NPASS drugs

Drug Information

Drug ID:	NPD5458
Drug Name:	GP-3269
Molecular Formula:	C23H21FN4O3
Canonical SMILES:	Fc1ccc(cc1)Nc1ncnc2c1c(cn2[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C)c1ccccc1
Standard InCHI:	InChI=1S/C23H21FN4O3/c1-13-19(29)20(30)23(31-13)28-11-17(14-5-3-2-4-6-14)18-21(25-12-26-22(18)28)27-16-9-7-15(24)8-10-16/h2-13,19-20,23,29-30H,1H3,(H,25,26,27)/t13-,19-,20-,23-/m1/s1
Standard InCHIKey:	MULTXXBUCOCYME-HYYMDVBZSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD5458

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	302
0.1-0.2	2008
0.2-0.3	12436
0.3-0.4	11494
0.4-0.5	2266
0.5-0.6	1800
0.6-0.7	570
0.7-0.8	14
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	0.7619	NPC168702
Intermediate Similarity	0.7619	NPC125659
Intermediate Similarity	0.7602	NPC158055
Intermediate Similarity	0.757	NPC250178
Intermediate Similarity	0.7569	NPC107160
Intermediate Similarity	0.7423	NPC317054
Intermediate Similarity	0.7352	NPC130570
Intermediate Similarity	0.7309	NPC160666
Intermediate Similarity	0.7292	NPC33382
Intermediate Similarity	0.7179	NPC222174
Intermediate Similarity	0.713	NPC471603
Intermediate Similarity	0.7129	NPC62510
Intermediate Similarity	0.708	NPC21461
Intermediate Similarity	0.7023	NPC314957
Remote Similarity	0.6981	NPC469308
Remote Similarity	0.6967	NPC474767
Remote Similarity	0.6888	NPC476446
Remote Similarity	0.6888	NPC469813
Remote Similarity	0.6888	NPC40779
Remote Similarity	0.6888	NPC78375
Remote Similarity	0.6878	NPC188387
Remote Similarity	0.6878	NPC163421
Remote Similarity	0.6869	NPC193761
Remote Similarity	0.686	NPC150447
Remote Similarity	0.686	NPC472289
Remote Similarity	0.6837	NPC71079
Remote Similarity	0.6832	NPC59269
Remote Similarity	0.6826	NPC89987
Remote Similarity	0.6823	NPC469975
Remote Similarity	0.6818	NPC49217
Remote Similarity	0.6802	NPC474217
Remote Similarity	0.6802	NPC311276
Remote Similarity	0.68	NPC470498
Remote Similarity	0.6796	NPC15102
Remote Similarity	0.6761	NPC149708
Remote Similarity	0.6745	NPC292361
Remote Similarity	0.6736	NPC470233
Remote Similarity	0.6734	NPC278366
Remote Similarity	0.6734	NPC127730
Remote Similarity	0.6732	NPC233936
Remote Similarity	0.6725	NPC476492
Remote Similarity	0.6716	NPC141377
Remote Similarity	0.6699	NPC472109
Remote Similarity	0.6699	NPC472110
Remote Similarity	0.6697	NPC320968
Remote Similarity	0.6684	NPC138018
Remote Similarity	0.6684	NPC469762
Remote Similarity	0.6683	NPC85918
Remote Similarity	0.6667	NPC68354
Remote Similarity	0.6667	NPC69843
Remote Similarity	0.6667	NPC95783
Remote Similarity	0.6667	NPC64216
Remote Similarity	0.665	NPC135141
Remote Similarity	0.665	NPC92796
Remote Similarity	0.6637	NPC54744
Remote Similarity	0.6636	NPC476874
Remote Similarity	0.6634	NPC133261
Remote Similarity	0.6633	NPC469785
Remote Similarity	0.6622	NPC54981
Remote Similarity	0.6622	NPC238945
Remote Similarity	0.6622	NPC267811
Remote Similarity	0.6617	NPC63751
Remote Similarity	0.6609	NPC103687
Remote Similarity	0.6609	NPC132631
Remote Similarity	0.6595	NPC470730
Remote Similarity	0.6595	NPC477176
Remote Similarity	0.6595	NPC477175
Remote Similarity	0.6595	NPC470729
Remote Similarity	0.6585	NPC151939
Remote Similarity	0.6583	NPC470203
Remote Similarity	0.6582	NPC120070
Remote Similarity	0.6582	NPC239737
Remote Similarity	0.6578	NPC470732
Remote Similarity	0.6578	NPC470731
Remote Similarity	0.6569	NPC189812
Remote Similarity	0.6569	NPC329688
Remote Similarity	0.6569	NPC37423
Remote Similarity	0.6569	NPC275305
Remote Similarity	0.6567	NPC474877
Remote Similarity	0.6567	NPC475969
Remote Similarity	0.6567	NPC475859
Remote Similarity	0.6567	NPC477177
Remote Similarity	0.6567	NPC54988
Remote Similarity	0.6562	NPC282247
Remote Similarity	0.6561	NPC116555
Remote Similarity	0.6557	NPC314882
Remote Similarity	0.655	NPC327095
Remote Similarity	0.655	NPC317105
Remote Similarity	0.655	NPC312942
Remote Similarity	0.6538	NPC469358
Remote Similarity	0.6538	NPC165743
Remote Similarity	0.6538	NPC48938
Remote Similarity	0.6538	NPC472108
Remote Similarity	0.6538	NPC139291
Remote Similarity	0.6537	NPC24594
Remote Similarity	0.6537	NPC472122
Remote Similarity	0.6535	NPC201700
Remote Similarity	0.6533	NPC470204
Remote Similarity	0.6533	NPC478157
Remote Similarity	0.6532	NPC478158
Remote Similarity	0.6531	NPC469765
Remote Similarity	0.6531	NPC73952
Remote Similarity	0.6531	NPC259644
Remote Similarity	0.6531	NPC469763
Remote Similarity	0.6531	NPC469786
Remote Similarity	0.6531	NPC469760
Remote Similarity	0.6531	NPC25008
Remote Similarity	0.6527	NPC39092
Remote Similarity	0.6524	NPC474707
Remote Similarity	0.6522	NPC40455
Remote Similarity	0.6522	NPC16659
Remote Similarity	0.6522	NPC300688
Remote Similarity	0.6522	NPC476817
Remote Similarity	0.652	NPC281049
Remote Similarity	0.6518	NPC478006
Remote Similarity	0.6515	NPC129721
Remote Similarity	0.6513	NPC53947
Remote Similarity	0.6511	NPC63279
Remote Similarity	0.6507	NPC471506
Remote Similarity	0.6502	NPC5145
Remote Similarity	0.65	NPC470500
Remote Similarity	0.6497	NPC212376
Remote Similarity	0.6497	NPC211572
Remote Similarity	0.6497	NPC75540
Remote Similarity	0.6497	NPC70922
Remote Similarity	0.6497	NPC476219
Remote Similarity	0.6497	NPC80597
Remote Similarity	0.6495	NPC474177
Remote Similarity	0.6494	NPC19170
Remote Similarity	0.6493	NPC204565
Remote Similarity	0.6493	NPC317030
Remote Similarity	0.649	NPC477891
Remote Similarity	0.6486	NPC71238
Remote Similarity	0.6485	NPC160105
Remote Similarity	0.6485	NPC474561
Remote Similarity	0.6485	NPC49954
Remote Similarity	0.6483	NPC297642
Remote Similarity	0.6477	NPC314372
Remote Similarity	0.6476	NPC477114
Remote Similarity	0.6475	NPC56271
Remote Similarity	0.6473	NPC265710
Remote Similarity	0.6473	NPC215795
Remote Similarity	0.6473	NPC176199
Remote Similarity	0.6471	NPC89562
Remote Similarity	0.6468	NPC478009
Remote Similarity	0.6468	NPC478010
Remote Similarity	0.6462	NPC321708
Remote Similarity	0.6462	NPC173028
Remote Similarity	0.6462	NPC65215
Remote Similarity	0.6459	NPC163055
Remote Similarity	0.6458	NPC171393
Remote Similarity	0.6458	NPC295452
Remote Similarity	0.6457	NPC162860
Remote Similarity	0.6456	NPC203754
Remote Similarity	0.6456	NPC150048
Remote Similarity	0.6453	NPC319456
Remote Similarity	0.6452	NPC265576
Remote Similarity	0.6445	NPC94752
Remote Similarity	0.6444	NPC75634
Remote Similarity	0.6443	NPC288838
Remote Similarity	0.6442	NPC187827
Remote Similarity	0.6442	NPC472105
Remote Similarity	0.6441	NPC323927
Remote Similarity	0.6439	NPC314603
Remote Similarity	0.6438	NPC475506
Remote Similarity	0.6432	NPC471192
Remote Similarity	0.6429	NPC315467
Remote Similarity	0.6425	NPC470505
Remote Similarity	0.6422	NPC98371
Remote Similarity	0.6422	NPC194411
Remote Similarity	0.6422	NPC313884
Remote Similarity	0.6418	NPC225018
Remote Similarity	0.6418	NPC282231
Remote Similarity	0.6415	NPC313514
Remote Similarity	0.6414	NPC476297
Remote Similarity	0.641	NPC297862
Remote Similarity	0.6409	NPC155143
Remote Similarity	0.6408	NPC469938
Remote Similarity	0.6407	NPC253987
Remote Similarity	0.6406	NPC229332
Remote Similarity	0.6404	NPC472285
Remote Similarity	0.64	NPC230869
Remote Similarity	0.6393	NPC106771
Remote Similarity	0.6393	NPC303820
Remote Similarity	0.6393	NPC471564
Remote Similarity	0.6393	NPC205254
Remote Similarity	0.6393	NPC23420
Remote Similarity	0.6389	NPC133366
Remote Similarity	0.6386	NPC102423
Remote Similarity	0.6377	NPC280852
Remote Similarity	0.6376	NPC470499
Remote Similarity	0.6376	NPC473640
Remote Similarity	0.6373	NPC190296
Remote Similarity	0.6372	NPC304187
Remote Similarity	0.6372	NPC477166
Remote Similarity	0.6372	NPC153980
Remote Similarity	0.6372	NPC473342
Remote Similarity	0.6372	NPC477167
Remote Similarity	0.6372	NPC6865
Remote Similarity	0.6368	NPC122141

Drug Structure

NPD5458 OpenBabel08211708292D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7935 4.1599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1026 3.2089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8154 4.3678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4334 2.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1463 3.6247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4582 -1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3242 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5921 -0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4582 0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7916 2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9941 -1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4553 2.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3242 -0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5921 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9941 0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8601 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1280 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1902 -1.0477 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 3.8601 -0.5477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1280 -0.5477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7261 0.9523 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1160 1.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 2.5772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7261 1.9523 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9250 0.9016 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0409 3.1650 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 28 1 0 0 0 0 12 25 2 0 0 0 0 12 26 1 0 0 0 0 13 1 1 6 0 0 0 13 19 1 0 0 0 0 13 31 1 0 0 0 0 14 17 1 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 1 0 0 0 20 23 1 0 0 0 0 20 30 1 1 0 0 0 21 25 1 0 0 0 0 21 27 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 28 1 6 0 0 0 23 31 1 0 0 0 0 27 32 1 0 0 0 0 29 33 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB002166
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	420.16
ALogP	-0.9699
MLogP	3.11
XLogP	5.14
HDA	7
HBD	3
Rotatable Bonds	8
TPSA	92.43
RO5 Violation	1