NPASS drugs

Drug Information

Drug ID:	NPD3442
Drug Name:	Prazosin
Molecular Formula:	C19H21N5O4
Canonical SMILES:	COc1cc2nc([nH]c(=N)c2cc1OC)N1CCN(CC1)C(=O)c1ccco1
Standard InCHI:	InChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)
Standard InCHIKey:	IENZQIKPVFGBNW-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3442

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	350
0.1-0.2	2839
0.2-0.3	9475
0.3-0.4	3351
0.4-0.5	11300
0.5-0.6	3135
0.6-0.7	433
0.7-0.8	7
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	0.7455	NPC473460
Intermediate Similarity	0.7287	NPC303374
Intermediate Similarity	0.7217	NPC313327
Intermediate Similarity	0.7137	NPC471561
Intermediate Similarity	0.7124	NPC16249
Intermediate Similarity	0.7111	NPC473422
Intermediate Similarity	0.7091	NPC198401
Remote Similarity	0.6987	NPC471762
Remote Similarity	0.6987	NPC66777
Remote Similarity	0.6946	NPC157931
Remote Similarity	0.6933	NPC122886
Remote Similarity	0.6916	NPC41216
Remote Similarity	0.6886	NPC268077
Remote Similarity	0.6864	NPC471650
Remote Similarity	0.6849	NPC148124
Remote Similarity	0.6842	NPC207971
Remote Similarity	0.684	NPC475133
Remote Similarity	0.6833	NPC174629
Remote Similarity	0.6807	NPC99724
Remote Similarity	0.6781	NPC471532
Remote Similarity	0.6777	NPC194740
Remote Similarity	0.677	NPC100863
Remote Similarity	0.677	NPC71124
Remote Similarity	0.6765	NPC476069
Remote Similarity	0.6748	NPC291173
Remote Similarity	0.6739	NPC163829
Remote Similarity	0.6739	NPC475147
Remote Similarity	0.6736	NPC248903
Remote Similarity	0.6736	NPC257851
Remote Similarity	0.6721	NPC217176
Remote Similarity	0.6721	NPC184680
Remote Similarity	0.6711	NPC127178
Remote Similarity	0.6709	NPC126556
Remote Similarity	0.6709	NPC471197
Remote Similarity	0.6709	NPC195636
Remote Similarity	0.6708	NPC71539
Remote Similarity	0.6708	NPC250960
Remote Similarity	0.6708	NPC74216
Remote Similarity	0.6707	NPC208898
Remote Similarity	0.6696	NPC204970
Remote Similarity	0.6694	NPC470785
Remote Similarity	0.6694	NPC266994
Remote Similarity	0.6694	NPC26928
Remote Similarity	0.6681	NPC471198
Remote Similarity	0.6681	NPC10732
Remote Similarity	0.6667	NPC46259
Remote Similarity	0.6667	NPC254957
Remote Similarity	0.6667	NPC5374
Remote Similarity	0.6653	NPC188400
Remote Similarity	0.6651	NPC471648
Remote Similarity	0.6638	NPC158551
Remote Similarity	0.6627	NPC56271
Remote Similarity	0.6621	NPC5167
Remote Similarity	0.6611	NPC77777
Remote Similarity	0.66	NPC41501
Remote Similarity	0.6597	NPC471531
Remote Similarity	0.6588	NPC203373
Remote Similarity	0.6583	NPC219397
Remote Similarity	0.6581	NPC285192
Remote Similarity	0.6575	NPC181905
Remote Similarity	0.6573	NPC34770
Remote Similarity	0.6567	NPC477161
Remote Similarity	0.656	NPC470784
Remote Similarity	0.6556	NPC128115
Remote Similarity	0.655	NPC112937
Remote Similarity	0.6548	NPC166712
Remote Similarity	0.6542	NPC87560
Remote Similarity	0.6542	NPC195120
Remote Similarity	0.654	NPC119722
Remote Similarity	0.654	NPC264176
Remote Similarity	0.654	NPC159815
Remote Similarity	0.6538	NPC308943
Remote Similarity	0.6534	NPC168922
Remote Similarity	0.6523	NPC51854
Remote Similarity	0.652	NPC472061
Remote Similarity	0.6516	NPC19175
Remote Similarity	0.6516	NPC231924
Remote Similarity	0.6513	NPC268223
Remote Similarity	0.6509	NPC295898
Remote Similarity	0.6502	NPC138083
Remote Similarity	0.6502	NPC473007
Remote Similarity	0.65	NPC287152
Remote Similarity	0.65	NPC244425
Remote Similarity	0.65	NPC15384
Remote Similarity	0.65	NPC305984
Remote Similarity	0.6498	NPC82541
Remote Similarity	0.6485	NPC55470
Remote Similarity	0.6485	NPC314817
Remote Similarity	0.6485	NPC66191
Remote Similarity	0.6485	NPC316297
Remote Similarity	0.6484	NPC9729
Remote Similarity	0.6478	NPC470821
Remote Similarity	0.6473	NPC248601
Remote Similarity	0.6473	NPC116007
Remote Similarity	0.6473	NPC303658
Remote Similarity	0.6471	NPC58209
Remote Similarity	0.6471	NPC85613
Remote Similarity	0.6468	NPC73280
Remote Similarity	0.6468	NPC222561
Remote Similarity	0.6465	NPC299582
Remote Similarity	0.646	NPC473008
Remote Similarity	0.646	NPC45389
Remote Similarity	0.6456	NPC269449
Remote Similarity	0.6455	NPC4669
Remote Similarity	0.6445	NPC1608
Remote Similarity	0.6441	NPC270301
Remote Similarity	0.6438	NPC164608
Remote Similarity	0.6434	NPC220851
Remote Similarity	0.6432	NPC57512
Remote Similarity	0.6429	NPC235194
Remote Similarity	0.6422	NPC471604
Remote Similarity	0.642	NPC157983
Remote Similarity	0.642	NPC118154
Remote Similarity	0.642	NPC472099
Remote Similarity	0.642	NPC173250
Remote Similarity	0.6414	NPC154922
Remote Similarity	0.6413	NPC314659
Remote Similarity	0.6404	NPC473004
Remote Similarity	0.6404	NPC79213
Remote Similarity	0.6402	NPC470482
Remote Similarity	0.6402	NPC470481
Remote Similarity	0.64	NPC172222
Remote Similarity	0.6398	NPC471155
Remote Similarity	0.6398	NPC478075
Remote Similarity	0.6396	NPC283810
Remote Similarity	0.6393	NPC128476
Remote Similarity	0.6392	NPC160100
Remote Similarity	0.6392	NPC208364
Remote Similarity	0.6388	NPC174122
Remote Similarity	0.6388	NPC473569
Remote Similarity	0.6388	NPC64140
Remote Similarity	0.6387	NPC476651
Remote Similarity	0.6379	NPC37957
Remote Similarity	0.6375	NPC151781
Remote Similarity	0.6375	NPC476220
Remote Similarity	0.6375	NPC160113
Remote Similarity	0.6375	NPC316181
Remote Similarity	0.6375	NPC74562
Remote Similarity	0.6375	NPC236668
Remote Similarity	0.6371	NPC270241
Remote Similarity	0.6371	NPC205926
Remote Similarity	0.6368	NPC476580
Remote Similarity	0.6368	NPC311357
Remote Similarity	0.6368	NPC197335
Remote Similarity	0.6364	NPC272706
Remote Similarity	0.6364	NPC474183
Remote Similarity	0.636	NPC220241
Remote Similarity	0.636	NPC295479
Remote Similarity	0.6356	NPC225400
Remote Similarity	0.6353	NPC100734
Remote Similarity	0.6353	NPC315634
Remote Similarity	0.6353	NPC88923
Remote Similarity	0.6352	NPC318525
Remote Similarity	0.6352	NPC478007
Remote Similarity	0.6352	NPC10653
Remote Similarity	0.6351	NPC13397
Remote Similarity	0.6349	NPC16066
Remote Similarity	0.6349	NPC146976
Remote Similarity	0.6348	NPC230313
Remote Similarity	0.6344	NPC234069
Remote Similarity	0.6342	NPC120239
Remote Similarity	0.6338	NPC471649
Remote Similarity	0.6337	NPC182853
Remote Similarity	0.6336	NPC120513
Remote Similarity	0.6331	NPC478078
Remote Similarity	0.633	NPC306669
Remote Similarity	0.633	NPC66490
Remote Similarity	0.6329	NPC472538
Remote Similarity	0.6329	NPC470786
Remote Similarity	0.6327	NPC150308
Remote Similarity	0.6327	NPC87391
Remote Similarity	0.6327	NPC276120
Remote Similarity	0.6327	NPC83511
Remote Similarity	0.6327	NPC118189
Remote Similarity	0.6325	NPC214368
Remote Similarity	0.6323	NPC32064
Remote Similarity	0.6323	NPC39822
Remote Similarity	0.6322	NPC244543
Remote Similarity	0.6318	NPC472068
Remote Similarity	0.6316	NPC21638
Remote Similarity	0.6311	NPC298436
Remote Similarity	0.6308	NPC133609
Remote Similarity	0.6307	NPC162530
Remote Similarity	0.6305	NPC311906
Remote Similarity	0.6301	NPC478008
Remote Similarity	0.6295	NPC28368
Remote Similarity	0.6293	NPC270515
Remote Similarity	0.6292	NPC146418
Remote Similarity	0.629	NPC476436
Remote Similarity	0.6289	NPC113455
Remote Similarity	0.6288	NPC92803
Remote Similarity	0.6286	NPC323969
Remote Similarity	0.6284	NPC476569
Remote Similarity	0.6284	NPC471652
Remote Similarity	0.6283	NPC102760
Remote Similarity	0.6282	NPC242728
Remote Similarity	0.6281	NPC50562
Remote Similarity	0.6281	NPC298449
Remote Similarity	0.6275	NPC304837
Remote Similarity	0.6275	NPC476258

Drug Structure

NPD3442 OpenBabel08211703112D 30 33 0 0 0 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -0.0055 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 -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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 -0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 2.0000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -4.3301 -1.5000 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 1.7321 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 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 3 9 2 0 0 0 0 4 14 2 0 0 0 0 5 7 1 0 0 0 0 5 23 1 0 0 0 0 6 8 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 24 1 0 0 0 0 9 28 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 28 1 0 0 0 0 15 16 2 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 18 25 2 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 29 1 0 0 0 0 22 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000300
DrugBank	DB00457
ChEMBL	CHEMBL2
IUPHAR/BPS	503
PharmaGKB	PA451093
KEGG Drug
PubChem CID	4893
ChEBI	8364
CAS Number	19216-56-9

Drug Properties

Molecular Weight	383.16
ALogP	-1.2809
MLogP	2.56
XLogP	2.505
HDA	6
HBD	2
Rotatable Bonds	7
TPSA	103.39
RO5 Violation	0