NPASS drugs

Drug Information

Drug ID:	NPD4022
Drug Name:
Molecular Formula:	C20H24FN3O4
Canonical SMILES:	CNC1CCCN(C1)c1c(F)cc2c(c1OC)n(cc(c2=O)C(=O)O)C1CC1
Standard InCHI:	InChI=1S/C20H24FN3O4/c1-22-11-4-3-7-23(9-11)17-15(21)8-13-16(19(17)28-2)24(12-5-6-12)10-14(18(13)25)20(26)27/h8,10-12,22H,3-7,9H2,1-2H3,(H,26,27)
Standard InCHIKey:	MGQLHRYJBWGORO-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4022

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	250
0.1-0.2	1680
0.2-0.3	7066
0.3-0.4	5756
0.4-0.5	10910
0.5-0.6	4728
0.6-0.7	470
0.7-0.8	27
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
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	0.9267	NPC330683
High Similarity	0.9267	NPC329567
Intermediate Similarity	0.8172	NPC292265
Intermediate Similarity	0.7538	NPC87391
Intermediate Similarity	0.7513	NPC318183
Intermediate Similarity	0.7512	NPC132874
Intermediate Similarity	0.7512	NPC195787
Intermediate Similarity	0.7512	NPC218733
Intermediate Similarity	0.7512	NPC138615
Intermediate Similarity	0.7512	NPC246140
Intermediate Similarity	0.7512	NPC265642
Intermediate Similarity	0.7476	NPC478075
Intermediate Similarity	0.7475	NPC314659
Intermediate Similarity	0.7424	NPC197335
Intermediate Similarity	0.74	NPC316141
Intermediate Similarity	0.7238	NPC469732
Intermediate Similarity	0.7209	NPC474366
Intermediate Similarity	0.7204	NPC1464
Intermediate Similarity	0.7171	NPC5630
Intermediate Similarity	0.715	NPC212123
Intermediate Similarity	0.711	NPC30749
Intermediate Similarity	0.7098	NPC115588
Intermediate Similarity	0.7095	NPC112937
Intermediate Similarity	0.7079	NPC472163
Intermediate Similarity	0.7078	NPC176113
Intermediate Similarity	0.7062	NPC93653
Intermediate Similarity	0.7053	NPC22476
Intermediate Similarity	0.7051	NPC269449
Intermediate Similarity	0.7026	NPC257763
Intermediate Similarity	0.7022	NPC122886
Remote Similarity	0.6995	NPC270301
Remote Similarity	0.6986	NPC305542
Remote Similarity	0.6986	NPC119722
Remote Similarity	0.6983	NPC151171
Remote Similarity	0.6977	NPC87714
Remote Similarity	0.6971	NPC203628
Remote Similarity	0.6967	NPC41488
Remote Similarity	0.6965	NPC8467
Remote Similarity	0.6964	NPC7560
Remote Similarity	0.6955	NPC114468
Remote Similarity	0.6947	NPC19175
Remote Similarity	0.6942	NPC262725
Remote Similarity	0.6941	NPC218303
Remote Similarity	0.6937	NPC126556
Remote Similarity	0.6923	NPC148391
Remote Similarity	0.6919	NPC303214
Remote Similarity	0.6916	NPC232600
Remote Similarity	0.6912	NPC116096
Remote Similarity	0.6911	NPC241392
Remote Similarity	0.6898	NPC475147
Remote Similarity	0.6887	NPC316282
Remote Similarity	0.6886	NPC13249
Remote Similarity	0.6875	NPC222046
Remote Similarity	0.6861	NPC195636
Remote Similarity	0.6854	NPC100863
Remote Similarity	0.6847	NPC2905
Remote Similarity	0.6837	NPC301163
Remote Similarity	0.683	NPC77777
Remote Similarity	0.683	NPC134702
Remote Similarity	0.6824	NPC154922
Remote Similarity	0.6824	NPC291173
Remote Similarity	0.6816	NPC234772
Remote Similarity	0.6814	NPC118189
Remote Similarity	0.6814	NPC76478
Remote Similarity	0.6784	NPC299582
Remote Similarity	0.6773	NPC475133
Remote Similarity	0.677	NPC476069
Remote Similarity	0.6769	NPC285254
Remote Similarity	0.6766	NPC301501
Remote Similarity	0.6765	NPC208522
Remote Similarity	0.6765	NPC127082
Remote Similarity	0.6761	NPC170333
Remote Similarity	0.6757	NPC127996
Remote Similarity	0.6756	NPC182853
Remote Similarity	0.6746	NPC21425
Remote Similarity	0.674	NPC128476
Remote Similarity	0.673	NPC1820
Remote Similarity	0.6726	NPC475609
Remote Similarity	0.6726	NPC268223
Remote Similarity	0.6723	NPC314702
Remote Similarity	0.6699	NPC283810
Remote Similarity	0.6699	NPC85613
Remote Similarity	0.6699	NPC5167
Remote Similarity	0.6696	NPC189661
Remote Similarity	0.6695	NPC139373
Remote Similarity	0.6682	NPC474059
Remote Similarity	0.6681	NPC223242
Remote Similarity	0.6681	NPC113455
Remote Similarity	0.6681	NPC469451
Remote Similarity	0.6681	NPC87560
Remote Similarity	0.6667	NPC313112
Remote Similarity	0.6667	NPC471513
Remote Similarity	0.6667	NPC301292
Remote Similarity	0.6667	NPC469450
Remote Similarity	0.6652	NPC288110
Remote Similarity	0.6649	NPC144691
Remote Similarity	0.6636	NPC469815
Remote Similarity	0.6636	NPC477161
Remote Similarity	0.6636	NPC469816
Remote Similarity	0.6635	NPC470317
Remote Similarity	0.6625	NPC329932
Remote Similarity	0.6624	NPC49547
Remote Similarity	0.662	NPC114039
Remote Similarity	0.662	NPC206109
Remote Similarity	0.6618	NPC166169
Remote Similarity	0.6611	NPC469452
Remote Similarity	0.6609	NPC477397
Remote Similarity	0.6608	NPC184408
Remote Similarity	0.6608	NPC195120
Remote Similarity	0.6607	NPC470482
Remote Similarity	0.6607	NPC470481
Remote Similarity	0.6604	NPC45389
Remote Similarity	0.6603	NPC97584
Remote Similarity	0.66	NPC293458
Remote Similarity	0.6598	NPC120239
Remote Similarity	0.6592	NPC25961
Remote Similarity	0.6591	NPC268077
Remote Similarity	0.6591	NPC133156
Remote Similarity	0.6588	NPC14994
Remote Similarity	0.6568	NPC160113
Remote Similarity	0.6568	NPC476220
Remote Similarity	0.6567	NPC204867
Remote Similarity	0.6562	NPC295479
Remote Similarity	0.6562	NPC220241
Remote Similarity	0.6558	NPC198401
Remote Similarity	0.655	NPC157983
Remote Similarity	0.655	NPC118154
Remote Similarity	0.6545	NPC207971
Remote Similarity	0.6545	NPC41216
Remote Similarity	0.6538	NPC98416
Remote Similarity	0.6537	NPC73280
Remote Similarity	0.6528	NPC125924
Remote Similarity	0.6526	NPC313293
Remote Similarity	0.6524	NPC302235
Remote Similarity	0.6513	NPC131977
Remote Similarity	0.6512	NPC203972
Remote Similarity	0.6509	NPC231924
Remote Similarity	0.6502	NPC472114
Remote Similarity	0.6502	NPC472115
Remote Similarity	0.6502	NPC285192
Remote Similarity	0.6502	NPC127362
Remote Similarity	0.6502	NPC476569
Remote Similarity	0.65	NPC15987
Remote Similarity	0.65	NPC288759
Remote Similarity	0.6496	NPC274640
Remote Similarity	0.6495	NPC28510
Remote Similarity	0.6495	NPC92803
Remote Similarity	0.6492	NPC43477
Remote Similarity	0.6481	NPC476436
Remote Similarity	0.6478	NPC185172
Remote Similarity	0.6476	NPC298449
Remote Similarity	0.6474	NPC319645
Remote Similarity	0.6473	NPC469722
Remote Similarity	0.6473	NPC477395
Remote Similarity	0.6471	NPC224970
Remote Similarity	0.6471	NPC223595
Remote Similarity	0.6471	NPC167724
Remote Similarity	0.6468	NPC71124
Remote Similarity	0.6459	NPC70092
Remote Similarity	0.6458	NPC41501
Remote Similarity	0.6458	NPC304837
Remote Similarity	0.6458	NPC476258
Remote Similarity	0.6457	NPC198160
Remote Similarity	0.6453	NPC257851
Remote Similarity	0.6453	NPC74575
Remote Similarity	0.6453	NPC473458
Remote Similarity	0.645	NPC123241
Remote Similarity	0.645	NPC61013
Remote Similarity	0.6447	NPC314223
Remote Similarity	0.6438	NPC241263
Remote Similarity	0.6432	NPC39500
Remote Similarity	0.6432	NPC148889
Remote Similarity	0.6432	NPC321166
Remote Similarity	0.6422	NPC161804
Remote Similarity	0.6422	NPC470021
Remote Similarity	0.6419	NPC25401
Remote Similarity	0.6418	NPC193410
Remote Similarity	0.6418	NPC36495
Remote Similarity	0.6413	NPC158551
Remote Similarity	0.641	NPC470018
Remote Similarity	0.6407	NPC472099
Remote Similarity	0.6406	NPC230313
Remote Similarity	0.6404	NPC158900
Remote Similarity	0.6402	NPC173295
Remote Similarity	0.6402	NPC18890
Remote Similarity	0.64	NPC477160
Remote Similarity	0.6398	NPC159963
Remote Similarity	0.6393	NPC234933
Remote Similarity	0.639	NPC33507
Remote Similarity	0.639	NPC470971
Remote Similarity	0.6389	NPC226708
Remote Similarity	0.6388	NPC116178
Remote Similarity	0.6386	NPC248117
Remote Similarity	0.6384	NPC222561
Remote Similarity	0.6383	NPC478078
Remote Similarity	0.638	NPC214368
Remote Similarity	0.6378	NPC315829
Remote Similarity	0.6376	NPC470023
Remote Similarity	0.6368	NPC471742
Remote Similarity	0.6368	NPC163829

Drug Structure

NPD4022 OpenBabel08211704332D 30 33 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 3.4641 0.0000 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 -1.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -1.8660 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 -0.0000 2.0000 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 -2.5981 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 3 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 -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 0.8660 1.5000 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 0.8660 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 0.0000 0.0000 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 1.7321 2.0000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 3.4641 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 28 1 0 0 0 0 3 4 1 0 0 0 0 3 7 1 0 0 0 0 4 11 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 12 1 0 0 0 0 7 23 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 24 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 25 2 0 0 0 0 19 28 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 22 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001458
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	65958
ChEBI
CAS Number

Drug Properties

Molecular Weight	389.18
ALogP	-1.8458
MLogP	2.78
XLogP	2.297
HDA	6
HBD	2
Rotatable Bonds	9
TPSA	82.11
RO5 Violation	0