NPASS drugs

Drug Information

Drug ID:	NPD4989
Drug Name:	Bradanicline
Molecular Formula:	C22H23N3O2
Canonical SMILES:	OC(=N[C@@H]1C2CCN([C@H]1Cc1cccnc1)CC2)c1cc2c(o1)cccc2
Standard InCHI:	InChI=1S/C22H23N3O2/c26-22(20-13-17-5-1-2-6-19(17)27-20)24-21-16-7-10-25(11-8-16)18(21)12-15-4-3-9-23-14-15/h1-6,9,13-14,16,18,21H,7-8,10-12H2,(H,24,26)/t18-,21+/m0/s1
Standard InCHIKey:	OXKRFEWMSWPKKV-GHTZIAJQSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4989

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	329
0.1-0.2	1592
0.2-0.3	7624
0.3-0.4	4799
0.4-0.5	8068
0.5-0.6	7257
0.6-0.7	1115
0.7-0.8	106
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	0.7595	NPC258048
Intermediate Similarity	0.7542	NPC328928
Intermediate Similarity	0.7523	NPC193238
Intermediate Similarity	0.7489	NPC471004
Intermediate Similarity	0.7436	NPC124542
Intermediate Similarity	0.7436	NPC475533
Intermediate Similarity	0.7436	NPC59779
Intermediate Similarity	0.7436	NPC471177
Intermediate Similarity	0.743	NPC274291
Intermediate Similarity	0.743	NPC264166
Intermediate Similarity	0.743	NPC47059
Intermediate Similarity	0.743	NPC118832
Intermediate Similarity	0.743	NPC165349
Intermediate Similarity	0.743	NPC329708
Intermediate Similarity	0.7425	NPC75179
Intermediate Similarity	0.7414	NPC210296
Intermediate Similarity	0.7404	NPC324619
Intermediate Similarity	0.7404	NPC475315
Intermediate Similarity	0.7397	NPC236668
Intermediate Similarity	0.7366	NPC216612
Intermediate Similarity	0.7364	NPC326930
Intermediate Similarity	0.7364	NPC475301
Intermediate Similarity	0.7364	NPC53255
Intermediate Similarity	0.7364	NPC146976
Intermediate Similarity	0.7364	NPC85879
Intermediate Similarity	0.736	NPC471178
Intermediate Similarity	0.7333	NPC13603
Intermediate Similarity	0.7333	NPC322482
Intermediate Similarity	0.7325	NPC24019
Intermediate Similarity	0.7292	NPC472435
Intermediate Similarity	0.7289	NPC210434
Intermediate Similarity	0.7281	NPC246381
Intermediate Similarity	0.7277	NPC15406
Intermediate Similarity	0.7273	NPC264176
Intermediate Similarity	0.7265	NPC314270
Intermediate Similarity	0.7265	NPC99891
Intermediate Similarity	0.726	NPC470020
Intermediate Similarity	0.7249	NPC278525
Intermediate Similarity	0.7246	NPC472434
Intermediate Similarity	0.7243	NPC473833
Intermediate Similarity	0.7241	NPC108342
Intermediate Similarity	0.722	NPC27041
Intermediate Similarity	0.7215	NPC472752
Intermediate Similarity	0.721	NPC182907
Intermediate Similarity	0.721	NPC189903
Intermediate Similarity	0.7207	NPC237740
Intermediate Similarity	0.7202	NPC472436
Intermediate Similarity	0.72	NPC128115
Intermediate Similarity	0.72	NPC472099
Intermediate Similarity	0.7178	NPC471015
Intermediate Similarity	0.7167	NPC183537
Intermediate Similarity	0.7167	NPC77878
Intermediate Similarity	0.7155	NPC329631
Intermediate Similarity	0.7155	NPC22481
Intermediate Similarity	0.7149	NPC478045
Intermediate Similarity	0.7143	NPC201508
Intermediate Similarity	0.7137	NPC477911
Intermediate Similarity	0.7136	NPC174672
Intermediate Similarity	0.7124	NPC54066
Intermediate Similarity	0.7124	NPC90875
Intermediate Similarity	0.7123	NPC289786
Intermediate Similarity	0.7119	NPC119134
Intermediate Similarity	0.7117	NPC202605
Intermediate Similarity	0.7117	NPC112206
Intermediate Similarity	0.7115	NPC295158
Intermediate Similarity	0.7112	NPC233334
Intermediate Similarity	0.711	NPC210256
Intermediate Similarity	0.7106	NPC166722
Intermediate Similarity	0.7101	NPC180668
Intermediate Similarity	0.7101	NPC148896
Intermediate Similarity	0.7101	NPC471013
Intermediate Similarity	0.7095	NPC44354
Intermediate Similarity	0.7091	NPC287208
Intermediate Similarity	0.7082	NPC96584
Intermediate Similarity	0.7082	NPC255800
Intermediate Similarity	0.7078	NPC472111
Intermediate Similarity	0.7071	NPC107123
Intermediate Similarity	0.707	NPC474916
Intermediate Similarity	0.7069	NPC477906
Intermediate Similarity	0.7067	NPC477908
Intermediate Similarity	0.7067	NPC206343
Intermediate Similarity	0.7059	NPC316224
Intermediate Similarity	0.7056	NPC473053
Intermediate Similarity	0.7054	NPC10904
Intermediate Similarity	0.7054	NPC165964
Intermediate Similarity	0.7048	NPC469439
Intermediate Similarity	0.7045	NPC471978
Intermediate Similarity	0.7042	NPC161801
Intermediate Similarity	0.704	NPC292517
Intermediate Similarity	0.7032	NPC472259
Intermediate Similarity	0.7031	NPC122436
Intermediate Similarity	0.7029	NPC124313
Intermediate Similarity	0.7028	NPC471979
Intermediate Similarity	0.7027	NPC290689
Intermediate Similarity	0.7022	NPC152768
Intermediate Similarity	0.7022	NPC148183
Intermediate Similarity	0.7021	NPC295228
Intermediate Similarity	0.7018	NPC477912
Intermediate Similarity	0.7017	NPC207283
Intermediate Similarity	0.7017	NPC84164
Intermediate Similarity	0.7014	NPC82548
Intermediate Similarity	0.7009	NPC146724
Intermediate Similarity	0.7005	NPC271792
Intermediate Similarity	0.7004	NPC472555
Intermediate Similarity	0.7	NPC309498
Intermediate Similarity	0.7	NPC328154
Remote Similarity	0.6995	NPC56170
Remote Similarity	0.6995	NPC471448
Remote Similarity	0.6991	NPC127085
Remote Similarity	0.6986	NPC200836
Remote Similarity	0.6982	NPC174758
Remote Similarity	0.6979	NPC182222
Remote Similarity	0.6979	NPC327769
Remote Similarity	0.6974	NPC477901
Remote Similarity	0.697	NPC148860
Remote Similarity	0.6966	NPC102593
Remote Similarity	0.6966	NPC196718
Remote Similarity	0.6964	NPC111732
Remote Similarity	0.6964	NPC472098
Remote Similarity	0.6962	NPC101350
Remote Similarity	0.696	NPC473822
Remote Similarity	0.6959	NPC160127
Remote Similarity	0.6959	NPC50997
Remote Similarity	0.6957	NPC164340
Remote Similarity	0.6955	NPC289086
Remote Similarity	0.6955	NPC16452
Remote Similarity	0.6955	NPC476581
Remote Similarity	0.6955	NPC36229
Remote Similarity	0.6953	NPC91125
Remote Similarity	0.6949	NPC477549
Remote Similarity	0.6947	NPC42678
Remote Similarity	0.6947	NPC477907
Remote Similarity	0.6947	NPC30570
Remote Similarity	0.6947	NPC477909
Remote Similarity	0.6947	NPC207531
Remote Similarity	0.6944	NPC78767
Remote Similarity	0.6944	NPC473814
Remote Similarity	0.694	NPC186351
Remote Similarity	0.693	NPC216428
Remote Similarity	0.693	NPC301368
Remote Similarity	0.693	NPC84815
Remote Similarity	0.693	NPC93390
Remote Similarity	0.6926	NPC473449
Remote Similarity	0.6926	NPC477900
Remote Similarity	0.6926	NPC477899
Remote Similarity	0.6926	NPC26881
Remote Similarity	0.6926	NPC21638
Remote Similarity	0.6923	NPC96801
Remote Similarity	0.6923	NPC317373
Remote Similarity	0.6923	NPC471997
Remote Similarity	0.6923	NPC150698
Remote Similarity	0.6923	NPC238457
Remote Similarity	0.692	NPC235685
Remote Similarity	0.6916	NPC469727
Remote Similarity	0.6916	NPC162812
Remote Similarity	0.6913	NPC127720
Remote Similarity	0.6913	NPC127026
Remote Similarity	0.6913	NPC235364
Remote Similarity	0.6912	NPC239954
Remote Similarity	0.6911	NPC53534
Remote Similarity	0.6907	NPC253675
Remote Similarity	0.6904	NPC148889
Remote Similarity	0.6903	NPC228331
Remote Similarity	0.6897	NPC470018
Remote Similarity	0.6892	NPC53344
Remote Similarity	0.6892	NPC475835
Remote Similarity	0.6889	NPC202768
Remote Similarity	0.6889	NPC296482
Remote Similarity	0.6889	NPC53069
Remote Similarity	0.6888	NPC78609
Remote Similarity	0.6886	NPC62367
Remote Similarity	0.6886	NPC319556
Remote Similarity	0.6885	NPC137353
Remote Similarity	0.6883	NPC471980
Remote Similarity	0.6881	NPC476578
Remote Similarity	0.6881	NPC476582
Remote Similarity	0.6881	NPC4071
Remote Similarity	0.688	NPC152620
Remote Similarity	0.6878	NPC327592
Remote Similarity	0.6877	NPC473639
Remote Similarity	0.6875	NPC72905
Remote Similarity	0.6872	NPC477910
Remote Similarity	0.6872	NPC91868
Remote Similarity	0.6872	NPC63971
Remote Similarity	0.687	NPC310118
Remote Similarity	0.687	NPC60621
Remote Similarity	0.6867	NPC110151
Remote Similarity	0.6867	NPC124029
Remote Similarity	0.6867	NPC74575
Remote Similarity	0.6867	NPC475601
Remote Similarity	0.6867	NPC211920
Remote Similarity	0.6866	NPC90229
Remote Similarity	0.6866	NPC74153
Remote Similarity	0.6866	NPC267928
Remote Similarity	0.6864	NPC57398
Remote Similarity	0.6864	NPC211813
Remote Similarity	0.6862	NPC477585
Remote Similarity	0.6862	NPC477590
Remote Similarity	0.6862	NPC477588
Remote Similarity	0.6862	NPC477586

Drug Structure

NPD4989 OpenBabel08211706322D 28 32 0 0 1 0 0 0 0 0999 V2000 2.3792 -1.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3338 -0.1455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8549 -3.7147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6632 -3.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6531 -1.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5624 0.2475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8005 -0.5665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8608 1.2697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1820 -3.1699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8606 -1.1786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9208 0.6576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6069 -2.2391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0734 -1.3990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1258 -2.0045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7986 -2.5493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8006 0.6578 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8817 -1.0886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0551 -0.5665 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8363 -0.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4715 -0.7261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2334 -0.0921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3361 -0.7715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3175 -2.3147 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0089 -1.3164 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9209 -0.5665 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.4716 0.0836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7988 0.6285 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 15 1 0 0 0 0 5 17 2 0 0 0 0 6 19 2 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 23 2 0 0 0 0 10 25 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 6 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 1 0 0 0 22 24 2 3 0 0 0 22 26 1 0 0 0 0 26 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000658
DrugBank	DB06090
ChEMBL	CHEMBL1258006
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	25147644
ChEBI
CAS Number	639489-84-2

Drug Properties

Molecular Weight	361.18
ALogP	-1.2319
MLogP	3.33
XLogP	4.237
HDA	4
HBD	1
Rotatable Bonds	5
TPSA	61.86
RO5 Violation	0