NPASS drugs

Drug Information

Drug ID:	NPD5144
Drug Name:	R-59494
Molecular Formula:	C22H27N3OS
Canonical SMILES:	CN(c1nc2c(s1)cccc2)C1CCN(C1)CCCCOc1ccccc1
Standard InCHI:	InChI=1S/C22H27N3OS/c1-24(22-23-20-11-5-6-12-21(20)27-22)18-13-15-25(17-18)14-7-8-16-26-19-9-3-2-4-10-19/h2-6,9-12,18H,7-8,13-17H2,1H3
Standard InCHIKey:	VVPJKZNOOONNDJ-UHFFFAOYSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD5144

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	563
0.1-0.2	10083
0.2-0.3	4232
0.3-0.4	11459
0.4-0.5	3327
0.5-0.6	1145
0.6-0.7	80
0.7-0.8	1
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	0.701	NPC188104
Remote Similarity	0.6893	NPC134079
Remote Similarity	0.6814	NPC153467
Remote Similarity	0.6754	NPC315822
Remote Similarity	0.6715	NPC206251
Remote Similarity	0.6715	NPC74382
Remote Similarity	0.6683	NPC224327
Remote Similarity	0.6667	NPC168486
Remote Similarity	0.6667	NPC222592
Remote Similarity	0.6582	NPC39092
Remote Similarity	0.6515	NPC285635
Remote Similarity	0.6494	NPC187145
Remote Similarity	0.6485	NPC316756
Remote Similarity	0.6473	NPC118776
Remote Similarity	0.6464	NPC273714
Remote Similarity	0.6384	NPC242923
Remote Similarity	0.6346	NPC249662
Remote Similarity	0.6339	NPC151779
Remote Similarity	0.6332	NPC26850
Remote Similarity	0.6324	NPC476518
Remote Similarity	0.6295	NPC469589
Remote Similarity	0.6293	NPC121658
Remote Similarity	0.6293	NPC14651
Remote Similarity	0.6293	NPC258773
Remote Similarity	0.6291	NPC110741
Remote Similarity	0.6281	NPC477806
Remote Similarity	0.6281	NPC477805
Remote Similarity	0.6281	NPC477795
Remote Similarity	0.6281	NPC477796
Remote Similarity	0.6281	NPC315257
Remote Similarity	0.6275	NPC1527
Remote Similarity	0.6271	NPC160666
Remote Similarity	0.627	NPC287895
Remote Similarity	0.6263	NPC26872
Remote Similarity	0.6262	NPC111624
Remote Similarity	0.6261	NPC257511
Remote Similarity	0.625	NPC84853
Remote Similarity	0.6238	NPC177404
Remote Similarity	0.6233	NPC472111
Remote Similarity	0.6221	NPC280638
Remote Similarity	0.6218	NPC470889
Remote Similarity	0.6216	NPC475774
Remote Similarity	0.6211	NPC472098
Remote Similarity	0.6196	NPC69277
Remote Similarity	0.619	NPC308906
Remote Similarity	0.6184	NPC471080
Remote Similarity	0.6184	NPC469592
Remote Similarity	0.6182	NPC187558
Remote Similarity	0.6168	NPC238242
Remote Similarity	0.6161	NPC219963
Remote Similarity	0.6154	NPC121772
Remote Similarity	0.6154	NPC329747
Remote Similarity	0.6154	NPC329793
Remote Similarity	0.6132	NPC176127
Remote Similarity	0.6111	NPC471593
Remote Similarity	0.6109	NPC18487
Remote Similarity	0.6106	NPC476465
Remote Similarity	0.6103	NPC320863
Remote Similarity	0.61	NPC161108
Remote Similarity	0.6095	NPC283152
Remote Similarity	0.6091	NPC267928
Remote Similarity	0.6087	NPC41982
Remote Similarity	0.6085	NPC161887
Remote Similarity	0.6085	NPC266551
Remote Similarity	0.6083	NPC92111
Remote Similarity	0.6078	NPC469594
Remote Similarity	0.6077	NPC312872
Remote Similarity	0.607	NPC94157
Remote Similarity	0.6037	NPC76748
Remote Similarity	0.6028	NPC84478
Remote Similarity	0.6026	NPC477533
Remote Similarity	0.6025	NPC471614
Remote Similarity	0.6009	NPC477891
Remote Similarity	0.6009	NPC19872
Remote Similarity	0.6009	NPC144114
Remote Similarity	0.6009	NPC176538
Remote Similarity	0.6008	NPC157931
Remote Similarity	0.6008	NPC257851
Remote Similarity	0.6	NPC264176
Remote Similarity	0.6	NPC49051
Remote Similarity	0.6	NPC20249
Remote Similarity	0.5992	NPC471615
Remote Similarity	0.5991	NPC72211
Remote Similarity	0.5991	NPC296527
Remote Similarity	0.5984	NPC30540
Remote Similarity	0.5983	NPC471304
Remote Similarity	0.5983	NPC314954
Remote Similarity	0.5981	NPC85482
Remote Similarity	0.5981	NPC105758
Remote Similarity	0.5981	NPC476686
Remote Similarity	0.5981	NPC476688
Remote Similarity	0.5973	NPC70259
Remote Similarity	0.5972	NPC204385
Remote Similarity	0.5971	NPC118511
Remote Similarity	0.5966	NPC305984
Remote Similarity	0.5965	NPC475910
Remote Similarity	0.5962	NPC278874
Remote Similarity	0.5958	NPC115595
Remote Similarity	0.5957	NPC132642
Remote Similarity	0.5956	NPC295898
Remote Similarity	0.5955	NPC307963
Remote Similarity	0.5952	NPC208060
Remote Similarity	0.595	NPC180504
Remote Similarity	0.5948	NPC470549
Remote Similarity	0.5948	NPC50511
Remote Similarity	0.5947	NPC471736
Remote Similarity	0.594	NPC303658
Remote Similarity	0.5936	NPC56271
Remote Similarity	0.5935	NPC206201
Remote Similarity	0.5931	NPC251036
Remote Similarity	0.5929	NPC162484
Remote Similarity	0.5929	NPC223427
Remote Similarity	0.5928	NPC205934
Remote Similarity	0.5928	NPC43787
Remote Similarity	0.5923	NPC170114
Remote Similarity	0.5923	NPC148183
Remote Similarity	0.5923	NPC152768
Remote Similarity	0.5922	NPC150447
Remote Similarity	0.5917	NPC471762
Remote Similarity	0.5917	NPC472289
Remote Similarity	0.5917	NPC66777
Remote Similarity	0.5915	NPC250178
Remote Similarity	0.5911	NPC232727
Remote Similarity	0.5905	NPC478074
Remote Similarity	0.5903	NPC285558
Remote Similarity	0.5895	NPC287208
Remote Similarity	0.5895	NPC82548
Remote Similarity	0.589	NPC472099
Remote Similarity	0.5882	NPC226202
Remote Similarity	0.5882	NPC279401
Remote Similarity	0.5882	NPC79293
Remote Similarity	0.5877	NPC475841
Remote Similarity	0.5877	NPC474145
Remote Similarity	0.587	NPC174672
Remote Similarity	0.5868	NPC475253
Remote Similarity	0.5867	NPC11017
Remote Similarity	0.5867	NPC315957
Remote Similarity	0.5862	NPC471603
Remote Similarity	0.5862	NPC36168
Remote Similarity	0.5859	NPC75498
Remote Similarity	0.5859	NPC476138
Remote Similarity	0.5859	NPC245816
Remote Similarity	0.5857	NPC164664
Remote Similarity	0.5845	NPC224632
Remote Similarity	0.5845	NPC242928
Remote Similarity	0.5844	NPC167860
Remote Similarity	0.5844	NPC123976
Remote Similarity	0.5841	NPC470586
Remote Similarity	0.5841	NPC476044
Remote Similarity	0.584	NPC280272
Remote Similarity	0.5837	NPC195268
Remote Similarity	0.5837	NPC133140
Remote Similarity	0.5833	NPC2497
Remote Similarity	0.5833	NPC264166
Remote Similarity	0.5833	NPC274291
Remote Similarity	0.5833	NPC165349
Remote Similarity	0.5833	NPC329708
Remote Similarity	0.5833	NPC472031
Remote Similarity	0.5833	NPC472066
Remote Similarity	0.5833	NPC118832
Remote Similarity	0.5833	NPC47059
Remote Similarity	0.5833	NPC472067
Remote Similarity	0.583	NPC13880
Remote Similarity	0.583	NPC251090
Remote Similarity	0.5826	NPC308392
Remote Similarity	0.5823	NPC128115
Remote Similarity	0.5822	NPC56618
Remote Similarity	0.5822	NPC288943
Remote Similarity	0.5822	NPC476582
Remote Similarity	0.5822	NPC476578
Remote Similarity	0.5822	NPC4071
Remote Similarity	0.5822	NPC287437
Remote Similarity	0.582	NPC141053
Remote Similarity	0.5819	NPC208284
Remote Similarity	0.5817	NPC472068
Remote Similarity	0.5816	NPC130570
Remote Similarity	0.5815	NPC475112
Remote Similarity	0.5815	NPC475085
Remote Similarity	0.5815	NPC291535
Remote Similarity	0.5812	NPC50562
Remote Similarity	0.5808	NPC476106
Remote Similarity	0.5805	NPC467439
Remote Similarity	0.5805	NPC96321
Remote Similarity	0.5804	NPC70956
Remote Similarity	0.5804	NPC243834
Remote Similarity	0.5802	NPC314557
Remote Similarity	0.5801	NPC14877
Remote Similarity	0.5801	NPC145178
Remote Similarity	0.5801	NPC473181
Remote Similarity	0.5801	NPC475350
Remote Similarity	0.5801	NPC174758
Remote Similarity	0.5799	NPC66083
Remote Similarity	0.5798	NPC477532
Remote Similarity	0.5797	NPC25899
Remote Similarity	0.5796	NPC477019
Remote Similarity	0.5794	NPC26679
Remote Similarity	0.5794	NPC161242
Remote Similarity	0.5787	NPC67658
Remote Similarity	0.5787	NPC474798
Remote Similarity	0.5785	NPC131017

Drug Structure

NPD5144 OpenBabel08211706322D 27 30 0 0 1 0 0 0 0 0999 V2000 0.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9378 -6.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1288 -5.6776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8513 -5.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7379 -1.1118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5469 -1.6995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2333 -4.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9558 -4.8642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0823 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8424 -0.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0334 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4423 -2.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0823 0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4945 0.9706 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.1468 -4.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0334 0.4706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2514 -3.2818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 21 2 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 25 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB012032
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	381.19
ALogP	-0.3028
MLogP	3.33
XLogP	5.346
HDA	3
HBD	0
Rotatable Bonds	9
TPSA	56.84
RO5 Violation	1