NPASS drugs

Drug Information

Drug ID:	NPD3569
Drug Name:	pibutidine
Molecular Formula:	C19H24N4O3
Canonical SMILES:	O=C1C(=C(C1=O)NC/C=CCOc1nccc(c1)CN1CCCCC1)N
Standard InCHI:	InChI=1S/C19H24N4O3/c20-16-17(19(25)18(16)24)22-7-2-5-11-26-15-12-14(6-8-21-15)13-23-9-3-1-4-10-23/h2,5-6,8,12,22H,1,3-4,7,9-11,13,20H2/b5-2-
Standard InCHIKey:	XMDYZASWLGWIPL-DJWKRKHSSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD3569

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	287
0.1-0.2	4518
0.2-0.3	8242
0.3-0.4	9066
0.4-0.5	5861
0.5-0.6	2157
0.6-0.7	744
0.7-0.8	15
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	0.7208	NPC103361
Intermediate Similarity	0.7163	NPC168209
Intermediate Similarity	0.7135	NPC107287
Intermediate Similarity	0.7113	NPC92111
Intermediate Similarity	0.7092	NPC135950
Intermediate Similarity	0.7081	NPC476518
Intermediate Similarity	0.7062	NPC243633
Intermediate Similarity	0.7062	NPC175150
Intermediate Similarity	0.7062	NPC76748
Intermediate Similarity	0.7043	NPC121658
Intermediate Similarity	0.7043	NPC14651
Intermediate Similarity	0.7041	NPC307963
Intermediate Similarity	0.7011	NPC471178
Intermediate Similarity	0.701	NPC296527
Intermediate Similarity	0.7	NPC315957
Remote Similarity	0.6963	NPC161887
Remote Similarity	0.6954	NPC289786
Remote Similarity	0.6952	NPC249614
Remote Similarity	0.6948	NPC122436
Remote Similarity	0.6942	NPC290689
Remote Similarity	0.6932	NPC471323
Remote Similarity	0.6923	NPC236668
Remote Similarity	0.6923	NPC213914
Remote Similarity	0.6915	NPC111624
Remote Similarity	0.691	NPC105811
Remote Similarity	0.691	NPC112741
Remote Similarity	0.6906	NPC209362
Remote Similarity	0.6904	NPC133140
Remote Similarity	0.6904	NPC195268
Remote Similarity	0.6902	NPC124542
Remote Similarity	0.6902	NPC177404
Remote Similarity	0.6902	NPC59779
Remote Similarity	0.6902	NPC471177
Remote Similarity	0.6893	NPC467188
Remote Similarity	0.689	NPC146976
Remote Similarity	0.6887	NPC472099
Remote Similarity	0.6884	NPC251090
Remote Similarity	0.6881	NPC196718
Remote Similarity	0.6875	NPC219963
Remote Similarity	0.6866	NPC476578
Remote Similarity	0.6866	NPC4071
Remote Similarity	0.6866	NPC476582
Remote Similarity	0.6863	NPC165349
Remote Similarity	0.6863	NPC118832
Remote Similarity	0.6863	NPC329708
Remote Similarity	0.6863	NPC47059
Remote Similarity	0.6863	NPC264166
Remote Similarity	0.6863	NPC274291
Remote Similarity	0.6842	NPC476419
Remote Similarity	0.6832	NPC176538
Remote Similarity	0.6804	NPC102593
Remote Similarity	0.6802	NPC101350
Remote Similarity	0.68	NPC13880
Remote Similarity	0.6788	NPC470474
Remote Similarity	0.6788	NPC266551
Remote Similarity	0.678	NPC476581
Remote Similarity	0.678	NPC285558
Remote Similarity	0.678	NPC36229
Remote Similarity	0.678	NPC16452
Remote Similarity	0.6774	NPC478078
Remote Similarity	0.6766	NPC473814
Remote Similarity	0.6766	NPC78767
Remote Similarity	0.6763	NPC82548
Remote Similarity	0.6757	NPC235685
Remote Similarity	0.675	NPC93390
Remote Similarity	0.6749	NPC19872
Remote Similarity	0.6744	NPC216612
Remote Similarity	0.6739	NPC138018
Remote Similarity	0.6731	NPC174672
Remote Similarity	0.673	NPC50562
Remote Similarity	0.6727	NPC49547
Remote Similarity	0.6724	NPC29702
Remote Similarity	0.6721	NPC75135
Remote Similarity	0.6721	NPC263455
Remote Similarity	0.6716	NPC232727
Remote Similarity	0.6714	NPC314270
Remote Similarity	0.6713	NPC322482
Remote Similarity	0.6703	NPC113812
Remote Similarity	0.67	NPC287437
Remote Similarity	0.67	NPC123395
Remote Similarity	0.6699	NPC470020
Remote Similarity	0.6699	NPC471304
Remote Similarity	0.6699	NPC167860
Remote Similarity	0.6699	NPC123976
Remote Similarity	0.6698	NPC67658
Remote Similarity	0.6698	NPC152768
Remote Similarity	0.6698	NPC148183
Remote Similarity	0.6685	NPC169586
Remote Similarity	0.6684	NPC20249
Remote Similarity	0.6684	NPC295158
Remote Similarity	0.6683	NPC476465
Remote Similarity	0.6683	NPC287208
Remote Similarity	0.6683	NPC74153
Remote Similarity	0.6683	NPC295898
Remote Similarity	0.6682	NPC260434
Remote Similarity	0.6682	NPC476287
Remote Similarity	0.6667	NPC329793
Remote Similarity	0.6667	NPC26872
Remote Similarity	0.6667	NPC469727
Remote Similarity	0.6667	NPC121772
Remote Similarity	0.6667	NPC477019
Remote Similarity	0.6667	NPC251391
Remote Similarity	0.6667	NPC312860
Remote Similarity	0.6667	NPC208284
Remote Similarity	0.6651	NPC472070
Remote Similarity	0.6651	NPC323969
Remote Similarity	0.6651	NPC174758
Remote Similarity	0.6648	NPC230085
Remote Similarity	0.6648	NPC159630
Remote Similarity	0.6647	NPC306397
Remote Similarity	0.6635	NPC264176
Remote Similarity	0.6635	NPC193238
Remote Similarity	0.6635	NPC313189
Remote Similarity	0.6634	NPC473053
Remote Similarity	0.6634	NPC31930
Remote Similarity	0.6633	NPC469489
Remote Similarity	0.6632	NPC283152
Remote Similarity	0.663	NPC229055
Remote Similarity	0.6627	NPC151489
Remote Similarity	0.6622	NPC141053
Remote Similarity	0.6621	NPC74575
Remote Similarity	0.662	NPC288349
Remote Similarity	0.662	NPC170114
Remote Similarity	0.6618	NPC289086
Remote Similarity	0.6617	NPC473821
Remote Similarity	0.6617	NPC84853
Remote Similarity	0.6616	NPC74382
Remote Similarity	0.6616	NPC206251
Remote Similarity	0.6609	NPC53534
Remote Similarity	0.6608	NPC316224
Remote Similarity	0.6605	NPC193267
Remote Similarity	0.6605	NPC213530
Remote Similarity	0.6604	NPC266931
Remote Similarity	0.6602	NPC472063
Remote Similarity	0.6602	NPC472069
Remote Similarity	0.6602	NPC472062
Remote Similarity	0.6601	NPC267928
Remote Similarity	0.6595	NPC74357
Remote Similarity	0.6591	NPC114310
Remote Similarity	0.6591	NPC314954
Remote Similarity	0.659	NPC210434
Remote Similarity	0.6589	NPC305984
Remote Similarity	0.6587	NPC323345
Remote Similarity	0.6587	NPC470164
Remote Similarity	0.6578	NPC63338
Remote Similarity	0.6578	NPC322976
Remote Similarity	0.6578	NPC324203
Remote Similarity	0.6573	NPC470549
Remote Similarity	0.657	NPC476138
Remote Similarity	0.657	NPC245816
Remote Similarity	0.6564	NPC61011
Remote Similarity	0.6564	NPC317010
Remote Similarity	0.6559	NPC26850
Remote Similarity	0.6557	NPC53069
Remote Similarity	0.6557	NPC26679
Remote Similarity	0.6557	NPC112206
Remote Similarity	0.6557	NPC472098
Remote Similarity	0.6557	NPC202605
Remote Similarity	0.6557	NPC202768
Remote Similarity	0.6557	NPC296482
Remote Similarity	0.6555	NPC135549
Remote Similarity	0.6552	NPC109922
Remote Similarity	0.655	NPC212125
Remote Similarity	0.655	NPC165370
Remote Similarity	0.6548	NPC284559
Remote Similarity	0.6547	NPC180504
Remote Similarity	0.6544	NPC60621
Remote Similarity	0.6538	NPC472259
Remote Similarity	0.6537	NPC284338
Remote Similarity	0.6537	NPC26543
Remote Similarity	0.6535	NPC226202
Remote Similarity	0.6529	NPC245244
Remote Similarity	0.6529	NPC146373
Remote Similarity	0.6529	NPC166424
Remote Similarity	0.6526	NPC162530
Remote Similarity	0.6524	NPC475910
Remote Similarity	0.6522	NPC70406
Remote Similarity	0.6519	NPC167400
Remote Similarity	0.6517	NPC138370
Remote Similarity	0.6513	NPC152620
Remote Similarity	0.6511	NPC258048
Remote Similarity	0.6508	NPC263439
Remote Similarity	0.6508	NPC473057
Remote Similarity	0.6507	NPC472111
Remote Similarity	0.6507	NPC472064
Remote Similarity	0.6507	NPC208522
Remote Similarity	0.6505	NPC234197
Remote Similarity	0.6503	NPC123906
Remote Similarity	0.6502	NPC469554
Remote Similarity	0.6502	NPC101543
Remote Similarity	0.65	NPC470018
Remote Similarity	0.65	NPC224327
Remote Similarity	0.6497	NPC176127
Remote Similarity	0.6495	NPC153452
Remote Similarity	0.6494	NPC63971
Remote Similarity	0.6494	NPC91868
Remote Similarity	0.6492	NPC319456
Remote Similarity	0.649	NPC475774
Remote Similarity	0.6489	NPC25899
Remote Similarity	0.6488	NPC127085

Drug Structure

NPD3569 OpenBabel08211703112D 29 31 0 0 0 0 0 0 0 0999 V2000 9.1416 0.6563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5176 1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4345 1.3634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8828 -0.3096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7956 1.5529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0884 2.2600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4686 1.1046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9169 -0.5684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1907 1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5708 0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2438 -0.1201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5367 0.5870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8637 1.0353 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.0012 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2098 0.1387 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -1.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8978 0.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 -1.4483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 -2.6730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 7 1 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 22 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 15 21 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 25 2 0 0 0 0 20 27 1 0 0 0 0 20 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB015753
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	356.18
ALogP	-2.6028
MLogP	2.78
XLogP	2.089
HDA	6
HBD	2
Rotatable Bonds	9
TPSA	97.55
RO5 Violation	0