NPASS drugs

Drug Information

Drug ID:	NPD5855
Drug Name:	Apatinib
Molecular Formula:	C24H23N5O
Canonical SMILES:	N#CC1(CCCC1)c1ccc(cc1)NC(=O)c1cccnc1NCc1ccncc1
Standard InCHI:	InChI=1S/C24H23N5O/c25-17-24(11-1-2-12-24)19-5-7-20(8-6-19)29-23(30)21-4-3-13-27-22(21)28-16-18-9-14-26-15-10-18/h3-10,13-15H,1-2,11-12,16H2,(H,27,28)(H,29,30)
Standard InCHIKey:	WPEWQEMJFLWMLV-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5855

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	558
0.1-0.2	4586
0.2-0.3	15627
0.3-0.4	6508
0.4-0.5	1438
0.5-0.6	1557
0.6-0.7	589
0.7-0.8	27
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	0.7461	NPC141612
Intermediate Similarity	0.7461	NPC17273
Intermediate Similarity	0.7461	NPC135601
Intermediate Similarity	0.7451	NPC116555
Intermediate Similarity	0.7358	NPC477003
Intermediate Similarity	0.7358	NPC21429
Intermediate Similarity	0.7222	NPC476460
Intermediate Similarity	0.7207	NPC467188
Intermediate Similarity	0.7204	NPC147983
Intermediate Similarity	0.7204	NPC177996
Intermediate Similarity	0.7177	NPC72956
Intermediate Similarity	0.7171	NPC317701
Intermediate Similarity	0.717	NPC267811
Intermediate Similarity	0.7143	NPC153980
Intermediate Similarity	0.7143	NPC6865
Intermediate Similarity	0.7127	NPC105811
Intermediate Similarity	0.7113	NPC16659
Intermediate Similarity	0.7098	NPC284775
Intermediate Similarity	0.7092	NPC467063
Intermediate Similarity	0.7074	NPC265100
Intermediate Similarity	0.7065	NPC304203
Intermediate Similarity	0.7062	NPC471194
Intermediate Similarity	0.7062	NPC265710
Intermediate Similarity	0.7062	NPC471193
Intermediate Similarity	0.7056	NPC133003
Intermediate Similarity	0.7042	NPC471192
Intermediate Similarity	0.7015	NPC216550
Remote Similarity	0.699	NPC191415
Remote Similarity	0.6986	NPC243850
Remote Similarity	0.6984	NPC478184
Remote Similarity	0.698	NPC326422
Remote Similarity	0.6973	NPC251391
Remote Similarity	0.697	NPC99939
Remote Similarity	0.697	NPC308931
Remote Similarity	0.6954	NPC102755
Remote Similarity	0.6952	NPC213914
Remote Similarity	0.695	NPC103119
Remote Similarity	0.6947	NPC42372
Remote Similarity	0.6939	NPC88110
Remote Similarity	0.6935	NPC209362
Remote Similarity	0.6931	NPC470203
Remote Similarity	0.6923	NPC237188
Remote Similarity	0.6923	NPC157583
Remote Similarity	0.6923	NPC240088
Remote Similarity	0.6923	NPC473380
Remote Similarity	0.6919	NPC70406
Remote Similarity	0.6915	NPC324091
Remote Similarity	0.6914	NPC101165
Remote Similarity	0.6911	NPC56233
Remote Similarity	0.6907	NPC317054
Remote Similarity	0.6895	NPC478182
Remote Similarity	0.6893	NPC477004
Remote Similarity	0.6878	NPC470204
Remote Similarity	0.6878	NPC167710
Remote Similarity	0.6875	NPC70949
Remote Similarity	0.685	NPC476527
Remote Similarity	0.6845	NPC229055
Remote Similarity	0.6845	NPC34837
Remote Similarity	0.6833	NPC2823
Remote Similarity	0.6825	NPC293487
Remote Similarity	0.6825	NPC80681
Remote Similarity	0.6823	NPC114637
Remote Similarity	0.6822	NPC470702
Remote Similarity	0.6822	NPC473218
Remote Similarity	0.6821	NPC293216
Remote Similarity	0.6816	NPC116622
Remote Similarity	0.6811	NPC123906
Remote Similarity	0.6809	NPC74357
Remote Similarity	0.6791	NPC470703
Remote Similarity	0.6786	NPC470323
Remote Similarity	0.6774	NPC313889
Remote Similarity	0.6768	NPC477042
Remote Similarity	0.6765	NPC272458
Remote Similarity	0.6763	NPC245244
Remote Similarity	0.6763	NPC166424
Remote Similarity	0.6763	NPC146373
Remote Similarity	0.6756	NPC267078
Remote Similarity	0.6756	NPC935
Remote Similarity	0.6755	NPC476219
Remote Similarity	0.6748	NPC128244
Remote Similarity	0.6738	NPC117032
Remote Similarity	0.6738	NPC470233
Remote Similarity	0.6737	NPC474492
Remote Similarity	0.6736	NPC478183
Remote Similarity	0.6735	NPC469529
Remote Similarity	0.6728	NPC470731
Remote Similarity	0.6726	NPC474357
Remote Similarity	0.6723	NPC471322
Remote Similarity	0.6713	NPC282247
Remote Similarity	0.6702	NPC122141
Remote Similarity	0.67	NPC470205
Remote Similarity	0.67	NPC255909
Remote Similarity	0.6683	NPC73994
Remote Similarity	0.6667	NPC282398
Remote Similarity	0.6667	NPC478185
Remote Similarity	0.6667	NPC476817
Remote Similarity	0.6667	NPC285923
Remote Similarity	0.6667	NPC225018
Remote Similarity	0.6667	NPC242116
Remote Similarity	0.6651	NPC88115
Remote Similarity	0.665	NPC470677
Remote Similarity	0.6648	NPC471589
Remote Similarity	0.6635	NPC475286
Remote Similarity	0.6635	NPC174281
Remote Similarity	0.6633	NPC262338
Remote Similarity	0.663	NPC314102
Remote Similarity	0.663	NPC65408
Remote Similarity	0.663	NPC251722
Remote Similarity	0.662	NPC471191
Remote Similarity	0.662	NPC472064
Remote Similarity	0.6616	NPC151635
Remote Similarity	0.6615	NPC470680
Remote Similarity	0.6615	NPC100104
Remote Similarity	0.6613	NPC143872
Remote Similarity	0.6612	NPC279081
Remote Similarity	0.66	NPC314281
Remote Similarity	0.66	NPC40530
Remote Similarity	0.6598	NPC233380
Remote Similarity	0.6596	NPC473878
Remote Similarity	0.6587	NPC79356
Remote Similarity	0.6587	NPC102592
Remote Similarity	0.6582	NPC32534
Remote Similarity	0.658	NPC194881
Remote Similarity	0.6575	NPC470732
Remote Similarity	0.6571	NPC19696
Remote Similarity	0.6571	NPC237414
Remote Similarity	0.6571	NPC136957
Remote Similarity	0.6564	NPC49217
Remote Similarity	0.6561	NPC472260
Remote Similarity	0.6559	NPC86288
Remote Similarity	0.6557	NPC106757
Remote Similarity	0.655	NPC11126
Remote Similarity	0.655	NPC248462
Remote Similarity	0.6544	NPC54981
Remote Similarity	0.6526	NPC325903
Remote Similarity	0.6522	NPC47190
Remote Similarity	0.6522	NPC230002
Remote Similarity	0.652	NPC94752
Remote Similarity	0.6515	NPC161861
Remote Similarity	0.6515	NPC252572
Remote Similarity	0.6514	NPC27740
Remote Similarity	0.6508	NPC40070
Remote Similarity	0.6508	NPC471655
Remote Similarity	0.6507	NPC476526
Remote Similarity	0.6507	NPC48117
Remote Similarity	0.6507	NPC329765
Remote Similarity	0.6502	NPC228835
Remote Similarity	0.6502	NPC108011
Remote Similarity	0.6502	NPC110158
Remote Similarity	0.65	NPC330326
Remote Similarity	0.65	NPC83774
Remote Similarity	0.6497	NPC471943
Remote Similarity	0.6497	NPC91895
Remote Similarity	0.6493	NPC220797
Remote Similarity	0.6493	NPC268744
Remote Similarity	0.6493	NPC474318
Remote Similarity	0.6493	NPC201266
Remote Similarity	0.6493	NPC475914
Remote Similarity	0.6493	NPC153123
Remote Similarity	0.6492	NPC476297
Remote Similarity	0.649	NPC188821
Remote Similarity	0.649	NPC474180
Remote Similarity	0.6489	NPC469811
Remote Similarity	0.6485	NPC307191
Remote Similarity	0.648	NPC69914
Remote Similarity	0.6479	NPC472062
Remote Similarity	0.6479	NPC472069
Remote Similarity	0.6479	NPC472063
Remote Similarity	0.6477	NPC135141
Remote Similarity	0.6477	NPC92796
Remote Similarity	0.6474	NPC217021
Remote Similarity	0.6474	NPC470679
Remote Similarity	0.6473	NPC312942
Remote Similarity	0.6473	NPC327095
Remote Similarity	0.6471	NPC204141
Remote Similarity	0.6471	NPC314372
Remote Similarity	0.6465	NPC201634
Remote Similarity	0.6464	NPC300299
Remote Similarity	0.6462	NPC77241
Remote Similarity	0.6462	NPC252338
Remote Similarity	0.6462	NPC13456
Remote Similarity	0.6462	NPC166209
Remote Similarity	0.6462	NPC21174
Remote Similarity	0.6462	NPC271797
Remote Similarity	0.6462	NPC269203
Remote Similarity	0.6461	NPC89490
Remote Similarity	0.6455	NPC321911
Remote Similarity	0.6452	NPC190296
Remote Similarity	0.6448	NPC105127
Remote Similarity	0.6448	NPC83214
Remote Similarity	0.6445	NPC474916
Remote Similarity	0.6445	NPC474389
Remote Similarity	0.6444	NPC40455
Remote Similarity	0.6443	NPC44773
Remote Similarity	0.6443	NPC215584
Remote Similarity	0.644	NPC200214
Remote Similarity	0.644	NPC138842
Remote Similarity	0.6438	NPC477413
Remote Similarity	0.6436	NPC79777
Remote Similarity	0.6436	NPC61011

Drug Structure

NPD5855 OpenBabel08211708292D 32 35 0 0 0 0 0 0 0 0999 V2000 -6.7350 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 1.5000 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 2.5981 -0.5000 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 -5.7839 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7839 1.8090 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 2.5981 -1.5000 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 -4.3301 0.5000 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 -4.3301 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 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 -3.4641 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -1.7321 3.0000 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 0.8660 2.5000 0.0000 H 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 1 2 1 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 13 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 5 19 2 0 0 0 0 6 8 2 0 0 0 0 6 19 1 0 0 0 0 7 20 2 0 0 0 0 8 20 1 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 15 2 0 0 0 0 10 18 1 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 26 1 0 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 24 1 0 0 0 0 17 25 3 0 0 0 0 19 24 1 0 0 0 0 20 29 1 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 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
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	397.19
ALogP	-1.8299
MLogP	3.44
XLogP	4.559
HDA	6
HBD	2
Rotatable Bonds	7
TPSA	90.7
RO5 Violation	0