NPASS drugs

Drug Information

Drug ID:	NPD5663
Drug Name:	apadoline
Molecular Formula:	C23H29N3OS
Canonical SMILES:	CCCN=C(c1ccc2c(c1)N([C@@H](CN1CCCC1)C)c1c(S2)cccc1)O
Standard InCHI:	InChI=1S/C23H29N3OS/c1-3-12-24-23(27)18-10-11-22-20(15-18)26(17(2)16-25-13-6-7-14-25)19-8-4-5-9-21(19)28-22/h4-5,8-11,15,17H,3,6-7,12-14,16H2,1-2H3,(H,24,27)/t17-/m1/s1
Standard InCHIKey:	KXMAIWXPZGQNCR-QGZVFWFLSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD5663

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	265
0.1-0.2	2207
0.2-0.3	10019
0.3-0.4	11409
0.4-0.5	4199
0.5-0.6	2620
0.6-0.7	166
0.7-0.8	5
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	0.7584	NPC473417
Intermediate Similarity	0.75	NPC184437
Intermediate Similarity	0.7188	NPC471741
Intermediate Similarity	0.7105	NPC476950
Intermediate Similarity	0.7012	NPC321617
Remote Similarity	0.6923	NPC476687
Remote Similarity	0.6923	NPC476685
Remote Similarity	0.6923	NPC476689
Remote Similarity	0.6867	NPC288445
Remote Similarity	0.6829	NPC470824
Remote Similarity	0.6747	NPC254798
Remote Similarity	0.6705	NPC476231
Remote Similarity	0.6688	NPC226662
Remote Similarity	0.6667	NPC476118
Remote Similarity	0.6648	NPC471743
Remote Similarity	0.66	NPC147957
Remote Similarity	0.6573	NPC158129
Remote Similarity	0.6554	NPC317430
Remote Similarity	0.6552	NPC27904
Remote Similarity	0.6549	NPC291610
Remote Similarity	0.6536	NPC471294
Remote Similarity	0.651	NPC296163
Remote Similarity	0.6453	NPC471132
Remote Similarity	0.6447	NPC192209
Remote Similarity	0.6441	NPC471130
Remote Similarity	0.6424	NPC243162
Remote Similarity	0.642	NPC59779
Remote Similarity	0.642	NPC471177
Remote Similarity	0.642	NPC124542
Remote Similarity	0.642	NPC85651
Remote Similarity	0.6404	NPC98187
Remote Similarity	0.6378	NPC143325
Remote Similarity	0.6374	NPC203754
Remote Similarity	0.6374	NPC150048
Remote Similarity	0.6374	NPC134586
Remote Similarity	0.6364	NPC255229
Remote Similarity	0.6364	NPC81229
Remote Similarity	0.6359	NPC168486
Remote Similarity	0.6359	NPC249662
Remote Similarity	0.6359	NPC222592
Remote Similarity	0.6345	NPC328877
Remote Similarity	0.6344	NPC471742
Remote Similarity	0.6344	NPC472294
Remote Similarity	0.6339	NPC326575
Remote Similarity	0.6339	NPC211997
Remote Similarity	0.6328	NPC289776
Remote Similarity	0.6328	NPC88970
Remote Similarity	0.6328	NPC133470
Remote Similarity	0.6328	NPC191863
Remote Similarity	0.6327	NPC37584
Remote Similarity	0.6313	NPC472115
Remote Similarity	0.6313	NPC472114
Remote Similarity	0.631	NPC88121
Remote Similarity	0.6299	NPC264580
Remote Similarity	0.6294	NPC472100
Remote Similarity	0.6291	NPC187036
Remote Similarity	0.629	NPC19679
Remote Similarity	0.629	NPC243058
Remote Similarity	0.6286	NPC141353
Remote Similarity	0.6271	NPC131718
Remote Similarity	0.6264	NPC472123
Remote Similarity	0.6264	NPC313791
Remote Similarity	0.6257	NPC471178
Remote Similarity	0.6257	NPC203635
Remote Similarity	0.625	NPC129721
Remote Similarity	0.625	NPC478079
Remote Similarity	0.6224	NPC249040
Remote Similarity	0.6221	NPC237649
Remote Similarity	0.6221	NPC300596
Remote Similarity	0.6216	NPC133261
Remote Similarity	0.6215	NPC471122
Remote Similarity	0.6213	NPC60553
Remote Similarity	0.6207	NPC193370
Remote Similarity	0.6199	NPC264589
Remote Similarity	0.6196	NPC472122
Remote Similarity	0.6196	NPC24594
Remote Similarity	0.619	NPC90415
Remote Similarity	0.619	NPC211551
Remote Similarity	0.6181	NPC475070
Remote Similarity	0.6178	NPC475915
Remote Similarity	0.6176	NPC472103
Remote Similarity	0.6162	NPC219848
Remote Similarity	0.6159	NPC324611
Remote Similarity	0.6158	NPC124636
Remote Similarity	0.6154	NPC33168
Remote Similarity	0.6141	NPC189812
Remote Similarity	0.6141	NPC329688
Remote Similarity	0.6139	NPC109151
Remote Similarity	0.6138	NPC476319
Remote Similarity	0.6138	NPC49051
Remote Similarity	0.6133	NPC278887
Remote Similarity	0.6133	NPC292758
Remote Similarity	0.6133	NPC65855
Remote Similarity	0.6129	NPC256268
Remote Similarity	0.6129	NPC313449
Remote Similarity	0.6124	NPC84508
Remote Similarity	0.6124	NPC216221
Remote Similarity	0.6117	NPC470317
Remote Similarity	0.6117	NPC48938
Remote Similarity	0.6114	NPC324149
Remote Similarity	0.6111	NPC102423
Remote Similarity	0.6111	NPC212125
Remote Similarity	0.6111	NPC159319
Remote Similarity	0.6111	NPC471313
Remote Similarity	0.6111	NPC471311
Remote Similarity	0.6108	NPC121903
Remote Similarity	0.6104	NPC288232
Remote Similarity	0.6103	NPC472193
Remote Similarity	0.6102	NPC315257
Remote Similarity	0.6096	NPC187827
Remote Similarity	0.6096	NPC15840
Remote Similarity	0.6096	NPC472105
Remote Similarity	0.6095	NPC22082
Remote Similarity	0.6095	NPC186284
Remote Similarity	0.6094	NPC95783
Remote Similarity	0.6092	NPC37548
Remote Similarity	0.6087	NPC34508
Remote Similarity	0.6087	NPC259545
Remote Similarity	0.6082	NPC20144
Remote Similarity	0.6082	NPC320863
Remote Similarity	0.608	NPC161108
Remote Similarity	0.6077	NPC77022
Remote Similarity	0.6077	NPC471124
Remote Similarity	0.6075	NPC248454
Remote Similarity	0.607	NPC475841
Remote Similarity	0.607	NPC474145
Remote Similarity	0.6069	NPC13470
Remote Similarity	0.6067	NPC211525
Remote Similarity	0.6067	NPC302790
Remote Similarity	0.6067	NPC153694
Remote Similarity	0.6059	NPC476116
Remote Similarity	0.6056	NPC47298
Remote Similarity	0.6056	NPC315214
Remote Similarity	0.6054	NPC469938
Remote Similarity	0.6054	NPC178681
Remote Similarity	0.6051	NPC195314
Remote Similarity	0.6047	NPC83790
Remote Similarity	0.6047	NPC128237
Remote Similarity	0.6043	NPC232340
Remote Similarity	0.6042	NPC188104
Remote Similarity	0.6041	NPC474916
Remote Similarity	0.6036	NPC472243
Remote Similarity	0.6032	NPC139291
Remote Similarity	0.6032	NPC472108
Remote Similarity	0.6032	NPC133306
Remote Similarity	0.6032	NPC472110
Remote Similarity	0.6032	NPC472109
Remote Similarity	0.6023	NPC471680
Remote Similarity	0.6022	NPC32028
Remote Similarity	0.6022	NPC189116
Remote Similarity	0.6021	NPC478077
Remote Similarity	0.6021	NPC314573
Remote Similarity	0.602	NPC472540
Remote Similarity	0.602	NPC470787
Remote Similarity	0.602	NPC472539
Remote Similarity	0.6012	NPC197680
Remote Similarity	0.6012	NPC259098
Remote Similarity	0.6012	NPC278451
Remote Similarity	0.6011	NPC44161
Remote Similarity	0.6011	NPC285469
Remote Similarity	0.6011	NPC33507
Remote Similarity	0.6011	NPC24990
Remote Similarity	0.601	NPC32200
Remote Similarity	0.601	NPC66699
Remote Similarity	0.6	NPC314113
Remote Similarity	0.6	NPC88097
Remote Similarity	0.6	NPC187951
Remote Similarity	0.6	NPC470003
Remote Similarity	0.6	NPC468984
Remote Similarity	0.6	NPC477185
Remote Similarity	0.6	NPC104483
Remote Similarity	0.599	NPC238242
Remote Similarity	0.599	NPC472541
Remote Similarity	0.599	NPC472542
Remote Similarity	0.599	NPC472111
Remote Similarity	0.5989	NPC477187
Remote Similarity	0.5989	NPC469763
Remote Similarity	0.5989	NPC469786
Remote Similarity	0.5989	NPC259644
Remote Similarity	0.5989	NPC469765
Remote Similarity	0.5989	NPC73952
Remote Similarity	0.5989	NPC25008
Remote Similarity	0.5989	NPC469760
Remote Similarity	0.5989	NPC293472
Remote Similarity	0.5988	NPC477890
Remote Similarity	0.5981	NPC149014
Remote Similarity	0.598	NPC469589
Remote Similarity	0.5979	NPC314394
Remote Similarity	0.5979	NPC113626
Remote Similarity	0.5978	NPC91895
Remote Similarity	0.5978	NPC288430
Remote Similarity	0.5978	NPC194411
Remote Similarity	0.5978	NPC469428
Remote Similarity	0.5976	NPC9856
Remote Similarity	0.5969	NPC15102
Remote Similarity	0.5967	NPC199737
Remote Similarity	0.5966	NPC33421
Remote Similarity	0.5964	NPC256893
Remote Similarity	0.5961	NPC53344
Remote Similarity	0.5961	NPC175916

Drug Structure

NPD5663 OpenBabel08211708292D 29 32 0 0 1 0 0 0 0 0999 V2000 -0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 19 2 0 0 0 0 9 21 2 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 25 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 2 1 1 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 28 1 0 0 0 0 22 28 1 0 0 0 0 23 24 2 3 0 0 0 23 27 1 0 0 0 0 27 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB010393
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	395.20
ALogP	-0.4542
MLogP	3.44
XLogP	5.195
HDA	4
HBD	1
Rotatable Bonds	9
TPSA	64.37
RO5 Violation	1