NPASS drugs

Drug Information

Drug ID:	NPD3363
Drug Name:
Molecular Formula:	C19H20ClN3O4
Canonical SMILES:	OCCN(CC(=O)N1c2ccc(cc2N=C(c2c1cccc2)O)Cl)CCO
Standard InCHI:	InChI=1S/C19H20ClN3O4/c20-13-5-6-17-15(11-13)21-19(27)14-3-1-2-4-16(14)23(17)18(26)12-22(7-9-24)8-10-25/h1-6,11,24-25H,7-10,12H2,(H,21,27)
Standard InCHIKey:	DDBKYWMANNIJRH-UHFFFAOYSA-N
Max Developmental Stage:	Clinical (unspecified phase)
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD3363

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	200
0.1-0.2	1982
0.2-0.3	10008
0.3-0.4	11626
0.4-0.5	4516
0.5-0.6	2436
0.6-0.7	117
0.7-0.8	5
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	0.7643	NPC325599
Intermediate Similarity	0.7394	NPC254798
Intermediate Similarity	0.7278	NPC471132
Intermediate Similarity	0.7081	NPC184437
Intermediate Similarity	0.7029	NPC88970
Remote Similarity	0.6957	NPC471785
Remote Similarity	0.6949	NPC471130
Remote Similarity	0.6932	NPC191863
Remote Similarity	0.6932	NPC289776
Remote Similarity	0.6932	NPC133470
Remote Similarity	0.6795	NPC317564
Remote Similarity	0.6748	NPC476687
Remote Similarity	0.6748	NPC476689
Remote Similarity	0.6748	NPC476685
Remote Similarity	0.6722	NPC182131
Remote Similarity	0.6708	NPC476950
Remote Similarity	0.6704	NPC189116
Remote Similarity	0.6648	NPC476231
Remote Similarity	0.6626	NPC226662
Remote Similarity	0.6592	NPC27904
Remote Similarity	0.6537	NPC471663
Remote Similarity	0.6514	NPC288445
Remote Similarity	0.6505	NPC471743
Remote Similarity	0.6474	NPC471742
Remote Similarity	0.6458	NPC232872
Remote Similarity	0.6442	NPC250476
Remote Similarity	0.6432	NPC158129
Remote Similarity	0.6425	NPC18890
Remote Similarity	0.6379	NPC470824
Remote Similarity	0.6359	NPC92803
Remote Similarity	0.6337	NPC43477
Remote Similarity	0.6329	NPC147957
Remote Similarity	0.6321	NPC90415
Remote Similarity	0.6275	NPC37584
Remote Similarity	0.6272	NPC313352
Remote Similarity	0.627	NPC472115
Remote Similarity	0.627	NPC472114
Remote Similarity	0.6265	NPC469666
Remote Similarity	0.6264	NPC471122
Remote Similarity	0.6256	NPC323198
Remote Similarity	0.625	NPC476118
Remote Similarity	0.625	NPC211551
Remote Similarity	0.6243	NPC203754
Remote Similarity	0.6243	NPC150048
Remote Similarity	0.6218	NPC470003
Remote Similarity	0.6211	NPC293472
Remote Similarity	0.6198	NPC192270
Remote Similarity	0.619	NPC469938
Remote Similarity	0.619	NPC231382
Remote Similarity	0.618	NPC300596
Remote Similarity	0.618	NPC237649
Remote Similarity	0.6178	NPC256268
Remote Similarity	0.6169	NPC212213
Remote Similarity	0.6168	NPC259098
Remote Similarity	0.6168	NPC197680
Remote Similarity	0.6166	NPC243058
Remote Similarity	0.6166	NPC48938
Remote Similarity	0.6163	NPC287358
Remote Similarity	0.6158	NPC129624
Remote Similarity	0.6158	NPC475607
Remote Similarity	0.6158	NPC134586
Remote Similarity	0.6154	NPC172937
Remote Similarity	0.6154	NPC94167
Remote Similarity	0.615	NPC472540
Remote Similarity	0.615	NPC472539
Remote Similarity	0.615	NPC470787
Remote Similarity	0.6149	NPC470301
Remote Similarity	0.6146	NPC39822
Remote Similarity	0.6141	NPC68650
Remote Similarity	0.6141	NPC320064
Remote Similarity	0.6136	NPC477890
Remote Similarity	0.6134	NPC203635
Remote Similarity	0.6129	NPC471124
Remote Similarity	0.6127	NPC311357
Remote Similarity	0.6126	NPC219848
Remote Similarity	0.6126	NPC211997
Remote Similarity	0.6126	NPC474081
Remote Similarity	0.6125	NPC470544
Remote Similarity	0.612	NPC299594
Remote Similarity	0.612	NPC104345
Remote Similarity	0.6119	NPC472541
Remote Similarity	0.6119	NPC472542
Remote Similarity	0.6108	NPC85651
Remote Similarity	0.6105	NPC475594
Remote Similarity	0.6098	NPC295548
Remote Similarity	0.6094	NPC474041
Remote Similarity	0.6094	NPC475761
Remote Similarity	0.6089	NPC473491
Remote Similarity	0.6087	NPC471155
Remote Similarity	0.6087	NPC470545
Remote Similarity	0.6085	NPC355
Remote Similarity	0.6084	NPC325013
Remote Similarity	0.6078	NPC471944
Remote Similarity	0.6074	NPC316582
Remote Similarity	0.6071	NPC94752
Remote Similarity	0.6069	NPC122553
Remote Similarity	0.6066	NPC141353
Remote Similarity	0.6062	NPC166169
Remote Similarity	0.6062	NPC475685
Remote Similarity	0.6061	NPC471196
Remote Similarity	0.6061	NPC471195
Remote Similarity	0.6058	NPC270241
Remote Similarity	0.6057	NPC22082
Remote Similarity	0.6057	NPC186284
Remote Similarity	0.6054	NPC322644
Remote Similarity	0.6051	NPC302235
Remote Similarity	0.6049	NPC470546
Remote Similarity	0.6049	NPC228515
Remote Similarity	0.6049	NPC220698
Remote Similarity	0.6039	NPC225400
Remote Similarity	0.6038	NPC296163
Remote Similarity	0.6034	NPC471312
Remote Similarity	0.6031	NPC314394
Remote Similarity	0.603	NPC243716
Remote Similarity	0.6021	NPC470548
Remote Similarity	0.6012	NPC469949
Remote Similarity	0.6012	NPC159589
Remote Similarity	0.601	NPC470786
Remote Similarity	0.601	NPC239954
Remote Similarity	0.601	NPC472538
Remote Similarity	0.6	NPC470317
Remote Similarity	0.6	NPC476989
Remote Similarity	0.599	NPC314573
Remote Similarity	0.5989	NPC271734
Remote Similarity	0.5989	NPC313757
Remote Similarity	0.5989	NPC102423
Remote Similarity	0.5989	NPC308197
Remote Similarity	0.5988	NPC192209
Remote Similarity	0.5979	NPC24864
Remote Similarity	0.5979	NPC317430
Remote Similarity	0.5976	NPC476990
Remote Similarity	0.597	NPC198673
Remote Similarity	0.5969	NPC207851
Remote Similarity	0.5969	NPC34508
Remote Similarity	0.5964	NPC283130
Remote Similarity	0.5964	NPC328683
Remote Similarity	0.596	NPC473815
Remote Similarity	0.5959	NPC326575
Remote Similarity	0.5951	NPC470497
Remote Similarity	0.595	NPC117244
Remote Similarity	0.595	NPC129909
Remote Similarity	0.595	NPC473763
Remote Similarity	0.5946	NPC300114
Remote Similarity	0.5944	NPC13470
Remote Similarity	0.5944	NPC212799
Remote Similarity	0.5939	NPC71684
Remote Similarity	0.5939	NPC202521
Remote Similarity	0.5931	NPC473640
Remote Similarity	0.5931	NPC168911
Remote Similarity	0.5928	NPC270009
Remote Similarity	0.5928	NPC133261
Remote Similarity	0.5926	NPC278887
Remote Similarity	0.5926	NPC238430
Remote Similarity	0.5926	NPC300631
Remote Similarity	0.5917	NPC319766
Remote Similarity	0.5915	NPC471741
Remote Similarity	0.5914	NPC84508
Remote Similarity	0.5913	NPC314648
Remote Similarity	0.5912	NPC321617
Remote Similarity	0.5909	NPC472243
Remote Similarity	0.5909	NPC469426
Remote Similarity	0.5909	NPC469427
Remote Similarity	0.5909	NPC214142
Remote Similarity	0.5907	NPC288785
Remote Similarity	0.5904	NPC252878
Remote Similarity	0.59	NPC313293
Remote Similarity	0.5899	NPC60553
Remote Similarity	0.5897	NPC15840
Remote Similarity	0.5897	NPC91179
Remote Similarity	0.5896	NPC474473
Remote Similarity	0.5896	NPC253476
Remote Similarity	0.5895	NPC33507
Remote Similarity	0.5894	NPC33168
Remote Similarity	0.5893	NPC474479
Remote Similarity	0.5893	NPC4974
Remote Similarity	0.5892	NPC315257
Remote Similarity	0.5889	NPC9373
Remote Similarity	0.5886	NPC316906
Remote Similarity	0.5886	NPC29702
Remote Similarity	0.5885	NPC313791
Remote Similarity	0.5882	NPC316282
Remote Similarity	0.5882	NPC131718
Remote Similarity	0.5882	NPC261251
Remote Similarity	0.588	NPC197141
Remote Similarity	0.5876	NPC14325
Remote Similarity	0.5876	NPC28848
Remote Similarity	0.5873	NPC471178
Remote Similarity	0.5872	NPC53044
Remote Similarity	0.587	NPC476268
Remote Similarity	0.5868	NPC6975
Remote Similarity	0.5868	NPC46427
Remote Similarity	0.5867	NPC113626
Remote Similarity	0.5866	NPC314186
Remote Similarity	0.5864	NPC116961
Remote Similarity	0.586	NPC211525
Remote Similarity	0.586	NPC153694
Remote Similarity	0.586	NPC244336
Remote Similarity	0.5859	NPC133591
Remote Similarity	0.5859	NPC307396
Remote Similarity	0.5856	NPC100547

Drug Structure

NPD3363 OpenBabel08211703112D 30 32 0 0 0 0 0 0 0 0999 V2000 3.4888 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0461 -5.3347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6425 -4.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1764 -6.3096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8650 -5.9242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4644 -3.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9944 -1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 -2.9994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 -1.5777 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6869 -4.6545 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1320 -6.6043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8206 -6.2189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1530 -3.2941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 1.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3545 -7.5793 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0431 -7.1939 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1530 1.4922 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 14 2 0 0 0 0 4 16 2 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 8 22 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 23 1 0 0 0 0 18 23 1 0 0 0 0 18 26 2 0 0 0 0 19 21 2 0 0 0 0 19 27 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB006574
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	389.11
ALogP	-1.0349
MLogP	2.67
XLogP	2.08
HDA	7
HBD	3
Rotatable Bonds	11
TPSA	96.6
RO5 Violation	0