NPASS drugs

Drug Information

Drug ID:	NPD3853
Drug Name:
Molecular Formula:	C20H20ClN3O3
Canonical SMILES:	COc1ccc(cc1)n1nc(cc1c1ccc(cc1)Cl)CCC(=O)N(O)C
Standard InCHI:	InChI=1S/C20H20ClN3O3/c1-23(26)20(25)12-7-16-13-19(14-3-5-15(21)6-4-14)24(22-16)17-8-10-18(27-2)11-9-17/h3-6,8-11,13,26H,7,12H2,1-2H3
Standard InCHIKey:	XYKWNRUXCOIMFZ-UHFFFAOYSA-N
Max Developmental Stage:	Clinical (unspecified phase)
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD3853

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	359
0.1-0.2	2566
0.2-0.3	10089
0.3-0.4	5326
0.4-0.5	9659
0.5-0.6	2281
0.6-0.7	604
0.7-0.8	5
0.8-0.85	0
0.85-0.9	1
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
High Similarity	0.8723	NPC471593
Intermediate Similarity	0.7292	NPC177404
Intermediate Similarity	0.7209	NPC471304
Intermediate Similarity	0.7135	NPC26850
Intermediate Similarity	0.7068	NPC26872
Intermediate Similarity	0.7064	NPC472098
Remote Similarity	0.6982	NPC96321
Remote Similarity	0.6961	NPC176127
Remote Similarity	0.696	NPC157931
Remote Similarity	0.6944	NPC45190
Remote Similarity	0.6944	NPC300156
Remote Similarity	0.692	NPC323969
Remote Similarity	0.6915	NPC312872
Remote Similarity	0.6906	NPC303658
Remote Similarity	0.6905	NPC307963
Remote Similarity	0.6887	NPC267928
Remote Similarity	0.6863	NPC168486
Remote Similarity	0.6863	NPC222592
Remote Similarity	0.6861	NPC305984
Remote Similarity	0.6856	NPC311906
Remote Similarity	0.6842	NPC76748
Remote Similarity	0.6835	NPC193238
Remote Similarity	0.6812	NPC257851
Remote Similarity	0.681	NPC92111
Remote Similarity	0.6806	NPC295898
Remote Similarity	0.6804	NPC82548
Remote Similarity	0.6794	NPC296527
Remote Similarity	0.6791	NPC329793
Remote Similarity	0.6786	NPC477887
Remote Similarity	0.6779	NPC204385
Remote Similarity	0.6774	NPC223427
Remote Similarity	0.6771	NPC16066
Remote Similarity	0.677	NPC472099
Remote Similarity	0.6757	NPC264176
Remote Similarity	0.6756	NPC473041
Remote Similarity	0.6748	NPC206201
Remote Similarity	0.6742	NPC269367
Remote Similarity	0.6741	NPC148183
Remote Similarity	0.6741	NPC152768
Remote Similarity	0.6739	NPC478078
Remote Similarity	0.6738	NPC323198
Remote Similarity	0.6737	NPC475816
Remote Similarity	0.6726	NPC151781
Remote Similarity	0.6726	NPC316181
Remote Similarity	0.6726	NPC74562
Remote Similarity	0.6714	NPC131017
Remote Similarity	0.6712	NPC472111
Remote Similarity	0.6711	NPC216612
Remote Similarity	0.671	NPC315822
Remote Similarity	0.671	NPC471762
Remote Similarity	0.671	NPC66777
Remote Similarity	0.6697	NPC475774
Remote Similarity	0.6696	NPC128115
Remote Similarity	0.6695	NPC474192
Remote Similarity	0.6695	NPC475720
Remote Similarity	0.6683	NPC283152
Remote Similarity	0.6683	NPC84478
Remote Similarity	0.6683	NPC477888
Remote Similarity	0.6682	NPC321428
Remote Similarity	0.6682	NPC53344
Remote Similarity	0.6682	NPC251090
Remote Similarity	0.6682	NPC194967
Remote Similarity	0.6682	NPC249583
Remote Similarity	0.6682	NPC4687
Remote Similarity	0.6667	NPC280799
Remote Similarity	0.6667	NPC470020
Remote Similarity	0.6667	NPC60621
Remote Similarity	0.6652	NPC266931
Remote Similarity	0.6652	NPC476465
Remote Similarity	0.6652	NPC287208
Remote Similarity	0.6651	NPC243834
Remote Similarity	0.6651	NPC70956
Remote Similarity	0.6651	NPC282103
Remote Similarity	0.665	NPC118511
Remote Similarity	0.6638	NPC194740
Remote Similarity	0.6637	NPC87413
Remote Similarity	0.6636	NPC323345
Remote Similarity	0.6636	NPC470164
Remote Similarity	0.6636	NPC176538
Remote Similarity	0.6636	NPC329747
Remote Similarity	0.6622	NPC174672
Remote Similarity	0.6621	NPC162484
Remote Similarity	0.662	NPC127085
Remote Similarity	0.6619	NPC194040
Remote Similarity	0.6609	NPC322482
Remote Similarity	0.6608	NPC46561
Remote Similarity	0.6606	NPC193777
Remote Similarity	0.6605	NPC472193
Remote Similarity	0.6596	NPC180504
Remote Similarity	0.6596	NPC141053
Remote Similarity	0.6593	NPC469928
Remote Similarity	0.659	NPC280714
Remote Similarity	0.659	NPC287437
Remote Similarity	0.6588	NPC66083
Remote Similarity	0.6578	NPC478074
Remote Similarity	0.6575	NPC199277
Remote Similarity	0.6575	NPC135887
Remote Similarity	0.6562	NPC187501
Remote Similarity	0.6562	NPC208284
Remote Similarity	0.6558	NPC276517
Remote Similarity	0.6557	NPC242928
Remote Similarity	0.6553	NPC84347
Remote Similarity	0.655	NPC150239
Remote Similarity	0.6547	NPC174758
Remote Similarity	0.6544	NPC72211
Remote Similarity	0.6542	NPC195268
Remote Similarity	0.6542	NPC72905
Remote Similarity	0.6542	NPC133140
Remote Similarity	0.6533	NPC308137
Remote Similarity	0.6533	NPC310211
Remote Similarity	0.6532	NPC270918
Remote Similarity	0.652	NPC274982
Remote Similarity	0.6516	NPC264166
Remote Similarity	0.6516	NPC165349
Remote Similarity	0.6516	NPC285558
Remote Similarity	0.6516	NPC118832
Remote Similarity	0.6516	NPC329708
Remote Similarity	0.6516	NPC47059
Remote Similarity	0.6516	NPC274291
Remote Similarity	0.6514	NPC18487
Remote Similarity	0.6513	NPC240384
Remote Similarity	0.6513	NPC184680
Remote Similarity	0.6511	NPC300114
Remote Similarity	0.6509	NPC473449
Remote Similarity	0.6507	NPC298436
Remote Similarity	0.6507	NPC474798
Remote Similarity	0.6504	NPC39500
Remote Similarity	0.6504	NPC236668
Remote Similarity	0.6502	NPC475910
Remote Similarity	0.65	NPC477066
Remote Similarity	0.6491	NPC169402
Remote Similarity	0.6489	NPC146418
Remote Similarity	0.6488	NPC121658
Remote Similarity	0.6488	NPC14651
Remote Similarity	0.6485	NPC474183
Remote Similarity	0.6485	NPC470785
Remote Similarity	0.6485	NPC470784
Remote Similarity	0.6484	NPC19872
Remote Similarity	0.6484	NPC121772
Remote Similarity	0.6483	NPC196718
Remote Similarity	0.6483	NPC473186
Remote Similarity	0.6478	NPC225279
Remote Similarity	0.6476	NPC146976
Remote Similarity	0.6476	NPC116238
Remote Similarity	0.6473	NPC478081
Remote Similarity	0.6473	NPC473540
Remote Similarity	0.6473	NPC477067
Remote Similarity	0.6473	NPC56618
Remote Similarity	0.6473	NPC288943
Remote Similarity	0.6473	NPC469589
Remote Similarity	0.6473	NPC478082
Remote Similarity	0.6471	NPC476098
Remote Similarity	0.6468	NPC285635
Remote Similarity	0.6465	NPC99666
Remote Similarity	0.6463	NPC247803
Remote Similarity	0.6463	NPC184408
Remote Similarity	0.646	NPC94157
Remote Similarity	0.6459	NPC271792
Remote Similarity	0.6452	NPC13880
Remote Similarity	0.6452	NPC70259
Remote Similarity	0.645	NPC198503
Remote Similarity	0.6447	NPC322064
Remote Similarity	0.6446	NPC142385
Remote Similarity	0.6445	NPC62069
Remote Similarity	0.6444	NPC477589
Remote Similarity	0.6444	NPC477587
Remote Similarity	0.6441	NPC210256
Remote Similarity	0.6441	NPC119006
Remote Similarity	0.6439	NPC476518
Remote Similarity	0.6438	NPC128823
Remote Similarity	0.6438	NPC97746
Remote Similarity	0.6438	NPC476578
Remote Similarity	0.6438	NPC4071
Remote Similarity	0.6438	NPC21638
Remote Similarity	0.6438	NPC476582
Remote Similarity	0.6435	NPC79293
Remote Similarity	0.6435	NPC475190
Remote Similarity	0.6435	NPC279401
Remote Similarity	0.6429	NPC39370
Remote Similarity	0.6429	NPC41382
Remote Similarity	0.6429	NPC39679
Remote Similarity	0.6429	NPC253675
Remote Similarity	0.6425	NPC291535
Remote Similarity	0.6425	NPC475085
Remote Similarity	0.6425	NPC475112
Remote Similarity	0.6423	NPC137353
Remote Similarity	0.6422	NPC144452
Remote Similarity	0.6422	NPC280272
Remote Similarity	0.6416	NPC9894
Remote Similarity	0.6414	NPC102593
Remote Similarity	0.6411	NPC88363
Remote Similarity	0.6411	NPC472168
Remote Similarity	0.6409	NPC45459
Remote Similarity	0.6409	NPC213308
Remote Similarity	0.6409	NPC234197
Remote Similarity	0.6409	NPC315491
Remote Similarity	0.6409	NPC477019
Remote Similarity	0.6407	NPC174760
Remote Similarity	0.6406	NPC43787
Remote Similarity	0.6406	NPC198401

Drug Structure

NPD3853 OpenBabel08211704332D 28 30 0 0 0 0 0 0 0 0999 V2000 -0.2739 -4.5430 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 0.3783 2.0540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0725 1.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5862 3.0322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2804 2.6720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4894 -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 -0.8660 1.5000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9016 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1215 1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5373 3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3084 -3.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7452 4.3193 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7206 -4.6476 0.0000 N 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 2.3029 -3.9431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1273 -5.5611 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 0.5395 -6.3701 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 27 1 0 0 0 0 3 5 1 0 0 0 0 3 14 2 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 16 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 20 1 0 0 0 0 13 16 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 22 24 1 0 0 0 0 23 26 1 0 0 0 0 26 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC001330; DNC001423
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	59757
ChEBI
CAS Number

Drug Properties

Molecular Weight	385.12
ALogP	0.0033
MLogP	2.89
XLogP	3.748
HDA	3
HBD	1
Rotatable Bonds	11
TPSA	67.07
RO5 Violation	0