NPASS drugs

Drug Information

Drug ID:	NPD6531
Drug Name:	Vilazodone
Molecular Formula:	C26H27N5O2
Canonical SMILES:	N#Cc1ccc2c(c1)c(CCCCN1CCN(CC1)c1ccc3c(c1)cc(o3)C(=N)O)c[nH]2
Standard InCHI:	InChI=1S/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32)
Standard InCHIKey:	SGEGOXDYSFKCPT-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6531

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	441
0.1-0.2	2771
0.2-0.3	9675
0.3-0.4	4206
0.4-0.5	10422
0.5-0.6	1938
0.6-0.7	1206
0.7-0.8	230
0.8-0.85	1
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	0.8226	NPC258048
Intermediate Similarity	0.7823	NPC78609
Intermediate Similarity	0.7806	NPC276657
Intermediate Similarity	0.7778	NPC207686
Intermediate Similarity	0.7699	NPC280799
Intermediate Similarity	0.7698	NPC165964
Intermediate Similarity	0.7692	NPC101350
Intermediate Similarity	0.7652	NPC235685
Intermediate Similarity	0.7589	NPC91868
Intermediate Similarity	0.7589	NPC63971
Intermediate Similarity	0.7581	NPC15801
Intermediate Similarity	0.7579	NPC178858
Intermediate Similarity	0.7563	NPC170114
Intermediate Similarity	0.7549	NPC53534
Intermediate Similarity	0.7542	NPC208284
Intermediate Similarity	0.7529	NPC89549
Intermediate Similarity	0.7521	NPC470549
Intermediate Similarity	0.751	NPC152620
Intermediate Similarity	0.751	NPC6786
Intermediate Similarity	0.75	NPC39370
Intermediate Similarity	0.749	NPC473186
Intermediate Similarity	0.7479	NPC60621
Intermediate Similarity	0.747	NPC208522
Intermediate Similarity	0.7459	NPC476818
Intermediate Similarity	0.7458	NPC27041
Intermediate Similarity	0.7443	NPC132385
Intermediate Similarity	0.7437	NPC219087
Intermediate Similarity	0.7429	NPC470018
Intermediate Similarity	0.7427	NPC264285
Intermediate Similarity	0.7419	NPC196718
Intermediate Similarity	0.7418	NPC229893
Intermediate Similarity	0.7404	NPC300156
Intermediate Similarity	0.7404	NPC45190
Intermediate Similarity	0.7398	NPC478078
Intermediate Similarity	0.7397	NPC74360
Intermediate Similarity	0.7395	NPC9894
Intermediate Similarity	0.7366	NPC150239
Intermediate Similarity	0.7359	NPC227582
Intermediate Similarity	0.7353	NPC11464
Intermediate Similarity	0.7352	NPC475844
Intermediate Similarity	0.7349	NPC49547
Intermediate Similarity	0.7349	NPC102593
Intermediate Similarity	0.7347	NPC122436
Intermediate Similarity	0.7336	NPC198503
Intermediate Similarity	0.7331	NPC477549
Intermediate Similarity	0.7322	NPC87413
Intermediate Similarity	0.7306	NPC16352
Intermediate Similarity	0.73	NPC193238
Intermediate Similarity	0.7295	NPC323969
Intermediate Similarity	0.7295	NPC472099
Intermediate Similarity	0.7291	NPC253675
Intermediate Similarity	0.729	NPC216369
Intermediate Similarity	0.7284	NPC247803
Intermediate Similarity	0.7283	NPC210296
Intermediate Similarity	0.728	NPC478083
Intermediate Similarity	0.728	NPC471304
Intermediate Similarity	0.7279	NPC9482
Intermediate Similarity	0.7273	NPC148183
Intermediate Similarity	0.7273	NPC152768
Intermediate Similarity	0.7273	NPC41679
Intermediate Similarity	0.7265	NPC252338
Intermediate Similarity	0.7265	NPC213308
Intermediate Similarity	0.7265	NPC310118
Intermediate Similarity	0.7262	NPC473187
Intermediate Similarity	0.7261	NPC266931
Intermediate Similarity	0.7258	NPC110151
Intermediate Similarity	0.7258	NPC74575
Intermediate Similarity	0.7255	NPC478081
Intermediate Similarity	0.7253	NPC131887
Intermediate Similarity	0.7253	NPC67288
Intermediate Similarity	0.7248	NPC270515
Intermediate Similarity	0.7243	NPC472285
Intermediate Similarity	0.7227	NPC270918
Intermediate Similarity	0.7227	NPC142385
Intermediate Similarity	0.7224	NPC174760
Intermediate Similarity	0.7222	NPC74413
Intermediate Similarity	0.7218	NPC227908
Intermediate Similarity	0.7216	NPC477066
Intermediate Similarity	0.7216	NPC217554
Intermediate Similarity	0.7215	NPC475070
Intermediate Similarity	0.7214	NPC13603
Intermediate Similarity	0.7213	NPC184408
Intermediate Similarity	0.7213	NPC46561
Intermediate Similarity	0.7211	NPC474192
Intermediate Similarity	0.7211	NPC475720
Intermediate Similarity	0.7209	NPC107836
Intermediate Similarity	0.7208	NPC470020
Intermediate Similarity	0.7205	NPC11408
Intermediate Similarity	0.7203	NPC260900
Intermediate Similarity	0.7203	NPC244543
Intermediate Similarity	0.72	NPC24019
Intermediate Similarity	0.7197	NPC171787
Intermediate Similarity	0.7194	NPC295228
Intermediate Similarity	0.7191	NPC176538
Intermediate Similarity	0.7189	NPC116701
Intermediate Similarity	0.7189	NPC157931
Intermediate Similarity	0.7188	NPC478082
Intermediate Similarity	0.7188	NPC477067
Intermediate Similarity	0.7184	NPC193267
Intermediate Similarity	0.7184	NPC213530
Intermediate Similarity	0.7183	NPC180504
Intermediate Similarity	0.7176	NPC475301
Intermediate Similarity	0.7176	NPC53255
Intermediate Similarity	0.7176	NPC85879
Intermediate Similarity	0.7176	NPC326930
Intermediate Similarity	0.7174	NPC83111
Intermediate Similarity	0.7171	NPC260434
Intermediate Similarity	0.7171	NPC474688
Intermediate Similarity	0.7167	NPC13880
Intermediate Similarity	0.7166	NPC210434
Intermediate Similarity	0.7165	NPC184680
Intermediate Similarity	0.716	NPC194740
Intermediate Similarity	0.716	NPC274640
Intermediate Similarity	0.716	NPC15406
Intermediate Similarity	0.7159	NPC74619
Intermediate Similarity	0.7155	NPC4687
Intermediate Similarity	0.7155	NPC249583
Intermediate Similarity	0.7155	NPC307963
Intermediate Similarity	0.7155	NPC88008
Intermediate Similarity	0.7154	NPC182222
Intermediate Similarity	0.7149	NPC308137
Intermediate Similarity	0.7149	NPC310211
Intermediate Similarity	0.7149	NPC48353
Intermediate Similarity	0.7149	NPC110182
Intermediate Similarity	0.7148	NPC148889
Intermediate Similarity	0.7143	NPC17437
Intermediate Similarity	0.7143	NPC96321
Intermediate Similarity	0.7143	NPC328928
Intermediate Similarity	0.7137	NPC470785
Intermediate Similarity	0.7137	NPC470784
Intermediate Similarity	0.7137	NPC322482
Intermediate Similarity	0.7137	NPC5145
Intermediate Similarity	0.7132	NPC284141
Intermediate Similarity	0.7131	NPC278525
Intermediate Similarity	0.7131	NPC322064
Intermediate Similarity	0.7126	NPC473800
Intermediate Similarity	0.7126	NPC137353
Intermediate Similarity	0.7126	NPC108342
Intermediate Similarity	0.7125	NPC39679
Intermediate Similarity	0.7121	NPC72905
Intermediate Similarity	0.7121	NPC473540
Intermediate Similarity	0.7119	NPC478074
Intermediate Similarity	0.7117	NPC45048
Intermediate Similarity	0.7113	NPC175602
Intermediate Similarity	0.711	NPC478080
Intermediate Similarity	0.7109	NPC475816
Intermediate Similarity	0.7107	NPC82370
Intermediate Similarity	0.7103	NPC474701
Intermediate Similarity	0.7102	NPC304926
Intermediate Similarity	0.7102	NPC169402
Intermediate Similarity	0.7102	NPC476041
Intermediate Similarity	0.7101	NPC223427
Intermediate Similarity	0.7098	NPC184225
Intermediate Similarity	0.7098	NPC189903
Intermediate Similarity	0.7098	NPC182907
Intermediate Similarity	0.7097	NPC144452
Intermediate Similarity	0.7095	NPC61038
Intermediate Similarity	0.7094	NPC251090
Intermediate Similarity	0.7092	NPC314954
Intermediate Similarity	0.7092	NPC252251
Intermediate Similarity	0.709	NPC116238
Intermediate Similarity	0.7085	NPC132642
Intermediate Similarity	0.7085	NPC86078
Intermediate Similarity	0.7085	NPC225279
Intermediate Similarity	0.7083	NPC321428
Intermediate Similarity	0.708	NPC279589
Intermediate Similarity	0.7078	NPC472098
Intermediate Similarity	0.7078	NPC118940
Intermediate Similarity	0.7075	NPC200553
Intermediate Similarity	0.7075	NPC132329
Intermediate Similarity	0.7075	NPC279189
Intermediate Similarity	0.7075	NPC469554
Intermediate Similarity	0.7071	NPC285558
Intermediate Similarity	0.7069	NPC92111
Intermediate Similarity	0.7068	NPC473833
Intermediate Similarity	0.7068	NPC51388
Intermediate Similarity	0.7068	NPC191489
Intermediate Similarity	0.7066	NPC160898
Intermediate Similarity	0.7065	NPC196449
Intermediate Similarity	0.7065	NPC314222
Intermediate Similarity	0.7063	NPC209174
Intermediate Similarity	0.7063	NPC326363
Intermediate Similarity	0.7061	NPC77878
Intermediate Similarity	0.7061	NPC36405
Intermediate Similarity	0.7061	NPC183537
Intermediate Similarity	0.7061	NPC3207
Intermediate Similarity	0.7061	NPC67401
Intermediate Similarity	0.7059	NPC291535
Intermediate Similarity	0.7059	NPC470017
Intermediate Similarity	0.7059	NPC475112
Intermediate Similarity	0.7059	NPC475085
Intermediate Similarity	0.7054	NPC82548
Intermediate Similarity	0.7054	NPC473312
Intermediate Similarity	0.7052	NPC473185
Intermediate Similarity	0.7049	NPC39500
Intermediate Similarity	0.7047	NPC329631
Intermediate Similarity	0.7047	NPC22481
Intermediate Similarity	0.7047	NPC323752
Intermediate Similarity	0.7046	NPC45459
Intermediate Similarity	0.7046	NPC315491

Drug Structure

NPD6531 OpenBabel08211710072D 36 40 0 0 0 0 0 0 0 0999 V2000 7.8793 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3339 6.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0030 5.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0467 5.0467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6866 6.7409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5249 2.9023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3557 5.9977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7158 4.3035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6940 4.5115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0175 7.4840 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.1940 3.6454 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 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 -3.0878 1.6750 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1885 3.5409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 8 1 0 0 0 0 3 19 1 0 0 0 0 4 6 2 0 0 0 0 4 18 1 0 0 0 0 5 7 1 0 0 0 0 5 21 2 0 0 0 0 6 23 1 0 0 0 0 7 24 2 0 0 0 0 8 30 1 0 0 0 0 9 11 1 0 0 0 0 9 30 1 0 0 0 0 10 12 1 0 0 0 0 10 30 1 0 0 0 0 11 31 1 0 0 0 0 12 31 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 25 2 0 0 0 0 16 18 1 0 0 0 0 16 27 3 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 19 22 1 0 0 0 0 20 24 1 0 0 0 0 21 31 1 0 0 0 0 22 23 2 0 0 0 0 23 29 1 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 33 1 0 0 0 0 26 28 2 0 0 0 0 26 32 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 32 36 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL001036
DrugBank	DB06684
ChEMBL	CHEMBL439849
IUPHAR/BPS	7427
PharmaGKB
KEGG Drug	D09698
PubChem CID	6918314
ChEBI	70707
CAS Number	163521-12-8

Drug Properties

Molecular Weight	441.22
ALogP	-1.0506
MLogP	3.55
XLogP	3.848
HDA	6
HBD	3
Rotatable Bonds	8
TPSA	103.28
RO5 Violation	0