NPASS drugs

Drug Information

Drug ID:	NPD4945
Drug Name:	HIV integrase inhibitors, Merck & Co
Molecular Formula:	C22H22FN5O5S
Canonical SMILES:	CN=C(c1cc(F)ccc1CN=C(c1nc(c2c(c1O)nccc2)N1CCCCS1(=O)=O)O)O
Standard InCHI:	InChI=1S/C22H22FN5O5S/c1-24-21(30)16-11-14(23)7-6-13(16)12-26-22(31)18-19(29)17-15(5-4-8-25-17)20(27-18)28-9-2-3-10-34(28,32)33/h4-8,11,29H,2-3,9-10,12H2,1H3,(H,24,30)(H,26,31)
Standard InCHIKey:	KBXRRIUYQIDSON-UHFFFAOYSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4945

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	463
0.1-0.2	4054
0.2-0.3	9094
0.3-0.4	12116
0.4-0.5	3054
0.5-0.6	1649
0.6-0.7	439
0.7-0.8	21
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	0.7723	NPC103687
Intermediate Similarity	0.7723	NPC132631
Intermediate Similarity	0.7397	NPC477111
Intermediate Similarity	0.7333	NPC472289
Intermediate Similarity	0.7249	NPC130570
Intermediate Similarity	0.7227	NPC477113
Intermediate Similarity	0.7196	NPC329541
Intermediate Similarity	0.717	NPC230805
Intermediate Similarity	0.7157	NPC314940
Intermediate Similarity	0.7157	NPC473764
Intermediate Similarity	0.7111	NPC471603
Intermediate Similarity	0.7101	NPC150048
Intermediate Similarity	0.7101	NPC203754
Intermediate Similarity	0.7073	NPC164664
Intermediate Similarity	0.7048	NPC477891
Intermediate Similarity	0.7048	NPC144114
Intermediate Similarity	0.7044	NPC97367
Intermediate Similarity	0.7042	NPC254762
Intermediate Similarity	0.7039	NPC252590
Intermediate Similarity	0.7018	NPC477110
Intermediate Similarity	0.7005	NPC208060
Remote Similarity	0.6957	NPC476688
Remote Similarity	0.6957	NPC105758
Remote Similarity	0.6957	NPC476686
Remote Similarity	0.6951	NPC264166
Remote Similarity	0.6951	NPC274291
Remote Similarity	0.6951	NPC165349
Remote Similarity	0.6951	NPC47059
Remote Similarity	0.6951	NPC329708
Remote Similarity	0.6951	NPC118832
Remote Similarity	0.6942	NPC278874
Remote Similarity	0.6927	NPC471178
Remote Similarity	0.6912	NPC124542
Remote Similarity	0.6912	NPC59779
Remote Similarity	0.6912	NPC471177
Remote Similarity	0.6898	NPC3715
Remote Similarity	0.6894	NPC2497
Remote Similarity	0.6878	NPC476167
Remote Similarity	0.686	NPC44161
Remote Similarity	0.6833	NPC192315
Remote Similarity	0.6829	NPC224632
Remote Similarity	0.6803	NPC39092
Remote Similarity	0.6786	NPC470678
Remote Similarity	0.6784	NPC18348
Remote Similarity	0.678	NPC25899
Remote Similarity	0.6778	NPC476451
Remote Similarity	0.6753	NPC237740
Remote Similarity	0.6739	NPC202605
Remote Similarity	0.6739	NPC112206
Remote Similarity	0.6726	NPC287437
Remote Similarity	0.6721	NPC477861
Remote Similarity	0.6715	NPC473057
Remote Similarity	0.6707	NPC472066
Remote Similarity	0.6707	NPC472031
Remote Similarity	0.6707	NPC472067
Remote Similarity	0.6695	NPC216612
Remote Similarity	0.6695	NPC304926
Remote Similarity	0.6695	NPC469727
Remote Similarity	0.6695	NPC476041
Remote Similarity	0.6683	NPC269919
Remote Similarity	0.6683	NPC132680
Remote Similarity	0.6681	NPC214980
Remote Similarity	0.668	NPC30540
Remote Similarity	0.6667	NPC284559
Remote Similarity	0.6667	NPC48192
Remote Similarity	0.6667	NPC295452
Remote Similarity	0.6667	NPC171393
Remote Similarity	0.6653	NPC186351
Remote Similarity	0.6652	NPC476582
Remote Similarity	0.6652	NPC476578
Remote Similarity	0.6652	NPC470500
Remote Similarity	0.6652	NPC5145
Remote Similarity	0.6652	NPC4071
Remote Similarity	0.6652	NPC475070
Remote Similarity	0.6639	NPC477112
Remote Similarity	0.6627	NPC472068
Remote Similarity	0.6623	NPC470164
Remote Similarity	0.6623	NPC323345
Remote Similarity	0.6608	NPC475774
Remote Similarity	0.6606	NPC324149
Remote Similarity	0.6606	NPC99666
Remote Similarity	0.6598	NPC116622
Remote Similarity	0.6596	NPC173080
Remote Similarity	0.6596	NPC314270
Remote Similarity	0.6585	NPC63562
Remote Similarity	0.6583	NPC6215
Remote Similarity	0.6582	NPC473317
Remote Similarity	0.6581	NPC476161
Remote Similarity	0.6579	NPC36229
Remote Similarity	0.6579	NPC16452
Remote Similarity	0.6579	NPC476581
Remote Similarity	0.6568	NPC250178
Remote Similarity	0.6562	NPC267928
Remote Similarity	0.656	NPC314002
Remote Similarity	0.6558	NPC42979
Remote Similarity	0.6555	NPC263439
Remote Similarity	0.6542	NPC224764
Remote Similarity	0.6538	NPC324203
Remote Similarity	0.6538	NPC322976
Remote Similarity	0.6538	NPC63338
Remote Similarity	0.6532	NPC133140
Remote Similarity	0.6532	NPC195268
Remote Similarity	0.6532	NPC473312
Remote Similarity	0.653	NPC171171
Remote Similarity	0.6518	NPC242209
Remote Similarity	0.6514	NPC204717
Remote Similarity	0.65	NPC125597
Remote Similarity	0.6498	NPC266551
Remote Similarity	0.6498	NPC161887
Remote Similarity	0.6498	NPC313804
Remote Similarity	0.6498	NPC315804
Remote Similarity	0.6498	NPC219963
Remote Similarity	0.6493	NPC108469
Remote Similarity	0.6491	NPC328596
Remote Similarity	0.6491	NPC328318
Remote Similarity	0.6491	NPC211813
Remote Similarity	0.6489	NPC77555
Remote Similarity	0.6488	NPC314954
Remote Similarity	0.6482	NPC56271
Remote Similarity	0.6476	NPC249040
Remote Similarity	0.6476	NPC211187
Remote Similarity	0.6475	NPC477516
Remote Similarity	0.6468	NPC220765
Remote Similarity	0.6453	NPC220523
Remote Similarity	0.6452	NPC478032
Remote Similarity	0.645	NPC313189
Remote Similarity	0.6447	NPC31930
Remote Similarity	0.6441	NPC8022
Remote Similarity	0.6441	NPC470799
Remote Similarity	0.6438	NPC290689
Remote Similarity	0.6435	NPC472259
Remote Similarity	0.6432	NPC256828
Remote Similarity	0.6429	NPC193267
Remote Similarity	0.6429	NPC471891
Remote Similarity	0.6429	NPC213530
Remote Similarity	0.6425	NPC46580
Remote Similarity	0.6415	NPC478012
Remote Similarity	0.6415	NPC478011
Remote Similarity	0.6414	NPC470504
Remote Similarity	0.641	NPC242923
Remote Similarity	0.6407	NPC317373
Remote Similarity	0.6406	NPC232340
Remote Similarity	0.6404	NPC19872
Remote Similarity	0.6402	NPC174049
Remote Similarity	0.6397	NPC295228
Remote Similarity	0.6395	NPC74619
Remote Similarity	0.6395	NPC150447
Remote Similarity	0.6393	NPC48938
Remote Similarity	0.6391	NPC200836
Remote Similarity	0.6391	NPC314176
Remote Similarity	0.6391	NPC53144
Remote Similarity	0.6388	NPC212213
Remote Similarity	0.6388	NPC478013
Remote Similarity	0.6388	NPC265576
Remote Similarity	0.6386	NPC470403
Remote Similarity	0.6386	NPC470394
Remote Similarity	0.6386	NPC470404
Remote Similarity	0.6383	NPC53069
Remote Similarity	0.6383	NPC202768
Remote Similarity	0.6383	NPC296482
Remote Similarity	0.638	NPC314573
Remote Similarity	0.6379	NPC107160
Remote Similarity	0.6376	NPC469308
Remote Similarity	0.6367	NPC160666
Remote Similarity	0.6367	NPC201508
Remote Similarity	0.6364	NPC327592
Remote Similarity	0.6359	NPC184964
Remote Similarity	0.6356	NPC226202
Remote Similarity	0.6356	NPC24802
Remote Similarity	0.6352	NPC287208
Remote Similarity	0.6349	NPC122463
Remote Similarity	0.6345	NPC41679
Remote Similarity	0.6344	NPC156704
Remote Similarity	0.6344	NPC224928
Remote Similarity	0.6337	NPC60006
Remote Similarity	0.6335	NPC20249
Remote Similarity	0.6335	NPC42591
Remote Similarity	0.6333	NPC84508
Remote Similarity	0.6324	NPC470395
Remote Similarity	0.6324	NPC477633
Remote Similarity	0.632	NPC245816
Remote Similarity	0.632	NPC476138
Remote Similarity	0.6318	NPC133306
Remote Similarity	0.6318	NPC473822
Remote Similarity	0.6316	NPC96584
Remote Similarity	0.6316	NPC255800
Remote Similarity	0.6316	NPC220852
Remote Similarity	0.631	NPC316756
Remote Similarity	0.6309	NPC135549
Remote Similarity	0.6305	NPC28945
Remote Similarity	0.6305	NPC285343
Remote Similarity	0.6296	NPC245348
Remote Similarity	0.6296	NPC471294
Remote Similarity	0.6295	NPC81175
Remote Similarity	0.6287	NPC317752
Remote Similarity	0.6287	NPC162530
Remote Similarity	0.6281	NPC478141
Remote Similarity	0.6276	NPC473513
Remote Similarity	0.6275	NPC469554
Remote Similarity	0.6275	NPC101543

Drug Structure

NPD4945 OpenBabel08211706322D 37 40 0 0 0 0 0 0 0 0999 V2000 -8.6603 3.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -0.8660 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 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 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 -7.7942 0.5000 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 -3.4641 -1.0000 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 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 -4.3301 -2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 15 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 25 2 0 0 0 0 9 28 1 0 0 0 0 10 34 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 16 2 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 18 27 1 0 0 0 0 19 29 1 0 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 24 2 3 0 0 0 21 30 1 0 0 0 0 22 26 2 3 0 0 0 22 31 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 37 1 0 0 0 0 32 34 2 0 0 0 0 33 34 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB000200
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	487.13
ALogP	-2.0797
MLogP	2.56
XLogP	2.699
HDA	9
HBD	3
Rotatable Bonds	10
TPSA	156.95
RO5 Violation	0