NPASS drugs

Drug Information

Drug ID:	NPD6548
Drug Name:	Cinnarizine
Molecular Formula:	C26H28N2
Canonical SMILES:	c1ccc(cc1)C=CCN1CCN(CC1)C(c1ccccc1)c1ccccc1
Standard InCHI:	InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2
Standard InCHIKey:	DERZBLKQOCDDDZ-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD6548

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	367
0.1-0.2	2434
0.2-0.3	9807
0.3-0.4	12297
0.4-0.5	4540
0.5-0.6	1264
0.6-0.7	160
0.7-0.8	16
0.8-0.85	4
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	0.8901	NPC470926
Intermediate Similarity	0.8469	NPC239854
Intermediate Similarity	0.8421	NPC329430
Intermediate Similarity	0.8022	NPC104070
Intermediate Similarity	0.8022	NPC119677
Intermediate Similarity	0.7935	NPC169016
Intermediate Similarity	0.7921	NPC291610
Intermediate Similarity	0.7864	NPC474695
Intermediate Similarity	0.7841	NPC271642
Intermediate Similarity	0.7727	NPC98976
Intermediate Similarity	0.7609	NPC231986
Intermediate Similarity	0.7579	NPC258046
Intermediate Similarity	0.7524	NPC473418
Intermediate Similarity	0.74	NPC322040
Intermediate Similarity	0.7391	NPC475915
Intermediate Similarity	0.7308	NPC474582
Intermediate Similarity	0.7283	NPC12857
Intermediate Similarity	0.7174	NPC325662
Intermediate Similarity	0.7174	NPC98269
Intermediate Similarity	0.7094	NPC314192
Intermediate Similarity	0.7037	NPC167336
Remote Similarity	0.699	NPC108339
Remote Similarity	0.697	NPC305602
Remote Similarity	0.697	NPC17497
Remote Similarity	0.6897	NPC192209
Remote Similarity	0.6889	NPC219246
Remote Similarity	0.6882	NPC139658
Remote Similarity	0.6848	NPC112609
Remote Similarity	0.6848	NPC299134
Remote Similarity	0.6848	NPC122327
Remote Similarity	0.6848	NPC113000
Remote Similarity	0.6838	NPC264580
Remote Similarity	0.6837	NPC133162
Remote Similarity	0.6809	NPC290638
Remote Similarity	0.6789	NPC469974
Remote Similarity	0.6786	NPC65855
Remote Similarity	0.6786	NPC292758
Remote Similarity	0.6762	NPC471320
Remote Similarity	0.6762	NPC471319
Remote Similarity	0.6752	NPC313449
Remote Similarity	0.6739	NPC244738
Remote Similarity	0.6731	NPC469330
Remote Similarity	0.6703	NPC229235
Remote Similarity	0.67	NPC203076
Remote Similarity	0.6698	NPC311242
Remote Similarity	0.6696	NPC302790
Remote Similarity	0.6696	NPC296163
Remote Similarity	0.6696	NPC187036
Remote Similarity	0.6667	NPC252794
Remote Similarity	0.6667	NPC22786
Remote Similarity	0.664	NPC9856
Remote Similarity	0.6638	NPC246904
Remote Similarity	0.6634	NPC60408
Remote Similarity	0.6634	NPC473031
Remote Similarity	0.6607	NPC434
Remote Similarity	0.6607	NPC79618
Remote Similarity	0.6602	NPC191444
Remote Similarity	0.6596	NPC276699
Remote Similarity	0.6585	NPC79698
Remote Similarity	0.6566	NPC474088
Remote Similarity	0.6555	NPC320656
Remote Similarity	0.6552	NPC246588
Remote Similarity	0.6525	NPC313673
Remote Similarity	0.6508	NPC473417
Remote Similarity	0.6505	NPC176858
Remote Similarity	0.6505	NPC470877
Remote Similarity	0.6476	NPC473661
Remote Similarity	0.6442	NPC159178
Remote Similarity	0.6442	NPC471307
Remote Similarity	0.6442	NPC141139
Remote Similarity	0.6442	NPC121872
Remote Similarity	0.6442	NPC209764
Remote Similarity	0.6442	NPC78041
Remote Similarity	0.6442	NPC74936
Remote Similarity	0.6441	NPC473573
Remote Similarity	0.6441	NPC288232
Remote Similarity	0.6429	NPC315216
Remote Similarity	0.6417	NPC220698
Remote Similarity	0.6415	NPC7067
Remote Similarity	0.6404	NPC113670
Remote Similarity	0.6392	NPC66270
Remote Similarity	0.6392	NPC245896
Remote Similarity	0.6389	NPC472258
Remote Similarity	0.6387	NPC470544
Remote Similarity	0.6364	NPC210849
Remote Similarity	0.6349	NPC478079
Remote Similarity	0.6344	NPC72670
Remote Similarity	0.6333	NPC470545
Remote Similarity	0.6328	NPC126458
Remote Similarity	0.6322	NPC114327
Remote Similarity	0.6322	NPC36357
Remote Similarity	0.6316	NPC96835
Remote Similarity	0.6316	NPC258492
Remote Similarity	0.6303	NPC101139
Remote Similarity	0.6286	NPC172128
Remote Similarity	0.6283	NPC476198
Remote Similarity	0.6281	NPC470546
Remote Similarity	0.6279	NPC473962
Remote Similarity	0.6263	NPC50063
Remote Similarity	0.6262	NPC471309
Remote Similarity	0.6261	NPC164802
Remote Similarity	0.625	NPC307195
Remote Similarity	0.623	NPC226143
Remote Similarity	0.6228	NPC45033
Remote Similarity	0.6226	NPC226438
Remote Similarity	0.6224	NPC255345
Remote Similarity	0.622	NPC476950
Remote Similarity	0.6204	NPC161972
Remote Similarity	0.6204	NPC256452
Remote Similarity	0.6204	NPC303045
Remote Similarity	0.6196	NPC267443
Remote Similarity	0.6183	NPC313352
Remote Similarity	0.6182	NPC322598
Remote Similarity	0.6172	NPC473322
Remote Similarity	0.6172	NPC111428
Remote Similarity	0.6168	NPC108800
Remote Similarity	0.6162	NPC159661
Remote Similarity	0.6154	NPC291066
Remote Similarity	0.6154	NPC471638
Remote Similarity	0.6154	NPC53044
Remote Similarity	0.6147	NPC25565
Remote Similarity	0.6132	NPC316108
Remote Similarity	0.6131	NPC20144
Remote Similarity	0.6129	NPC71684
Remote Similarity	0.6124	NPC124802
Remote Similarity	0.6122	NPC249018
Remote Similarity	0.6122	NPC3190
Remote Similarity	0.6121	NPC77294
Remote Similarity	0.6119	NPC314102
Remote Similarity	0.6119	NPC251722
Remote Similarity	0.6111	NPC200745
Remote Similarity	0.6111	NPC307020
Remote Similarity	0.6111	NPC71009
Remote Similarity	0.6103	NPC470925
Remote Similarity	0.6098	NPC162689
Remote Similarity	0.6098	NPC54102
Remote Similarity	0.6095	NPC12429
Remote Similarity	0.6095	NPC30445
Remote Similarity	0.6094	NPC145754
Remote Similarity	0.6092	NPC198841
Remote Similarity	0.6091	NPC475439
Remote Similarity	0.6091	NPC473501
Remote Similarity	0.6087	NPC473498
Remote Similarity	0.6077	NPC259665
Remote Similarity	0.6077	NPC255447
Remote Similarity	0.6077	NPC89769
Remote Similarity	0.6077	NPC126859
Remote Similarity	0.6071	NPC214200
Remote Similarity	0.6071	NPC228400
Remote Similarity	0.6064	NPC213570
Remote Similarity	0.6064	NPC139416
Remote Similarity	0.6064	NPC246822
Remote Similarity	0.6064	NPC473206
Remote Similarity	0.6063	NPC52764
Remote Similarity	0.6048	NPC27833
Remote Similarity	0.6044	NPC50266
Remote Similarity	0.6043	NPC469735
Remote Similarity	0.6042	NPC54269
Remote Similarity	0.6032	NPC329825
Remote Similarity	0.6031	NPC257390
Remote Similarity	0.6031	NPC69914
Remote Similarity	0.6029	NPC22082
Remote Similarity	0.6029	NPC186284
Remote Similarity	0.6029	NPC88097
Remote Similarity	0.6023	NPC120441
Remote Similarity	0.6023	NPC65873
Remote Similarity	0.6023	NPC300345
Remote Similarity	0.6023	NPC212114
Remote Similarity	0.6016	NPC240136
Remote Similarity	0.6016	NPC136453
Remote Similarity	0.6016	NPC471402
Remote Similarity	0.6016	NPC297486
Remote Similarity	0.6	NPC257490
Remote Similarity	0.6	NPC248705
Remote Similarity	0.6	NPC469740
Remote Similarity	0.6	NPC135924
Remote Similarity	0.6	NPC263385
Remote Similarity	0.6	NPC150196
Remote Similarity	0.6	NPC54368
Remote Similarity	0.6	NPC211551
Remote Similarity	0.6	NPC251490
Remote Similarity	0.5986	NPC66936
Remote Similarity	0.5984	NPC14672
Remote Similarity	0.5984	NPC315276
Remote Similarity	0.5984	NPC285394
Remote Similarity	0.5984	NPC285926
Remote Similarity	0.598	NPC14326
Remote Similarity	0.5978	NPC155172
Remote Similarity	0.5978	NPC198023
Remote Similarity	0.5978	NPC32312
Remote Similarity	0.5977	NPC149436
Remote Similarity	0.5969	NPC239990
Remote Similarity	0.5969	NPC105114
Remote Similarity	0.5969	NPC152850
Remote Similarity	0.5969	NPC89923
Remote Similarity	0.5969	NPC71933
Remote Similarity	0.5968	NPC91958
Remote Similarity	0.5963	NPC474974
Remote Similarity	0.5962	NPC229477
Remote Similarity	0.596	NPC9796

Drug Structure

NPD6548 OpenBabel08211710072D 28 31 0 0 0 0 0 0 0 0999 V2000 6.0622 1.5000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -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 -1.7321 -2.0000 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 2.5981 1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 1 4 2 0 0 0 0 1 5 1 0 0 0 0 2 6 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 13 2 3 0 0 0 10 18 1 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 24 2 0 0 0 0 15 24 1 0 0 0 0 16 25 2 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 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 28 1 0 0 0 0 22 28 1 0 0 0 0 24 26 1 0 0 0 0 25 26 1 0 0 0 0 26 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000325
DrugBank	DB00568
ChEMBL	CHEMBL43064
IUPHAR/BPS
PharmaGKB	PA164749342
KEGG Drug	D01295
PubChem CID
ChEBI	31403
CAS Number	298-57-7

Drug Properties

Molecular Weight	368.23
ALogP	0.5018
MLogP	4.1
XLogP	9.866
HDA	2
HBD	0
Rotatable Bonds	6
TPSA	6.48
RO5 Violation	1