NPASS drugs

Drug Information

Drug ID:	NPD5418
Drug Name:	sibopirdine
Molecular Formula:	C23H18N4
Canonical SMILES:	n1ccc(cc1)CC1(Cc2ccncc2)c2cccnc2c2c1cccn2
Standard InCHI:	InChI=1S/C23H18N4/c1-3-19-21(26-9-1)22-20(4-2-10-27-22)23(19,15-17-5-11-24-12-6-17)16-18-7-13-25-14-8-18/h1-14H,15-16H2
Standard InCHIKey:	FJYRSJDIZKTXKB-UHFFFAOYSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD5418

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	870
0.1-0.2	7475
0.2-0.3	16062
0.3-0.4	3419
0.4-0.5	1271
0.5-0.6	1203
0.6-0.7	486
0.7-0.8	100
0.8-0.85	4
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	0.8312	NPC86288
Intermediate Similarity	0.8193	NPC297034
Intermediate Similarity	0.8036	NPC280852
Intermediate Similarity	0.8	NPC138842
Intermediate Similarity	0.7933	NPC69914
Intermediate Similarity	0.7888	NPC325903
Intermediate Similarity	0.7875	NPC40070
Intermediate Similarity	0.7867	NPC476131
Intermediate Similarity	0.7862	NPC470111
Intermediate Similarity	0.7799	NPC63545
Intermediate Similarity	0.775	NPC469811
Intermediate Similarity	0.775	NPC201380
Intermediate Similarity	0.775	NPC179787
Intermediate Similarity	0.7742	NPC251722
Intermediate Similarity	0.7742	NPC314102
Intermediate Similarity	0.7722	NPC20144
Intermediate Similarity	0.7702	NPC321911
Intermediate Similarity	0.7665	NPC317105
Intermediate Similarity	0.7661	NPC471579
Intermediate Similarity	0.7607	NPC470233
Intermediate Similarity	0.7605	NPC470203
Intermediate Similarity	0.756	NPC478182
Intermediate Similarity	0.7545	NPC122141
Intermediate Similarity	0.7545	NPC470204
Intermediate Similarity	0.7533	NPC476322
Intermediate Similarity	0.75	NPC225018
Intermediate Similarity	0.7485	NPC293487
Intermediate Similarity	0.7485	NPC474897
Intermediate Similarity	0.7471	NPC56233
Intermediate Similarity	0.7467	NPC46358
Intermediate Similarity	0.7444	NPC231536
Intermediate Similarity	0.7442	NPC201634
Intermediate Similarity	0.7425	NPC236711
Intermediate Similarity	0.741	NPC476219
Intermediate Similarity	0.7381	NPC477591
Intermediate Similarity	0.7368	NPC478183
Intermediate Similarity	0.7365	NPC91958
Intermediate Similarity	0.7358	NPC169433
Intermediate Similarity	0.7353	NPC478184
Intermediate Similarity	0.7337	NPC229173
Intermediate Similarity	0.7297	NPC297486
Intermediate Similarity	0.7297	NPC240136
Intermediate Similarity	0.7297	NPC471402
Intermediate Similarity	0.7296	NPC150259
Intermediate Similarity	0.7294	NPC478185
Intermediate Similarity	0.7285	NPC329825
Intermediate Similarity	0.7256	NPC288838
Intermediate Similarity	0.7255	NPC146373
Intermediate Similarity	0.7255	NPC245244
Intermediate Similarity	0.7255	NPC166424
Intermediate Similarity	0.7235	NPC81229
Intermediate Similarity	0.7235	NPC255229
Intermediate Similarity	0.7229	NPC53947
Intermediate Similarity	0.7219	NPC216643
Intermediate Similarity	0.7209	NPC274229
Intermediate Similarity	0.7205	NPC88097
Intermediate Similarity	0.7205	NPC315348
Intermediate Similarity	0.7205	NPC316811
Intermediate Similarity	0.7205	NPC32002
Intermediate Similarity	0.7184	NPC91895
Intermediate Similarity	0.7184	NPC32534
Intermediate Similarity	0.7176	NPC221786
Intermediate Similarity	0.7176	NPC474880
Intermediate Similarity	0.716	NPC469780
Intermediate Similarity	0.716	NPC469767
Intermediate Similarity	0.716	NPC469783
Intermediate Similarity	0.716	NPC115611
Intermediate Similarity	0.716	NPC469761
Intermediate Similarity	0.716	NPC469779
Intermediate Similarity	0.716	NPC469768
Intermediate Similarity	0.716	NPC469784
Intermediate Similarity	0.7143	NPC82331
Intermediate Similarity	0.7135	NPC44773
Intermediate Similarity	0.7135	NPC215584
Intermediate Similarity	0.7134	NPC282398
Intermediate Similarity	0.7133	NPC143603
Intermediate Similarity	0.7125	NPC96102
Intermediate Similarity	0.7124	NPC290094
Intermediate Similarity	0.7119	NPC474958
Intermediate Similarity	0.7118	NPC167635
Intermediate Similarity	0.7117	NPC469766
Intermediate Similarity	0.7105	NPC182570
Intermediate Similarity	0.7105	NPC48564
Intermediate Similarity	0.7105	NPC265605
Intermediate Similarity	0.7101	NPC476297
Intermediate Similarity	0.7099	NPC73767
Intermediate Similarity	0.7099	NPC104483
Intermediate Similarity	0.7093	NPC194881
Intermediate Similarity	0.7091	NPC469525
Intermediate Similarity	0.7089	NPC256893
Intermediate Similarity	0.7086	NPC97343
Intermediate Similarity	0.7081	NPC84911
Intermediate Similarity	0.7081	NPC105127
Intermediate Similarity	0.7074	NPC265576
Intermediate Similarity	0.7062	NPC317054
Intermediate Similarity	0.7059	NPC128244
Intermediate Similarity	0.7056	NPC307191
Intermediate Similarity	0.7055	NPC284635
Intermediate Similarity	0.702	NPC162689
Intermediate Similarity	0.702	NPC54102
Intermediate Similarity	0.7019	NPC29886
Intermediate Similarity	0.7019	NPC261195
Intermediate Similarity	0.7018	NPC286427
Intermediate Similarity	0.7018	NPC129721
Remote Similarity	0.6994	NPC110126
Remote Similarity	0.6987	NPC202957
Remote Similarity	0.6987	NPC169625
Remote Similarity	0.6981	NPC101165
Remote Similarity	0.6978	NPC108011
Remote Similarity	0.6977	NPC56765
Remote Similarity	0.6977	NPC92796
Remote Similarity	0.6977	NPC41257
Remote Similarity	0.6977	NPC475990
Remote Similarity	0.6977	NPC135141
Remote Similarity	0.6968	NPC27740
Remote Similarity	0.6957	NPC198988
Remote Similarity	0.6954	NPC265100
Remote Similarity	0.6954	NPC81561
Remote Similarity	0.6951	NPC279081
Remote Similarity	0.6951	NPC2949
Remote Similarity	0.6946	NPC143872
Remote Similarity	0.6944	NPC12649
Remote Similarity	0.6939	NPC27802
Remote Similarity	0.6927	NPC150048
Remote Similarity	0.6927	NPC203754
Remote Similarity	0.6919	NPC193740
Remote Similarity	0.6914	NPC325252
Remote Similarity	0.6906	NPC24864
Remote Similarity	0.6899	NPC89490
Remote Similarity	0.6887	NPC148140
Remote Similarity	0.6886	NPC314372
Remote Similarity	0.6885	NPC467063
Remote Similarity	0.6879	NPC80681
Remote Similarity	0.6875	NPC82295
Remote Similarity	0.6867	NPC190296
Remote Similarity	0.6867	NPC143156
Remote Similarity	0.686	NPC51054
Remote Similarity	0.6859	NPC122718
Remote Similarity	0.6855	NPC329896
Remote Similarity	0.6855	NPC475105
Remote Similarity	0.6855	NPC475090
Remote Similarity	0.6848	NPC230002
Remote Similarity	0.6845	NPC478186
Remote Similarity	0.6824	NPC24678
Remote Similarity	0.6824	NPC105818
Remote Similarity	0.6821	NPC475288
Remote Similarity	0.6818	NPC195507
Remote Similarity	0.6818	NPC2165
Remote Similarity	0.6805	NPC21605
Remote Similarity	0.6796	NPC157583
Remote Similarity	0.6786	NPC204141
Remote Similarity	0.6786	NPC285731
Remote Similarity	0.6786	NPC159856
Remote Similarity	0.6786	NPC166492
Remote Similarity	0.6786	NPC473362
Remote Similarity	0.6782	NPC206819
Remote Similarity	0.6782	NPC318065
Remote Similarity	0.678	NPC98187
Remote Similarity	0.6776	NPC476566
Remote Similarity	0.6776	NPC191415
Remote Similarity	0.6772	NPC326422
Remote Similarity	0.6772	NPC329541
Remote Similarity	0.6761	NPC90723
Remote Similarity	0.6758	NPC133261
Remote Similarity	0.6747	NPC59084
Remote Similarity	0.6744	NPC259644
Remote Similarity	0.6744	NPC469760
Remote Similarity	0.6744	NPC469786
Remote Similarity	0.6744	NPC469765
Remote Similarity	0.6744	NPC469763
Remote Similarity	0.6744	NPC73952
Remote Similarity	0.6744	NPC25008
Remote Similarity	0.6739	NPC102755
Remote Similarity	0.6739	NPC48938
Remote Similarity	0.6735	NPC76540
Remote Similarity	0.6735	NPC231655
Remote Similarity	0.673	NPC471313
Remote Similarity	0.673	NPC471311
Remote Similarity	0.6725	NPC33421
Remote Similarity	0.6722	NPC477611
Remote Similarity	0.672	NPC324149
Remote Similarity	0.671	NPC215519
Remote Similarity	0.6707	NPC218268
Remote Similarity	0.6707	NPC473868
Remote Similarity	0.6707	NPC63157
Remote Similarity	0.6706	NPC471957
Remote Similarity	0.6706	NPC477974
Remote Similarity	0.6705	NPC80597
Remote Similarity	0.6705	NPC211572
Remote Similarity	0.6705	NPC75540
Remote Similarity	0.6705	NPC212376
Remote Similarity	0.6705	NPC70922
Remote Similarity	0.6703	NPC59269
Remote Similarity	0.6703	NPC237188
Remote Similarity	0.6703	NPC284678
Remote Similarity	0.6667	NPC469541
Remote Similarity	0.6667	NPC308931
Remote Similarity	0.6667	NPC469785
Remote Similarity	0.6667	NPC15102
Remote Similarity	0.6667	NPC476464

Drug Structure

NPD5418 OpenBabel08211708292D 27 31 0 0 0 0 0 0 0 0999 V2000 3.3849 2.9312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3849 1.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6924 -0.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7534 -0.9940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2079 -1.6821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9300 1.6658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7535 -0.0167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5385 3.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1507 -1.8863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6052 -2.5744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9015 1.5639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7250 -0.1186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3847 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3846 0.9774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7820 -0.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3561 0.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 1.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6926 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 1.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5766 -2.6765 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2989 0.6717 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 2.9315 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 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 5 17 2 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 18 2 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 26 2 0 0 0 0 10 27 2 0 0 0 0 11 24 2 0 0 0 0 12 24 1 0 0 0 0 13 25 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB013893
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	350.15
ALogP	0.5426
MLogP	3.55
XLogP	5.006
HDA	4
HBD	0
Rotatable Bonds	4
TPSA	51.56
RO5 Violation	1