NPASS drugs

Drug Information

Drug ID:	NPD4885
Drug Name:	Tadalafil
Molecular Formula:	C22H19N3O4
Canonical SMILES:	O=C1N(C)CC(=O)N2[C@@H]1Cc1c([C@H]2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
Standard InCHI:	InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
Standard InCHIKey:	WOXKDUGGOYFFRN-IIBYNOLFSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4885

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	380
0.1-0.2	1893
0.2-0.3	9659
0.3-0.4	4114
0.4-0.5	10286
0.5-0.6	2582
0.6-0.7	1545
0.7-0.8	408
0.8-0.85	19
0.85-0.9	4
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
High Similarity	0.8905	NPC305984
High Similarity	0.8565	NPC184680
High Similarity	0.8528	NPC303374
High Similarity	0.8527	NPC470785
Intermediate Similarity	0.8444	NPC470784
Intermediate Similarity	0.8341	NPC303658
Intermediate Similarity	0.8273	NPC280272
Intermediate Similarity	0.8251	NPC311906
Intermediate Similarity	0.8249	NPC148183
Intermediate Similarity	0.8249	NPC152768
Intermediate Similarity	0.823	NPC253675
Intermediate Similarity	0.8198	NPC21638
Intermediate Similarity	0.817	NPC194740
Intermediate Similarity	0.8111	NPC472098
Intermediate Similarity	0.8109	NPC284685
Intermediate Similarity	0.8102	NPC471304
Intermediate Similarity	0.81	NPC472099
Intermediate Similarity	0.8075	NPC191489
Intermediate Similarity	0.8047	NPC313189
Intermediate Similarity	0.8047	NPC135549
Intermediate Similarity	0.8044	NPC157931
Intermediate Similarity	0.8018	NPC323969
Intermediate Similarity	0.8009	NPC96321
Intermediate Similarity	0.7965	NPC478078
Intermediate Similarity	0.7945	NPC171409
Intermediate Similarity	0.7945	NPC96405
Intermediate Similarity	0.7945	NPC202768
Intermediate Similarity	0.7945	NPC53069
Intermediate Similarity	0.7945	NPC296482
Intermediate Similarity	0.7942	NPC315634
Intermediate Similarity	0.7942	NPC88923
Intermediate Similarity	0.7942	NPC100734
Intermediate Similarity	0.793	NPC471762
Intermediate Similarity	0.7928	NPC473041
Intermediate Similarity	0.7909	NPC471080
Intermediate Similarity	0.7909	NPC469592
Intermediate Similarity	0.7888	NPC474183
Intermediate Similarity	0.7879	NPC295228
Intermediate Similarity	0.7874	NPC204385
Intermediate Similarity	0.7864	NPC264176
Intermediate Similarity	0.7854	NPC475816
Intermediate Similarity	0.7854	NPC206201
Intermediate Similarity	0.785	NPC234197
Intermediate Similarity	0.785	NPC329793
Intermediate Similarity	0.7848	NPC469594
Intermediate Similarity	0.7821	NPC477066
Intermediate Similarity	0.7797	NPC81939
Intermediate Similarity	0.7787	NPC477067
Intermediate Similarity	0.7787	NPC478081
Intermediate Similarity	0.7787	NPC478082
Intermediate Similarity	0.7773	NPC66777
Intermediate Similarity	0.7767	NPC477019
Intermediate Similarity	0.7764	NPC475666
Intermediate Similarity	0.7748	NPC266931
Intermediate Similarity	0.7743	NPC60621
Intermediate Similarity	0.7742	NPC476098
Intermediate Similarity	0.7742	NPC223427
Intermediate Similarity	0.7735	NPC82472
Intermediate Similarity	0.7731	NPC17437
Intermediate Similarity	0.7729	NPC257851
Intermediate Similarity	0.7721	NPC4071
Intermediate Similarity	0.7721	NPC476582
Intermediate Similarity	0.7721	NPC476578
Intermediate Similarity	0.7717	NPC270918
Intermediate Similarity	0.7712	NPC473540
Intermediate Similarity	0.7685	NPC329747
Intermediate Similarity	0.7672	NPC474192
Intermediate Similarity	0.7672	NPC475720
Intermediate Similarity	0.7671	NPC300156
Intermediate Similarity	0.7668	NPC149471
Intermediate Similarity	0.7668	NPC271215
Intermediate Similarity	0.7654	NPC478083
Intermediate Similarity	0.7639	NPC22481
Intermediate Similarity	0.7639	NPC473105
Intermediate Similarity	0.763	NPC63199
Intermediate Similarity	0.763	NPC196251
Intermediate Similarity	0.763	NPC111602
Intermediate Similarity	0.763	NPC102338
Intermediate Similarity	0.7626	NPC16452
Intermediate Similarity	0.7626	NPC476581
Intermediate Similarity	0.7626	NPC36229
Intermediate Similarity	0.7615	NPC199277
Intermediate Similarity	0.7615	NPC135887
Intermediate Similarity	0.7613	NPC167860
Intermediate Similarity	0.7613	NPC123976
Intermediate Similarity	0.7613	NPC188420
Intermediate Similarity	0.761	NPC312872
Intermediate Similarity	0.7607	NPC39370
Intermediate Similarity	0.7602	NPC475910
Intermediate Similarity	0.7597	NPC473186
Intermediate Similarity	0.7591	NPC45190
Intermediate Similarity	0.7589	NPC236668
Intermediate Similarity	0.7586	NPC278525
Intermediate Similarity	0.7585	NPC101350
Intermediate Similarity	0.7577	NPC46451
Intermediate Similarity	0.7574	NPC272549
Intermediate Similarity	0.7574	NPC108342
Intermediate Similarity	0.7562	NPC133609
Intermediate Similarity	0.756	NPC176127
Intermediate Similarity	0.7558	NPC5374
Intermediate Similarity	0.7557	NPC4687
Intermediate Similarity	0.7556	NPC146976
Intermediate Similarity	0.755	NPC315467
Intermediate Similarity	0.7545	NPC251160
Intermediate Similarity	0.7545	NPC285558
Intermediate Similarity	0.7545	NPC94157
Intermediate Similarity	0.7542	NPC235685
Intermediate Similarity	0.7542	NPC189903
Intermediate Similarity	0.7542	NPC182907
Intermediate Similarity	0.7541	NPC478080
Intermediate Similarity	0.7534	NPC295898
Intermediate Similarity	0.7533	NPC23614
Intermediate Similarity	0.7533	NPC174788
Intermediate Similarity	0.7533	NPC100079
Intermediate Similarity	0.7532	NPC24370
Intermediate Similarity	0.7532	NPC319232
Intermediate Similarity	0.7531	NPC189079
Intermediate Similarity	0.7523	NPC195268
Intermediate Similarity	0.7523	NPC176538
Intermediate Similarity	0.7523	NPC249040
Intermediate Similarity	0.7523	NPC133140
Intermediate Similarity	0.7522	NPC122436
Intermediate Similarity	0.7522	NPC469928
Intermediate Similarity	0.752	NPC478009
Intermediate Similarity	0.7512	NPC71124
Intermediate Similarity	0.7512	NPC472112
Intermediate Similarity	0.7511	NPC166722
Intermediate Similarity	0.7511	NPC326363
Intermediate Similarity	0.751	NPC53534
Intermediate Similarity	0.75	NPC261251
Intermediate Similarity	0.75	NPC124920
Intermediate Similarity	0.75	NPC304307
Intermediate Similarity	0.75	NPC193267
Intermediate Similarity	0.75	NPC118559
Intermediate Similarity	0.75	NPC34580
Intermediate Similarity	0.75	NPC213530
Intermediate Similarity	0.75	NPC82541
Intermediate Similarity	0.749	NPC473800
Intermediate Similarity	0.7489	NPC323198
Intermediate Similarity	0.7489	NPC469589
Intermediate Similarity	0.7489	NPC323752
Intermediate Similarity	0.7489	NPC31930
Intermediate Similarity	0.7478	NPC235076
Intermediate Similarity	0.7477	NPC249583
Intermediate Similarity	0.7476	NPC161861
Intermediate Similarity	0.747	NPC152620
Intermediate Similarity	0.7468	NPC100547
Intermediate Similarity	0.7468	NPC473183
Intermediate Similarity	0.7457	NPC214142
Intermediate Similarity	0.7449	NPC478006
Intermediate Similarity	0.7446	NPC475271
Intermediate Similarity	0.7445	NPC322064
Intermediate Similarity	0.7445	NPC330009
Intermediate Similarity	0.7443	NPC254240
Intermediate Similarity	0.7443	NPC199851
Intermediate Similarity	0.7443	NPC128265
Intermediate Similarity	0.7443	NPC294909
Intermediate Similarity	0.7443	NPC312870
Intermediate Similarity	0.7442	NPC472113
Intermediate Similarity	0.7441	NPC84478
Intermediate Similarity	0.7437	NPC131486
Intermediate Similarity	0.7436	NPC95240
Intermediate Similarity	0.7436	NPC322135
Intermediate Similarity	0.7436	NPC223409
Intermediate Similarity	0.7435	NPC280799
Intermediate Similarity	0.7434	NPC478074
Intermediate Similarity	0.7432	NPC472111
Intermediate Similarity	0.7424	NPC52254
Intermediate Similarity	0.7424	NPC288987
Intermediate Similarity	0.7422	NPC87413
Intermediate Similarity	0.7421	NPC207971
Intermediate Similarity	0.7412	NPC169402
Intermediate Similarity	0.7411	NPC476116
Intermediate Similarity	0.7409	NPC232727
Intermediate Similarity	0.7407	NPC254957
Intermediate Similarity	0.7406	NPC168922
Intermediate Similarity	0.7404	NPC14288
Intermediate Similarity	0.7404	NPC260434
Intermediate Similarity	0.7403	NPC144452
Intermediate Similarity	0.7399	NPC321428
Intermediate Similarity	0.7395	NPC184225
Intermediate Similarity	0.7395	NPC92111
Intermediate Similarity	0.7393	NPC314954
Intermediate Similarity	0.7389	NPC112206
Intermediate Similarity	0.7389	NPC202605
Intermediate Similarity	0.7389	NPC316981
Intermediate Similarity	0.7387	NPC268077
Intermediate Similarity	0.7384	NPC473184
Intermediate Similarity	0.7384	NPC325976
Intermediate Similarity	0.7381	NPC478010
Intermediate Similarity	0.738	NPC46561
Intermediate Similarity	0.738	NPC204446
Intermediate Similarity	0.738	NPC82070
Intermediate Similarity	0.7378	NPC290689
Intermediate Similarity	0.7377	NPC26543
Intermediate Similarity	0.7375	NPC210296
Intermediate Similarity	0.7373	NPC469554
Intermediate Similarity	0.7373	NPC54803
Intermediate Similarity	0.7373	NPC321592
Intermediate Similarity	0.7373	NPC131017

Drug Structure

NPD4885 OpenBabel08211706322D 30 35 0 0 1 0 0 0 0 0999 V2000 0.0001 1.0225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3768 -5.8496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5322 -6.3371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3769 -4.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6883 -5.8498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7711 -3.1109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4954 -3.7629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6417 -4.3654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6884 -1.9501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2929 -6.2931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8443 -3.4121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5327 -4.3873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6885 -2.9251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6881 -4.8749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4628 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2928 -4.7162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -5.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 -1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 -3.4126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -2.9249 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8445 -0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 -4.3876 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 -0.0001 -1.9503 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7301 -1.9739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7300 0.0235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8657 -5.5046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -5.9920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0219 -4.8876 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 13 2 0 0 0 0 5 15 2 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 10 24 1 0 0 0 0 11 28 1 0 0 0 0 11 29 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 20 2 0 0 0 0 15 23 1 0 0 0 0 16 9 1 1 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 18 2 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 26 2 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 12 1 1 0 0 0 21 25 1 0 0 0 0 22 24 1 0 0 0 0 22 27 2 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000615
DrugBank	DB00820
ChEMBL	CHEMBL779
IUPHAR/BPS	7299
PharmaGKB	PA10333
KEGG Drug	D02008
PubChem CID	110635
ChEBI	71940
CAS Number	171596-29-5

Drug Properties

Molecular Weight	389.14
ALogP	-2.2373
MLogP	3.11
XLogP	2.233
HDA	5
HBD	1
Rotatable Bonds	2
TPSA	74.87
RO5 Violation	0