NPASS drugs

Drug Information

Drug ID:	NPD8296
Drug Name:	Digoxin
Molecular Formula:	C41H64O14
Canonical SMILES:	O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)[C@H](O)C[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O)O
Standard InCHI:	"InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1"
Standard InCHIKey:	LTMHDMANZUZIPE-PUGKRICDSA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD8296

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	58441
0.1-0.2	131268
0.2-0.3	20761
0.3-0.4	631
0.4-0.5	326
0.5-0.6	131
0.6-0.7	33
0.7-0.8	18
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	7

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC312977
High Similarity	1.0	NPC173555
High Similarity	1.0	NPC60091
High Similarity	1.0	NPC236993
High Similarity	1.0	NPC535419
High Similarity	1.0	NPC561796
High Similarity	1.0	NPC611686
Intermediate Similarity	0.8395	NPC72260
Intermediate Similarity	0.8395	NPC71838
Intermediate Similarity	0.8395	NPC531292
Intermediate Similarity	0.8395	NPC564438
Intermediate Similarity	0.8395	NPC611742
Intermediate Similarity	0.8235	NPC97027
Intermediate Similarity	0.8235	NPC208193
Intermediate Similarity	0.8235	NPC611890
Intermediate Similarity	0.8193	NPC147543
Intermediate Similarity	0.8171	NPC574959
Intermediate Similarity	0.8171	NPC596953
Intermediate Similarity	0.7667	NPC183529
Intermediate Similarity	0.7634	NPC307150
Intermediate Similarity	0.7634	NPC117445
Intermediate Similarity	0.7634	NPC60450
Intermediate Similarity	0.7634	NPC308262
Intermediate Similarity	0.7634	NPC264741
Intermediate Similarity	0.7634	NPC292379
Intermediate Similarity	0.7634	NPC611633
Intermediate Similarity	0.7619	NPC193893
Intermediate Similarity	0.7619	NPC4949
Intermediate Similarity	0.7619	NPC585498
Intermediate Similarity	0.7531	NPC471633
Intermediate Similarity	0.732	NPC537701
Intermediate Similarity	0.7033	NPC222736
Intermediate Similarity	0.7033	NPC41586
Intermediate Similarity	0.7033	NPC118715
Intermediate Similarity	0.7033	NPC198909
Intermediate Similarity	0.7033	NPC149410
Remote Similarity	0.6923	NPC253997
Remote Similarity	0.6897	NPC197872
Remote Similarity	0.6897	NPC179412
Remote Similarity	0.6897	NPC471356
Remote Similarity	0.6897	NPC471353
Remote Similarity	0.6774	NPC138125
Remote Similarity	0.6742	NPC146787
Remote Similarity	0.6667	NPC55532
Remote Similarity	0.6465	NPC120390
Remote Similarity	0.6465	NPC74259
Remote Similarity	0.6465	NPC146414
Remote Similarity	0.6465	NPC203375
Remote Similarity	0.6465	NPC58848
Remote Similarity	0.6429	NPC475590
Remote Similarity	0.6383	NPC93973
Remote Similarity	0.6383	NPC543980
Remote Similarity	0.6337	NPC308492
Remote Similarity	0.6322	NPC64235
Remote Similarity	0.6322	NPC99620
Remote Similarity	0.6322	NPC473852
Remote Similarity	0.6322	NPC571074
Remote Similarity	0.6322	NPC579794
Remote Similarity	0.6277	NPC581084
Remote Similarity	0.619	NPC55777
Remote Similarity	0.6186	NPC4192
Remote Similarity	0.6146	NPC125077
Remote Similarity	0.61	NPC586189
Remote Similarity	0.6061	NPC475219
Remote Similarity	0.6061	NPC562580
Remote Similarity	0.6044	NPC77319
Remote Similarity	0.6044	NPC471351
Remote Similarity	0.6044	NPC471355
Remote Similarity	0.6044	NPC568691
Remote Similarity	0.5978	NPC9499
Remote Similarity	0.5978	NPC471360
Remote Similarity	0.5978	NPC469751
Remote Similarity	0.5978	NPC63703
Remote Similarity	0.5978	NPC471361
Remote Similarity	0.5978	NPC86159
Remote Similarity	0.5978	NPC469752
Remote Similarity	0.5978	NPC310768
Remote Similarity	0.5978	NPC469754
Remote Similarity	0.5978	NPC302930
Remote Similarity	0.5978	NPC70542
Remote Similarity	0.5978	NPC511665
Remote Similarity	0.5978	NPC579803
Remote Similarity	0.5934	NPC84949
Remote Similarity	0.5934	NPC277628
Remote Similarity	0.5934	NPC480562
Remote Similarity	0.5934	NPC74945
Remote Similarity	0.5934	NPC31354
Remote Similarity	0.5934	NPC69576
Remote Similarity	0.5934	NPC143797
Remote Similarity	0.5934	NPC174052
Remote Similarity	0.5926	NPC189588
Remote Similarity	0.5926	NPC558927
Remote Similarity	0.5926	NPC600289
Remote Similarity	0.5914	NPC471354
Remote Similarity	0.5914	NPC27507
Remote Similarity	0.5882	NPC172644
Remote Similarity	0.5882	NPC28024
Remote Similarity	0.5882	NPC60056
Remote Similarity	0.5882	NPC242031
Remote Similarity	0.5882	NPC295558
Remote Similarity	0.5843	NPC474418
Remote Similarity	0.5842	NPC539423
Remote Similarity	0.5833	NPC236973
Remote Similarity	0.5833	NPC143842
Remote Similarity	0.5833	NPC587232
Remote Similarity	0.5824	NPC5311
Remote Similarity	0.5824	NPC505575
Remote Similarity	0.5789	NPC233712
Remote Similarity	0.5758	NPC304259
Remote Similarity	0.5758	NPC2509
Remote Similarity	0.5758	NPC74221
Remote Similarity	0.5758	NPC549357
Remote Similarity	0.5714	NPC288328
Remote Similarity	0.5714	NPC139489
Remote Similarity	0.5714	NPC197963
Remote Similarity	0.5714	NPC16920
Remote Similarity	0.5714	NPC94659
Remote Similarity	0.5714	NPC93361
Remote Similarity	0.5714	NPC73483
Remote Similarity	0.5714	NPC234796
Remote Similarity	0.5714	NPC27613
Remote Similarity	0.5714	NPC101638
Remote Similarity	0.5714	NPC59541
Remote Similarity	0.5714	NPC294540
Remote Similarity	0.5714	NPC528731
Remote Similarity	0.5714	NPC534493
Remote Similarity	0.5714	NPC552261
Remote Similarity	0.5714	NPC576313
Remote Similarity	0.5657	NPC486143
Remote Similarity	0.5657	NPC190120
Remote Similarity	0.5657	NPC486142
Remote Similarity	0.5657	NPC115721
Remote Similarity	0.5657	NPC486149
Remote Similarity	0.5652	NPC469750
Remote Similarity	0.5652	NPC210121
Remote Similarity	0.5652	NPC57795
Remote Similarity	0.5652	NPC95062
Remote Similarity	0.5652	NPC106071
Remote Similarity	0.5652	NPC509241
Remote Similarity	0.5652	NPC560725
Remote Similarity	0.5652	NPC597833
Remote Similarity	0.5648	NPC53288
Remote Similarity	0.5638	NPC471359
Remote Similarity	0.5638	NPC93883
Remote Similarity	0.5607	NPC566190
Remote Similarity	0.5591	NPC199428
Remote Similarity	0.5591	NPC81423
Remote Similarity	0.5591	NPC112630
Remote Similarity	0.5591	NPC109448
Remote Similarity	0.5591	NPC76572
Remote Similarity	0.5591	NPC310341
Remote Similarity	0.5591	NPC253568
Remote Similarity	0.5591	NPC193382
Remote Similarity	0.5591	NPC149375
Remote Similarity	0.5591	NPC271482
Remote Similarity	0.5591	NPC497390
Remote Similarity	0.5591	NPC503503
Remote Similarity	0.5591	NPC511596
Remote Similarity	0.5591	NPC552901
Remote Similarity	0.5591	NPC570645
Remote Similarity	0.5591	NPC583210
Remote Similarity	0.5591	NPC607739
Remote Similarity	0.5579	NPC70897
Remote Similarity	0.5579	NPC138660
Remote Similarity	0.5556	NPC255569
Remote Similarity	0.5545	NPC579251
Remote Similarity	0.5529	NPC196471
Remote Similarity	0.5474	NPC484202
Remote Similarity	0.5474	NPC216693
Remote Similarity	0.5474	NPC208343
Remote Similarity	0.5474	NPC196134
Remote Similarity	0.5474	NPC135733
Remote Similarity	0.5474	NPC260365
Remote Similarity	0.5474	NPC558996
Remote Similarity	0.5474	NPC570813
Remote Similarity	0.5474	NPC592129
Remote Similarity	0.5472	NPC474908
Remote Similarity	0.5463	NPC474423
Remote Similarity	0.5455	NPC475556
Remote Similarity	0.5455	NPC311706
Remote Similarity	0.5455	NPC609198
Remote Similarity	0.5446	NPC563540
Remote Similarity	0.5417	NPC469753
Remote Similarity	0.5417	NPC550636
Remote Similarity	0.5408	NPC79068
Remote Similarity	0.5408	NPC30483
Remote Similarity	0.5408	NPC470897
Remote Similarity	0.5408	NPC513498
Remote Similarity	0.5402	NPC475030
Remote Similarity	0.5402	NPC287241
Remote Similarity	0.5392	NPC105339
Remote Similarity	0.5392	NPC184044
Remote Similarity	0.5392	NPC486146
Remote Similarity	0.5392	NPC170291
Remote Similarity	0.5392	NPC596281
Remote Similarity	0.5377	NPC259960
Remote Similarity	0.5377	NPC475419
Remote Similarity	0.5377	NPC227900
Remote Similarity	0.5376	NPC196429
Remote Similarity	0.5368	NPC263072

Drug Structure

NPD8296 OpenBabel08211713002D 61 68 0 0 1 0 0 0 0 0999 V2000 3.5880 -7.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4471 -0.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1017 -5.7140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3665 3.5005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3007 6.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0118 3.5516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8039 4.5298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7824 1.5442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6449 7.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5745 2.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2327 6.6260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1151 8.7137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4766 1.9044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1586 4.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7348 -7.9793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4061 -1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1277 -3.7066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0662 7.4047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6369 -7.3613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4960 -0.7722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3586 -5.0449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1151 7.7137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2687 2.8825 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7334 1.2352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6939 7.1260 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8528 4.8388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1097 4.1697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4780 -8.6484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6630 -2.0593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3356 -4.6848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0493 5.4568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0662 9.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1982 -0.4121 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9427 -7.0012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8233 -3.3976 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4290 -8.3394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2881 -1.7503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4075 -5.3539 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3176 3.1915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6939 6.1260 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6449 5.8169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2701 -9.6266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8709 -3.0375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2867 -4.9938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0003 5.7658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3752 9.9738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1722 -9.0086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6540 8.2137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8938 -6.6921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2471 -0.1030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5665 -4.0667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9413 0.2571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1996 -6.3320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0312 -2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0132 -10.2957 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1277 -3.7066 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4946 -5.9719 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2082 6.7440 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9643 -9.9867 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5 40 1 0 0 0 0 6 7 1 0 0 0 0 6 23 1 0 0 0 0 7 26 1 0 0 0 0 8 10 1 0 0 0 0 8 24 1 0 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 39 1 0 0 0 0 11 41 1 0 0 0 0 12 22 2 0 0 0 0 12 32 1 0 0 0 0 13 23 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 14 31 1 0 0 0 0 15 28 1 0 0 0 0 15 34 1 0 0 0 0 16 29 1 0 0 0 0 16 33 1 0 0 0 0 17 30 1 0 0 0 0 17 35 1 0 0 0 0 18 22 1 0 0 0 0 18 49 1 0 0 0 0 19 1 1 6 0 0 0 19 36 1 0 0 0 0 19 50 1 0 0 0 0 20 2 1 6 0 0 0 20 37 1 0 0 0 0 20 51 1 0 0 0 0 21 3 1 6 0 0 0 21 38 1 0 0 0 0 21 52 1 0 0 0 0 22 25 1 0 0 0 0 23 39 1 1 0 0 0 24 53 1 6 0 0 0 25 40 1 6 0 0 0 26 27 1 0 0 0 0 26 41 1 1 0 0 0 27 39 1 6 0 0 0 28 36 1 0 0 0 0 28 42 1 1 0 0 0 29 37 1 0 0 0 0 29 43 1 1 0 0 0 30 38 1 0 0 0 0 30 44 1 1 0 0 0 31 40 1 6 0 0 0 31 45 1 0 0 0 0 32 46 2 0 0 0 0 32 49 1 0 0 0 0 33 51 1 0 0 0 0 33 53 1 6 0 0 0 34 50 1 0 0 0 0 34 54 1 6 0 0 0 35 52 1 0 0 0 0 35 55 1 6 0 0 0 36 47 1 1 0 0 0 37 55 1 1 0 0 0 38 54 1 1 0 0 0 39 4 1 6 0 0 0 40 41 1 6 0 0 0 41 48 1 6 0 0 0 42 56 1 0 0 0 0 43 57 1 0 0 0 0 44 58 1 0 0 0 0 45 59 1 0 0 0 0 47 60 1 0 0 0 0 48 61 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000744
DrugBank	DB00390
ChEMBL	CHEMBL1751
IUPHAR/BPS	4726
PharmaGKB	PA449319
KEGG Drug	D00298
PubChem CID	2724385
ChEBI	4551
CAS Number	20830-75-5

Drug Properties

Molecular Weight	780.43
ALogP	-3.6782
MLogP	4.43
XLogP	2.174
HDA	14
HBD	6
Rotatable Bonds	18
TPSA	203.06
RO5 Violation	2