NPASS drugs

Drug Information

Drug ID:	NPD4421
Drug Name:	Crizotinib
Molecular Formula:	C21H22Cl2FN5O
Canonical SMILES:	Nc1ncc(cc1O[C@@H](c1c(Cl)ccc(c1Cl)F)C)c1cnn(c1)C1CCNCC1
Standard InCHI:	InChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1
Standard InCHIKey:	KTEIFNKAUNYNJU-GFCCVEGCSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4421

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	584
0.1-0.2	5958
0.2-0.3	7340
0.3-0.4	12239
0.4-0.5	3049
0.5-0.6	1568
0.6-0.7	150
0.7-0.8	2
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	0.7511	NPC180504
Intermediate Similarity	0.7229	NPC56271
Remote Similarity	0.6867	NPC471614
Remote Similarity	0.683	NPC471593
Remote Similarity	0.6783	NPC19872
Remote Similarity	0.6776	NPC314954
Remote Similarity	0.6723	NPC476465
Remote Similarity	0.6694	NPC469554
Remote Similarity	0.6681	NPC26679
Remote Similarity	0.6653	NPC160666
Remote Similarity	0.6624	NPC476138
Remote Similarity	0.6624	NPC245816
Remote Similarity	0.658	NPC267928
Remote Similarity	0.6562	NPC228206
Remote Similarity	0.6559	NPC103687
Remote Similarity	0.6559	NPC132631
Remote Similarity	0.6555	NPC185782
Remote Similarity	0.6535	NPC76748
Remote Similarity	0.6525	NPC285558
Remote Similarity	0.6524	NPC287437
Remote Similarity	0.6515	NPC476287
Remote Similarity	0.6507	NPC92111
Remote Similarity	0.6496	NPC30540
Remote Similarity	0.6496	NPC176538
Remote Similarity	0.6494	NPC101543
Remote Similarity	0.6491	NPC296527
Remote Similarity	0.6483	NPC475774
Remote Similarity	0.6458	NPC123976
Remote Similarity	0.6458	NPC167860
Remote Similarity	0.645	NPC307963
Remote Similarity	0.6444	NPC470474
Remote Similarity	0.6432	NPC208284
Remote Similarity	0.6411	NPC130570
Remote Similarity	0.6398	NPC232727
Remote Similarity	0.6395	NPC194967
Remote Similarity	0.6393	NPC8022
Remote Similarity	0.6393	NPC288349
Remote Similarity	0.6393	NPC470799
Remote Similarity	0.6379	NPC162530
Remote Similarity	0.6375	NPC287208
Remote Similarity	0.636	NPC323345
Remote Similarity	0.636	NPC470164
Remote Similarity	0.6356	NPC329793
Remote Similarity	0.6356	NPC121772
Remote Similarity	0.6325	NPC13880
Remote Similarity	0.6325	NPC473053
Remote Similarity	0.6325	NPC251090
Remote Similarity	0.6322	NPC290689
Remote Similarity	0.6318	NPC329708
Remote Similarity	0.6318	NPC264166
Remote Similarity	0.6318	NPC274291
Remote Similarity	0.6318	NPC118832
Remote Similarity	0.6318	NPC165349
Remote Similarity	0.6318	NPC47059
Remote Similarity	0.6316	NPC193267
Remote Similarity	0.6316	NPC213530
Remote Similarity	0.6314	NPC24802
Remote Similarity	0.6309	NPC84853
Remote Similarity	0.6287	NPC315957
Remote Similarity	0.6286	NPC470549
Remote Similarity	0.627	NPC471603
Remote Similarity	0.627	NPC94157
Remote Similarity	0.6266	NPC195268
Remote Similarity	0.6266	NPC133140
Remote Similarity	0.626	NPC477110
Remote Similarity	0.626	NPC170114
Remote Similarity	0.6245	NPC469592
Remote Similarity	0.6245	NPC471080
Remote Similarity	0.6245	NPC284559
Remote Similarity	0.624	NPC216612
Remote Similarity	0.624	NPC477111
Remote Similarity	0.6239	NPC289786
Remote Similarity	0.6224	NPC477113
Remote Similarity	0.6198	NPC471891
Remote Similarity	0.6192	NPC31930
Remote Similarity	0.6189	NPC11464
Remote Similarity	0.6189	NPC5145
Remote Similarity	0.6185	NPC250178
Remote Similarity	0.6185	NPC292958
Remote Similarity	0.6179	NPC266931
Remote Similarity	0.6176	NPC4071
Remote Similarity	0.6176	NPC476578
Remote Similarity	0.6176	NPC187558
Remote Similarity	0.6176	NPC476582
Remote Similarity	0.6174	NPC284678
Remote Similarity	0.6173	NPC475910
Remote Similarity	0.6172	NPC196718
Remote Similarity	0.616	NPC132642
Remote Similarity	0.6157	NPC472111
Remote Similarity	0.6157	NPC474798
Remote Similarity	0.6157	NPC115595
Remote Similarity	0.6151	NPC472067
Remote Similarity	0.6151	NPC472031
Remote Similarity	0.6151	NPC472066
Remote Similarity	0.6151	NPC329747
Remote Similarity	0.6151	NPC477019
Remote Similarity	0.6148	NPC469589
Remote Similarity	0.6145	NPC469594
Remote Similarity	0.6145	NPC75179
Remote Similarity	0.6139	NPC240384
Remote Similarity	0.6137	NPC472289
Remote Similarity	0.6136	NPC472068
Remote Similarity	0.6135	NPC310118
Remote Similarity	0.6132	NPC313189
Remote Similarity	0.6126	NPC97367
Remote Similarity	0.6116	NPC36229
Remote Similarity	0.6116	NPC476581
Remote Similarity	0.6116	NPC470930
Remote Similarity	0.6116	NPC16452
Remote Similarity	0.6116	NPC475070
Remote Similarity	0.6109	NPC102593
Remote Similarity	0.6107	NPC82548
Remote Similarity	0.6102	NPC475190
Remote Similarity	0.61	NPC295228
Remote Similarity	0.6099	NPC471178
Remote Similarity	0.6096	NPC472099
Remote Similarity	0.6087	NPC161887
Remote Similarity	0.6085	NPC141053
Remote Similarity	0.6082	NPC174672
Remote Similarity	0.6081	NPC152620
Remote Similarity	0.6081	NPC59779
Remote Similarity	0.6081	NPC124542
Remote Similarity	0.6081	NPC471177
Remote Similarity	0.608	NPC197141
Remote Similarity	0.608	NPC314270
Remote Similarity	0.6078	NPC110151
Remote Similarity	0.6078	NPC20249
Remote Similarity	0.6073	NPC202768
Remote Similarity	0.6073	NPC296482
Remote Similarity	0.6073	NPC53069
Remote Similarity	0.607	NPC475253
Remote Similarity	0.6068	NPC242928
Remote Similarity	0.6063	NPC125597
Remote Similarity	0.6061	NPC176127
Remote Similarity	0.6061	NPC472434
Remote Similarity	0.6049	NPC470500
Remote Similarity	0.6042	NPC476167
Remote Similarity	0.6037	NPC53534
Remote Similarity	0.6032	NPC242923
Remote Similarity	0.603	NPC26543
Remote Similarity	0.6023	NPC329631
Remote Similarity	0.6017	NPC234197
Remote Similarity	0.6017	NPC219963
Remote Similarity	0.6016	NPC174758
Remote Similarity	0.6008	NPC148889
Remote Similarity	0.6008	NPC60621
Remote Similarity	0.6008	NPC260434
Remote Similarity	0.6008	NPC300114
Remote Similarity	0.6	NPC152768
Remote Similarity	0.6	NPC192315
Remote Similarity	0.6	NPC148183
Remote Similarity	0.6	NPC135549
Remote Similarity	0.5992	NPC471304
Remote Similarity	0.5992	NPC99666
Remote Similarity	0.5992	NPC324149
Remote Similarity	0.5985	NPC295452
Remote Similarity	0.5985	NPC171393
Remote Similarity	0.5983	NPC242209
Remote Similarity	0.5983	NPC171171
Remote Similarity	0.5983	NPC224764
Remote Similarity	0.5982	NPC118511
Remote Similarity	0.5976	NPC304926
Remote Similarity	0.5976	NPC476041
Remote Similarity	0.5976	NPC473513
Remote Similarity	0.5975	NPC128823
Remote Similarity	0.5967	NPC470678
Remote Similarity	0.5966	NPC204717
Remote Similarity	0.5966	NPC226202
Remote Similarity	0.5966	NPC329541
Remote Similarity	0.5966	NPC84478
Remote Similarity	0.5962	NPC316756
Remote Similarity	0.5953	NPC473185
Remote Similarity	0.5953	NPC192712
Remote Similarity	0.5952	NPC173080
Remote Similarity	0.5951	NPC473181
Remote Similarity	0.5948	NPC266551
Remote Similarity	0.5947	NPC476518
Remote Similarity	0.5947	NPC81175
Remote Similarity	0.5946	NPC315062
Remote Similarity	0.5946	NPC476451
Remote Similarity	0.5945	NPC473317
Remote Similarity	0.5944	NPC316981
Remote Similarity	0.5944	NPC171409
Remote Similarity	0.5944	NPC202605
Remote Similarity	0.5944	NPC112206
Remote Similarity	0.5944	NPC96405
Remote Similarity	0.5944	NPC472098
Remote Similarity	0.5944	NPC251160
Remote Similarity	0.5943	NPC223427
Remote Similarity	0.5941	NPC472435
Remote Similarity	0.594	NPC314002
Remote Similarity	0.5938	NPC177404
Remote Similarity	0.5936	NPC472027
Remote Similarity	0.5934	NPC72211
Remote Similarity	0.5931	NPC42979
Remote Similarity	0.5927	NPC188420
Remote Similarity	0.5927	NPC199667
Remote Similarity	0.5923	NPC244897
Remote Similarity	0.5923	NPC49547
Remote Similarity	0.5923	NPC220765

Drug Structure

NPD4421 OpenBabel08211705262D 33 36 0 0 1 0 0 0 0 0999 V2000 3.6808 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2257 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 -1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 0.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 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 6.2788 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 1.2024 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -1.7976 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -2.7976 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 -2.7406 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 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 4.5468 1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 2.7024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 4.2024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6269 -3.6542 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 6 1 0 0 0 0 4 15 1 0 0 0 0 5 7 1 0 0 0 0 5 15 1 0 0 0 0 6 26 1 0 0 0 0 7 26 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 13 1 0 0 0 0 9 27 2 0 0 0 0 10 14 1 0 0 0 0 10 28 2 0 0 0 0 11 14 2 0 0 0 0 11 29 1 0 0 0 0 12 1 1 1 0 0 0 12 19 1 0 0 0 0 12 30 1 0 0 0 0 13 14 1 0 0 0 0 15 29 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 21 27 1 0 0 0 0 25 31 1 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 28 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNAP001679
DrugBank	DB08700
ChEMBL
IUPHAR/BPS	4903
PharmaGKB
KEGG Drug
PubChem CID	11626560
ChEBI
CAS Number

Drug Properties

Molecular Weight	449.12
ALogP	0.0548
MLogP	2.78
XLogP	2.834
HDA	5
HBD	2
Rotatable Bonds	10
TPSA	77.99
RO5 Violation	0