NPASS drugs

Drug Information

Drug ID:	NPD5253
Drug Name:	Aprindine
Molecular Formula:	C22H30N2
Canonical SMILES:	CCN(CCCN(C1Cc2c(C1)cccc2)c1ccccc1)CC
Standard InCHI:	InChI=1S/C22H30N2/c1-3-23(4-2)15-10-16-24(21-13-6-5-7-14-21)22-17-19-11-8-9-12-20(19)18-22/h5-9,11-14,22H,3-4,10,15-18H2,1-2H3
Standard InCHIKey:	NZLBHDRPUJLHCE-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; DrugBank

Structural Similarity Between NPASS Natural Products and NPD5253

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	415
0.1-0.2	2403
0.2-0.3	11109
0.3-0.4	11343
0.4-0.5	4106
0.5-0.6	1230
0.6-0.7	256
0.7-0.8	27
0.8-0.85	0
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	0.8922	NPC291610
Intermediate Similarity	0.7966	NPC475915
Intermediate Similarity	0.7864	NPC470926
Intermediate Similarity	0.7739	NPC187036
Intermediate Similarity	0.7679	NPC434
Intermediate Similarity	0.7679	NPC79618
Intermediate Similarity	0.7627	NPC192209
Intermediate Similarity	0.7627	NPC313449
Intermediate Similarity	0.7607	NPC288232
Intermediate Similarity	0.7586	NPC296163
Intermediate Similarity	0.7426	NPC104070
Intermediate Similarity	0.7395	NPC313673
Intermediate Similarity	0.7345	NPC474695
Intermediate Similarity	0.7315	NPC329430
Intermediate Similarity	0.7302	NPC476950
Intermediate Similarity	0.7302	NPC145754
Intermediate Similarity	0.729	NPC108800
Intermediate Similarity	0.7273	NPC264580
Intermediate Similarity	0.7264	NPC191444
Intermediate Similarity	0.7232	NPC239854
Intermediate Similarity	0.7222	NPC252794
Intermediate Similarity	0.7213	NPC226143
Intermediate Similarity	0.717	NPC176858
Intermediate Similarity	0.7155	NPC164802
Intermediate Similarity	0.7155	NPC302790
Intermediate Similarity	0.7115	NPC229477
Intermediate Similarity	0.7071	NPC271642
Intermediate Similarity	0.7019	NPC169016
Remote Similarity	0.697	NPC98976
Remote Similarity	0.696	NPC257490
Remote Similarity	0.6935	NPC291962
Remote Similarity	0.6935	NPC177684
Remote Similarity	0.6923	NPC134825
Remote Similarity	0.6923	NPC9856
Remote Similarity	0.6923	NPC473417
Remote Similarity	0.6916	NPC30445
Remote Similarity	0.6893	NPC231986
Remote Similarity	0.6887	NPC258046
Remote Similarity	0.688	NPC258531
Remote Similarity	0.688	NPC112373
Remote Similarity	0.688	NPC161956
Remote Similarity	0.6842	NPC313352
Remote Similarity	0.6842	NPC474582
Remote Similarity	0.6838	NPC130251
Remote Similarity	0.6822	NPC262295
Remote Similarity	0.6818	NPC53044
Remote Similarity	0.6788	NPC301760
Remote Similarity	0.6786	NPC469735
Remote Similarity	0.6769	NPC478079
Remote Similarity	0.6763	NPC311330
Remote Similarity	0.6762	NPC119677
Remote Similarity	0.6757	NPC322040
Remote Similarity	0.6754	NPC323726
Remote Similarity	0.6738	NPC212799
Remote Similarity	0.6738	NPC469740
Remote Similarity	0.6724	NPC474430
Remote Similarity	0.6691	NPC63157
Remote Similarity	0.6691	NPC473868
Remote Similarity	0.669	NPC109787
Remote Similarity	0.6667	NPC186284
Remote Similarity	0.6667	NPC192533
Remote Similarity	0.6667	NPC264589
Remote Similarity	0.6667	NPC22082
Remote Similarity	0.6642	NPC314102
Remote Similarity	0.6642	NPC251722
Remote Similarity	0.6641	NPC48564
Remote Similarity	0.6641	NPC182570
Remote Similarity	0.6641	NPC265605
Remote Similarity	0.6636	NPC78154
Remote Similarity	0.6619	NPC59084
Remote Similarity	0.6618	NPC471123
Remote Similarity	0.6614	NPC316582
Remote Similarity	0.6609	NPC75496
Remote Similarity	0.6606	NPC111233
Remote Similarity	0.6602	NPC12857
Remote Similarity	0.6597	NPC33421
Remote Similarity	0.6597	NPC206592
Remote Similarity	0.6587	NPC81561
Remote Similarity	0.6587	NPC228515
Remote Similarity	0.6585	NPC314141
Remote Similarity	0.6585	NPC57051
Remote Similarity	0.6567	NPC282398
Remote Similarity	0.6552	NPC326792
Remote Similarity	0.6549	NPC86288
Remote Similarity	0.6547	NPC104483
Remote Similarity	0.6545	NPC173991
Remote Similarity	0.6544	NPC300299
Remote Similarity	0.6542	NPC133162
Remote Similarity	0.6535	NPC143603
Remote Similarity	0.6525	NPC20144
Remote Similarity	0.6522	NPC150259
Remote Similarity	0.6508	NPC476566
Remote Similarity	0.6508	NPC148140
Remote Similarity	0.6505	NPC98269
Remote Similarity	0.6505	NPC325662
Remote Similarity	0.65	NPC2949
Remote Similarity	0.65	NPC20322
Remote Similarity	0.6496	NPC267508
Remote Similarity	0.6496	NPC198988
Remote Similarity	0.6496	NPC325599
Remote Similarity	0.6484	NPC279385
Remote Similarity	0.6484	NPC179605
Remote Similarity	0.6471	NPC162417
Remote Similarity	0.6471	NPC316104
Remote Similarity	0.6471	NPC184437
Remote Similarity	0.6466	NPC328590
Remote Similarity	0.6458	NPC21605
Remote Similarity	0.6454	NPC469537
Remote Similarity	0.6449	NPC325252
Remote Similarity	0.6444	NPC22079
Remote Similarity	0.6434	NPC103292
Remote Similarity	0.6429	NPC88097
Remote Similarity	0.6419	NPC51054
Remote Similarity	0.6406	NPC162689
Remote Similarity	0.6406	NPC54102
Remote Similarity	0.6406	NPC91958
Remote Similarity	0.6403	NPC469560
Remote Similarity	0.6397	NPC475450
Remote Similarity	0.6385	NPC39818
Remote Similarity	0.637	NPC154602
Remote Similarity	0.637	NPC243756
Remote Similarity	0.637	NPC40070
Remote Similarity	0.637	NPC66936
Remote Similarity	0.6364	NPC470343
Remote Similarity	0.6364	NPC122718
Remote Similarity	0.6364	NPC472244
Remote Similarity	0.6364	NPC476322
Remote Similarity	0.6357	NPC243162
Remote Similarity	0.6343	NPC150863
Remote Similarity	0.6343	NPC209389
Remote Similarity	0.6336	NPC283130
Remote Similarity	0.6336	NPC328683
Remote Similarity	0.6333	NPC56765
Remote Similarity	0.6333	NPC206819
Remote Similarity	0.6333	NPC318065
Remote Similarity	0.6333	NPC6436
Remote Similarity	0.6333	NPC313362
Remote Similarity	0.6331	NPC218268
Remote Similarity	0.6328	NPC240136
Remote Similarity	0.6328	NPC471402
Remote Similarity	0.6328	NPC297486
Remote Similarity	0.6327	NPC285381
Remote Similarity	0.6327	NPC122106
Remote Similarity	0.6312	NPC316811
Remote Similarity	0.6312	NPC32002
Remote Similarity	0.6312	NPC471574
Remote Similarity	0.6312	NPC315348
Remote Similarity	0.6312	NPC110126
Remote Similarity	0.6312	NPC73767
Remote Similarity	0.6308	NPC215519
Remote Similarity	0.6296	NPC314431
Remote Similarity	0.6296	NPC472245
Remote Similarity	0.6296	NPC280807
Remote Similarity	0.6288	NPC46358
Remote Similarity	0.6284	NPC478076
Remote Similarity	0.6284	NPC138842
Remote Similarity	0.627	NPC246904
Remote Similarity	0.6269	NPC250361
Remote Similarity	0.6268	NPC469767
Remote Similarity	0.6268	NPC469761
Remote Similarity	0.6268	NPC469784
Remote Similarity	0.6268	NPC469768
Remote Similarity	0.6268	NPC469779
Remote Similarity	0.6268	NPC469780
Remote Similarity	0.6268	NPC469783
Remote Similarity	0.6261	NPC108339
Remote Similarity	0.626	NPC268534
Remote Similarity	0.6259	NPC475763
Remote Similarity	0.625	NPC473587
Remote Similarity	0.625	NPC139658
Remote Similarity	0.625	NPC469741
Remote Similarity	0.6241	NPC169433
Remote Similarity	0.6241	NPC315051
Remote Similarity	0.6241	NPC27740
Remote Similarity	0.6241	NPC79698
Remote Similarity	0.6225	NPC41257
Remote Similarity	0.6224	NPC469766
Remote Similarity	0.6214	NPC122327
Remote Similarity	0.6214	NPC112609
Remote Similarity	0.6214	NPC113000
Remote Similarity	0.6212	NPC41174
Remote Similarity	0.6212	NPC329825
Remote Similarity	0.6207	NPC471320
Remote Similarity	0.6207	NPC471319
Remote Similarity	0.6204	NPC476687
Remote Similarity	0.6204	NPC476689
Remote Similarity	0.6204	NPC476685
Remote Similarity	0.6204	NPC475428
Remote Similarity	0.6198	NPC473418
Remote Similarity	0.6194	NPC250476
Remote Similarity	0.6194	NPC146373
Remote Similarity	0.6194	NPC245244
Remote Similarity	0.6194	NPC166424
Remote Similarity	0.6184	NPC225319
Remote Similarity	0.6183	NPC314192
Remote Similarity	0.6181	NPC136002
Remote Similarity	0.6176	NPC187231
Remote Similarity	0.6176	NPC473762
Remote Similarity	0.6172	NPC147957
Remote Similarity	0.6172	NPC125416

Drug Structure

NPD5253 OpenBabel08211706322D 24 26 0 0 0 0 0 0 0 0999 V2000 2.3814 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5154 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5154 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6494 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -0.2976 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 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2167 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 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 -2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6494 3.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 1.7024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 21 2 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 21 24 1 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000954
DrugBank	DB01429
ChEMBL	CHEMBL1213033
IUPHAR/BPS
PharmaGKB	PA164764496
KEGG Drug	D01326
PubChem CID	2218
ChEBI	135370
CAS Number	37640-71-4

Drug Properties

Molecular Weight	322.24
ALogP	0.5414
MLogP	3.66
XLogP	7.014
HDA	2
HBD	0
Rotatable Bonds	10
TPSA	6.48
RO5 Violation	1