NPASS drugs

Drug Information

Drug ID:	NPD3931
Drug Name:	Amodiaquine
Molecular Formula:	C20H22ClN3O
Canonical SMILES:	CCN(Cc1cc(ccc1O)Nc1ccnc2c1ccc(c2)Cl)CC
Standard InCHI:	InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)
Standard InCHIKey:	OVCDSSHSILBFBN-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD3931

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	452
0.1-0.2	4200
0.2-0.3	8761
0.3-0.4	11046
0.4-0.5	3712
0.5-0.6	1569
0.6-0.7	1021
0.7-0.8	129
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	0.791	NPC475070
Intermediate Similarity	0.7882	NPC477111
Intermediate Similarity	0.7869	NPC124542
Intermediate Similarity	0.7869	NPC59779
Intermediate Similarity	0.7869	NPC471177
Intermediate Similarity	0.7845	NPC476464
Intermediate Similarity	0.7824	NPC171171
Intermediate Similarity	0.7806	NPC99666
Intermediate Similarity	0.7784	NPC471178
Intermediate Similarity	0.7783	NPC477113
Intermediate Similarity	0.772	NPC204717
Intermediate Similarity	0.7716	NPC324149
Intermediate Similarity	0.768	NPC314002
Intermediate Similarity	0.7668	NPC220765
Intermediate Similarity	0.765	NPC77555
Intermediate Similarity	0.7644	NPC184964
Intermediate Similarity	0.7548	NPC5145
Intermediate Similarity	0.7536	NPC477110
Intermediate Similarity	0.7474	NPC473764
Intermediate Similarity	0.7474	NPC314940
Intermediate Similarity	0.7426	NPC242209
Intermediate Similarity	0.7424	NPC46580
Intermediate Similarity	0.7418	NPC476041
Intermediate Similarity	0.7418	NPC469727
Intermediate Similarity	0.7418	NPC304926
Intermediate Similarity	0.7391	NPC470500
Intermediate Similarity	0.7387	NPC246700
Intermediate Similarity	0.7387	NPC128751
Intermediate Similarity	0.7387	NPC32771
Intermediate Similarity	0.7371	NPC96890
Intermediate Similarity	0.7368	NPC18348
Intermediate Similarity	0.7366	NPC315957
Intermediate Similarity	0.7354	NPC97367
Intermediate Similarity	0.735	NPC469497
Intermediate Similarity	0.735	NPC106833
Intermediate Similarity	0.734	NPC131718
Intermediate Similarity	0.7327	NPC329541
Intermediate Similarity	0.7327	NPC106937
Intermediate Similarity	0.7306	NPC214980
Intermediate Similarity	0.7306	NPC313791
Intermediate Similarity	0.7306	NPC474409
Intermediate Similarity	0.7304	NPC156704
Intermediate Similarity	0.7302	NPC477609
Intermediate Similarity	0.7299	NPC309845
Intermediate Similarity	0.7282	NPC249040
Intermediate Similarity	0.7264	NPC208284
Intermediate Similarity	0.726	NPC200836
Intermediate Similarity	0.7254	NPC252590
Intermediate Similarity	0.7252	NPC300114
Intermediate Similarity	0.7249	NPC25899
Intermediate Similarity	0.7241	NPC307963
Intermediate Similarity	0.7233	NPC476167
Intermediate Similarity	0.7231	NPC203754
Intermediate Similarity	0.7231	NPC150048
Intermediate Similarity	0.7228	NPC92111
Intermediate Similarity	0.7225	NPC47059
Intermediate Similarity	0.7225	NPC165349
Intermediate Similarity	0.7225	NPC329708
Intermediate Similarity	0.7225	NPC264166
Intermediate Similarity	0.7225	NPC274291
Intermediate Similarity	0.7225	NPC118832
Intermediate Similarity	0.722	NPC153042
Intermediate Similarity	0.7215	NPC130570
Intermediate Similarity	0.7212	NPC211813
Intermediate Similarity	0.7206	NPC326634
Intermediate Similarity	0.7196	NPC477610
Intermediate Similarity	0.7196	NPC266931
Intermediate Similarity	0.7184	NPC192315
Intermediate Similarity	0.7178	NPC471593
Intermediate Similarity	0.7178	NPC76748
Intermediate Similarity	0.7173	NPC102423
Intermediate Similarity	0.7171	NPC472193
Intermediate Similarity	0.717	NPC476116
Intermediate Similarity	0.7162	NPC477607
Intermediate Similarity	0.7162	NPC477608
Intermediate Similarity	0.7157	NPC88363
Intermediate Similarity	0.715	NPC94943
Intermediate Similarity	0.7143	NPC285558
Intermediate Similarity	0.7143	NPC60553
Intermediate Similarity	0.7136	NPC133306
Intermediate Similarity	0.7129	NPC470678
Intermediate Similarity	0.7129	NPC296527
Intermediate Similarity	0.7128	NPC259545
Intermediate Similarity	0.712	NPC48192
Intermediate Similarity	0.7116	NPC478074
Intermediate Similarity	0.7115	NPC176538
Intermediate Similarity	0.7115	NPC121772
Intermediate Similarity	0.7115	NPC315491
Intermediate Similarity	0.7115	NPC45459
Intermediate Similarity	0.7111	NPC471312
Intermediate Similarity	0.711	NPC193267
Intermediate Similarity	0.711	NPC213530
Intermediate Similarity	0.71	NPC190007
Intermediate Similarity	0.7097	NPC288445
Intermediate Similarity	0.7094	NPC95783
Intermediate Similarity	0.7087	NPC251090
Intermediate Similarity	0.7087	NPC222018
Intermediate Similarity	0.7083	NPC159319
Intermediate Similarity	0.7083	NPC473057
Intermediate Similarity	0.7072	NPC132631
Intermediate Similarity	0.7072	NPC103687
Intermediate Similarity	0.7071	NPC232340
Intermediate Similarity	0.7071	NPC42979
Intermediate Similarity	0.7071	NPC72980
Intermediate Similarity	0.707	NPC202605
Intermediate Similarity	0.707	NPC112206
Intermediate Similarity	0.7056	NPC11464
Intermediate Similarity	0.7056	NPC224764
Intermediate Similarity	0.7053	NPC474188
Intermediate Similarity	0.7053	NPC26850
Intermediate Similarity	0.7053	NPC90229
Intermediate Similarity	0.705	NPC212535
Intermediate Similarity	0.705	NPC48938
Intermediate Similarity	0.704	NPC6215
Intermediate Similarity	0.7033	NPC32002
Intermediate Similarity	0.7033	NPC213308
Intermediate Similarity	0.7033	NPC19872
Intermediate Similarity	0.7033	NPC315348
Intermediate Similarity	0.7031	NPC315214
Intermediate Similarity	0.7031	NPC47298
Intermediate Similarity	0.7028	NPC476121
Intermediate Similarity	0.7028	NPC476124
Intermediate Similarity	0.7026	NPC164664
Intermediate Similarity	0.7022	NPC477112
Intermediate Similarity	0.7014	NPC53144
Intermediate Similarity	0.7009	NPC253580
Intermediate Similarity	0.7005	NPC237740
Intermediate Similarity	0.7005	NPC13880
Intermediate Similarity	0.7	NPC144114
Remote Similarity	0.6996	NPC60006
Remote Similarity	0.6995	NPC32028
Remote Similarity	0.6986	NPC173080
Remote Similarity	0.6984	NPC469760
Remote Similarity	0.6984	NPC73952
Remote Similarity	0.6984	NPC469763
Remote Similarity	0.6984	NPC469786
Remote Similarity	0.6984	NPC259644
Remote Similarity	0.6984	NPC469765
Remote Similarity	0.6984	NPC25008
Remote Similarity	0.6974	NPC477549
Remote Similarity	0.6974	NPC44161
Remote Similarity	0.6972	NPC469928
Remote Similarity	0.6972	NPC183407
Remote Similarity	0.6968	NPC310118
Remote Similarity	0.6964	NPC470126
Remote Similarity	0.6961	NPC472289
Remote Similarity	0.6957	NPC477861
Remote Similarity	0.6954	NPC471294
Remote Similarity	0.6954	NPC208060
Remote Similarity	0.6947	NPC70922
Remote Similarity	0.6947	NPC75540
Remote Similarity	0.6947	NPC80597
Remote Similarity	0.6947	NPC211572
Remote Similarity	0.6947	NPC212376
Remote Similarity	0.6946	NPC314573
Remote Similarity	0.6943	NPC177056
Remote Similarity	0.6943	NPC177404
Remote Similarity	0.6941	NPC27041
Remote Similarity	0.6939	NPC194411
Remote Similarity	0.6937	NPC162748
Remote Similarity	0.6934	NPC223427
Remote Similarity	0.6919	NPC232727
Remote Similarity	0.6916	NPC193777
Remote Similarity	0.6915	NPC477891
Remote Similarity	0.6912	NPC128084
Remote Similarity	0.6912	NPC254762
Remote Similarity	0.6912	NPC316981
Remote Similarity	0.6907	NPC311276
Remote Similarity	0.6907	NPC56271
Remote Similarity	0.6905	NPC476175
Remote Similarity	0.6901	NPC36229
Remote Similarity	0.6901	NPC476581
Remote Similarity	0.6901	NPC16452
Remote Similarity	0.69	NPC295228
Remote Similarity	0.69	NPC215795
Remote Similarity	0.69	NPC176199
Remote Similarity	0.6898	NPC167860
Remote Similarity	0.6898	NPC123976
Remote Similarity	0.6895	NPC476161
Remote Similarity	0.6895	NPC26872
Remote Similarity	0.689	NPC473814
Remote Similarity	0.689	NPC78767
Remote Similarity	0.6888	NPC63751
Remote Similarity	0.6881	NPC162530
Remote Similarity	0.6878	NPC24678
Remote Similarity	0.6878	NPC105818
Remote Similarity	0.6875	NPC245348
Remote Similarity	0.6872	NPC329793
Remote Similarity	0.687	NPC184225
Remote Similarity	0.6861	NPC470501
Remote Similarity	0.6854	NPC475774
Remote Similarity	0.6853	NPC126481
Remote Similarity	0.6849	NPC470549
Remote Similarity	0.6847	NPC276657
Remote Similarity	0.6839	NPC135141
Remote Similarity	0.6839	NPC92796
Remote Similarity	0.6837	NPC88008
Remote Similarity	0.6837	NPC108469
Remote Similarity	0.6835	NPC48353
Remote Similarity	0.6834	NPC275305

Drug Structure

NPD3931 OpenBabel08211704332D 27 29 0 0 0 0 0 0 0 0999 V2000 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 3.4641 -0.0000 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 4.3301 -0.5000 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 1.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 -2.0000 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 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 Cl 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 2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 16 2 0 0 0 0 7 17 1 0 0 0 0 8 20 2 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 20 25 1 0 0 0 0 23 26 1 0 0 0 0 25 27 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000699
DrugBank	DB00613
ChEMBL	CHEMBL682
IUPHAR/BPS
PharmaGKB	PA448404
KEGG Drug	D02922
PubChem CID	2165
ChEBI	2674
CAS Number	86-42-0

Drug Properties

Molecular Weight	355.15
ALogP	0.5938
MLogP	3.11
XLogP	4.03
HDA	3
HBD	2
Rotatable Bonds	10
TPSA	48.39
RO5 Violation	0