NPASS drugs

Drug Information

Drug ID:	NPD3358
Drug Name:	Macitentan
Molecular Formula:	C19H20Br2N6O4S
Canonical SMILES:	CCCNS(=O)(=O)N=c1nc[nH]c(c1c1ccc(cc1)Br)OCCOc1ncc(cn1)Br
Standard InCHI:	InChI=1S/C19H20Br2N6O4S/c1-2-7-26-32(28,29)27-17-16(13-3-5-14(20)6-4-13)18(25-12-24-17)30-8-9-31-19-22-10-15(21)11-23-19/h3-6,10-12,26H,2,7-9H2,1H3,(H,24,25,27)
Standard InCHIKey:	JGCMEBMXRHSZKX-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3358

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	355
0.1-0.2	5289
0.2-0.3	13519
0.3-0.4	8408
0.4-0.5	2374
0.5-0.6	899
0.6-0.7	46
0.7-0.8	0
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
Remote Similarity	0.6608	NPC101165
Remote Similarity	0.6608	NPC471322
Remote Similarity	0.6534	NPC316811
Remote Similarity	0.65	NPC477166
Remote Similarity	0.65	NPC304187
Remote Similarity	0.65	NPC477167
Remote Similarity	0.65	NPC473342
Remote Similarity	0.6489	NPC17751
Remote Similarity	0.648	NPC108011
Remote Similarity	0.6462	NPC307191
Remote Similarity	0.6448	NPC469975
Remote Similarity	0.6425	NPC115595
Remote Similarity	0.6378	NPC120070
Remote Similarity	0.6316	NPC280864
Remote Similarity	0.6289	NPC280297
Remote Similarity	0.6243	NPC89490
Remote Similarity	0.6207	NPC475090
Remote Similarity	0.6207	NPC475105
Remote Similarity	0.6207	NPC329896
Remote Similarity	0.6205	NPC317054
Remote Similarity	0.6178	NPC247987
Remote Similarity	0.6173	NPC474958
Remote Similarity	0.6162	NPC282531
Remote Similarity	0.6154	NPC477611
Remote Similarity	0.615	NPC141926
Remote Similarity	0.6146	NPC474180
Remote Similarity	0.6146	NPC188821
Remote Similarity	0.6126	NPC253687
Remote Similarity	0.6123	NPC474357
Remote Similarity	0.6106	NPC470323
Remote Similarity	0.6103	NPC82331
Remote Similarity	0.6093	NPC113369
Remote Similarity	0.6079	NPC267078
Remote Similarity	0.6079	NPC935
Remote Similarity	0.6069	NPC166424
Remote Similarity	0.6069	NPC146373
Remote Similarity	0.6069	NPC245244
Remote Similarity	0.6064	NPC232798
Remote Similarity	0.605	NPC275292
Remote Similarity	0.605	NPC243381
Remote Similarity	0.603	NPC233050
Remote Similarity	0.603	NPC276540
Remote Similarity	0.6029	NPC474389
Remote Similarity	0.6018	NPC250178
Remote Similarity	0.6012	NPC27740
Remote Similarity	0.6	NPC231536
Remote Similarity	0.5979	NPC274229
Remote Similarity	0.5979	NPC2165
Remote Similarity	0.5969	NPC469897
Remote Similarity	0.5968	NPC143872
Remote Similarity	0.5965	NPC160666
Remote Similarity	0.5959	NPC470203
Remote Similarity	0.5947	NPC34844
Remote Similarity	0.5943	NPC475935
Remote Similarity	0.5943	NPC94211
Remote Similarity	0.5943	NPC52909
Remote Similarity	0.5939	NPC470498
Remote Similarity	0.5928	NPC149265
Remote Similarity	0.5928	NPC477114
Remote Similarity	0.5909	NPC471311
Remote Similarity	0.5909	NPC471313
Remote Similarity	0.5907	NPC470204
Remote Similarity	0.5907	NPC122141
Remote Similarity	0.5896	NPC166209
Remote Similarity	0.5896	NPC23420
Remote Similarity	0.5896	NPC205254
Remote Similarity	0.5896	NPC13456
Remote Similarity	0.5896	NPC106771
Remote Similarity	0.5896	NPC269203
Remote Similarity	0.5896	NPC77241
Remote Similarity	0.5896	NPC303820
Remote Similarity	0.589	NPC207020
Remote Similarity	0.5888	NPC164664
Remote Similarity	0.5885	NPC474196
Remote Similarity	0.5882	NPC316069
Remote Similarity	0.5877	NPC156003
Remote Similarity	0.5876	NPC225018
Remote Similarity	0.5874	NPC472289
Remote Similarity	0.5869	NPC469308
Remote Similarity	0.5867	NPC49217
Remote Similarity	0.5866	NPC256893
Remote Similarity	0.5862	NPC290094
Remote Similarity	0.5858	NPC84268
Remote Similarity	0.5855	NPC300238
Remote Similarity	0.5849	NPC474318
Remote Similarity	0.5849	NPC201266
Remote Similarity	0.5849	NPC220797
Remote Similarity	0.5849	NPC268744
Remote Similarity	0.5849	NPC475914
Remote Similarity	0.5849	NPC153123
Remote Similarity	0.5848	NPC91958
Remote Similarity	0.5842	NPC16659
Remote Similarity	0.5841	NPC130570
Remote Similarity	0.5833	NPC476464
Remote Similarity	0.5829	NPC476322
Remote Similarity	0.582	NPC2272
Remote Similarity	0.5816	NPC195507
Remote Similarity	0.581	NPC282398
Remote Similarity	0.5805	NPC329825
Remote Similarity	0.5803	NPC193740
Remote Similarity	0.5795	NPC71079
Remote Similarity	0.5792	NPC470703
Remote Similarity	0.5792	NPC265710
Remote Similarity	0.5789	NPC297486
Remote Similarity	0.5789	NPC240136
Remote Similarity	0.5789	NPC471402
Remote Similarity	0.5781	NPC75135
Remote Similarity	0.5778	NPC474195
Remote Similarity	0.5767	NPC471617
Remote Similarity	0.5765	NPC311276
Remote Similarity	0.5765	NPC476446
Remote Similarity	0.5765	NPC78375
Remote Similarity	0.5765	NPC474217
Remote Similarity	0.5765	NPC469813
Remote Similarity	0.5763	NPC202957
Remote Similarity	0.5763	NPC169625
Remote Similarity	0.5756	NPC143603
Remote Similarity	0.5754	NPC476131
Remote Similarity	0.5751	NPC158055
Remote Similarity	0.5749	NPC254762
Remote Similarity	0.5747	NPC48564
Remote Similarity	0.5747	NPC182570
Remote Similarity	0.5747	NPC470702
Remote Similarity	0.5747	NPC473218
Remote Similarity	0.5747	NPC265605
Remote Similarity	0.5745	NPC314372
Remote Similarity	0.5743	NPC68354
Remote Similarity	0.5736	NPC85918
Remote Similarity	0.5729	NPC97343
Remote Similarity	0.5722	NPC190296
Remote Similarity	0.5722	NPC69914
Remote Similarity	0.5722	NPC469762
Remote Similarity	0.5721	NPC275305
Remote Similarity	0.5721	NPC37423
Remote Similarity	0.5714	NPC88115
Remote Similarity	0.5708	NPC116555
Remote Similarity	0.5707	NPC314102
Remote Similarity	0.5707	NPC251722
Remote Similarity	0.5707	NPC24678
Remote Similarity	0.5707	NPC49954
Remote Similarity	0.5707	NPC125746
Remote Similarity	0.5707	NPC127730
Remote Similarity	0.5707	NPC278366
Remote Similarity	0.5707	NPC105818
Remote Similarity	0.5707	NPC474561
Remote Similarity	0.5701	NPC54981
Remote Similarity	0.5701	NPC477004
Remote Similarity	0.57	NPC105758
Remote Similarity	0.57	NPC201634
Remote Similarity	0.57	NPC476688
Remote Similarity	0.57	NPC476686
Remote Similarity	0.5699	NPC477815
Remote Similarity	0.5699	NPC469780
Remote Similarity	0.5699	NPC469783
Remote Similarity	0.5699	NPC476219
Remote Similarity	0.5699	NPC469779
Remote Similarity	0.5699	NPC469784
Remote Similarity	0.5699	NPC469767
Remote Similarity	0.5699	NPC469768
Remote Similarity	0.5699	NPC469761
Remote Similarity	0.5691	NPC471323
Remote Similarity	0.5687	NPC88315
Remote Similarity	0.5685	NPC194640
Remote Similarity	0.5685	NPC40779
Remote Similarity	0.5684	NPC114209
Remote Similarity	0.5684	NPC223223
Remote Similarity	0.568	NPC110158
Remote Similarity	0.568	NPC467063
Remote Similarity	0.5678	NPC63751
Remote Similarity	0.5678	NPC278874
Remote Similarity	0.5677	NPC470233
Remote Similarity	0.5676	NPC128084
Remote Similarity	0.5672	NPC208060
Remote Similarity	0.567	NPC469785
Remote Similarity	0.567	NPC147983
Remote Similarity	0.567	NPC177996
Remote Similarity	0.567	NPC74357
Remote Similarity	0.5668	NPC469766
Remote Similarity	0.5665	NPC240088
Remote Similarity	0.5665	NPC473380
Remote Similarity	0.5661	NPC204141
Remote Similarity	0.5659	NPC477891
Remote Similarity	0.5655	NPC27802
Remote Similarity	0.5652	NPC163421
Remote Similarity	0.5652	NPC188387
Remote Similarity	0.565	NPC194411
Remote Similarity	0.565	NPC116961
Remote Similarity	0.5648	NPC73952
Remote Similarity	0.5648	NPC469765
Remote Similarity	0.5648	NPC469760
Remote Similarity	0.5648	NPC469763
Remote Similarity	0.5648	NPC259644
Remote Similarity	0.5648	NPC25008
Remote Similarity	0.5648	NPC469786
Remote Similarity	0.5645	NPC73767
Remote Similarity	0.5645	NPC110126
Remote Similarity	0.5644	NPC267811
Remote Similarity	0.5641	NPC167635
Remote Similarity	0.5637	NPC176199
Remote Similarity	0.5637	NPC215795

Drug Structure

NPD3358 OpenBabel08211703112D 34 36 0 0 0 0 0 0 0 0999 V2000 -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 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 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 -1.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5000 -6.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -7.0000 -5.1962 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -6.0622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -4.3301 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -3.4641 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 7 1 0 0 0 0 3 5 1 0 0 0 0 3 13 2 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 26 1 0 0 0 0 8 9 1 0 0 0 0 8 30 1 0 0 0 0 9 31 1 0 0 0 0 10 15 2 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 23 2 0 0 0 0 12 24 2 0 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 24 1 0 0 0 0 17 27 2 3 0 0 0 18 25 1 0 0 0 0 18 30 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 25 33 1 0 0 0 0 26 32 1 0 0 0 0 26 34 1 0 0 0 0 27 32 1 0 0 0 0 28 32 2 0 0 0 0 29 32 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DNCL001904
DrugBank	DB08932
ChEMBL	CHEMBL2103873
IUPHAR/BPS	7352
PharmaGKB
KEGG Drug	D10135
PubChem CID	16004692
ChEBI	76607
CAS Number	441798-33-0

Drug Properties

Molecular Weight	585.96
ALogP	-1.1907
MLogP	2.12
XLogP	3.938
HDA	9
HBD	2
Rotatable Bonds	13
TPSA	135.54
RO5 Violation	0