NPASS drugs

Drug Information

Drug ID:	NPD4404
Drug Name:	ipragliflozin
Molecular Formula:	C21H21FO5S
Canonical SMILES:	OC[C@H]1O[C@@H](c2ccc(c(c2)Cc2cc3c(s2)cccc3)F)[C@@H]([C@H]([C@@H]1O)O)O
Standard InCHI:	InChI=1S/C21H21FO5S/c22-15-6-5-12(21-20(26)19(25)18(24)16(10-23)27-21)7-13(15)9-14-8-11-3-1-2-4-17(11)28-14/h1-8,16,18-21,23-26H,9-10H2/t16-,18-,19+,20-,21+/m1/s1
Standard InCHIKey:	AHFWIQIYAXSLBA-RQXATKFSSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4404

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	212
0.1-0.2	1060
0.2-0.3	2415
0.3-0.4	8159
0.4-0.5	8710
0.5-0.6	9373
0.6-0.7	958
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	0.7059	NPC301651
Intermediate Similarity	0.7059	NPC473556
Intermediate Similarity	0.7015	NPC265002
Remote Similarity	0.6992	NPC264784
Remote Similarity	0.694	NPC234376
Remote Similarity	0.6917	NPC276061
Remote Similarity	0.6917	NPC474148
Remote Similarity	0.6899	NPC154905
Remote Similarity	0.6899	NPC60373
Remote Similarity	0.687	NPC37714
Remote Similarity	0.687	NPC152384
Remote Similarity	0.6866	NPC30563
Remote Similarity	0.6809	NPC229600
Remote Similarity	0.6794	NPC148060
Remote Similarity	0.6767	NPC277788
Remote Similarity	0.6765	NPC153795
Remote Similarity	0.6765	NPC42911
Remote Similarity	0.6765	NPC290353
Remote Similarity	0.6763	NPC476266
Remote Similarity	0.6692	NPC475086
Remote Similarity	0.669	NPC476033
Remote Similarity	0.6667	NPC473137
Remote Similarity	0.6667	NPC472170
Remote Similarity	0.6667	NPC471064
Remote Similarity	0.6667	NPC473451
Remote Similarity	0.6644	NPC103799
Remote Similarity	0.6643	NPC216605
Remote Similarity	0.6643	NPC266389
Remote Similarity	0.6643	NPC122245
Remote Similarity	0.6623	NPC124085
Remote Similarity	0.6623	NPC117048
Remote Similarity	0.6597	NPC471067
Remote Similarity	0.6594	NPC169616
Remote Similarity	0.6594	NPC120217
Remote Similarity	0.6589	NPC474934
Remote Similarity	0.6579	NPC79957
Remote Similarity	0.6575	NPC79608
Remote Similarity	0.6569	NPC185840
Remote Similarity	0.6567	NPC37115
Remote Similarity	0.6567	NPC472315
Remote Similarity	0.6567	NPC475203
Remote Similarity	0.6567	NPC472316
Remote Similarity	0.6567	NPC474376
Remote Similarity	0.6566	NPC145990
Remote Similarity	0.6558	NPC475836
Remote Similarity	0.6556	NPC85435
Remote Similarity	0.6554	NPC474178
Remote Similarity	0.6554	NPC470084
Remote Similarity	0.6554	NPC245826
Remote Similarity	0.6554	NPC148366
Remote Similarity	0.6554	NPC311293
Remote Similarity	0.6554	NPC252307
Remote Similarity	0.6552	NPC470907
Remote Similarity	0.6552	NPC232454
Remote Similarity	0.6552	NPC178449
Remote Similarity	0.6547	NPC12656
Remote Similarity	0.6541	NPC47286
Remote Similarity	0.6536	NPC262585
Remote Similarity	0.6536	NPC20829
Remote Similarity	0.6536	NPC3049
Remote Similarity	0.6536	NPC18189
Remote Similarity	0.6531	NPC206882
Remote Similarity	0.651	NPC475875
Remote Similarity	0.6507	NPC131747
Remote Similarity	0.6507	NPC257682
Remote Similarity	0.6507	NPC146355
Remote Similarity	0.6494	NPC474687
Remote Similarity	0.649	NPC230219
Remote Similarity	0.6483	NPC174977
Remote Similarity	0.6475	NPC176730
Remote Similarity	0.6475	NPC172525
Remote Similarity	0.6475	NPC123175
Remote Similarity	0.6467	NPC145305
Remote Similarity	0.6467	NPC77040
Remote Similarity	0.6467	NPC92164
Remote Similarity	0.6467	NPC153739
Remote Similarity	0.6467	NPC257582
Remote Similarity	0.6467	NPC187998
Remote Similarity	0.6467	NPC42300
Remote Similarity	0.6467	NPC64201
Remote Similarity	0.6467	NPC174495
Remote Similarity	0.6467	NPC241522
Remote Similarity	0.6467	NPC242807
Remote Similarity	0.6466	NPC469527
Remote Similarity	0.6463	NPC81641
Remote Similarity	0.6458	NPC160854
Remote Similarity	0.6458	NPC201402
Remote Similarity	0.6458	NPC469704
Remote Similarity	0.6458	NPC469703
Remote Similarity	0.6449	NPC308689
Remote Similarity	0.6447	NPC26394
Remote Similarity	0.6446	NPC46067
Remote Similarity	0.6444	NPC136962
Remote Similarity	0.6443	NPC274717
Remote Similarity	0.6443	NPC72529
Remote Similarity	0.6438	NPC138798
Remote Similarity	0.6429	NPC321285
Remote Similarity	0.6429	NPC32356
Remote Similarity	0.6429	NPC263367
Remote Similarity	0.6429	NPC54743
Remote Similarity	0.6429	NPC477939
Remote Similarity	0.6429	NPC177160
Remote Similarity	0.6429	NPC10737
Remote Similarity	0.6429	NPC209985
Remote Similarity	0.6429	NPC156502
Remote Similarity	0.6429	NPC29799
Remote Similarity	0.6424	NPC150011
Remote Similarity	0.6424	NPC476166
Remote Similarity	0.6424	NPC277804
Remote Similarity	0.6424	NPC129784
Remote Similarity	0.6424	NPC196765
Remote Similarity	0.6424	NPC236014
Remote Similarity	0.6424	NPC129106
Remote Similarity	0.6424	NPC280653
Remote Similarity	0.6424	NPC207892
Remote Similarity	0.6424	NPC475067
Remote Similarity	0.6424	NPC162801
Remote Similarity	0.6424	NPC228369
Remote Similarity	0.6424	NPC300875
Remote Similarity	0.6424	NPC268917
Remote Similarity	0.6424	NPC17343
Remote Similarity	0.6424	NPC118114
Remote Similarity	0.6424	NPC12875
Remote Similarity	0.6424	NPC164574
Remote Similarity	0.6424	NPC206224
Remote Similarity	0.6423	NPC306045
Remote Similarity	0.6423	NPC265211
Remote Similarity	0.6418	NPC171831
Remote Similarity	0.6418	NPC280616
Remote Similarity	0.6418	NPC242913
Remote Similarity	0.6414	NPC469686
Remote Similarity	0.6412	NPC262826
Remote Similarity	0.641	NPC55793
Remote Similarity	0.6405	NPC184269
Remote Similarity	0.64	NPC5851
Remote Similarity	0.64	NPC86030
Remote Similarity	0.6389	NPC146673
Remote Similarity	0.6389	NPC233923
Remote Similarity	0.6386	NPC186595
Remote Similarity	0.6383	NPC473507
Remote Similarity	0.6382	NPC201587
Remote Similarity	0.6382	NPC254275
Remote Similarity	0.6382	NPC13005
Remote Similarity	0.6382	NPC253105
Remote Similarity	0.6377	NPC44732
Remote Similarity	0.6376	NPC469687
Remote Similarity	0.637	NPC473871
Remote Similarity	0.637	NPC472919
Remote Similarity	0.637	NPC476142
Remote Similarity	0.637	NPC255026
Remote Similarity	0.637	NPC473870
Remote Similarity	0.6369	NPC100482
Remote Similarity	0.6369	NPC277331
Remote Similarity	0.6364	NPC93783
Remote Similarity	0.6358	NPC143483
Remote Similarity	0.6358	NPC27187
Remote Similarity	0.6358	NPC470225
Remote Similarity	0.6352	NPC217635
Remote Similarity	0.6352	NPC79429
Remote Similarity	0.6352	NPC471667
Remote Similarity	0.6351	NPC278552
Remote Similarity	0.6351	NPC167571
Remote Similarity	0.6351	NPC207179
Remote Similarity	0.6346	NPC156376
Remote Similarity	0.6345	NPC470414
Remote Similarity	0.6343	NPC234305
Remote Similarity	0.6343	NPC472172
Remote Similarity	0.634	NPC263064
Remote Similarity	0.634	NPC92805
Remote Similarity	0.6338	NPC175771
Remote Similarity	0.6333	NPC11258
Remote Similarity	0.6333	NPC282703
Remote Similarity	0.6333	NPC87224
Remote Similarity	0.6333	NPC301857
Remote Similarity	0.6333	NPC21867
Remote Similarity	0.6333	NPC128208
Remote Similarity	0.6333	NPC222572
Remote Similarity	0.6333	NPC184733
Remote Similarity	0.6333	NPC45774
Remote Similarity	0.6333	NPC129570
Remote Similarity	0.6331	NPC111108
Remote Similarity	0.6324	NPC135464
Remote Similarity	0.6324	NPC92623
Remote Similarity	0.6323	NPC77861
Remote Similarity	0.6323	NPC470802
Remote Similarity	0.632	NPC148231
Remote Similarity	0.6319	NPC85059
Remote Similarity	0.6319	NPC121866
Remote Similarity	0.6319	NPC238582
Remote Similarity	0.6316	NPC40432
Remote Similarity	0.6316	NPC158079
Remote Similarity	0.6316	NPC27843
Remote Similarity	0.6316	NPC7171
Remote Similarity	0.6316	NPC478255
Remote Similarity	0.6316	NPC161557
Remote Similarity	0.6316	NPC271945
Remote Similarity	0.6316	NPC228346
Remote Similarity	0.6316	NPC115207
Remote Similarity	0.6316	NPC181497
Remote Similarity	0.6312	NPC181615

Drug Structure

NPD4404 OpenBabel08211705262D 32 35 0 0 1 0 0 0 0 0999 V2000 6.9128 3.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 3.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9128 1.8364 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 1.7321 3.0000 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 4.4347 2.4945 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 -0.8660 -1.5000 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 0.8660 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 4.3301 1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 F 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 5.2437 1.0933 0.0000 S 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 -2.5981 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 11 2 0 0 0 0 4 17 2 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 13 15 2 0 0 0 0 14 28 1 0 0 0 0 15 22 1 0 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 21 12 1 6 0 0 0 21 27 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNCL002834
DrugBank
ChEMBL
IUPHAR/BPS	9394
PharmaGKB
KEGG Drug
PubChem CID	57339444
ChEBI
CAS Number

Drug Properties

Molecular Weight	404.11
ALogP	-0.8442
MLogP	3
XLogP	3.568
HDA	5
HBD	4
Rotatable Bonds	9
TPSA	118.39
RO5 Violation	0