NPASS drugs

Drug Information

Drug ID:	NPD4925
Drug Name:	Icotinib
Molecular Formula:	C22H21N3O4
Canonical SMILES:	C#Cc1cccc(c1)Nc1ncnc2c1cc1OCCOCCOCCOc1c2
Standard InCHI:	InChI=1S/C22H21N3O4/c1-2-16-4-3-5-17(12-16)25-22-18-13-20-21(14-19(18)23-15-24-22)29-11-9-27-7-6-26-8-10-28-20/h1,3-5,12-15H,6-11H2,(H,23,24,25)
Standard InCHIKey:	QQLKULDARVNMAL-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4925

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	613
0.1-0.2	5683
0.2-0.3	7475
0.3-0.4	7984
0.4-0.5	6387
0.5-0.6	2155
0.6-0.7	532
0.7-0.8	60
0.8-0.85	0
0.85-0.9	1
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
High Similarity	0.8634	NPC56271
Intermediate Similarity	0.7658	NPC162530
Intermediate Similarity	0.751	NPC472067
Intermediate Similarity	0.751	NPC472031
Intermediate Similarity	0.751	NPC472066
Intermediate Similarity	0.75	NPC472068
Intermediate Similarity	0.7431	NPC315957
Intermediate Similarity	0.743	NPC195268
Intermediate Similarity	0.743	NPC133140
Intermediate Similarity	0.7401	NPC473513
Intermediate Similarity	0.7376	NPC16452
Intermediate Similarity	0.7376	NPC36229
Intermediate Similarity	0.7376	NPC476581
Intermediate Similarity	0.7353	NPC30540
Intermediate Similarity	0.7345	NPC266931
Intermediate Similarity	0.7343	NPC312872
Intermediate Similarity	0.7306	NPC476582
Intermediate Similarity	0.7306	NPC4071
Intermediate Similarity	0.7306	NPC476578
Intermediate Similarity	0.7301	NPC316981
Intermediate Similarity	0.7293	NPC173080
Intermediate Similarity	0.7285	NPC135887
Intermediate Similarity	0.7285	NPC199277
Intermediate Similarity	0.7284	NPC130570
Intermediate Similarity	0.7273	NPC234197
Intermediate Similarity	0.7252	NPC162484
Intermediate Similarity	0.724	NPC31930
Intermediate Similarity	0.722	NPC285558
Intermediate Similarity	0.7212	NPC290689
Intermediate Similarity	0.7196	NPC204385
Intermediate Similarity	0.717	NPC144114
Intermediate Similarity	0.7168	NPC201697
Intermediate Similarity	0.7149	NPC296482
Intermediate Similarity	0.7149	NPC112206
Intermediate Similarity	0.7149	NPC202768
Intermediate Similarity	0.7149	NPC202605
Intermediate Similarity	0.7149	NPC53069
Intermediate Similarity	0.7112	NPC308906
Intermediate Similarity	0.7105	NPC208284
Intermediate Similarity	0.7101	NPC160666
Intermediate Similarity	0.7089	NPC206201
Intermediate Similarity	0.7087	NPC235076
Intermediate Similarity	0.708	NPC313189
Intermediate Similarity	0.7074	NPC171409
Intermediate Similarity	0.7074	NPC96405
Intermediate Similarity	0.7074	NPC48353
Intermediate Similarity	0.7069	NPC23614
Intermediate Similarity	0.7069	NPC100079
Intermediate Similarity	0.7061	NPC188420
Intermediate Similarity	0.7045	NPC131017
Intermediate Similarity	0.7043	NPC271215
Intermediate Similarity	0.7043	NPC149471
Intermediate Similarity	0.704	NPC329747
Intermediate Similarity	0.704	NPC477019
Intermediate Similarity	0.704	NPC303374
Intermediate Similarity	0.7027	NPC72211
Intermediate Similarity	0.7021	NPC280272
Intermediate Similarity	0.7016	NPC51854
Intermediate Similarity	0.7009	NPC232727
Intermediate Similarity	0.7004	NPC135549
Intermediate Similarity	0.7004	NPC193777
Remote Similarity	0.6996	NPC473822
Remote Similarity	0.6987	NPC123976
Remote Similarity	0.6987	NPC167860
Remote Similarity	0.6983	NPC295228
Remote Similarity	0.6976	NPC9729
Remote Similarity	0.6975	NPC187145
Remote Similarity	0.6974	NPC476465
Remote Similarity	0.6974	NPC18348
Remote Similarity	0.6966	NPC46451
Remote Similarity	0.6964	NPC176538
Remote Similarity	0.6952	NPC164664
Remote Similarity	0.6947	NPC223427
Remote Similarity	0.6941	NPC76748
Remote Similarity	0.6937	NPC70259
Remote Similarity	0.693	NPC477891
Remote Similarity	0.6926	NPC251160
Remote Similarity	0.6923	NPC307963
Remote Similarity	0.6919	NPC258773
Remote Similarity	0.6909	NPC92111
Remote Similarity	0.6908	NPC270515
Remote Similarity	0.69	NPC475910
Remote Similarity	0.6895	NPC296527
Remote Similarity	0.6894	NPC213530
Remote Similarity	0.6894	NPC193267
Remote Similarity	0.6894	NPC250178
Remote Similarity	0.6892	NPC43787
Remote Similarity	0.6892	NPC205934
Remote Similarity	0.6889	NPC329793
Remote Similarity	0.6887	NPC208060
Remote Similarity	0.6883	NPC477796
Remote Similarity	0.6883	NPC477805
Remote Similarity	0.6883	NPC477795
Remote Similarity	0.6883	NPC477806
Remote Similarity	0.6878	NPC118121
Remote Similarity	0.6875	NPC252251
Remote Similarity	0.6866	NPC84478
Remote Similarity	0.6861	NPC251090
Remote Similarity	0.6858	NPC470586
Remote Similarity	0.6858	NPC267423
Remote Similarity	0.6851	NPC204446
Remote Similarity	0.6849	NPC66083
Remote Similarity	0.6849	NPC254762
Remote Similarity	0.6844	NPC287437
Remote Similarity	0.684	NPC219664
Remote Similarity	0.6838	NPC170114
Remote Similarity	0.6829	NPC41501
Remote Similarity	0.6828	NPC291535
Remote Similarity	0.6828	NPC475085
Remote Similarity	0.6828	NPC475112
Remote Similarity	0.6824	NPC469592
Remote Similarity	0.6824	NPC236668
Remote Similarity	0.6824	NPC478074
Remote Similarity	0.6824	NPC471080
Remote Similarity	0.682	NPC176127
Remote Similarity	0.6818	NPC477531
Remote Similarity	0.6818	NPC201508
Remote Similarity	0.6816	NPC326634
Remote Similarity	0.6814	NPC121772
Remote Similarity	0.6812	NPC26850
Remote Similarity	0.6812	NPC476106
Remote Similarity	0.6805	NPC471762
Remote Similarity	0.6795	NPC146976
Remote Similarity	0.6795	NPC470549
Remote Similarity	0.6793	NPC477533
Remote Similarity	0.6786	NPC194967
Remote Similarity	0.6784	NPC476044
Remote Similarity	0.6781	NPC471603
Remote Similarity	0.6781	NPC203168
Remote Similarity	0.678	NPC469594
Remote Similarity	0.6777	NPC209174
Remote Similarity	0.6767	NPC471304
Remote Similarity	0.6763	NPC157931
Remote Similarity	0.6762	NPC255800
Remote Similarity	0.6762	NPC96584
Remote Similarity	0.6761	NPC105758
Remote Similarity	0.6761	NPC476688
Remote Similarity	0.6761	NPC476686
Remote Similarity	0.6756	NPC70956
Remote Similarity	0.6756	NPC243834
Remote Similarity	0.6754	NPC66815
Remote Similarity	0.6751	NPC17565
Remote Similarity	0.6748	NPC473183
Remote Similarity	0.6747	NPC316756
Remote Similarity	0.6745	NPC278874
Remote Similarity	0.6742	NPC230805
Remote Similarity	0.6739	NPC323345
Remote Similarity	0.6739	NPC472111
Remote Similarity	0.6739	NPC470164
Remote Similarity	0.6736	NPC66777
Remote Similarity	0.6736	NPC122463
Remote Similarity	0.6735	NPC277351
Remote Similarity	0.6726	NPC99666
Remote Similarity	0.6724	NPC469589
Remote Similarity	0.6723	NPC174049
Remote Similarity	0.6722	NPC214980
Remote Similarity	0.6722	NPC200888
Remote Similarity	0.6718	NPC132385
Remote Similarity	0.6714	NPC224632
Remote Similarity	0.6713	NPC283152
Remote Similarity	0.6712	NPC62069
Remote Similarity	0.6711	NPC13880
Remote Similarity	0.6708	NPC115595
Remote Similarity	0.6696	NPC79293
Remote Similarity	0.6696	NPC279401
Remote Similarity	0.6696	NPC470930
Remote Similarity	0.6695	NPC11464
Remote Similarity	0.6694	NPC110151
Remote Similarity	0.6694	NPC473182
Remote Similarity	0.668	NPC475253
Remote Similarity	0.6667	NPC472289
Remote Similarity	0.6667	NPC473184
Remote Similarity	0.6667	NPC26872
Remote Similarity	0.6667	NPC11017
Remote Similarity	0.6653	NPC472099
Remote Similarity	0.6652	NPC174758
Remote Similarity	0.6639	NPC473041
Remote Similarity	0.6639	NPC96321
Remote Similarity	0.6639	NPC65277
Remote Similarity	0.6638	NPC26679
Remote Similarity	0.6626	NPC470889
Remote Similarity	0.6625	NPC17305
Remote Similarity	0.6625	NPC477532
Remote Similarity	0.6625	NPC60621
Remote Similarity	0.6625	NPC310118
Remote Similarity	0.6624	NPC477110
Remote Similarity	0.6624	NPC5145
Remote Similarity	0.6623	NPC274291
Remote Similarity	0.6623	NPC329708
Remote Similarity	0.6623	NPC264166
Remote Similarity	0.6623	NPC165349
Remote Similarity	0.6623	NPC47059
Remote Similarity	0.6623	NPC118832
Remote Similarity	0.6621	NPC118776
Remote Similarity	0.6613	NPC472061
Remote Similarity	0.6612	NPC217176
Remote Similarity	0.6609	NPC470931
Remote Similarity	0.6609	NPC82548
Remote Similarity	0.6608	NPC474188
Remote Similarity	0.6608	NPC153042

Drug Structure

NPD4925 OpenBabel08211706322D 30 33 0 0 0 0 0 0 0 0999 V2000 -1.7320 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7320 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7320 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3303 -5.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3305 -4.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5984 -5.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1964 -3.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5983 -4.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8661 -2.5001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5982 -1.5001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8661 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 -0.8661 -1.5001 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 -1.7321 -3.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5982 -2.5001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4642 -6.0002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1963 -4.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7322 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4643 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7320 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 0 0 0 0 2 16 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 16 1 0 0 0 0 5 17 2 0 0 0 0 6 7 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 10 1 0 0 0 0 8 26 1 0 0 0 0 9 11 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB015104
DrugBank	DB11737
ChEMBL	CHEMBL2087361
IUPHAR/BPS	7641
PharmaGKB
KEGG Drug
PubChem CID	22024915
ChEBI
CAS Number	610798-31-7

Drug Properties

Molecular Weight	391.15
ALogP	-0.2023
MLogP	3.11
XLogP	2.934
HDA	5
HBD	1
Rotatable Bonds	2
TPSA	74.73
RO5 Violation	0