NPASS drugs

Drug Information

Drug ID:	NPD5445
Drug Name:	Bentiromide
Molecular Formula:	C23H20N2O5
Canonical SMILES:	O=C([C@@H](N=C(c1ccccc1)O)Cc1ccc(cc1)O)Nc1ccc(cc1)C(=O)O
Standard InCHI:	InChI=1S/C23H20N2O5/c26-19-12-6-15(7-13-19)14-20(25-21(27)16-4-2-1-3-5-16)22(28)24-18-10-8-17(9-11-18)23(29)30/h1-13,20,26H,14H2,(H,24,28)(H,25,27)(H,29,30)/t20-/m0/s1
Standard InCHIKey:	SPPTWHFVYKCNNK-FQEVSTJZSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5445

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	226
0.1-0.2	1365
0.2-0.3	6319
0.3-0.4	6023
0.4-0.5	9320
0.5-0.6	6434
0.6-0.7	1126
0.7-0.8	77
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	0.7791	NPC242933
Intermediate Similarity	0.7701	NPC191863
Intermediate Similarity	0.7701	NPC133470
Intermediate Similarity	0.7701	NPC289776
Intermediate Similarity	0.75	NPC199737
Intermediate Similarity	0.7485	NPC144691
Intermediate Similarity	0.7458	NPC189116
Intermediate Similarity	0.7301	NPC314098
Intermediate Similarity	0.7291	NPC322064
Intermediate Similarity	0.7286	NPC39679
Intermediate Similarity	0.7278	NPC472241
Intermediate Similarity	0.7267	NPC315829
Intermediate Similarity	0.7253	NPC474814
Intermediate Similarity	0.7253	NPC112336
Intermediate Similarity	0.7251	NPC472242
Intermediate Similarity	0.7243	NPC474815
Intermediate Similarity	0.7239	NPC325651
Intermediate Similarity	0.7236	NPC270918
Intermediate Similarity	0.7225	NPC203628
Intermediate Similarity	0.7225	NPC92803
Intermediate Similarity	0.7219	NPC470317
Intermediate Similarity	0.7211	NPC18890
Intermediate Similarity	0.7202	NPC238412
Intermediate Similarity	0.7198	NPC471778
Intermediate Similarity	0.7181	NPC471742
Intermediate Similarity	0.7179	NPC306376
Intermediate Similarity	0.7174	NPC328611
Intermediate Similarity	0.7167	NPC223207
Intermediate Similarity	0.7165	NPC303214
Intermediate Similarity	0.716	NPC472243
Intermediate Similarity	0.7143	NPC287358
Intermediate Similarity	0.7135	NPC196243
Intermediate Similarity	0.7127	NPC290755
Intermediate Similarity	0.7127	NPC471771
Intermediate Similarity	0.7127	NPC304074
Intermediate Similarity	0.7127	NPC471130
Intermediate Similarity	0.7126	NPC237649
Intermediate Similarity	0.7126	NPC300596
Intermediate Similarity	0.7111	NPC88970
Intermediate Similarity	0.711	NPC478039
Intermediate Similarity	0.7108	NPC244866
Intermediate Similarity	0.7108	NPC250448
Intermediate Similarity	0.7105	NPC150308
Intermediate Similarity	0.7099	NPC205946
Intermediate Similarity	0.7097	NPC14849
Intermediate Similarity	0.7094	NPC87413
Intermediate Similarity	0.7094	NPC23294
Intermediate Similarity	0.7083	NPC313293
Intermediate Similarity	0.7083	NPC5630
Intermediate Similarity	0.7076	NPC301702
Intermediate Similarity	0.7071	NPC471944
Intermediate Similarity	0.7071	NPC232600
Intermediate Similarity	0.7069	NPC254798
Intermediate Similarity	0.7059	NPC194671
Intermediate Similarity	0.7059	NPC147298
Intermediate Similarity	0.7059	NPC182057
Intermediate Similarity	0.7059	NPC131450
Intermediate Similarity	0.7059	NPC269750
Intermediate Similarity	0.7049	NPC66490
Intermediate Similarity	0.7044	NPC303951
Intermediate Similarity	0.7043	NPC471743
Intermediate Similarity	0.7039	NPC3207
Intermediate Similarity	0.703	NPC210828
Intermediate Similarity	0.703	NPC86834
Intermediate Similarity	0.7027	NPC73280
Intermediate Similarity	0.7021	NPC39822
Intermediate Similarity	0.7018	NPC43477
Intermediate Similarity	0.7017	NPC475983
Intermediate Similarity	0.7011	NPC146370
Intermediate Similarity	0.7011	NPC198254
Intermediate Similarity	0.7011	NPC274198
Intermediate Similarity	0.7005	NPC472284
Intermediate Similarity	0.7	NPC220851
Intermediate Similarity	0.7	NPC150323
Intermediate Similarity	0.7	NPC103250
Intermediate Similarity	0.7	NPC476098
Intermediate Similarity	0.7	NPC469243
Remote Similarity	0.699	NPC298449
Remote Similarity	0.6989	NPC279871
Remote Similarity	0.6989	NPC233702
Remote Similarity	0.6989	NPC248862
Remote Similarity	0.6981	NPC24370
Remote Similarity	0.6981	NPC319232
Remote Similarity	0.6981	NPC214142
Remote Similarity	0.6978	NPC204867
Remote Similarity	0.6977	NPC132329
Remote Similarity	0.6974	NPC45850
Remote Similarity	0.6973	NPC89831
Remote Similarity	0.6967	NPC51388
Remote Similarity	0.6963	NPC235194
Remote Similarity	0.6963	NPC241025
Remote Similarity	0.6961	NPC27904
Remote Similarity	0.6957	NPC330009
Remote Similarity	0.6954	NPC119569
Remote Similarity	0.6954	NPC16188
Remote Similarity	0.6948	NPC304307
Remote Similarity	0.6948	NPC118559
Remote Similarity	0.6948	NPC261251
Remote Similarity	0.6948	NPC34580
Remote Similarity	0.6948	NPC124920
Remote Similarity	0.6946	NPC326966
Remote Similarity	0.6946	NPC257390
Remote Similarity	0.6944	NPC284888
Remote Similarity	0.6942	NPC471741
Remote Similarity	0.6927	NPC9894
Remote Similarity	0.6919	NPC276506
Remote Similarity	0.6919	NPC478141
Remote Similarity	0.6916	NPC100547
Remote Similarity	0.6916	NPC194740
Remote Similarity	0.6915	NPC9475
Remote Similarity	0.6911	NPC294951
Remote Similarity	0.6908	NPC118228
Remote Similarity	0.6906	NPC475544
Remote Similarity	0.6905	NPC174760
Remote Similarity	0.6902	NPC182131
Remote Similarity	0.6902	NPC328649
Remote Similarity	0.6898	NPC303225
Remote Similarity	0.6897	NPC473804
Remote Similarity	0.6897	NPC4687
Remote Similarity	0.6895	NPC288305
Remote Similarity	0.6893	NPC241392
Remote Similarity	0.6891	NPC473815
Remote Similarity	0.6886	NPC120251
Remote Similarity	0.6884	NPC223409
Remote Similarity	0.6884	NPC95240
Remote Similarity	0.6884	NPC322135
Remote Similarity	0.6882	NPC292265
Remote Similarity	0.6879	NPC13696
Remote Similarity	0.6869	NPC74153
Remote Similarity	0.6869	NPC473814
Remote Similarity	0.6869	NPC78767
Remote Similarity	0.6865	NPC315388
Remote Similarity	0.6864	NPC474473
Remote Similarity	0.6864	NPC253476
Remote Similarity	0.6853	NPC276517
Remote Similarity	0.6852	NPC14288
Remote Similarity	0.6845	NPC306804
Remote Similarity	0.6842	NPC293151
Remote Similarity	0.6842	NPC313694
Remote Similarity	0.6842	NPC242159
Remote Similarity	0.6842	NPC271792
Remote Similarity	0.6842	NPC27041
Remote Similarity	0.6832	NPC473460
Remote Similarity	0.6829	NPC325297
Remote Similarity	0.6826	NPC472245
Remote Similarity	0.6825	NPC150239
Remote Similarity	0.6824	NPC473360
Remote Similarity	0.682	NPC54803
Remote Similarity	0.682	NPC321592
Remote Similarity	0.6814	NPC222561
Remote Similarity	0.6814	NPC283117
Remote Similarity	0.6814	NPC471155
Remote Similarity	0.681	NPC264285
Remote Similarity	0.681	NPC27581
Remote Similarity	0.6809	NPC159767
Remote Similarity	0.6809	NPC158277
Remote Similarity	0.6809	NPC155506
Remote Similarity	0.6809	NPC165285
Remote Similarity	0.6804	NPC206186
Remote Similarity	0.6802	NPC48202
Remote Similarity	0.68	NPC314186
Remote Similarity	0.68	NPC323798
Remote Similarity	0.6798	NPC473422
Remote Similarity	0.6796	NPC309845
Remote Similarity	0.6794	NPC74969
Remote Similarity	0.6794	NPC469928
Remote Similarity	0.6793	NPC139506
Remote Similarity	0.6793	NPC292143
Remote Similarity	0.6793	NPC63931
Remote Similarity	0.6791	NPC318183
Remote Similarity	0.6791	NPC469671
Remote Similarity	0.6791	NPC126676
Remote Similarity	0.6789	NPC323198
Remote Similarity	0.6789	NPC474041
Remote Similarity	0.6789	NPC323752
Remote Similarity	0.6786	NPC22476
Remote Similarity	0.6784	NPC6913
Remote Similarity	0.6784	NPC141454
Remote Similarity	0.678	NPC270241
Remote Similarity	0.6778	NPC473580
Remote Similarity	0.6774	NPC470971
Remote Similarity	0.6774	NPC474701
Remote Similarity	0.6771	NPC471785
Remote Similarity	0.6769	NPC183805
Remote Similarity	0.6768	NPC93390
Remote Similarity	0.6768	NPC146724
Remote Similarity	0.6766	NPC150863
Remote Similarity	0.6765	NPC225400
Remote Similarity	0.6765	NPC472287
Remote Similarity	0.6765	NPC300156
Remote Similarity	0.6765	NPC472286
Remote Similarity	0.6763	NPC314252
Remote Similarity	0.6763	NPC294375
Remote Similarity	0.6763	NPC47986
Remote Similarity	0.6762	NPC169402
Remote Similarity	0.6762	NPC126556
Remote Similarity	0.676	NPC202198
Remote Similarity	0.6759	NPC274640
Remote Similarity	0.6758	NPC33064
Remote Similarity	0.6758	NPC245055

Drug Structure

NPD5445 OpenBabel08211708292D 34 36 0 0 1 0 0 0 0 0999 V2000 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -1.5000 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 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 N 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 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 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 3.4641 -5.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 5 2 0 0 0 0 4 16 2 0 0 0 0 5 16 1 0 0 0 0 6 12 1 0 0 0 0 6 15 2 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 17 2 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 14 1 6 0 0 0 20 22 1 0 0 0 0 20 25 1 0 0 0 0 21 25 2 3 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 23 30 2 0 0 0 0 24 31 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB013892
DrugBank	DB00522
ChEMBL	CHEMBL1200368
IUPHAR/BPS
PharmaGKB	PA164750572
KEGG Drug	D01346
PubChem CID
ChEBI	31263
CAS Number	37106-97-1

Drug Properties

Molecular Weight	404.14
ALogP	-1.5112
MLogP	3.22
XLogP	5.15
HDA	6
HBD	4
Rotatable Bonds	11
TPSA	119.22
RO5 Violation	1