NPASS drugs

Drug Information

Drug ID:	NPD6513
Drug Name:	Lofepramine
Molecular Formula:	C26H27ClN2O
Canonical SMILES:	CN(CC(=O)c1ccc(cc1)Cl)CCCN1c2ccccc2CCc2c1cccc2
Standard InCHI:	InChI=1S/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3
Standard InCHIKey:	SAPNXPWPAUFAJU-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6513

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	272
0.1-0.2	2043
0.2-0.3	9185
0.3-0.4	11986
0.4-0.5	5769
0.5-0.6	1432
0.6-0.7	178
0.7-0.8	25
0.8-0.85	0
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	0.7883	NPC257490
Intermediate Similarity	0.7868	NPC226143
Intermediate Similarity	0.7737	NPC291962
Intermediate Similarity	0.7737	NPC177684
Intermediate Similarity	0.7681	NPC258531
Intermediate Similarity	0.7681	NPC161956
Intermediate Similarity	0.7681	NPC112373
Intermediate Similarity	0.7447	NPC268534
Intermediate Similarity	0.7305	NPC279385
Intermediate Similarity	0.7305	NPC179605
Intermediate Similarity	0.7303	NPC471574
Intermediate Similarity	0.726	NPC209389
Intermediate Similarity	0.7254	NPC103292
Intermediate Similarity	0.7222	NPC192533
Intermediate Similarity	0.7203	NPC39818
Intermediate Similarity	0.72	NPC300299
Intermediate Similarity	0.7161	NPC136002
Intermediate Similarity	0.7152	NPC325599
Intermediate Similarity	0.7133	NPC162417
Intermediate Similarity	0.7133	NPC316104
Intermediate Similarity	0.7055	NPC472244
Intermediate Similarity	0.7055	NPC470343
Intermediate Similarity	0.7027	NPC150863
Intermediate Similarity	0.702	NPC313352
Intermediate Similarity	0.7013	NPC207554
Remote Similarity	0.698	NPC472245
Remote Similarity	0.698	NPC280807
Remote Similarity	0.698	NPC314431
Remote Similarity	0.6948	NPC83214
Remote Similarity	0.6929	NPC57051
Remote Similarity	0.6879	NPC113099
Remote Similarity	0.681	NPC295021
Remote Similarity	0.6803	NPC254698
Remote Similarity	0.6788	NPC477887
Remote Similarity	0.6741	NPC291610
Remote Similarity	0.6739	NPC172170
Remote Similarity	0.6715	NPC167336
Remote Similarity	0.6646	NPC117032
Remote Similarity	0.6646	NPC471164
Remote Similarity	0.6646	NPC2823
Remote Similarity	0.6645	NPC194562
Remote Similarity	0.6626	NPC144691
Remote Similarity	0.6624	NPC469560
Remote Similarity	0.6582	NPC472243
Remote Similarity	0.6582	NPC315051
Remote Similarity	0.657	NPC472118
Remote Similarity	0.6562	NPC478040
Remote Similarity	0.6558	NPC53044
Remote Similarity	0.6543	NPC478039
Remote Similarity	0.6532	NPC318183
Remote Similarity	0.6522	NPC314186
Remote Similarity	0.6522	NPC470822
Remote Similarity	0.6514	NPC471743
Remote Similarity	0.6497	NPC471123
Remote Similarity	0.6463	NPC237649
Remote Similarity	0.6463	NPC300596
Remote Similarity	0.6452	NPC207428
Remote Similarity	0.6425	NPC470317
Remote Similarity	0.6398	NPC472241
Remote Similarity	0.6386	NPC66936
Remote Similarity	0.6384	NPC157583
Remote Similarity	0.6376	NPC317564
Remote Similarity	0.6375	NPC130251
Remote Similarity	0.6374	NPC469741
Remote Similarity	0.6354	NPC133003
Remote Similarity	0.6351	NPC228515
Remote Similarity	0.6345	NPC187036
Remote Similarity	0.6343	NPC355
Remote Similarity	0.634	NPC322433
Remote Similarity	0.6337	NPC204867
Remote Similarity	0.6335	NPC301760
Remote Similarity	0.6323	NPC187231
Remote Similarity	0.6316	NPC93653
Remote Similarity	0.6299	NPC476950
Remote Similarity	0.6292	NPC237188
Remote Similarity	0.6292	NPC284775
Remote Similarity	0.6286	NPC471943
Remote Similarity	0.6284	NPC192209
Remote Similarity	0.6284	NPC313449
Remote Similarity	0.6282	NPC316746
Remote Similarity	0.628	NPC472242
Remote Similarity	0.6275	NPC79698
Remote Similarity	0.6268	NPC79618
Remote Similarity	0.6267	NPC316582
Remote Similarity	0.6265	NPC242000
Remote Similarity	0.6258	NPC308197
Remote Similarity	0.6257	NPC475094
Remote Similarity	0.625	NPC316906
Remote Similarity	0.625	NPC122553
Remote Similarity	0.6243	NPC113056
Remote Similarity	0.6243	NPC138293
Remote Similarity	0.6235	NPC315348
Remote Similarity	0.6235	NPC29285
Remote Similarity	0.6235	NPC32002
Remote Similarity	0.6235	NPC43477
Remote Similarity	0.6229	NPC63047
Remote Similarity	0.6229	NPC70949
Remote Similarity	0.6229	NPC475248
Remote Similarity	0.6228	NPC473329
Remote Similarity	0.6221	NPC474058
Remote Similarity	0.6221	NPC27904
Remote Similarity	0.6216	NPC324091
Remote Similarity	0.6216	NPC313293
Remote Similarity	0.6215	NPC252572
Remote Similarity	0.6207	NPC471130
Remote Similarity	0.6207	NPC299582
Remote Similarity	0.6203	NPC304203
Remote Similarity	0.6199	NPC222029
Remote Similarity	0.6199	NPC113946
Remote Similarity	0.6194	NPC58827
Remote Similarity	0.6194	NPC72473
Remote Similarity	0.6194	NPC307437
Remote Similarity	0.619	NPC134657
Remote Similarity	0.619	NPC471318
Remote Similarity	0.6185	NPC293458
Remote Similarity	0.6185	NPC88970
Remote Similarity	0.6185	NPC199737
Remote Similarity	0.618	NPC470548
Remote Similarity	0.6178	NPC314098
Remote Similarity	0.6171	NPC214960
Remote Similarity	0.6171	NPC279527
Remote Similarity	0.6167	NPC474041
Remote Similarity	0.6164	NPC253476
Remote Similarity	0.6163	NPC80681
Remote Similarity	0.6163	NPC276085
Remote Similarity	0.6162	NPC473666
Remote Similarity	0.6162	NPC255909
Remote Similarity	0.6154	NPC117027
Remote Similarity	0.6149	NPC288232
Remote Similarity	0.6145	NPC475607
Remote Similarity	0.6141	NPC17273
Remote Similarity	0.6141	NPC141612
Remote Similarity	0.6141	NPC135601
Remote Similarity	0.6139	NPC40364
Remote Similarity	0.6136	NPC473484
Remote Similarity	0.6135	NPC470301
Remote Similarity	0.6133	NPC73994
Remote Similarity	0.6127	NPC473418
Remote Similarity	0.6125	NPC173295
Remote Similarity	0.6122	NPC296163
Remote Similarity	0.6121	NPC130797
Remote Similarity	0.6118	NPC200743
Remote Similarity	0.6118	NPC281094
Remote Similarity	0.6118	NPC475915
Remote Similarity	0.6111	NPC474081
Remote Similarity	0.6111	NPC302790
Remote Similarity	0.6105	NPC123241
Remote Similarity	0.6105	NPC61013
Remote Similarity	0.6105	NPC104345
Remote Similarity	0.6092	NPC476231
Remote Similarity	0.6089	NPC475594
Remote Similarity	0.6087	NPC316141
Remote Similarity	0.6076	NPC126458
Remote Similarity	0.6075	NPC103119
Remote Similarity	0.6071	NPC109787
Remote Similarity	0.6069	NPC154478
Remote Similarity	0.6069	NPC36495
Remote Similarity	0.6069	NPC193410
Remote Similarity	0.6066	NPC159125
Remote Similarity	0.6066	NPC470205
Remote Similarity	0.6061	NPC469537
Remote Similarity	0.6057	NPC271797
Remote Similarity	0.6057	NPC21174
Remote Similarity	0.6048	NPC324445
Remote Similarity	0.6048	NPC470579
Remote Similarity	0.6047	NPC84317
Remote Similarity	0.6047	NPC476464
Remote Similarity	0.6045	NPC223595
Remote Similarity	0.6045	NPC224970
Remote Similarity	0.6045	NPC167724
Remote Similarity	0.6044	NPC475685
Remote Similarity	0.6044	NPC85613
Remote Similarity	0.6042	NPC434
Remote Similarity	0.6038	NPC473962
Remote Similarity	0.6037	NPC22082
Remote Similarity	0.6037	NPC186284
Remote Similarity	0.6037	NPC316202
Remote Similarity	0.6036	NPC102664
Remote Similarity	0.6034	NPC242269
Remote Similarity	0.6034	NPC248117
Remote Similarity	0.6034	NPC225319
Remote Similarity	0.6033	NPC21429
Remote Similarity	0.6033	NPC477003
Remote Similarity	0.6026	NPC252794
Remote Similarity	0.6023	NPC115232
Remote Similarity	0.6023	NPC71132
Remote Similarity	0.6022	NPC234987
Remote Similarity	0.6013	NPC9856
Remote Similarity	0.6011	NPC191415
Remote Similarity	0.6011	NPC116961
Remote Similarity	0.6011	NPC476460
Remote Similarity	0.6	NPC75496
Remote Similarity	0.6	NPC469529
Remote Similarity	0.6	NPC472117
Remote Similarity	0.6	NPC282339
Remote Similarity	0.6	NPC35510
Remote Similarity	0.6	NPC313673
Remote Similarity	0.6	NPC472101
Remote Similarity	0.6	NPC243756
Remote Similarity	0.6	NPC154602

Drug Structure

NPD6513 OpenBabel08211710072D 30 33 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 -1.1625 2.7575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6629 -1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7258 1.9313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7969 -1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6886 -0.3854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1653 2.6828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6629 -0.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2920 1.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9309 -1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2658 1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2440 0.1134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0659 -1.1563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9770 -0.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7989 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9111 0.5895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7331 -0.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5998 0.2041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2686 1.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7969 0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2884 -0.1813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7545 -1.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2948 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9309 -0.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5553 0.4988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4876 -2.2218 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.8667 0.8843 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 -4.7779 1.4738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 6 17 1 0 0 0 0 6 18 1 0 0 0 0 7 20 2 0 0 0 0 8 21 2 0 0 0 0 9 24 2 0 0 0 0 10 25 2 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 22 2 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 23 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 29 1 0 0 0 0 25 29 1 0 0 0 0 26 30 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB000496
DrugBank
ChEMBL
IUPHAR/BPS	7551
PharmaGKB
KEGG Drug
PubChem CID	3947
ChEBI
CAS Number

Drug Properties

Molecular Weight	418.18
ALogP	0.2674
MLogP	3.88
XLogP	7.1
HDA	3
HBD	0
Rotatable Bonds	9
TPSA	23.55
RO5 Violation	1