NPASS drugs

Drug Information

Drug ID:	NPD4000
Drug Name:	Amitriptylinoxide
Molecular Formula:	C20H23NO
Canonical SMILES:	CN(=O)(CCC=C1c2ccccc2CCc2c1cccc2)C
Standard InCHI:	InChI=1S/C20H23NO/c1-21(2,22)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:	ZPMKQFOGINQDAM-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4000

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	174
0.1-0.2	2001
0.2-0.3	7713
0.3-0.4	15767
0.4-0.5	4461
0.5-0.6	630
0.6-0.7	138
0.7-0.8	5
0.8-0.85	1
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	0.8023	NPC133162
Intermediate Similarity	0.7303	NPC104070
Intermediate Similarity	0.7273	NPC231986
Intermediate Similarity	0.7234	NPC470926
Intermediate Similarity	0.7125	NPC155172
Intermediate Similarity	0.7093	NPC271642
Remote Similarity	0.6977	NPC98976
Remote Similarity	0.6962	NPC210849
Remote Similarity	0.6962	NPC238023
Remote Similarity	0.6962	NPC310758
Remote Similarity	0.6941	NPC54269
Remote Similarity	0.6897	NPC139658
Remote Similarity	0.6875	NPC71009
Remote Similarity	0.6809	NPC60408
Remote Similarity	0.6786	NPC246822
Remote Similarity	0.6786	NPC200936
Remote Similarity	0.6786	NPC213570
Remote Similarity	0.6786	NPC139416
Remote Similarity	0.675	NPC135924
Remote Similarity	0.6747	NPC6107
Remote Similarity	0.6739	NPC474088
Remote Similarity	0.6707	NPC291066
Remote Similarity	0.6707	NPC32312
Remote Similarity	0.6707	NPC198023
Remote Similarity	0.6705	NPC110264
Remote Similarity	0.6702	NPC258046
Remote Similarity	0.6667	NPC22786
Remote Similarity	0.6667	NPC29680
Remote Similarity	0.6667	NPC66517
Remote Similarity	0.6667	NPC329430
Remote Similarity	0.6667	NPC22760
Remote Similarity	0.663	NPC14326
Remote Similarity	0.6629	NPC3190
Remote Similarity	0.6629	NPC249018
Remote Similarity	0.6628	NPC87099
Remote Similarity	0.6628	NPC193578
Remote Similarity	0.6628	NPC158028
Remote Similarity	0.6628	NPC280135
Remote Similarity	0.6628	NPC1008
Remote Similarity	0.6628	NPC39799
Remote Similarity	0.6628	NPC135433
Remote Similarity	0.6628	NPC226999
Remote Similarity	0.6627	NPC289915
Remote Similarity	0.6627	NPC113837
Remote Similarity	0.6627	NPC178527
Remote Similarity	0.6602	NPC239854
Remote Similarity	0.6593	NPC475289
Remote Similarity	0.6593	NPC475573
Remote Similarity	0.6591	NPC276699
Remote Similarity	0.6588	NPC297358
Remote Similarity	0.6585	NPC113670
Remote Similarity	0.6585	NPC21211
Remote Similarity	0.6585	NPC88566
Remote Similarity	0.6585	NPC45756
Remote Similarity	0.6582	NPC212114
Remote Similarity	0.6582	NPC65873
Remote Similarity	0.6582	NPC120441
Remote Similarity	0.6582	NPC300345
Remote Similarity	0.6556	NPC12857
Remote Similarity	0.6552	NPC244738
Remote Similarity	0.6548	NPC267443
Remote Similarity	0.6543	NPC246588
Remote Similarity	0.6543	NPC150196
Remote Similarity	0.6543	NPC54368
Remote Similarity	0.6543	NPC248705
Remote Similarity	0.6512	NPC263385
Remote Similarity	0.6512	NPC72670
Remote Similarity	0.6512	NPC229235
Remote Similarity	0.6512	NPC251490
Remote Similarity	0.6506	NPC264470
Remote Similarity	0.6505	NPC474582
Remote Similarity	0.6489	NPC169016
Remote Similarity	0.6484	NPC159661
Remote Similarity	0.6477	NPC122327
Remote Similarity	0.6477	NPC113000
Remote Similarity	0.6477	NPC112609
Remote Similarity	0.6458	NPC17497
Remote Similarity	0.6458	NPC305602
Remote Similarity	0.6456	NPC269586
Remote Similarity	0.6456	NPC198841
Remote Similarity	0.6444	NPC290638
Remote Similarity	0.6437	NPC121708
Remote Similarity	0.6437	NPC125144
Remote Similarity	0.6421	NPC3210
Remote Similarity	0.642	NPC147062
Remote Similarity	0.6413	NPC315216
Remote Similarity	0.6404	NPC307195
Remote Similarity	0.64	NPC322040
Remote Similarity	0.6386	NPC50266
Remote Similarity	0.6364	NPC1901
Remote Similarity	0.6354	NPC203076
Remote Similarity	0.6344	NPC242628
Remote Similarity	0.6329	NPC149436
Remote Similarity	0.6329	NPC277704
Remote Similarity	0.63	NPC473661
Remote Similarity	0.6296	NPC8235
Remote Similarity	0.6296	NPC114327
Remote Similarity	0.6296	NPC64270
Remote Similarity	0.6296	NPC36357
Remote Similarity	0.6292	NPC96835
Remote Similarity	0.6292	NPC258492
Remote Similarity	0.6289	NPC473031
Remote Similarity	0.6289	NPC471638
Remote Similarity	0.6264	NPC98269
Remote Similarity	0.6264	NPC325662
Remote Similarity	0.6262	NPC474695
Remote Similarity	0.6224	NPC12429
Remote Similarity	0.622	NPC169110
Remote Similarity	0.6211	NPC119677
Remote Similarity	0.6207	NPC473206
Remote Similarity	0.6196	NPC245896
Remote Similarity	0.6196	NPC255345
Remote Similarity	0.6196	NPC66270
Remote Similarity	0.619	NPC316797
Remote Similarity	0.6162	NPC470877
Remote Similarity	0.6146	NPC267704
Remote Similarity	0.6136	NPC219246
Remote Similarity	0.6122	NPC53492
Remote Similarity	0.6117	NPC471319
Remote Similarity	0.6117	NPC471320
Remote Similarity	0.6111	NPC299134
Remote Similarity	0.6111	NPC474559
Remote Similarity	0.6111	NPC167336
Remote Similarity	0.61	NPC74936
Remote Similarity	0.61	NPC78041
Remote Similarity	0.61	NPC141139
Remote Similarity	0.61	NPC121872
Remote Similarity	0.61	NPC209764
Remote Similarity	0.61	NPC471307
Remote Similarity	0.61	NPC159178
Remote Similarity	0.61	NPC172128
Remote Similarity	0.6087	NPC9796
Remote Similarity	0.6078	NPC474974
Remote Similarity	0.6071	NPC200745
Remote Similarity	0.6064	NPC50063
Remote Similarity	0.6058	NPC472258
Remote Similarity	0.604	NPC284475
Remote Similarity	0.6038	NPC469457
Remote Similarity	0.6022	NPC103488
Remote Similarity	0.6019	NPC256452
Remote Similarity	0.6019	NPC260233
Remote Similarity	0.6	NPC322598
Remote Similarity	0.6	NPC212463
Remote Similarity	0.6	NPC298115
Remote Similarity	0.598	NPC155232
Remote Similarity	0.598	NPC153885
Remote Similarity	0.598	NPC1682
Remote Similarity	0.598	NPC188844
Remote Similarity	0.5979	NPC95429
Remote Similarity	0.5963	NPC473418
Remote Similarity	0.5957	NPC272260
Remote Similarity	0.5941	NPC26224
Remote Similarity	0.5922	NPC238219
Remote Similarity	0.5922	NPC471309
Remote Similarity	0.5922	NPC71140
Remote Similarity	0.5914	NPC298023
Remote Similarity	0.5913	NPC246904
Remote Similarity	0.5909	NPC311343
Remote Similarity	0.5909	NPC45033
Remote Similarity	0.59	NPC157778
Remote Similarity	0.5895	NPC17408
Remote Similarity	0.5895	NPC157055
Remote Similarity	0.5895	NPC184030
Remote Similarity	0.5895	NPC285716
Remote Similarity	0.5895	NPC164449
Remote Similarity	0.5893	NPC158854
Remote Similarity	0.5893	NPC65855
Remote Similarity	0.5893	NPC292758
Remote Similarity	0.5889	NPC74458
Remote Similarity	0.5888	NPC228400
Remote Similarity	0.5888	NPC214200
Remote Similarity	0.5882	NPC133461
Remote Similarity	0.5882	NPC220596
Remote Similarity	0.5882	NPC245259
Remote Similarity	0.5882	NPC125226
Remote Similarity	0.5882	NPC475059
Remote Similarity	0.5882	NPC475023
Remote Similarity	0.5876	NPC477770
Remote Similarity	0.587	NPC189371
Remote Similarity	0.5865	NPC58674
Remote Similarity	0.5865	NPC303045
Remote Similarity	0.5865	NPC161972
Remote Similarity	0.5865	NPC108339
Remote Similarity	0.5862	NPC36440
Remote Similarity	0.5862	NPC473573
Remote Similarity	0.5851	NPC224544
Remote Similarity	0.5849	NPC75724
Remote Similarity	0.5843	NPC98880
Remote Similarity	0.5833	NPC291610
Remote Similarity	0.5825	NPC59677
Remote Similarity	0.5825	NPC475057
Remote Similarity	0.5824	NPC285679
Remote Similarity	0.581	NPC25565
Remote Similarity	0.58	NPC43945
Remote Similarity	0.5795	NPC52330
Remote Similarity	0.5794	NPC323726
Remote Similarity	0.5789	NPC151405
Remote Similarity	0.5789	NPC139901
Remote Similarity	0.5784	NPC316108
Remote Similarity	0.5784	NPC173413

Drug Structure

NPD4000 OpenBabel08211704332D 22 24 0 0 0 0 0 0 0 0999 V2000 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8904 -0.4237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0783 4.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9348 -0.7184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3453 3.7669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1129 0.5513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0339 4.1523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2018 -0.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5678 2.7920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7452 2.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2452 3.0283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 1.2314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2564 3.1774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4243 0.9367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5233 2.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 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 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 21 22 2 0 0 0 0 M END $$$$

External Identifiers

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

Drug Properties

Molecular Weight	293.18
ALogP
MLogP	3.44
XLogP
HDA	0
HBD	0
Rotatable Bonds	5
TPSA	17.07
RO5 Violation	0