NPASS drugs

Drug Information

Drug ID:	NPD6209
Drug Name:	Apixaban
Molecular Formula:	C25H25N5O4
Canonical SMILES:	COc1ccc(cc1)n1nc(c2c1C(=O)N(CC2)c1ccc(cc1)N1CCCCC1=O)C(=N)O
Standard InCHI:	InChI=1S/C25H25N5O4/c1-34-19-11-9-18(10-12-19)30-23-20(22(27-30)24(26)32)13-15-29(25(23)33)17-7-5-16(6-8-17)28-14-3-2-4-21(28)31/h5-12H,2-4,13-15H2,1H3,(H2,26,32)
Standard InCHIKey:	QNZCBYKSOIHPEH-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6209

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	340
0.1-0.2	3082
0.2-0.3	9498
0.3-0.4	6068
0.4-0.5	8593
0.5-0.6	2370
0.6-0.7	907
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	0.738	NPC157931
Intermediate Similarity	0.7348	NPC194740
Intermediate Similarity	0.7345	NPC323969
Intermediate Similarity	0.7304	NPC478078
Intermediate Similarity	0.7273	NPC270918
Intermediate Similarity	0.7212	NPC305984
Intermediate Similarity	0.7198	NPC66777
Intermediate Similarity	0.7195	NPC321428
Intermediate Similarity	0.7193	NPC128115
Intermediate Similarity	0.7193	NPC472099
Intermediate Similarity	0.7173	NPC470784
Intermediate Similarity	0.7161	NPC477549
Intermediate Similarity	0.7155	NPC257851
Intermediate Similarity	0.7131	NPC184680
Intermediate Similarity	0.713	NPC216612
Intermediate Similarity	0.7124	NPC471762
Intermediate Similarity	0.7124	NPC311906
Intermediate Similarity	0.7101	NPC470785
Intermediate Similarity	0.7093	NPC322064
Intermediate Similarity	0.708	NPC316181
Intermediate Similarity	0.708	NPC151781
Intermediate Similarity	0.708	NPC74562
Intermediate Similarity	0.7035	NPC264176
Intermediate Similarity	0.7035	NPC472098
Intermediate Similarity	0.7034	NPC477516
Intermediate Similarity	0.7031	NPC303658
Intermediate Similarity	0.7029	NPC474183
Intermediate Similarity	0.7018	NPC152768
Intermediate Similarity	0.7018	NPC148183
Intermediate Similarity	0.7012	NPC72905
Intermediate Similarity	0.7009	NPC186351
Intermediate Similarity	0.7	NPC475816
Remote Similarity	0.6996	NPC472111
Remote Similarity	0.6996	NPC472287
Remote Similarity	0.6996	NPC472286
Remote Similarity	0.6983	NPC142385
Remote Similarity	0.6983	NPC478141
Remote Similarity	0.6974	NPC50562
Remote Similarity	0.6953	NPC322482
Remote Similarity	0.6951	NPC137353
Remote Similarity	0.6947	NPC471304
Remote Similarity	0.6943	NPC67658
Remote Similarity	0.6937	NPC295898
Remote Similarity	0.6933	NPC82548
Remote Similarity	0.6926	NPC288987
Remote Similarity	0.691	NPC280272
Remote Similarity	0.691	NPC220851
Remote Similarity	0.6908	NPC478083
Remote Similarity	0.6906	NPC223427
Remote Similarity	0.6898	NPC471593
Remote Similarity	0.6891	NPC474192
Remote Similarity	0.6891	NPC475720
Remote Similarity	0.6889	NPC53344
Remote Similarity	0.6883	NPC96321
Remote Similarity	0.6875	NPC473639
Remote Similarity	0.6869	NPC241025
Remote Similarity	0.6867	NPC303374
Remote Similarity	0.6865	NPC215837
Remote Similarity	0.6862	NPC329631
Remote Similarity	0.6862	NPC141053
Remote Similarity	0.6856	NPC469592
Remote Similarity	0.6856	NPC471080
Remote Similarity	0.6853	NPC168209
Remote Similarity	0.6851	NPC21638
Remote Similarity	0.6847	NPC329793
Remote Similarity	0.6846	NPC15801
Remote Similarity	0.6844	NPC75179
Remote Similarity	0.684	NPC53534
Remote Similarity	0.6833	NPC472284
Remote Similarity	0.6829	NPC161801
Remote Similarity	0.6828	NPC469589
Remote Similarity	0.6824	NPC54066
Remote Similarity	0.6815	NPC67401
Remote Similarity	0.6815	NPC473800
Remote Similarity	0.6814	NPC193238
Remote Similarity	0.681	NPC469594
Remote Similarity	0.6802	NPC63971
Remote Similarity	0.6802	NPC91868
Remote Similarity	0.679	NPC41501
Remote Similarity	0.6784	NPC287208
Remote Similarity	0.6783	NPC236668
Remote Similarity	0.6783	NPC250448
Remote Similarity	0.678	NPC473449
Remote Similarity	0.6777	NPC184225
Remote Similarity	0.6773	NPC93390
Remote Similarity	0.6771	NPC249040
Remote Similarity	0.677	NPC45190
Remote Similarity	0.677	NPC300156
Remote Similarity	0.677	NPC317373
Remote Similarity	0.6766	NPC243633
Remote Similarity	0.6766	NPC175150
Remote Similarity	0.676	NPC244543
Remote Similarity	0.676	NPC329982
Remote Similarity	0.6756	NPC476098
Remote Similarity	0.6754	NPC174672
Remote Similarity	0.6753	NPC146976
Remote Similarity	0.6753	NPC237740
Remote Similarity	0.6749	NPC101350
Remote Similarity	0.6747	NPC315893
Remote Similarity	0.6747	NPC313587
Remote Similarity	0.6747	NPC316110
Remote Similarity	0.6745	NPC152620
Remote Similarity	0.6737	NPC122436
Remote Similarity	0.6726	NPC472259
Remote Similarity	0.6726	NPC327592
Remote Similarity	0.6724	NPC469928
Remote Similarity	0.6722	NPC473105
Remote Similarity	0.6712	NPC78767
Remote Similarity	0.6712	NPC473814
Remote Similarity	0.6711	NPC475910
Remote Similarity	0.6709	NPC193267
Remote Similarity	0.6709	NPC213530
Remote Similarity	0.6709	NPC313804
Remote Similarity	0.6709	NPC315804
Remote Similarity	0.6708	NPC260434
Remote Similarity	0.6708	NPC235685
Remote Similarity	0.6707	NPC26543
Remote Similarity	0.6707	NPC316224
Remote Similarity	0.6696	NPC146418
Remote Similarity	0.6696	NPC87413
Remote Similarity	0.6695	NPC469727
Remote Similarity	0.6695	NPC312645
Remote Similarity	0.6694	NPC39370
Remote Similarity	0.6681	NPC174758
Remote Similarity	0.6681	NPC477979
Remote Similarity	0.668	NPC473186
Remote Similarity	0.668	NPC207686
Remote Similarity	0.6667	NPC471944
Remote Similarity	0.6667	NPC473041
Remote Similarity	0.6667	NPC184408
Remote Similarity	0.6653	NPC477588
Remote Similarity	0.6653	NPC477590
Remote Similarity	0.6653	NPC60621
Remote Similarity	0.6653	NPC180504
Remote Similarity	0.6653	NPC477585
Remote Similarity	0.6653	NPC477586
Remote Similarity	0.6652	NPC165349
Remote Similarity	0.6652	NPC274291
Remote Similarity	0.6652	NPC47059
Remote Similarity	0.6652	NPC264166
Remote Similarity	0.6652	NPC470020
Remote Similarity	0.6652	NPC280714
Remote Similarity	0.6652	NPC329708
Remote Similarity	0.6652	NPC230403
Remote Similarity	0.6652	NPC118832
Remote Similarity	0.6652	NPC192674
Remote Similarity	0.6651	NPC161887
Remote Similarity	0.6642	NPC196449
Remote Similarity	0.6642	NPC314222
Remote Similarity	0.6638	NPC478074
Remote Similarity	0.6638	NPC89508
Remote Similarity	0.6638	NPC317752
Remote Similarity	0.6637	NPC211813
Remote Similarity	0.6637	NPC328318
Remote Similarity	0.6637	NPC328596
Remote Similarity	0.6627	NPC17437
Remote Similarity	0.6626	NPC253675
Remote Similarity	0.6626	NPC182222
Remote Similarity	0.6626	NPC477066
Remote Similarity	0.6625	NPC314954
Remote Similarity	0.6624	NPC27041
Remote Similarity	0.6623	NPC220337
Remote Similarity	0.6623	NPC472064
Remote Similarity	0.6621	NPC110741
Remote Similarity	0.6618	NPC285635
Remote Similarity	0.6612	NPC196718
Remote Similarity	0.6611	NPC24370
Remote Similarity	0.6611	NPC470018
Remote Similarity	0.6611	NPC319232
Remote Similarity	0.661	NPC150239
Remote Similarity	0.6609	NPC16066
Remote Similarity	0.6609	NPC476116
Remote Similarity	0.6606	NPC478077
Remote Similarity	0.6601	NPC478080
Remote Similarity	0.6599	NPC478082
Remote Similarity	0.6599	NPC478081
Remote Similarity	0.6599	NPC477067
Remote Similarity	0.6598	NPC272549
Remote Similarity	0.6598	NPC295228
Remote Similarity	0.6598	NPC326363
Remote Similarity	0.6595	NPC318299
Remote Similarity	0.6594	NPC316403
Remote Similarity	0.6588	NPC477888
Remote Similarity	0.6587	NPC189079
Remote Similarity	0.6584	NPC172222
Remote Similarity	0.6584	NPC284888
Remote Similarity	0.6583	NPC118559
Remote Similarity	0.6583	NPC304307
Remote Similarity	0.6583	NPC124920
Remote Similarity	0.6583	NPC261251
Remote Similarity	0.6583	NPC34580
Remote Similarity	0.6582	NPC280799
Remote Similarity	0.658	NPC269367
Remote Similarity	0.6577	NPC473821
Remote Similarity	0.6577	NPC307963
Remote Similarity	0.6574	NPC165964
Remote Similarity	0.6573	NPC291609
Remote Similarity	0.6571	NPC477589
Remote Similarity	0.6571	NPC477587
Remote Similarity	0.657	NPC477112

Drug Structure

NPD6209 OpenBabel08211709092D 36 40 0 0 0 0 0 0 0 0999 V2000 0.5669 -4.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -2.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 -2.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 2.7770 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.6910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 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 -5.2812 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2361 -3.8042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 3.7281 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 4.2633 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 5 16 2 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 18 2 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 34 1 0 0 0 0 20 22 1 0 0 0 0 20 23 2 0 0 0 0 21 28 1 0 0 0 0 21 31 2 0 0 0 0 22 24 1 0 0 0 0 22 27 2 0 0 0 0 23 25 1 0 0 0 0 23 30 1 0 0 0 0 24 26 2 0 0 0 0 24 32 1 0 0 0 0 25 29 1 0 0 0 0 25 33 2 0 0 0 0 26 35 1 0 0 0 0 27 30 1 0 0 0 0 32 36 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000438
DrugBank	DB06605
ChEMBL	CHEMBL231779
IUPHAR/BPS	6390
PharmaGKB
KEGG Drug	D03213
PubChem CID	10182969
ChEBI	72296
CAS Number	503612-47-3

Drug Properties

Molecular Weight	459.19
ALogP	-1.6522
MLogP	3.22
XLogP	3.566
HDA	8
HBD	2
Rotatable Bonds	7
TPSA	111.23
RO5 Violation	0