NPASS drugs

Drug Information

Drug ID:	NPD4454
Drug Name:	Rafabegron
Molecular Formula:	C21H23ClN2O4
Canonical SMILES:	C[C@H](Cc1c[nH]c2c1cccc2OCC(=O)O)NC[C@@H](c1cccc(c1)Cl)O
Standard InCHI:	InChI=1S/C21H23ClN2O4/c1-13(23-11-18(25)14-4-2-5-16(22)9-14)8-15-10-24-21-17(15)6-3-7-19(21)28-12-20(26)27/h2-7,9-10,13,18,23-25H,8,11-12H2,1H3,(H,26,27)/t13-,18+/m1/s1
Standard InCHIKey:	FHEYFIGWYQJVDR-ACJLOTCBSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4454

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	284
0.1-0.2	1785
0.2-0.3	9710
0.3-0.4	4273
0.4-0.5	11344
0.5-0.6	2326
0.6-0.7	1057
0.7-0.8	111
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	0.7964	NPC476287
Intermediate Similarity	0.7877	NPC475190
Intermediate Similarity	0.7812	NPC288349
Intermediate Similarity	0.7803	NPC266931
Intermediate Similarity	0.7717	NPC475774
Intermediate Similarity	0.7679	NPC26679
Intermediate Similarity	0.7655	NPC470799
Intermediate Similarity	0.7655	NPC8022
Intermediate Similarity	0.7639	NPC251090
Intermediate Similarity	0.7636	NPC245816
Intermediate Similarity	0.7636	NPC476138
Intermediate Similarity	0.7628	NPC307963
Intermediate Similarity	0.7617	NPC323752
Intermediate Similarity	0.7617	NPC323198
Intermediate Similarity	0.7615	NPC128823
Intermediate Similarity	0.7545	NPC185782
Intermediate Similarity	0.7534	NPC88008
Intermediate Similarity	0.7522	NPC132642
Intermediate Similarity	0.7488	NPC474798
Intermediate Similarity	0.7488	NPC76748
Intermediate Similarity	0.7454	NPC92111
Intermediate Similarity	0.7442	NPC296527
Intermediate Similarity	0.7435	NPC197141
Intermediate Similarity	0.7393	NPC125597
Intermediate Similarity	0.7368	NPC316981
Intermediate Similarity	0.7364	NPC156704
Intermediate Similarity	0.7362	NPC24370
Intermediate Similarity	0.7362	NPC319232
Intermediate Similarity	0.7361	NPC242928
Intermediate Similarity	0.7357	NPC11464
Intermediate Similarity	0.7353	NPC469554
Intermediate Similarity	0.7342	NPC19872
Intermediate Similarity	0.7339	NPC99666
Intermediate Similarity	0.7313	NPC209769
Intermediate Similarity	0.7303	NPC15801
Intermediate Similarity	0.7297	NPC476167
Intermediate Similarity	0.7293	NPC94157
Intermediate Similarity	0.7289	NPC470930
Intermediate Similarity	0.7284	NPC184408
Intermediate Similarity	0.7284	NPC475844
Intermediate Similarity	0.7284	NPC148889
Intermediate Similarity	0.7281	NPC5145
Intermediate Similarity	0.7265	NPC45459
Intermediate Similarity	0.7265	NPC473317
Intermediate Similarity	0.7265	NPC315491
Intermediate Similarity	0.7252	NPC192315
Intermediate Similarity	0.7251	NPC258048
Intermediate Similarity	0.725	NPC180504
Intermediate Similarity	0.7249	NPC116701
Intermediate Similarity	0.7238	NPC267853
Intermediate Similarity	0.7222	NPC314002
Intermediate Similarity	0.7209	NPC469358
Intermediate Similarity	0.7208	NPC101543
Intermediate Similarity	0.7208	NPC244897
Intermediate Similarity	0.7189	NPC171171
Intermediate Similarity	0.7188	NPC176538
Intermediate Similarity	0.7186	NPC469592
Intermediate Similarity	0.7186	NPC471080
Intermediate Similarity	0.7185	NPC473185
Intermediate Similarity	0.7185	NPC192712
Intermediate Similarity	0.7176	NPC204717
Intermediate Similarity	0.7167	NPC300114
Intermediate Similarity	0.7167	NPC315062
Intermediate Similarity	0.716	NPC473183
Intermediate Similarity	0.7155	NPC274640
Intermediate Similarity	0.7149	NPC316411
Intermediate Similarity	0.7149	NPC473184
Intermediate Similarity	0.7137	NPC264166
Intermediate Similarity	0.7137	NPC274291
Intermediate Similarity	0.7137	NPC469594
Intermediate Similarity	0.7137	NPC285558
Intermediate Similarity	0.7137	NPC165349
Intermediate Similarity	0.7137	NPC47059
Intermediate Similarity	0.7137	NPC470500
Intermediate Similarity	0.7137	NPC118832
Intermediate Similarity	0.7137	NPC329708
Intermediate Similarity	0.713	NPC220765
Intermediate Similarity	0.713	NPC77555
Intermediate Similarity	0.7124	NPC193761
Intermediate Similarity	0.7119	NPC60621
Intermediate Similarity	0.7113	NPC110151
Intermediate Similarity	0.7112	NPC39500
Intermediate Similarity	0.7106	NPC473179
Intermediate Similarity	0.7106	NPC292958
Intermediate Similarity	0.71	NPC208284
Intermediate Similarity	0.7091	NPC9482
Intermediate Similarity	0.7087	NPC478006
Intermediate Similarity	0.7069	NPC203168
Intermediate Similarity	0.7069	NPC207020
Intermediate Similarity	0.7063	NPC314882
Intermediate Similarity	0.7056	NPC199667
Intermediate Similarity	0.7056	NPC284141
Intermediate Similarity	0.7049	NPC295228
Intermediate Similarity	0.7048	NPC476874
Intermediate Similarity	0.7043	NPC152620
Intermediate Similarity	0.7043	NPC476465
Intermediate Similarity	0.7035	NPC213308
Intermediate Similarity	0.7034	NPC193267
Intermediate Similarity	0.7034	NPC213530
Intermediate Similarity	0.7031	NPC476106
Intermediate Similarity	0.7026	NPC187501
Intermediate Similarity	0.7025	NPC474688
Intermediate Similarity	0.7025	NPC475253
Intermediate Similarity	0.7021	NPC314552
Intermediate Similarity	0.7017	NPC144452
Intermediate Similarity	0.7013	NPC473181
Intermediate Similarity	0.7012	NPC165964
Intermediate Similarity	0.7012	NPC314954
Intermediate Similarity	0.7009	NPC118228
Intermediate Similarity	0.7009	NPC13880
Intermediate Similarity	0.7004	NPC232727
Remote Similarity	0.6996	NPC473180
Remote Similarity	0.6996	NPC475720
Remote Similarity	0.6996	NPC473186
Remote Similarity	0.6996	NPC474192
Remote Similarity	0.6992	NPC314270
Remote Similarity	0.6988	NPC472434
Remote Similarity	0.6987	NPC475070
Remote Similarity	0.6983	NPC219664
Remote Similarity	0.698	NPC272549
Remote Similarity	0.6979	NPC477110
Remote Similarity	0.6979	NPC170114
Remote Similarity	0.6978	NPC267928
Remote Similarity	0.6974	NPC199277
Remote Similarity	0.6974	NPC135887
Remote Similarity	0.6972	NPC176127
Remote Similarity	0.697	NPC477111
Remote Similarity	0.6969	NPC472435
Remote Similarity	0.6967	NPC473182
Remote Similarity	0.6962	NPC74360
Remote Similarity	0.6958	NPC235885
Remote Similarity	0.6955	NPC315555
Remote Similarity	0.6955	NPC260434
Remote Similarity	0.6953	NPC216369
Remote Similarity	0.6951	NPC184680
Remote Similarity	0.6951	NPC104712
Remote Similarity	0.6951	NPC177056
Remote Similarity	0.695	NPC314056
Remote Similarity	0.6946	NPC280272
Remote Similarity	0.6944	NPC26543
Remote Similarity	0.6944	NPC184964
Remote Similarity	0.6943	NPC223427
Remote Similarity	0.6939	NPC182222
Remote Similarity	0.6939	NPC39370
Remote Similarity	0.6936	NPC470549
Remote Similarity	0.6935	NPC217554
Remote Similarity	0.6933	NPC225279
Remote Similarity	0.6932	NPC471891
Remote Similarity	0.6929	NPC196449
Remote Similarity	0.6929	NPC314222
Remote Similarity	0.6926	NPC196718
Remote Similarity	0.6923	NPC470785
Remote Similarity	0.6923	NPC315467
Remote Similarity	0.6923	NPC11408
Remote Similarity	0.6923	NPC470784
Remote Similarity	0.6923	NPC46580
Remote Similarity	0.692	NPC204446
Remote Similarity	0.692	NPC208522
Remote Similarity	0.6917	NPC167908
Remote Similarity	0.6917	NPC51388
Remote Similarity	0.6916	NPC470498
Remote Similarity	0.6912	NPC42979
Remote Similarity	0.691	NPC167860
Remote Similarity	0.691	NPC123976
Remote Similarity	0.6907	NPC74969
Remote Similarity	0.6904	NPC310118
Remote Similarity	0.6903	NPC243834
Remote Similarity	0.6903	NPC70956
Remote Similarity	0.69	NPC475085
Remote Similarity	0.69	NPC291535
Remote Similarity	0.69	NPC475112
Remote Similarity	0.6898	NPC224764
Remote Similarity	0.6897	NPC478010
Remote Similarity	0.6897	NPC478009
Remote Similarity	0.6897	NPC475910
Remote Similarity	0.6888	NPC179287
Remote Similarity	0.6887	NPC472436
Remote Similarity	0.6885	NPC474701
Remote Similarity	0.6883	NPC240384
Remote Similarity	0.6883	NPC477113
Remote Similarity	0.688	NPC316224
Remote Similarity	0.6875	NPC324149
Remote Similarity	0.6872	NPC470499
Remote Similarity	0.687	NPC478013
Remote Similarity	0.687	NPC476098
Remote Similarity	0.6867	NPC469589
Remote Similarity	0.6867	NPC478158
Remote Similarity	0.6864	NPC284678
Remote Similarity	0.6864	NPC478157
Remote Similarity	0.686	NPC202503
Remote Similarity	0.6857	NPC102593
Remote Similarity	0.6853	NPC321428
Remote Similarity	0.6851	NPC219087
Remote Similarity	0.6849	NPC96321
Remote Similarity	0.684	NPC311276
Remote Similarity	0.6838	NPC471304
Remote Similarity	0.6837	NPC252590
Remote Similarity	0.6835	NPC36405
Remote Similarity	0.6833	NPC2395
Remote Similarity	0.6827	NPC475816

Drug Structure

NPD4454 OpenBabel08211705262D 32 34 0 0 1 0 0 0 0 0999 V2000 3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 -2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 -2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -1.7024 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 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8383 0.6203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4128 0.2976 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 7.1449 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -0.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5074 1.3634 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 8.0109 -0.2024 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -0.2024 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 4.5468 -1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1984 2.3145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4855 1.1555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1473 -0.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 0.2976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.7024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1547 1.8986 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 14 1 0 0 0 0 5 16 2 0 0 0 0 6 17 1 0 0 0 0 7 19 2 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 12 20 1 0 0 0 0 12 28 1 0 0 0 0 13 1 1 6 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 18 11 1 1 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 28 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB016776
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	402.13
ALogP	-1.128
MLogP	3
XLogP	2.997
HDA	5
HBD	4
Rotatable Bonds	13
TPSA	94.58
RO5 Violation	0