NPASS drugs

Drug Information

Drug ID:	NPD3546
Drug Name:	Imipramine
Molecular Formula:	C19H24N2
Canonical SMILES:	CN(CCCN1c2ccccc2CCc2c1cccc2)C
Standard InCHI:	InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
Standard InCHIKey:	BCGWQEUPMDMJNV-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3546

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	430
0.1-0.2	3172
0.2-0.3	11243
0.3-0.4	10682
0.4-0.5	3764
0.5-0.6	1234
0.6-0.7	321
0.7-0.8	40
0.8-0.85	3
0.85-0.9	1
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
High Similarity	0.8824	NPC291610
Intermediate Similarity	0.8125	NPC187036
Intermediate Similarity	0.8	NPC192209
Intermediate Similarity	0.8	NPC313449
Intermediate Similarity	0.7838	NPC302790
Intermediate Similarity	0.7826	NPC288232
Intermediate Similarity	0.7807	NPC296163
Intermediate Similarity	0.7759	NPC313673
Intermediate Similarity	0.7748	NPC79618
Intermediate Similarity	0.7731	NPC475915
Intermediate Similarity	0.7561	NPC252794
Intermediate Similarity	0.75	NPC476950
Intermediate Similarity	0.75	NPC145754
Intermediate Similarity	0.7434	NPC434
Intermediate Similarity	0.7429	NPC470926
Intermediate Similarity	0.7417	NPC226143
Intermediate Similarity	0.7368	NPC164802
Intermediate Similarity	0.7353	NPC229477
Intermediate Similarity	0.7333	NPC264580
Intermediate Similarity	0.7333	NPC191444
Intermediate Similarity	0.7295	NPC257490
Intermediate Similarity	0.7273	NPC291962
Intermediate Similarity	0.7273	NPC177684
Intermediate Similarity	0.7244	NPC9856
Intermediate Similarity	0.7239	NPC473868
Intermediate Similarity	0.7239	NPC63157
Intermediate Similarity	0.7238	NPC176858
Intermediate Similarity	0.7213	NPC258531
Intermediate Similarity	0.7213	NPC112373
Intermediate Similarity	0.7213	NPC161956
Intermediate Similarity	0.7212	NPC262295
Intermediate Similarity	0.7196	NPC108800
Intermediate Similarity	0.719	NPC81561
Intermediate Similarity	0.7143	NPC111233
Intermediate Similarity	0.7143	NPC271642
Intermediate Similarity	0.7109	NPC473417
Intermediate Similarity	0.7107	NPC148140
Intermediate Similarity	0.7087	NPC169016
Intermediate Similarity	0.7068	NPC314102
Intermediate Similarity	0.7068	NPC251722
Intermediate Similarity	0.7049	NPC228515
Intermediate Similarity	0.7045	NPC325599
Intermediate Similarity	0.7041	NPC98976
Intermediate Similarity	0.7009	NPC78154
Remote Similarity	0.6992	NPC162689
Remote Similarity	0.6992	NPC54102
Remote Similarity	0.6991	NPC239854
Remote Similarity	0.699	NPC104070
Remote Similarity	0.699	NPC134825
Remote Similarity	0.6981	NPC30445
Remote Similarity	0.6978	NPC21605
Remote Similarity	0.6935	NPC316582
Remote Similarity	0.6929	NPC122718
Remote Similarity	0.6917	NPC314141
Remote Similarity	0.6912	NPC59084
Remote Similarity	0.6909	NPC329430
Remote Similarity	0.6894	NPC162417
Remote Similarity	0.6894	NPC313352
Remote Similarity	0.6894	NPC316104
Remote Similarity	0.688	NPC215519
Remote Similarity	0.6857	NPC109787
Remote Similarity	0.6842	NPC300299
Remote Similarity	0.6838	NPC104483
Remote Similarity	0.6827	NPC119677
Remote Similarity	0.6825	NPC268534
Remote Similarity	0.6822	NPC478079
Remote Similarity	0.6815	NPC150259
Remote Similarity	0.68	NPC279385
Remote Similarity	0.68	NPC179605
Remote Similarity	0.6796	NPC231986
Remote Similarity	0.6791	NPC471123
Remote Similarity	0.6791	NPC198988
Remote Similarity	0.6788	NPC2949
Remote Similarity	0.6783	NPC474430
Remote Similarity	0.6765	NPC130251
Remote Similarity	0.6746	NPC103292
Remote Similarity	0.6742	NPC22079
Remote Similarity	0.6742	NPC53044
Remote Similarity	0.6736	NPC476297
Remote Similarity	0.6719	NPC46358
Remote Similarity	0.6715	NPC186284
Remote Similarity	0.6715	NPC22082
Remote Similarity	0.6715	NPC301760
Remote Similarity	0.6714	NPC469735
Remote Similarity	0.6693	NPC39818
Remote Similarity	0.6692	NPC475450
Remote Similarity	0.6691	NPC20144
Remote Similarity	0.6691	NPC469560
Remote Similarity	0.6667	NPC474695
Remote Similarity	0.6667	NPC267508
Remote Similarity	0.6667	NPC323726
Remote Similarity	0.6667	NPC12857
Remote Similarity	0.6667	NPC469740
Remote Similarity	0.6643	NPC40070
Remote Similarity	0.6642	NPC184437
Remote Similarity	0.664	NPC471402
Remote Similarity	0.664	NPC240136
Remote Similarity	0.664	NPC297486
Remote Similarity	0.6639	NPC57051
Remote Similarity	0.6618	NPC325252
Remote Similarity	0.6606	NPC173991
Remote Similarity	0.6596	NPC264589
Remote Similarity	0.6594	NPC88097
Remote Similarity	0.6594	NPC110126
Remote Similarity	0.6594	NPC73767
Remote Similarity	0.6587	NPC91958
Remote Similarity	0.6569	NPC83214
Remote Similarity	0.6565	NPC250361
Remote Similarity	0.6562	NPC265605
Remote Similarity	0.6562	NPC48564
Remote Similarity	0.6562	NPC182570
Remote Similarity	0.656	NPC476566
Remote Similarity	0.6547	NPC469767
Remote Similarity	0.6547	NPC469784
Remote Similarity	0.6547	NPC469779
Remote Similarity	0.6547	NPC469783
Remote Similarity	0.6547	NPC469780
Remote Similarity	0.6547	NPC469761
Remote Similarity	0.6547	NPC469768
Remote Similarity	0.6541	NPC473587
Remote Similarity	0.6538	NPC470343
Remote Similarity	0.6538	NPC472244
Remote Similarity	0.6538	NPC476322
Remote Similarity	0.6535	NPC317564
Remote Similarity	0.6528	NPC33421
Remote Similarity	0.6528	NPC206592
Remote Similarity	0.6522	NPC75496
Remote Similarity	0.6515	NPC150863
Remote Similarity	0.6515	NPC328590
Remote Similarity	0.6515	NPC209389
Remote Similarity	0.6512	NPC41174
Remote Similarity	0.6512	NPC283130
Remote Similarity	0.6512	NPC328683
Remote Similarity	0.65	NPC469766
Remote Similarity	0.6496	NPC218268
Remote Similarity	0.6493	NPC476685
Remote Similarity	0.6493	NPC476689
Remote Similarity	0.6493	NPC476687
Remote Similarity	0.6493	NPC475428
Remote Similarity	0.6489	NPC250476
Remote Similarity	0.6481	NPC258046
Remote Similarity	0.6475	NPC315348
Remote Similarity	0.6475	NPC316811
Remote Similarity	0.6475	NPC471574
Remote Similarity	0.6475	NPC32002
Remote Similarity	0.6466	NPC472245
Remote Similarity	0.6466	NPC473762
Remote Similarity	0.6466	NPC326792
Remote Similarity	0.6466	NPC314431
Remote Similarity	0.6466	NPC280807
Remote Similarity	0.6462	NPC290094
Remote Similarity	0.6449	NPC133162
Remote Similarity	0.6449	NPC105127
Remote Similarity	0.6449	NPC84911
Remote Similarity	0.6444	NPC179365
Remote Similarity	0.6439	NPC476140
Remote Similarity	0.6429	NPC115611
Remote Similarity	0.6417	NPC20322
Remote Similarity	0.6414	NPC53947
Remote Similarity	0.6408	NPC325662
Remote Similarity	0.6408	NPC98269
Remote Similarity	0.6403	NPC315051
Remote Similarity	0.6403	NPC169433
Remote Similarity	0.6397	NPC473930
Remote Similarity	0.6395	NPC476219
Remote Similarity	0.6387	NPC313362
Remote Similarity	0.6385	NPC329825
Remote Similarity	0.6383	NPC469537
Remote Similarity	0.6377	NPC96102
Remote Similarity	0.6377	NPC29886
Remote Similarity	0.6377	NPC261195
Remote Similarity	0.6372	NPC322040
Remote Similarity	0.637	NPC282398
Remote Similarity	0.637	NPC69914
Remote Similarity	0.6364	NPC146373
Remote Similarity	0.6364	NPC245244
Remote Similarity	0.6364	NPC166424
Remote Similarity	0.6364	NPC470440
Remote Similarity	0.6351	NPC51054
Remote Similarity	0.6349	NPC147957
Remote Similarity	0.6343	NPC187231
Remote Similarity	0.6338	NPC136002
Remote Similarity	0.6338	NPC311330
Remote Similarity	0.6336	NPC192533
Remote Similarity	0.6331	NPC125746
Remote Similarity	0.6328	NPC143603
Remote Similarity	0.6319	NPC212799
Remote Similarity	0.6319	NPC288838
Remote Similarity	0.6316	NPC108339
Remote Similarity	0.6316	NPC202957
Remote Similarity	0.6316	NPC169625
Remote Similarity	0.6312	NPC238499
Remote Similarity	0.6311	NPC139658
Remote Similarity	0.6303	NPC328877
Remote Similarity	0.6301	NPC243756
Remote Similarity	0.6301	NPC154602
Remote Similarity	0.6301	NPC66936
Remote Similarity	0.6296	NPC231382
Remote Similarity	0.6296	NPC476131
Remote Similarity	0.6286	NPC243162

Drug Structure

NPD3546 OpenBabel08211703112D 21 23 0 0 0 0 0 0 0 0999 V2000 3.0892 1.8592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5787 3.5143 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 -2.9693 -0.3720 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 -2.5355 0.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1781 1.2697 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 -2.4060 -1.1982 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 -1.5382 0.6037 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 -0.9749 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4006 2.2446 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 0.7818 -1.6235 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 -0.6235 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 2.3562 2.5394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 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 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 14 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 13 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 20 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 21 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001154
DrugBank	DB00458
ChEMBL	CHEMBL11
IUPHAR/BPS	357
PharmaGKB	PA449969
KEGG Drug
PubChem CID	3696
ChEBI	47499
CAS Number	50-49-7

Drug Properties

Molecular Weight	280.19
ALogP	0.091
MLogP	3.33
XLogP	5.244
HDA	2
HBD	0
Rotatable Bonds	6
TPSA	6.48
RO5 Violation	1