NPASS drugs

Drug Information

Drug ID:	NPD3831
Drug Name:	Riociguat
Molecular Formula:	C20H19FN8O2
Canonical SMILES:	COC(=O)N(c1c(N)nc([nH]c1=N)c1nn(c2c1cccn2)Cc1ccccc1F)C
Standard InCHI:	InChI=1S/C20H19FN8O2/c1-28(20(30)31-2)15-16(22)25-18(26-17(15)23)14-12-7-5-9-24-19(12)29(27-14)10-11-6-3-4-8-13(11)21/h3-9H,10H2,1-2H3,(H4,22,23,25,26)
Standard InCHIKey:	WXXSNCNJFUAIDG-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3831

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	573
0.1-0.2	10607
0.2-0.3	13978
0.3-0.4	2435
0.4-0.5	1713
0.5-0.6	1298
0.6-0.7	283
0.7-0.8	3
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	0.7579	NPC317054
Intermediate Similarity	0.7351	NPC120070
Intermediate Similarity	0.7282	NPC469308
Remote Similarity	0.6891	NPC470203
Remote Similarity	0.6891	NPC225018
Remote Similarity	0.6869	NPC471579
Remote Similarity	0.6866	NPC471603
Remote Similarity	0.6839	NPC122141
Remote Similarity	0.6839	NPC470204
Remote Similarity	0.6789	NPC470233
Remote Similarity	0.6769	NPC478184
Remote Similarity	0.6769	NPC478182
Remote Similarity	0.6733	NPC16659
Remote Similarity	0.6718	NPC478185
Remote Similarity	0.6683	NPC265710
Remote Similarity	0.6634	NPC473380
Remote Similarity	0.6634	NPC240088
Remote Similarity	0.6632	NPC476219
Remote Similarity	0.6615	NPC293487
Remote Similarity	0.6615	NPC469975
Remote Similarity	0.6593	NPC101165
Remote Similarity	0.6579	NPC143872
Remote Similarity	0.6562	NPC40070
Remote Similarity	0.6546	NPC476297
Remote Similarity	0.6545	NPC114209
Remote Similarity	0.6533	NPC478183
Remote Similarity	0.653	NPC116555
Remote Similarity	0.652	NPC12649
Remote Similarity	0.6518	NPC267811
Remote Similarity	0.6516	NPC54981
Remote Similarity	0.651	NPC282531
Remote Similarity	0.6507	NPC472289
Remote Similarity	0.6491	NPC130570
Remote Similarity	0.6473	NPC108011
Remote Similarity	0.6473	NPC147983
Remote Similarity	0.6473	NPC177996
Remote Similarity	0.6468	NPC32534
Remote Similarity	0.6468	NPC91895
Remote Similarity	0.6458	NPC201380
Remote Similarity	0.6458	NPC179787
Remote Similarity	0.6456	NPC307191
Remote Similarity	0.6453	NPC158055
Remote Similarity	0.6442	NPC308931
Remote Similarity	0.6442	NPC99939
Remote Similarity	0.644	NPC204141
Remote Similarity	0.6432	NPC317105
Remote Similarity	0.6425	NPC321911
Remote Similarity	0.6422	NPC69843
Remote Similarity	0.6413	NPC471322
Remote Similarity	0.641	NPC200214
Remote Similarity	0.641	NPC325903
Remote Similarity	0.6406	NPC63545
Remote Similarity	0.6394	NPC21429
Remote Similarity	0.638	NPC71238
Remote Similarity	0.6373	NPC469811
Remote Similarity	0.6373	NPC470111
Remote Similarity	0.6368	NPC49217
Remote Similarity	0.6364	NPC300238
Remote Similarity	0.6359	NPC11126
Remote Similarity	0.6354	NPC470440
Remote Similarity	0.6339	NPC6865
Remote Similarity	0.6339	NPC153980
Remote Similarity	0.6336	NPC107160
Remote Similarity	0.633	NPC125746
Remote Similarity	0.633	NPC314102
Remote Similarity	0.633	NPC251722
Remote Similarity	0.6329	NPC24864
Remote Similarity	0.6318	NPC473376
Remote Similarity	0.6316	NPC228835
Remote Similarity	0.6313	NPC236711
Remote Similarity	0.6311	NPC28848
Remote Similarity	0.6311	NPC14325
Remote Similarity	0.6311	NPC282247
Remote Similarity	0.6305	NPC116961
Remote Similarity	0.6295	NPC72956
Remote Similarity	0.6287	NPC56233
Remote Similarity	0.6283	NPC197068
Remote Similarity	0.6277	NPC64216
Remote Similarity	0.6263	NPC51054
Remote Similarity	0.6263	NPC110126
Remote Similarity	0.6263	NPC73767
Remote Similarity	0.6262	NPC280852
Remote Similarity	0.6256	NPC17273
Remote Similarity	0.6256	NPC141612
Remote Similarity	0.6256	NPC471192
Remote Similarity	0.6256	NPC94752
Remote Similarity	0.6256	NPC135601
Remote Similarity	0.6256	NPC62995
Remote Similarity	0.625	NPC314281
Remote Similarity	0.625	NPC42483
Remote Similarity	0.625	NPC40530
Remote Similarity	0.625	NPC20144
Remote Similarity	0.6243	NPC65408
Remote Similarity	0.6239	NPC54744
Remote Similarity	0.6238	NPC467063
Remote Similarity	0.6233	NPC188821
Remote Similarity	0.6233	NPC474180
Remote Similarity	0.623	NPC469780
Remote Similarity	0.623	NPC469767
Remote Similarity	0.623	NPC469784
Remote Similarity	0.623	NPC469768
Remote Similarity	0.623	NPC469783
Remote Similarity	0.623	NPC469779
Remote Similarity	0.623	NPC469761
Remote Similarity	0.6224	NPC53947
Remote Similarity	0.6222	NPC265605
Remote Similarity	0.6222	NPC48564
Remote Similarity	0.6222	NPC182570
Remote Similarity	0.6214	NPC469938
Remote Similarity	0.6209	NPC27740
Remote Similarity	0.62	NPC318065
Remote Similarity	0.62	NPC56765
Remote Similarity	0.62	NPC206819
Remote Similarity	0.6198	NPC469766
Remote Similarity	0.6195	NPC82331
Remote Similarity	0.6195	NPC471193
Remote Similarity	0.6195	NPC471194
Remote Similarity	0.619	NPC216159
Remote Similarity	0.6188	NPC243850
Remote Similarity	0.6186	NPC470323
Remote Similarity	0.6186	NPC86288
Remote Similarity	0.6186	NPC314372
Remote Similarity	0.6184	NPC470732
Remote Similarity	0.6184	NPC470731
Remote Similarity	0.6181	NPC476464
Remote Similarity	0.6179	NPC476527
Remote Similarity	0.6178	NPC104483
Remote Similarity	0.6176	NPC63751
Remote Similarity	0.6174	NPC250178
Remote Similarity	0.6172	NPC73994
Remote Similarity	0.6169	NPC44773
Remote Similarity	0.6169	NPC215584
Remote Similarity	0.6166	NPC190296
Remote Similarity	0.616	NPC267078
Remote Similarity	0.616	NPC935
Remote Similarity	0.6158	NPC84911
Remote Similarity	0.6158	NPC105127
Remote Similarity	0.6158	NPC17751
Remote Similarity	0.6158	NPC280864
Remote Similarity	0.6158	NPC150259
Remote Similarity	0.6157	NPC198673
Remote Similarity	0.6154	NPC68354
Remote Similarity	0.6154	NPC59269
Remote Similarity	0.6154	NPC478186
Remote Similarity	0.6154	NPC288838
Remote Similarity	0.615	NPC17059
Remote Similarity	0.615	NPC242923
Remote Similarity	0.615	NPC320968
Remote Similarity	0.6147	NPC167710
Remote Similarity	0.6146	NPC238499
Remote Similarity	0.6146	NPC194411
Remote Similarity	0.6144	NPC115595
Remote Similarity	0.6142	NPC105818
Remote Similarity	0.6142	NPC24678
Remote Similarity	0.6139	NPC253687
Remote Similarity	0.6138	NPC198988
Remote Similarity	0.6135	NPC275305
Remote Similarity	0.6135	NPC37423
Remote Similarity	0.6134	NPC474357
Remote Similarity	0.6132	NPC15102
Remote Similarity	0.6129	NPC294693
Remote Similarity	0.6127	NPC49954
Remote Similarity	0.6127	NPC474561
Remote Similarity	0.6119	NPC92796
Remote Similarity	0.6119	NPC135141
Remote Similarity	0.6119	NPC474389
Remote Similarity	0.6119	NPC475990
Remote Similarity	0.6119	NPC168911
Remote Similarity	0.6111	NPC477166
Remote Similarity	0.6111	NPC472260
Remote Similarity	0.6111	NPC473342
Remote Similarity	0.6111	NPC304187
Remote Similarity	0.6111	NPC477167
Remote Similarity	0.6108	NPC311276
Remote Similarity	0.6106	NPC474958
Remote Similarity	0.6105	NPC29886
Remote Similarity	0.6105	NPC261195
Remote Similarity	0.6105	NPC96102
Remote Similarity	0.6103	NPC311858
Remote Similarity	0.6094	NPC312942
Remote Similarity	0.6094	NPC327095
Remote Similarity	0.6094	NPC88097
Remote Similarity	0.6092	NPC89987
Remote Similarity	0.6091	NPC192674
Remote Similarity	0.6091	NPC295452
Remote Similarity	0.6091	NPC171393
Remote Similarity	0.6087	NPC238945
Remote Similarity	0.6087	NPC161861
Remote Similarity	0.6085	NPC165495
Remote Similarity	0.6085	NPC470003
Remote Similarity	0.608	NPC281094
Remote Similarity	0.608	NPC469760
Remote Similarity	0.608	NPC25008
Remote Similarity	0.608	NPC469763
Remote Similarity	0.608	NPC469786
Remote Similarity	0.608	NPC73952
Remote Similarity	0.608	NPC469765
Remote Similarity	0.608	NPC138842
Remote Similarity	0.608	NPC259644
Remote Similarity	0.6078	NPC195507

Drug Structure

NPD3831 OpenBabel08211704332D 35 38 0 0 0 0 0 0 0 0999 V2000 -5.9675 0.9953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3296 -2.4499 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 -0.7226 -2.8966 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 -1.3917 -2.1535 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 0.2556 -2.6887 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 1.7321 0.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5662 -0.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9785 0.7862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1595 -0.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5772 -0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1485 -0.7273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -4.3852 1.6997 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7473 -1.7454 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5646 -1.7377 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9839 0.6817 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1650 -1.0409 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5608 0.0817 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 -7.1431 -0.6228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7418 -1.6409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7974 2.5088 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3797 1.8043 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3406 -2.6589 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7582 -1.9544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 31 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 24 2 0 0 0 0 10 11 1 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 19 2 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 27 2 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 29 1 0 0 0 0 20 28 1 0 0 0 0 20 30 2 0 0 0 0 20 31 1 0 0 0 0 22 32 1 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 26 35 1 0 0 0 0 27 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNCL001915
DrugBank	DB08931
ChEMBL	CHEMBL2107834
IUPHAR/BPS	5257
PharmaGKB
KEGG Drug	D09572
PubChem CID	11304743
ChEBI	76018
CAS Number	625115-55-1

Drug Properties

Molecular Weight	422.16
ALogP	-0.5364
MLogP	2.45
XLogP	2.739
HDA	10
HBD	3
Rotatable Bonds	10
TPSA	134.51
RO5 Violation	0