NPASS drugs

Drug Information

Drug ID:	NPD2514
Drug Name:	Bumetanide
Molecular Formula:	C17H20N2O5S
Canonical SMILES:	CCCCNc1cc(cc(c1Oc1ccccc1)S(=O)(=O)N)C(=O)O
Standard InCHI:	InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
Standard InCHIKey:	MAEIEVLCKWDQJH-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2514

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	253
0.1-0.2	1777
0.2-0.3	7601
0.3-0.4	4912
0.4-0.5	8403
0.5-0.6	7705
0.6-0.7	235
0.7-0.8	4
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	0.75	NPC108847
Intermediate Similarity	0.736	NPC315631
Intermediate Similarity	0.7236	NPC474815
Intermediate Similarity	0.7121	NPC73280
Remote Similarity	0.6976	NPC235194
Remote Similarity	0.6931	NPC17760
Remote Similarity	0.6887	NPC314948
Remote Similarity	0.6882	NPC314252
Remote Similarity	0.6856	NPC203424
Remote Similarity	0.6856	NPC206372
Remote Similarity	0.6834	NPC314861
Remote Similarity	0.6829	NPC472163
Remote Similarity	0.6808	NPC478049
Remote Similarity	0.6784	NPC314725
Remote Similarity	0.6784	NPC313375
Remote Similarity	0.6766	NPC471778
Remote Similarity	0.6759	NPC214368
Remote Similarity	0.6683	NPC199737
Remote Similarity	0.6667	NPC288305
Remote Similarity	0.6578	NPC30749
Remote Similarity	0.6575	NPC288759
Remote Similarity	0.6573	NPC475411
Remote Similarity	0.6562	NPC218303
Remote Similarity	0.6555	NPC314659
Remote Similarity	0.655	NPC231862
Remote Similarity	0.6549	NPC176113
Remote Similarity	0.6533	NPC305542
Remote Similarity	0.6524	NPC469829
Remote Similarity	0.6522	NPC9475
Remote Similarity	0.6516	NPC301292
Remote Similarity	0.6516	NPC313112
Remote Similarity	0.6507	NPC197335
Remote Similarity	0.65	NPC15987
Remote Similarity	0.6494	NPC251071
Remote Similarity	0.6488	NPC474814
Remote Similarity	0.6488	NPC112336
Remote Similarity	0.6486	NPC195787
Remote Similarity	0.6486	NPC246140
Remote Similarity	0.6471	NPC154922
Remote Similarity	0.6462	NPC87391
Remote Similarity	0.6457	NPC198160
Remote Similarity	0.6457	NPC212123
Remote Similarity	0.6453	NPC299582
Remote Similarity	0.6444	NPC474366
Remote Similarity	0.6441	NPC87714
Remote Similarity	0.6438	NPC241263
Remote Similarity	0.6436	NPC57105
Remote Similarity	0.6435	NPC471825
Remote Similarity	0.6406	NPC43477
Remote Similarity	0.6406	NPC314113
Remote Similarity	0.6394	NPC8467
Remote Similarity	0.6389	NPC206109
Remote Similarity	0.6389	NPC114039
Remote Similarity	0.6388	NPC116178
Remote Similarity	0.6386	NPC93653
Remote Similarity	0.6375	NPC314702
Remote Similarity	0.6372	NPC25961
Remote Similarity	0.6372	NPC474059
Remote Similarity	0.636	NPC321166
Remote Similarity	0.636	NPC217903
Remote Similarity	0.6355	NPC257763
Remote Similarity	0.6343	NPC1820
Remote Similarity	0.6338	NPC313886
Remote Similarity	0.6337	NPC301163
Remote Similarity	0.6337	NPC113455
Remote Similarity	0.6327	NPC477160
Remote Similarity	0.6323	NPC207971
Remote Similarity	0.6321	NPC469831
Remote Similarity	0.632	NPC182853
Remote Similarity	0.632	NPC134702
Remote Similarity	0.6318	NPC234933
Remote Similarity	0.6313	NPC144691
Remote Similarity	0.6311	NPC470971
Remote Similarity	0.6311	NPC257266
Remote Similarity	0.6309	NPC118189
Remote Similarity	0.6308	NPC262725
Remote Similarity	0.6303	NPC283810
Remote Similarity	0.6303	NPC98416
Remote Similarity	0.6295	NPC473422
Remote Similarity	0.6283	NPC257728
Remote Similarity	0.6281	NPC301501
Remote Similarity	0.627	NPC469451
Remote Similarity	0.6269	NPC181526
Remote Similarity	0.6263	NPC253476
Remote Similarity	0.6262	NPC471652
Remote Similarity	0.6261	NPC148391
Remote Similarity	0.626	NPC120239
Remote Similarity	0.6256	NPC153365
Remote Similarity	0.6255	NPC469450
Remote Similarity	0.625	NPC77777
Remote Similarity	0.6245	NPC13249
Remote Similarity	0.6244	NPC158900
Remote Similarity	0.6239	NPC478075
Remote Similarity	0.6239	NPC193238
Remote Similarity	0.6239	NPC76478
Remote Similarity	0.6234	NPC234772
Remote Similarity	0.6231	NPC214239
Remote Similarity	0.623	NPC173295
Remote Similarity	0.6229	NPC19175
Remote Similarity	0.6226	NPC85613
Remote Similarity	0.6224	NPC476220
Remote Similarity	0.6224	NPC160113
Remote Similarity	0.6223	NPC2596
Remote Similarity	0.6222	NPC268077
Remote Similarity	0.622	NPC329932
Remote Similarity	0.6218	NPC319645
Remote Similarity	0.6218	NPC274640
Remote Similarity	0.6218	NPC238412
Remote Similarity	0.6217	NPC268223
Remote Similarity	0.6214	NPC204179
Remote Similarity	0.6213	NPC148124
Remote Similarity	0.6211	NPC330683
Remote Similarity	0.6211	NPC329567
Remote Similarity	0.6208	NPC139373
Remote Similarity	0.6205	NPC1464
Remote Similarity	0.6204	NPC469722
Remote Similarity	0.6204	NPC469830
Remote Similarity	0.6204	NPC469452
Remote Similarity	0.62	NPC314223
Remote Similarity	0.6198	NPC17160
Remote Similarity	0.6198	NPC313720
Remote Similarity	0.6197	NPC327005
Remote Similarity	0.6197	NPC476069
Remote Similarity	0.6192	NPC223242
Remote Similarity	0.619	NPC298449
Remote Similarity	0.619	NPC189661
Remote Similarity	0.6183	NPC221798
Remote Similarity	0.618	NPC87560
Remote Similarity	0.618	NPC195120
Remote Similarity	0.6179	NPC291609
Remote Similarity	0.6178	NPC266425
Remote Similarity	0.6174	NPC470481
Remote Similarity	0.6174	NPC470482
Remote Similarity	0.617	NPC329830
Remote Similarity	0.617	NPC99724
Remote Similarity	0.6168	NPC470317
Remote Similarity	0.6163	NPC475844
Remote Similarity	0.6154	NPC208522
Remote Similarity	0.615	NPC241392
Remote Similarity	0.615	NPC5167
Remote Similarity	0.6147	NPC114468
Remote Similarity	0.6147	NPC471741
Remote Similarity	0.6147	NPC469437
Remote Similarity	0.6146	NPC470441
Remote Similarity	0.614	NPC207873
Remote Similarity	0.614	NPC100573
Remote Similarity	0.6138	NPC124300
Remote Similarity	0.6137	NPC195636
Remote Similarity	0.613	NPC220241
Remote Similarity	0.613	NPC295479
Remote Similarity	0.6123	NPC477161
Remote Similarity	0.6122	NPC476258
Remote Similarity	0.6122	NPC304837
Remote Similarity	0.6121	NPC270301
Remote Similarity	0.6121	NPC309692
Remote Similarity	0.6121	NPC2905
Remote Similarity	0.6119	NPC22476
Remote Similarity	0.6111	NPC132751
Remote Similarity	0.6109	NPC230313
Remote Similarity	0.6109	NPC243626
Remote Similarity	0.6109	NPC248903
Remote Similarity	0.6107	NPC131977
Remote Similarity	0.6106	NPC182131
Remote Similarity	0.6106	NPC41216
Remote Similarity	0.6103	NPC282087
Remote Similarity	0.6103	NPC318984
Remote Similarity	0.6103	NPC259800
Remote Similarity	0.6103	NPC328137
Remote Similarity	0.6103	NPC241086
Remote Similarity	0.6103	NPC317741
Remote Similarity	0.6103	NPC318028
Remote Similarity	0.6102	NPC128476
Remote Similarity	0.6102	NPC7560
Remote Similarity	0.61	NPC474688
Remote Similarity	0.6099	NPC71124
Remote Similarity	0.6099	NPC100863
Remote Similarity	0.6096	NPC222561
Remote Similarity	0.6095	NPC471648
Remote Similarity	0.6092	NPC231924
Remote Similarity	0.6092	NPC122886
Remote Similarity	0.6087	NPC139506
Remote Similarity	0.6087	NPC292143
Remote Similarity	0.6085	NPC473432
Remote Similarity	0.6083	NPC149571
Remote Similarity	0.6082	NPC151171
Remote Similarity	0.6082	NPC316574
Remote Similarity	0.6081	NPC170333
Remote Similarity	0.6079	NPC133156
Remote Similarity	0.6078	NPC216369
Remote Similarity	0.6078	NPC63370
Remote Similarity	0.6078	NPC36836
Remote Similarity	0.6077	NPC35345
Remote Similarity	0.6076	NPC144452
Remote Similarity	0.6075	NPC69403
Remote Similarity	0.6075	NPC291189
Remote Similarity	0.6073	NPC313293
Remote Similarity	0.607	NPC90185
Remote Similarity	0.6068	NPC306366
Remote Similarity	0.6067	NPC26928
Remote Similarity	0.6067	NPC285254

Drug Structure

NPD2514 OpenBabel08211702172D 29 30 0 0 0 0 0 0 0 0999 V2000 6.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 1.7321 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 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 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 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 9 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 15 2 0 0 0 0 12 17 1 0 0 0 0 13 24 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 21 29 1 0 0 0 0 22 25 2 0 0 0 0 23 25 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000361
DrugBank	DB00887
ChEMBL	CHEMBL1072
IUPHAR/BPS	4837
PharmaGKB	PA448682
KEGG Drug	D00247
PubChem CID	2471
ChEBI	3213
CAS Number	28395-03-1

Drug Properties

Molecular Weight	364.11
ALogP	-2.2639
MLogP	2.45
XLogP	2.926
HDA	6
HBD	3
Rotatable Bonds	11
TPSA	127.1
RO5 Violation	0