NPASS drugs

Drug Information

Drug ID:	NPD5854
Drug Name:	apatinib
Molecular Formula:	C24H23N5O
Canonical SMILES:	N#CC1(CCCC1)c1ccc(cc1)NC(=O)c1cccnc1Nc1cnccc1C
Standard InCHI:	InChI=1S/C24H23N5O/c1-17-10-14-26-15-21(17)29-22-20(5-4-13-27-22)23(30)28-19-8-6-18(7-9-19)24(16-25)11-2-3-12-24/h4-10,13-15H,2-3,11-12H2,1H3,(H,27,29)(H,28,30)
Standard InCHIKey:	MGZNERAVOCFMCU-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5854

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	523
0.1-0.2	4396
0.2-0.3	15952
0.3-0.4	6348
0.4-0.5	1481
0.5-0.6	1592
0.6-0.7	566
0.7-0.8	32
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	0.7577	NPC135601
Intermediate Similarity	0.7577	NPC141612
Intermediate Similarity	0.7577	NPC17273
Intermediate Similarity	0.7561	NPC116555
Intermediate Similarity	0.7385	NPC21429
Intermediate Similarity	0.7366	NPC317701
Intermediate Similarity	0.7311	NPC177996
Intermediate Similarity	0.7311	NPC147983
Intermediate Similarity	0.7282	NPC191415
Intermediate Similarity	0.7277	NPC267811
Intermediate Similarity	0.7202	NPC317054
Intermediate Similarity	0.7196	NPC478184
Intermediate Similarity	0.7196	NPC478182
Intermediate Similarity	0.717	NPC153980
Intermediate Similarity	0.717	NPC6865
Intermediate Similarity	0.7157	NPC102755
Intermediate Similarity	0.7143	NPC16659
Intermediate Similarity	0.7123	NPC72956
Intermediate Similarity	0.7121	NPC477003
Intermediate Similarity	0.712	NPC56233
Intermediate Similarity	0.7114	NPC324091
Intermediate Similarity	0.7094	NPC326422
Intermediate Similarity	0.7092	NPC265710
Intermediate Similarity	0.7085	NPC133003
Intermediate Similarity	0.7053	NPC470203
Intermediate Similarity	0.7049	NPC467188
Intermediate Similarity	0.7037	NPC293487
Intermediate Similarity	0.7035	NPC467063
Intermediate Similarity	0.7016	NPC265100
Intermediate Similarity	0.7009	NPC471193
Intermediate Similarity	0.7009	NPC471194
Intermediate Similarity	0.7	NPC470204
Remote Similarity	0.6995	NPC476460
Remote Similarity	0.6991	NPC471192
Remote Similarity	0.6973	NPC105811
Remote Similarity	0.697	NPC73994
Remote Similarity	0.697	NPC88110
Remote Similarity	0.6968	NPC476219
Remote Similarity	0.6961	NPC216550
Remote Similarity	0.6961	NPC272458
Remote Similarity	0.6954	NPC240088
Remote Similarity	0.6954	NPC473380
Remote Similarity	0.6943	NPC478183
Remote Similarity	0.6942	NPC128244
Remote Similarity	0.6934	NPC243850
Remote Similarity	0.6915	NPC99939
Remote Similarity	0.6915	NPC308931
Remote Similarity	0.6904	NPC151635
Remote Similarity	0.6889	NPC470323
Remote Similarity	0.6875	NPC478185
Remote Similarity	0.6869	NPC157583
Remote Similarity	0.6869	NPC284775
Remote Similarity	0.6862	NPC70406
Remote Similarity	0.6858	NPC935
Remote Similarity	0.6858	NPC267078
Remote Similarity	0.6853	NPC469529
Remote Similarity	0.6845	NPC304203
Remote Similarity	0.6842	NPC237414
Remote Similarity	0.6828	NPC474357
Remote Similarity	0.6827	NPC167710
Remote Similarity	0.6825	NPC251391
Remote Similarity	0.6823	NPC122141
Remote Similarity	0.6821	NPC70949
Remote Similarity	0.682	NPC282247
Remote Similarity	0.6814	NPC103119
Remote Similarity	0.6808	NPC472064
Remote Similarity	0.68	NPC40530
Remote Similarity	0.68	NPC314281
Remote Similarity	0.6798	NPC476527
Remote Similarity	0.6789	NPC209362
Remote Similarity	0.6788	NPC225018
Remote Similarity	0.6786	NPC91895
Remote Similarity	0.6786	NPC32534
Remote Similarity	0.6784	NPC237188
Remote Similarity	0.6784	NPC83774
Remote Similarity	0.6779	NPC79356
Remote Similarity	0.6779	NPC102592
Remote Similarity	0.6774	NPC473218
Remote Similarity	0.6774	NPC470702
Remote Similarity	0.6771	NPC80681
Remote Similarity	0.6769	NPC114637
Remote Similarity	0.6758	NPC470731
Remote Similarity	0.6743	NPC470703
Remote Similarity	0.6728	NPC54981
Remote Similarity	0.672	NPC313889
Remote Similarity	0.6719	NPC213914
Remote Similarity	0.6718	NPC42372
Remote Similarity	0.6717	NPC252572
Remote Similarity	0.6716	NPC61011
Remote Similarity	0.6714	NPC34837
Remote Similarity	0.6702	NPC229055
Remote Similarity	0.6702	NPC476297
Remote Similarity	0.6702	NPC201380
Remote Similarity	0.6702	NPC179787
Remote Similarity	0.6701	NPC194881
Remote Similarity	0.6696	NPC476817
Remote Similarity	0.6696	NPC116622
Remote Similarity	0.6685	NPC2823
Remote Similarity	0.6684	NPC470233
Remote Similarity	0.6684	NPC472260
Remote Similarity	0.6684	NPC117032
Remote Similarity	0.6683	NPC293216
Remote Similarity	0.6682	NPC477004
Remote Similarity	0.6667	NPC321911
Remote Similarity	0.6667	NPC101165
Remote Similarity	0.6667	NPC472062
Remote Similarity	0.6667	NPC472063
Remote Similarity	0.6667	NPC472069
Remote Similarity	0.6667	NPC74357
Remote Similarity	0.6667	NPC123906
Remote Similarity	0.6667	NPC12649
Remote Similarity	0.6651	NPC471191
Remote Similarity	0.6651	NPC121327
Remote Similarity	0.665	NPC255909
Remote Similarity	0.665	NPC470205
Remote Similarity	0.6649	NPC63545
Remote Similarity	0.6649	NPC325903
Remote Similarity	0.6635	NPC474916
Remote Similarity	0.6634	NPC477042
Remote Similarity	0.6634	NPC24864
Remote Similarity	0.6633	NPC161861
Remote Similarity	0.6632	NPC40070
Remote Similarity	0.662	NPC469308
Remote Similarity	0.6618	NPC46895
Remote Similarity	0.6618	NPC285923
Remote Similarity	0.6618	NPC108011
Remote Similarity	0.6615	NPC242116
Remote Similarity	0.6615	NPC120070
Remote Similarity	0.6614	NPC469811
Remote Similarity	0.6606	NPC470732
Remote Similarity	0.6604	NPC81535
Remote Similarity	0.6604	NPC284338
Remote Similarity	0.6601	NPC307191
Remote Similarity	0.659	NPC71238
Remote Similarity	0.6589	NPC143977
Remote Similarity	0.6588	NPC174281
Remote Similarity	0.6588	NPC106824
Remote Similarity	0.6588	NPC475286
Remote Similarity	0.6585	NPC476341
Remote Similarity	0.6584	NPC11126
Remote Similarity	0.6582	NPC271797
Remote Similarity	0.6582	NPC21174
Remote Similarity	0.6576	NPC251722
Remote Similarity	0.6576	NPC65408
Remote Similarity	0.6576	NPC314102
Remote Similarity	0.6575	NPC471322
Remote Similarity	0.6574	NPC472065
Remote Similarity	0.6567	NPC280852
Remote Similarity	0.6561	NPC478186
Remote Similarity	0.6553	NPC94752
Remote Similarity	0.655	NPC69843
Remote Similarity	0.6548	NPC233380
Remote Similarity	0.6546	NPC236711
Remote Similarity	0.6545	NPC473878
Remote Similarity	0.6537	NPC228835
Remote Similarity	0.6535	NPC476491
Remote Similarity	0.6528	NPC88115
Remote Similarity	0.6526	NPC136957
Remote Similarity	0.6526	NPC19696
Remote Similarity	0.6526	NPC470111
Remote Similarity	0.6524	NPC474180
Remote Similarity	0.6524	NPC188821
Remote Similarity	0.652	NPC470677
Remote Similarity	0.6519	NPC282398
Remote Similarity	0.6517	NPC245244
Remote Similarity	0.6517	NPC146373
Remote Similarity	0.6517	NPC166424
Remote Similarity	0.6514	NPC266249
Remote Similarity	0.6513	NPC474492
Remote Similarity	0.6508	NPC470440
Remote Similarity	0.6504	NPC312942
Remote Similarity	0.6504	NPC327095
Remote Similarity	0.6502	NPC248462
Remote Similarity	0.65	NPC471589
Remote Similarity	0.6497	NPC317105
Remote Similarity	0.6488	NPC270834
Remote Similarity	0.6484	NPC472070
Remote Similarity	0.6481	NPC477549
Remote Similarity	0.648	NPC470680
Remote Similarity	0.648	NPC100104
Remote Similarity	0.6479	NPC474389
Remote Similarity	0.6479	NPC265576
Remote Similarity	0.6476	NPC40455
Remote Similarity	0.6473	NPC62749
Remote Similarity	0.6462	NPC48117
Remote Similarity	0.6462	NPC329765
Remote Similarity	0.6462	NPC476526
Remote Similarity	0.6455	NPC123839
Remote Similarity	0.6452	NPC473376
Remote Similarity	0.6449	NPC153123
Remote Similarity	0.6449	NPC474318
Remote Similarity	0.6449	NPC268744
Remote Similarity	0.6449	NPC201266
Remote Similarity	0.6449	NPC475914
Remote Similarity	0.6449	NPC220797
Remote Similarity	0.6447	NPC19170
Remote Similarity	0.6435	NPC106757
Remote Similarity	0.6435	NPC156003
Remote Similarity	0.6432	NPC49217
Remote Similarity	0.6429	NPC300238

Drug Structure

NPD5854 OpenBabel08211708292D 32 35 0 0 0 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8120 -0.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5531 -1.8812 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 3.4641 -3.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9733 -0.3707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5545 -1.9336 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 -3.4641 0.0000 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 4.8784 -0.0518 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 -1.7321 -1.0000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5607 0.8964 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 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 3 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 18 2 0 0 0 0 7 9 2 0 0 0 0 7 18 1 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 11 24 1 0 0 0 0 12 24 1 0 0 0 0 13 27 2 0 0 0 0 14 26 2 0 0 0 0 15 21 2 0 0 0 0 15 26 1 0 0 0 0 16 24 1 0 0 0 0 16 25 3 0 0 0 0 17 21 1 0 0 0 0 18 24 1 0 0 0 0 19 28 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 29 1 0 0 0 0 22 27 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 23 30 2 0 0 0 0 28 31 1 0 0 0 0 29 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB005388
DrugBank
ChEMBL
IUPHAR/BPS	7648
PharmaGKB
KEGG Drug
PubChem CID	66577012
ChEBI
CAS Number

Drug Properties

Molecular Weight	397.19
ALogP	-1.1995
MLogP	3.44
XLogP	4.728
HDA	6
HBD	2
Rotatable Bonds	7
TPSA	90.7
RO5 Violation	0