NPASS drugs

Drug Information

Drug ID:	NPD5886
Drug Name:	Canagliflozin
Molecular Formula:	C24H25FO5S
Canonical SMILES:	OC[C@H]1O[C@@H](c2ccc(c(c2)Cc2ccc(s2)c2ccc(cc2)F)C)[C@@H]([C@H]([C@@H]1O)O)O
Standard InCHI:	InChI=1S/C24H25FO5S/c1-13-2-3-15(24-23(29)22(28)21(27)19(12-26)30-24)10-16(13)11-18-8-9-20(31-18)14-4-6-17(25)7-5-14/h2-10,19,21-24,26-29H,11-12H2,1H3/t19-,21-,22+,23-,24+/m1/s1
Standard InCHIKey:	XTNGUQKDFGDXSJ-ZXGKGEBGSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5886

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	209
0.1-0.2	1035
0.2-0.3	2152
0.3-0.4	6740
0.4-0.5	9431
0.5-0.6	9857
0.6-0.7	1463
0.7-0.8	3
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	0.7209	NPC154905
Intermediate Similarity	0.7209	NPC60373
Intermediate Similarity	0.7132	NPC169616
Remote Similarity	0.6901	NPC233923
Remote Similarity	0.6901	NPC146673
Remote Similarity	0.6861	NPC111108
Remote Similarity	0.6857	NPC473556
Remote Similarity	0.6857	NPC301651
Remote Similarity	0.6831	NPC238582
Remote Similarity	0.6812	NPC265002
Remote Similarity	0.6809	NPC476266
Remote Similarity	0.6788	NPC30563
Remote Similarity	0.6788	NPC264784
Remote Similarity	0.6765	NPC149455
Remote Similarity	0.6765	NPC64642
Remote Similarity	0.6765	NPC472982
Remote Similarity	0.6757	NPC469386
Remote Similarity	0.6739	NPC234376
Remote Similarity	0.6738	NPC472862
Remote Similarity	0.6715	NPC474148
Remote Similarity	0.6715	NPC276061
Remote Similarity	0.6712	NPC307139
Remote Similarity	0.6711	NPC471064
Remote Similarity	0.6711	NPC148366
Remote Similarity	0.6711	NPC311293
Remote Similarity	0.6707	NPC145990
Remote Similarity	0.6689	NPC78575
Remote Similarity	0.6689	NPC5486
Remote Similarity	0.6687	NPC474442
Remote Similarity	0.6667	NPC221318
Remote Similarity	0.6667	NPC152384
Remote Similarity	0.6667	NPC37714
Remote Similarity	0.6667	NPC124085
Remote Similarity	0.6667	NPC471942
Remote Similarity	0.6667	NPC117048
Remote Similarity	0.6646	NPC258083
Remote Similarity	0.6645	NPC59239
Remote Similarity	0.6644	NPC473870
Remote Similarity	0.6644	NPC473871
Remote Similarity	0.6643	NPC254233
Remote Similarity	0.6642	NPC19856
Remote Similarity	0.6625	NPC215678
Remote Similarity	0.6625	NPC274454
Remote Similarity	0.6623	NPC11089
Remote Similarity	0.6622	NPC124030
Remote Similarity	0.6621	NPC229600
Remote Similarity	0.6618	NPC475086
Remote Similarity	0.6603	NPC475836
Remote Similarity	0.6601	NPC85435
Remote Similarity	0.66	NPC470084
Remote Similarity	0.6599	NPC473451
Remote Similarity	0.6596	NPC473137
Remote Similarity	0.6596	NPC12656
Remote Similarity	0.6593	NPC148060
Remote Similarity	0.6589	NPC128645
Remote Similarity	0.6584	NPC174251
Remote Similarity	0.6584	NPC153182
Remote Similarity	0.6582	NPC186033
Remote Similarity	0.6581	NPC18189
Remote Similarity	0.6581	NPC262585
Remote Similarity	0.6581	NPC20829
Remote Similarity	0.6581	NPC3049
Remote Similarity	0.6579	NPC312341
Remote Similarity	0.6579	NPC103799
Remote Similarity	0.6577	NPC206882
Remote Similarity	0.6575	NPC473889
Remote Similarity	0.6571	NPC290353
Remote Similarity	0.6571	NPC153795
Remote Similarity	0.6571	NPC42911
Remote Similarity	0.6569	NPC27252
Remote Similarity	0.6569	NPC472980
Remote Similarity	0.6569	NPC472979
Remote Similarity	0.6569	NPC277788
Remote Similarity	0.6559	NPC473803
Remote Similarity	0.6556	NPC475875
Remote Similarity	0.6544	NPC243601
Remote Similarity	0.6544	NPC471133
Remote Similarity	0.6538	NPC474687
Remote Similarity	0.6536	NPC230219
Remote Similarity	0.6533	NPC471077
Remote Similarity	0.6531	NPC182333
Remote Similarity	0.6531	NPC273336
Remote Similarity	0.6525	NPC123175
Remote Similarity	0.6525	NPC176730
Remote Similarity	0.6519	NPC265075
Remote Similarity	0.6516	NPC79957
Remote Similarity	0.6515	NPC474934
Remote Similarity	0.6513	NPC145305
Remote Similarity	0.6513	NPC99795
Remote Similarity	0.6513	NPC174495
Remote Similarity	0.6513	NPC241522
Remote Similarity	0.6513	NPC187998
Remote Similarity	0.6513	NPC42300
Remote Similarity	0.6513	NPC153739
Remote Similarity	0.6513	NPC64201
Remote Similarity	0.6513	NPC92164
Remote Similarity	0.6513	NPC77040
Remote Similarity	0.6513	NPC196193
Remote Similarity	0.6513	NPC257582
Remote Similarity	0.6513	NPC242807
Remote Similarity	0.6513	NPC470727
Remote Similarity	0.651	NPC81641
Remote Similarity	0.651	NPC470158
Remote Similarity	0.651	NPC475933
Remote Similarity	0.651	NPC476033
Remote Similarity	0.6507	NPC470414
Remote Similarity	0.6497	NPC275592
Remote Similarity	0.6497	NPC476643
Remote Similarity	0.6497	NPC183781
Remote Similarity	0.6497	NPC100913
Remote Similarity	0.6496	NPC472316
Remote Similarity	0.6496	NPC475203
Remote Similarity	0.6496	NPC472315
Remote Similarity	0.6496	NPC474376
Remote Similarity	0.6494	NPC26394
Remote Similarity	0.6493	NPC245927
Remote Similarity	0.6493	NPC289117
Remote Similarity	0.649	NPC245826
Remote Similarity	0.649	NPC252307
Remote Similarity	0.649	NPC474178
Remote Similarity	0.6486	NPC77691
Remote Similarity	0.6483	NPC121866
Remote Similarity	0.6481	NPC474397
Remote Similarity	0.6475	NPC273837
Remote Similarity	0.6474	NPC54743
Remote Similarity	0.6474	NPC177160
Remote Similarity	0.6474	NPC126101
Remote Similarity	0.6474	NPC263367
Remote Similarity	0.6474	NPC10737
Remote Similarity	0.6474	NPC327735
Remote Similarity	0.6474	NPC477939
Remote Similarity	0.6474	NPC29799
Remote Similarity	0.6474	NPC156502
Remote Similarity	0.6474	NPC209985
Remote Similarity	0.6471	NPC129106
Remote Similarity	0.6471	NPC268917
Remote Similarity	0.6471	NPC164574
Remote Similarity	0.6471	NPC476166
Remote Similarity	0.6471	NPC277804
Remote Similarity	0.6471	NPC129784
Remote Similarity	0.6471	NPC118114
Remote Similarity	0.6471	NPC300875
Remote Similarity	0.6471	NPC206224
Remote Similarity	0.6471	NPC12875
Remote Similarity	0.6471	NPC207892
Remote Similarity	0.6471	NPC472170
Remote Similarity	0.6471	NPC280653
Remote Similarity	0.6471	NPC162801
Remote Similarity	0.6471	NPC228369
Remote Similarity	0.6471	NPC236014
Remote Similarity	0.6471	NPC150011
Remote Similarity	0.6471	NPC196765
Remote Similarity	0.6471	NPC315794
Remote Similarity	0.6471	NPC17343
Remote Similarity	0.6467	NPC253681
Remote Similarity	0.6467	NPC476972
Remote Similarity	0.6467	NPC476971
Remote Similarity	0.6467	NPC470724
Remote Similarity	0.6463	NPC85059
Remote Similarity	0.6458	NPC45794
Remote Similarity	0.6458	NPC122245
Remote Similarity	0.6458	NPC216605
Remote Similarity	0.6458	NPC266389
Remote Similarity	0.6456	NPC118080
Remote Similarity	0.6456	NPC472576
Remote Similarity	0.6456	NPC308768
Remote Similarity	0.6456	NPC97947
Remote Similarity	0.6456	NPC291599
Remote Similarity	0.6456	NPC27377
Remote Similarity	0.6456	NPC12668
Remote Similarity	0.6456	NPC41481
Remote Similarity	0.6456	NPC87448
Remote Similarity	0.6452	NPC184269
Remote Similarity	0.6452	NPC311256
Remote Similarity	0.6447	NPC27712
Remote Similarity	0.6443	NPC131747
Remote Similarity	0.6443	NPC146355
Remote Similarity	0.6443	NPC257682
Remote Similarity	0.6438	NPC103916
Remote Similarity	0.6438	NPC475122
Remote Similarity	0.6438	NPC241951
Remote Similarity	0.6438	NPC471139
Remote Similarity	0.6438	NPC475759
Remote Similarity	0.6438	NPC470152
Remote Similarity	0.6433	NPC266006
Remote Similarity	0.6429	NPC228843
Remote Similarity	0.6429	NPC13005
Remote Similarity	0.6424	NPC186889
Remote Similarity	0.642	NPC233980
Remote Similarity	0.6419	NPC471067
Remote Similarity	0.6419	NPC174977
Remote Similarity	0.6415	NPC76871
Remote Similarity	0.6414	NPC329980
Remote Similarity	0.641	NPC93783
Remote Similarity	0.641	NPC309056
Remote Similarity	0.6408	NPC120217
Remote Similarity	0.6405	NPC27187
Remote Similarity	0.6405	NPC143483
Remote Similarity	0.6405	NPC470225
Remote Similarity	0.64	NPC79608

Drug Structure

NPD5886 OpenBabel08211708292D 35 38 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6801 2.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0978 2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0868 3.1341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5045 3.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 0.3364 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 -4.3301 -0.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6856 2.1160 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4990 3.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2788 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9058 4.8566 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 0.9945 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 3 2 0 0 0 0 2 13 1 0 0 0 0 3 15 1 0 0 0 0 4 6 1 0 0 0 0 4 14 2 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 20 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 26 1 0 0 0 0 13 16 2 0 0 0 0 14 20 1 0 0 0 0 17 25 1 0 0 0 0 18 31 1 0 0 0 0 19 12 1 6 0 0 0 19 21 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 6 0 0 0 23 24 1 0 0 0 0 23 29 1 1 0 0 0 24 15 1 6 0 0 0 24 30 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL001169; DNCL002839
DrugBank	DB08907
ChEMBL	CHEMBL2048484
IUPHAR/BPS	4582
PharmaGKB
KEGG Drug	D09592
PubChem CID	24812758
ChEBI	73274
CAS Number	842133-18-0

Drug Properties

Molecular Weight	444.14
ALogP	-0.2022
MLogP	3.33
XLogP	5.034
HDA	5
HBD	4
Rotatable Bonds	11
TPSA	118.39
RO5 Violation	1