	NPC475199
Remote Similarity	0.6292	NPC298023
Remote Similarity	0.6289	NPC277277
Remote Similarity	0.6289	NPC191444
Remote Similarity	0.6283	NPC320656
Remote Similarity	0.6279	NPC74458
Remote Similarity	0.6277	NPC99482
Remote Similarity	0.6264	NPC285716
Remote Similarity	0.6264	NPC95868
Remote Similarity	0.6264	NPC17408
Remote Similarity	0.6264	NPC157055
Remote Similarity	0.6264	NPC477703
Remote Similarity	0.6263	NPC71140
Remote Similarity	0.6263	NPC469330
Remote Similarity	0.6263	NPC471309
Remote Similarity	0.6261	NPC316896
Remote Similarity	0.625	NPC147578
Remote Similarity	0.625	NPC267262
Remote Similarity	0.625	NPC189371
Remote Similarity	0.625	NPC262393
Remote Similarity	0.6238	NPC33168
Remote Similarity	0.6237	NPC477770
Remote Similarity	0.6235	NPC98880
Remote Similarity	0.6224	NPC245259
Remote Similarity	0.6224	NPC284475
Remote Similarity	0.6222	NPC224544
Remote Similarity	0.6214	NPC469457

Drug Structure

NPD3981 OpenBabel08211704332D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.9766 -3.0154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7985 -4.2851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 0.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 -0.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5105 -1.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.1982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 -0.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 -0.9749 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 2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2880 -2.6300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.6235 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 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0211 -3.3102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 6 2 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC001466; DAP000864
DrugBank	DB00321
ChEMBL	CHEMBL629
IUPHAR/BPS	200
PharmaGKB	PA448385
KEGG Drug
PubChem CID	2160
ChEBI	2666
CAS Number	50-48-6

Drug Properties

Molecular Weight	277.18
ALogP	0.3384
MLogP	3.55
XLogP	8.275
HDA	1
HBD	0
Rotatable Bonds	5
TPSA	3.24
RO5 Violation	1