NPASS drugs

Drug Information

Drug ID:	NPD4332
Drug Name:	Linifanib
Molecular Formula:	C21H18FN5O
Canonical SMILES:	Cc1ccc(c(c1)N=C(Nc1ccc(cc1)c1cccc2c1c(N)n[nH]2)O)F
Standard InCHI:	InChI=1S/C21H18FN5O/c1-12-5-10-16(22)18(11-12)25-21(28)24-14-8-6-13(7-9-14)15-3-2-4-17-19(15)20(23)27-26-17/h2-11H,1H3,(H3,23,26,27)(H2,24,25,28)
Standard InCHIKey:	MPVGZUGXCQEXTM-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4332

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	617
0.1-0.2	6119
0.2-0.3	15474
0.3-0.4	5528
0.4-0.5	1856
0.5-0.6	1086
0.6-0.7	209
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	0.7041	NPC312092
Remote Similarity	0.691	NPC184476
Remote Similarity	0.6886	NPC473930
Remote Similarity	0.6857	NPC477134
Remote Similarity	0.6826	NPC475450
Remote Similarity	0.6826	NPC179365
Remote Similarity	0.678	NPC33421
Remote Similarity	0.6738	NPC471579
Remote Similarity	0.6727	NPC250361
Remote Similarity	0.6723	NPC124005
Remote Similarity	0.6707	NPC473587
Remote Similarity	0.6705	NPC284635
Remote Similarity	0.6703	NPC215584
Remote Similarity	0.6703	NPC44773
Remote Similarity	0.6686	NPC242556
Remote Similarity	0.6667	NPC194411
Remote Similarity	0.6667	NPC475428
Remote Similarity	0.6647	NPC473762
Remote Similarity	0.6578	NPC280548
Remote Similarity	0.6575	NPC38736
Remote Similarity	0.6568	NPC22079
Remote Similarity	0.6561	NPC37423
Remote Similarity	0.6561	NPC275305
Remote Similarity	0.6557	NPC318065
Remote Similarity	0.6557	NPC206819
Remote Similarity	0.6557	NPC56765
Remote Similarity	0.6557	NPC41257
Remote Similarity	0.6554	NPC204141
Remote Similarity	0.6541	NPC472587
Remote Similarity	0.6536	NPC37548
Remote Similarity	0.6517	NPC129042
Remote Similarity	0.6514	NPC59084
Remote Similarity	0.6503	NPC286427
Remote Similarity	0.6503	NPC316910
Remote Similarity	0.6492	NPC68354
Remote Similarity	0.6485	NPC41174
Remote Similarity	0.648	NPC21605
Remote Similarity	0.6477	NPC63157
Remote Similarity	0.6477	NPC473868
Remote Similarity	0.6467	NPC135141
Remote Similarity	0.6467	NPC92796
Remote Similarity	0.6461	NPC314372
Remote Similarity	0.6458	NPC176199
Remote Similarity	0.6458	NPC215795
Remote Similarity	0.6441	NPC190296
Remote Similarity	0.6437	NPC125746
Remote Similarity	0.6432	NPC473320
Remote Similarity	0.642	NPC115611
Remote Similarity	0.642	NPC2949
Remote Similarity	0.6416	NPC198988
Remote Similarity	0.6409	NPC53947
Remote Similarity	0.6409	NPC105818
Remote Similarity	0.6409	NPC24678
Remote Similarity	0.6398	NPC16667
Remote Similarity	0.6398	NPC317031
Remote Similarity	0.6393	NPC470507
Remote Similarity	0.6393	NPC471458
Remote Similarity	0.6383	NPC49217
Remote Similarity	0.6379	NPC325252
Remote Similarity	0.6374	NPC470233
Remote Similarity	0.6364	NPC271734
Remote Similarity	0.6364	NPC162799
Remote Similarity	0.6364	NPC90723
Remote Similarity	0.6364	NPC88097
Remote Similarity	0.6359	NPC285469
Remote Similarity	0.6359	NPC19679
Remote Similarity	0.6354	NPC187951
Remote Similarity	0.6349	NPC154293
Remote Similarity	0.6344	NPC229173
Remote Similarity	0.634	NPC88110
Remote Similarity	0.6339	NPC469763
Remote Similarity	0.6339	NPC73952
Remote Similarity	0.6339	NPC469765
Remote Similarity	0.6339	NPC25008
Remote Similarity	0.6339	NPC259644
Remote Similarity	0.6339	NPC469786
Remote Similarity	0.6339	NPC469760
Remote Similarity	0.6333	NPC143872
Remote Similarity	0.6333	NPC288838
Remote Similarity	0.6328	NPC469768
Remote Similarity	0.6328	NPC469761
Remote Similarity	0.6328	NPC469779
Remote Similarity	0.6328	NPC469784
Remote Similarity	0.6328	NPC469780
Remote Similarity	0.6328	NPC469767
Remote Similarity	0.6328	NPC469783
Remote Similarity	0.6324	NPC299594
Remote Similarity	0.6324	NPC216643
Remote Similarity	0.631	NPC470203
Remote Similarity	0.631	NPC122718
Remote Similarity	0.6304	NPC70922
Remote Similarity	0.6304	NPC212376
Remote Similarity	0.6304	NPC80597
Remote Similarity	0.6304	NPC211572
Remote Similarity	0.6304	NPC75540
Remote Similarity	0.6302	NPC189812
Remote Similarity	0.6302	NPC329688
Remote Similarity	0.6298	NPC114209
Remote Similarity	0.6298	NPC471957
Remote Similarity	0.6294	NPC476319
Remote Similarity	0.6292	NPC469766
Remote Similarity	0.629	NPC474880
Remote Similarity	0.629	NPC300238
Remote Similarity	0.629	NPC475990
Remote Similarity	0.629	NPC221786
Remote Similarity	0.6286	NPC218268
Remote Similarity	0.6278	NPC470440
Remote Similarity	0.6278	NPC159856
Remote Similarity	0.6277	NPC317105
Remote Similarity	0.6271	NPC73767
Remote Similarity	0.6271	NPC110126
Remote Similarity	0.627	NPC51054
Remote Similarity	0.6263	NPC63751
Remote Similarity	0.6257	NPC470204
Remote Similarity	0.625	NPC84911
Remote Similarity	0.625	NPC105127
Remote Similarity	0.625	NPC325903
Remote Similarity	0.625	NPC97525
Remote Similarity	0.6244	NPC21429
Remote Similarity	0.6237	NPC59269
Remote Similarity	0.6216	NPC476219
Remote Similarity	0.6207	NPC85066
Remote Similarity	0.6207	NPC195314
Remote Similarity	0.6207	NPC181502
Remote Similarity	0.6203	NPC67056
Remote Similarity	0.6203	NPC6436
Remote Similarity	0.62	NPC246700
Remote Similarity	0.6198	NPC6982
Remote Similarity	0.6193	NPC261195
Remote Similarity	0.6193	NPC29886
Remote Similarity	0.6193	NPC96102
Remote Similarity	0.6183	NPC469785
Remote Similarity	0.6178	NPC201700
Remote Similarity	0.617	NPC122141
Remote Similarity	0.6169	NPC95783
Remote Similarity	0.6166	NPC34508
Remote Similarity	0.6162	NPC200743
Remote Similarity	0.6158	NPC314102
Remote Similarity	0.6158	NPC251722
Remote Similarity	0.615	NPC477887
Remote Similarity	0.615	NPC76982
Remote Similarity	0.615	NPC469762
Remote Similarity	0.6146	NPC474897
Remote Similarity	0.6145	NPC162689
Remote Similarity	0.6145	NPC54102
Remote Similarity	0.6131	NPC473189
Remote Similarity	0.6131	NPC15102
Remote Similarity	0.6129	NPC207726
Remote Similarity	0.6129	NPC476297
Remote Similarity	0.6126	NPC474561
Remote Similarity	0.6126	NPC160105
Remote Similarity	0.6126	NPC49954
Remote Similarity	0.6124	NPC169433
Remote Similarity	0.612	NPC179787
Remote Similarity	0.612	NPC201380
Remote Similarity	0.6108	NPC216713
Remote Similarity	0.6105	NPC247987
Remote Similarity	0.6105	NPC8104
Remote Similarity	0.6105	NPC476118
Remote Similarity	0.6105	NPC271797
Remote Similarity	0.6105	NPC21174
Remote Similarity	0.6105	NPC311276
Remote Similarity	0.6103	NPC288785
Remote Similarity	0.6101	NPC434
Remote Similarity	0.6101	NPC79618
Remote Similarity	0.6098	NPC472193
Remote Similarity	0.6096	NPC141353
Remote Similarity	0.6094	NPC317430
Remote Similarity	0.6091	NPC198339
Remote Similarity	0.6091	NPC16659
Remote Similarity	0.6091	NPC300688
Remote Similarity	0.6089	NPC104483
Remote Similarity	0.6087	NPC2272
Remote Similarity	0.6087	NPC321911
Remote Similarity	0.6084	NPC81561
Remote Similarity	0.6082	NPC472123
Remote Similarity	0.608	NPC472294
Remote Similarity	0.6077	NPC477890
Remote Similarity	0.6075	NPC200214
Remote Similarity	0.6074	NPC314141
Remote Similarity	0.6073	NPC470508
Remote Similarity	0.6071	NPC151939
Remote Similarity	0.6071	NPC215519
Remote Similarity	0.6068	NPC229332
Remote Similarity	0.6066	NPC63545
Remote Similarity	0.6061	NPC302191
Remote Similarity	0.6056	NPC279081
Remote Similarity	0.6054	NPC148592
Remote Similarity	0.6053	NPC282231
Remote Similarity	0.6053	NPC225018
Remote Similarity	0.6042	NPC109447
Remote Similarity	0.6041	NPC270009
Remote Similarity	0.6041	NPC265710
Remote Similarity	0.604	NPC128751
Remote Similarity	0.6033	NPC469811
Remote Similarity	0.6031	NPC201634
Remote Similarity	0.603	NPC117027
Remote Similarity	0.6024	NPC148140
Remote Similarity	0.6021	NPC40779
Remote Similarity	0.602	NPC280852

Drug Structure

NPD4332 OpenBabel08211705262D 33 36 0 0 0 0 0 0 0 0999 V2000 -7.4578 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5918 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7258 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7258 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5918 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8597 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8597 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9937 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9937 -1.0827 0.0000 F 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 -3.1277 -4.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9937 -3.0827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 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 -4.8597 -4.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0540 -0.3783 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6939 -2.0725 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1277 -5.5827 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8597 -5.5827 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 15 1 0 0 0 0 4 17 2 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 13 15 1 0 0 0 0 14 24 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 20 23 1 0 0 0 0 20 27 2 0 0 0 0 21 24 1 0 0 0 0 21 25 2 3 0 0 0 21 28 1 0 0 0 0 23 29 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 26 27 1 0 0 0 0 26 32 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000029
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	11485656
ChEBI
CAS Number

Drug Properties

Molecular Weight	375.15
ALogP	-0.1231
MLogP	3
XLogP	6.243
HDA	6
HBD	4
Rotatable Bonds	8
TPSA	99.32
RO5 Violation	1