NPASS Natural Product

Natural Product: NPC152166

Natural Product ID:	NPC152166
Common Name:	Ternatin
IUPAC Name:	5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxychromen-4-one
Synonyms:	Ternatin
Molecular Formula:	C19H18O8
Standard InCHIKey:	DGUWNYKZOJRCQQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O8/c1-23-12-7-9(5-6-10(12)20)16-19(26-4)15(22)14-11(21)8-13(24-2)17(25-3)18(14)27-16/h5-8,20-21H,1-4H3
Canonical SMILES:	COc1cc(ccc1O)c1oc2c(OC)c(OC)cc(c2c(=O)c1OC)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO28242	Amomum latifolium	Species	Zingiberaceae	Eukaryota	UNPD*
NPO15715	Astragalus mongholicus	Species	Fabaceae	Eukaryota	UNPD*
NPO4248	Maytenus canariensis	Species	Celastraceae	Eukaryota	UNPD*
NPO16513	Trachyopsis aplysinoides	NA	NA	NA	UNPD*
NPO11913	Melicope spp.	Species	Rutaceae	Eukaryota	TCMID*
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	TCMID*
NPO25088	Larrea tridentata	Species	Zygophyllaceae	Eukaryota	TCMID*
NPO10285	Evodia madagascariensis	NA	NA	NA	TCMID*
NPO24100	Egletes viscosa	Species	Asteraceae	Eukaryota	TCMID*
NPO10285	Evodia madagascariensis	NA	NA	NA	HerDing*
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	HerDing*
NPO24100	Egletes viscosa	Species	Asteraceae	Eukaryota	HerDing*
NPO25088	Larrea tridentata	Species	Zygophyllaceae	Eukaryota	HerDing*
NPO31469	Melicope spp	Species	Rutaceae	Eukaryota	HerDing*
NPO8672	Ophiura ophiura	Species	Ophiuridae	Eukaryota	UNPD*
NPO20235	Recordia reitzii	Species	Verbenaceae	Eukaryota	UNPD*
NPO19690	Selinum vaginatum	Species	Apiaceae	Eukaryota	UNPD*
NPO19154	Maytenus ebenifolia	Species	Celastraceae	Eukaryota	UNPD*
NPO27887	Striga asiatica	Species	Orobanchaceae	Eukaryota	UNPD*
NPO14146	Lupinus hirsutus	Species	Fabaceae	Eukaryota	UNPD*
NPO28296	Dryopteris dickinsii	Species	Dryopteridaceae	Eukaryota	UNPD*
NPO28277	Diospyros maingayi	Species	Ebenaceae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
ED50	9
GI50	105
IC50	1
Others	6

Activity Type	# Activity
Cell Line	105
Organism	14
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	9500	nM	9632366
NPT518	Protein Complex	Tubulin	Homo sapiens	IC50	>	40000	nM	9632366
NPT518	Protein Complex	Tubulin	Homo sapiens	Inhibition	=	0	%	9632366
NPT4194	Organism	Human adenovirus type 2	Human adenovirus 2	ED50	=	0.01	nM	10.1021/np50070a036
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	ED50	=	0.044	nM	10.1021/np50070a036
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	ED50	=	0.1	nM	10.1021/np50070a036
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	ED50	=	0.014	nM	10.1021/np50070a036
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	ED50	=	0.048	nM	10.1021/np50070a036
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	ED50	=	0.038	nM	10.1021/np50070a036
NPT1859	Organism	Human poliovirus 2	Human poliovirus 2	ED50	=	0.004	nM	10.1021/np50070a036
NPT1859	Organism	Human poliovirus 2	Human poliovirus 2	ED50	=	0.003	nM	10.1021/np50070a036
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	1		10.1021/np50070a036
NPT1859	Organism	Human poliovirus 2	Human poliovirus 2	Activity	=	5		10.1021/np50070a036
NPT4194	Organism	Human adenovirus type 2	Human adenovirus 2	Activity	=	3		10.1021/np50070a036
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	Activity	=	2		10.1021/np50070a036
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	2		10.1021/np50070a036
NPT367	Cell Line	MDA-N	Homo sapiens	GI50		15240.53	nM	PubChem BioAssay data set
NPT368	Cell Line	SN12C	Homo sapiens	GI50		3732.5	nM	PubChem BioAssay data set
NPT369	Cell Line	ACHN	Homo sapiens	GI50		1840.77	nM	PubChem BioAssay data set
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50		7379.04	nM	PubChem BioAssay data set
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50		35075.19	nM	PubChem BioAssay data set
NPT368	Cell Line	SN12C	Homo sapiens	GI50		12416.52	nM	PubChem BioAssay data set
NPT369	Cell Line	ACHN	Homo sapiens	GI50		4709.77	nM	PubChem BioAssay data set
NPT371	Cell Line	UO-31	Homo sapiens	GI50		3881.5	nM	PubChem BioAssay data set
NPT372	Cell Line	HOP-92	Homo sapiens	GI50		2741.57	nM	PubChem BioAssay data set
NPT371	Cell Line	UO-31	Homo sapiens	GI50		8203.52	nM	PubChem BioAssay data set
NPT372	Cell Line	HOP-92	Homo sapiens	GI50		5847.9	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		1238.8	nM	PubChem BioAssay data set
NPT374	Cell Line	SF-539	Homo sapiens	GI50		6180.16	nM	PubChem BioAssay data set
NPT90	Cell Line	DU-145	Homo sapiens	GI50		7430.19	nM	PubChem BioAssay data set
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50		2371.37	nM	PubChem BioAssay data set
NPT374	Cell Line	SF-539	Homo sapiens	GI50		7498.94	nM	PubChem BioAssay data set
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50		13091.82	nM	PubChem BioAssay data set
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50		9120.11	nM	PubChem BioAssay data set
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50		9594.01	nM	PubChem BioAssay data set
NPT376	Cell Line	A498	Homo sapiens	GI50		3380.65	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		27542.29	nM	PubChem BioAssay data set
NPT376	Cell Line	A498	Homo sapiens	GI50		16595.87	nM	PubChem BioAssay data set
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50		11694.99	nM	PubChem BioAssay data set
NPT379	Cell Line	HOP-62	Homo sapiens	GI50		14689.26	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		12676.52	nM	PubChem BioAssay data set
NPT379	Cell Line	HOP-62	Homo sapiens	GI50		4008.67	nM	PubChem BioAssay data set
NPT380	Cell Line	U-251	Homo sapiens	GI50		5970.35	nM	PubChem BioAssay data set
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50		38815.04	nM	PubChem BioAssay data set
NPT380	Cell Line	U-251	Homo sapiens	GI50		12676.52	nM	PubChem BioAssay data set
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50		20653.8	nM	PubChem BioAssay data set
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50		34593.94	nM	PubChem BioAssay data set
NPT383	Cell Line	SNB-19	Homo sapiens	GI50		41591.06	nM	PubChem BioAssay data set
NPT383	Cell Line	SNB-19	Homo sapiens	GI50		49773.71	nM	PubChem BioAssay data set
NPT384	Cell Line	TK-10	Homo sapiens	GI50		4841.72	nM	PubChem BioAssay data set
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50		15240.53	nM	PubChem BioAssay data set
NPT384	Cell Line	TK-10	Homo sapiens	GI50		8689.6	nM	PubChem BioAssay data set
NPT323	Cell Line	SW-620	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT323	Cell Line	SW-620	Homo sapiens	GI50		37757.22	nM	PubChem BioAssay data set
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50		2113.49	nM	PubChem BioAssay data set
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50		22080.05	nM	PubChem BioAssay data set
NPT386	Cell Line	KM12	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT387	Cell Line	M14	Homo sapiens	GI50		6266.14	nM	PubChem BioAssay data set
NPT386	Cell Line	KM12	Homo sapiens	GI50		19010.78	nM	PubChem BioAssay data set
NPT574	Cell Line	XF498	Homo sapiens	GI50		2202.93	nM	PubChem BioAssay data set
NPT387	Cell Line	M14	Homo sapiens	GI50		2999.16	nM	PubChem BioAssay data set
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50		9840.11	nM	PubChem BioAssay data set
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50		1883.65	nM	PubChem BioAssay data set
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50		11350.11	nM	PubChem BioAssay data set
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50		7961.59	nM	PubChem BioAssay data set
NPT457	Cell Line	BT-549	Homo sapiens	GI50		5011.87	nM	PubChem BioAssay data set
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		2523.48	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		6902.4	nM	PubChem BioAssay data set
NPT81	Cell Line	A549	Homo sapiens	GI50		14893.61	nM	PubChem BioAssay data set
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT392	Cell Line	SNB-75	Homo sapiens	GI50		5000.35	nM	PubChem BioAssay data set
NPT392	Cell Line	SNB-75	Homo sapiens	GI50		1698.24	nM	PubChem BioAssay data set
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50		30974.19	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		4539.42	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		6237.35	nM	PubChem BioAssay data set
NPT393	Cell Line	HCT-116	Homo sapiens	GI50		5035.01	nM	PubChem BioAssay data set
NPT393	Cell Line	HCT-116	Homo sapiens	GI50		8689.6	nM	PubChem BioAssay data set
NPT395	Cell Line	SF-268	Homo sapiens	GI50		34434.99	nM	PubChem BioAssay data set
NPT395	Cell Line	SF-268	Homo sapiens	GI50		15275.66	nM	PubChem BioAssay data set
NPT394	Cell Line	EKVX	Homo sapiens	GI50		11350.11	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	GI50		21086.28	nM	PubChem BioAssay data set
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50		3981.07	nM	PubChem BioAssay data set
NPT576	Cell Line	DMS-114	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		1174.9	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50		20417.38	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		2192.8	nM	PubChem BioAssay data set
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50		3999.45	nM	PubChem BioAssay data set
NPT396	Cell Line	T47D	Homo sapiens	GI50		8317.64	nM	PubChem BioAssay data set
NPT398	Cell Line	UACC-62	Homo sapiens	GI50		8394.6	nM	PubChem BioAssay data set
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50		8511.38	nM	PubChem BioAssay data set
NPT398	Cell Line	UACC-62	Homo sapiens	GI50		4698.94	nM	PubChem BioAssay data set
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50		10568.18	nM	PubChem BioAssay data set
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50		6998.42	nM	PubChem BioAssay data set
NPT399	Cell Line	SF-295	Homo sapiens	GI50		3243.4	nM	PubChem BioAssay data set
NPT399	Cell Line	SF-295	Homo sapiens	GI50		8336.81	nM	PubChem BioAssay data set
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50		4886.52	nM	PubChem BioAssay data set
NPT577	Cell Line	RXF 631	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50		4102.04	nM	PubChem BioAssay data set
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50		3926.45	nM	PubChem BioAssay data set
NPT401	Cell Line	786-0	Homo sapiens	GI50		6324.12	nM	PubChem BioAssay data set
NPT401	Cell Line	786-0	Homo sapiens	GI50		11994.99	nM	PubChem BioAssay data set
NPT403	Cell Line	UACC-257	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT578	Cell Line	SNB-78	Homo sapiens	GI50		6486.34	nM	PubChem BioAssay data set
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50		3380.65	nM	PubChem BioAssay data set
NPT579	Cell Line	DLD-1	Homo sapiens	GI50		3698.28	nM	PubChem BioAssay data set
NPT403	Cell Line	UACC-257	Homo sapiens	GI50		50003.45	nM	PubChem BioAssay data set
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50		2415.46	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50		3881.5	nM	PubChem BioAssay data set
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50		12445.15	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		50003.45	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		19998.62	nM	PubChem BioAssay data set
NPT406	Cell Line	RXF 393	Homo sapiens	GI50		6180.16	nM	PubChem BioAssay data set
NPT406	Cell Line	RXF 393	Homo sapiens	GI50		3872.58	nM	PubChem BioAssay data set
NPT407	Cell Line	COLO 205	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT407	Cell Line	COLO 205	Homo sapiens	GI50		50003.45	nM	PubChem BioAssay data set

Similar Natural Products in NPASS

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

● The left chart: Distribution of similarity level between NPC152166 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	1282
0.2-0.3	3013
0.3-0.4	6987
0.4-0.5	5694
0.5-0.6	2582
0.6-0.7	3567
0.7-0.8	4026
0.8-0.85	1745
0.85-0.9	974
0.9-0.95	530
0.95-1	156

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC253634
1.0	High Similarity	NPC19687
1.0	High Similarity	NPC288669
1.0	High Similarity	NPC143828
1.0	High Similarity	NPC191459
1.0	High Similarity	NPC18607
1.0	High Similarity	NPC115798
1.0	High Similarity	NPC9609
1.0	High Similarity	NPC18772
1.0	High Similarity	NPC130894
1.0	High Similarity	NPC300943
1.0	High Similarity	NPC4481
1.0	High Similarity	NPC105242
1.0	High Similarity	NPC176300
1.0	High Similarity	NPC22472
1.0	High Similarity	NPC261004
1.0	High Similarity	NPC204854
1.0	High Similarity	NPC7846
1.0	High Similarity	NPC25495
0.9933	High Similarity	NPC101830
0.9933	High Similarity	NPC176665
0.9933	High Similarity	NPC189179
0.9933	High Similarity	NPC7973
0.9933	High Similarity	NPC227192
0.9933	High Similarity	NPC78302
0.9933	High Similarity	NPC163524
0.9933	High Similarity	NPC93376
0.9933	High Similarity	NPC203891
0.9933	High Similarity	NPC29841
0.9933	High Similarity	NPC235215
0.9933	High Similarity	NPC472438
0.9933	High Similarity	NPC110070
0.9933	High Similarity	NPC224137
0.9933	High Similarity	NPC287979
0.9933	High Similarity	NPC305663
0.9933	High Similarity	NPC75215
0.9868	High Similarity	NPC193842
0.9867	High Similarity	NPC43243
0.9867	High Similarity	NPC55619
0.9867	High Similarity	NPC200388
0.9867	High Similarity	NPC100916
0.9867	High Similarity	NPC474520
0.9867	High Similarity	NPC247017
0.9867	High Similarity	NPC268161
0.9867	High Similarity	NPC178854
0.9867	High Similarity	NPC266960
0.9867	High Similarity	NPC49824
0.9867	High Similarity	NPC245546
0.9867	High Similarity	NPC292107
0.9867	High Similarity	NPC98661
0.98	High Similarity	NPC214138
0.98	High Similarity	NPC196439
0.98	High Similarity	NPC50715
0.98	High Similarity	NPC32557
0.98	High Similarity	NPC189960
0.98	High Similarity	NPC167815
0.98	High Similarity	NPC92659
0.98	High Similarity	NPC4455
0.98	High Similarity	NPC2476
0.98	High Similarity	NPC44079
0.98	High Similarity	NPC280339
0.98	High Similarity	NPC201136
0.98	High Similarity	NPC138360
0.98	High Similarity	NPC163780
0.98	High Similarity	NPC26227
0.98	High Similarity	NPC128863
0.98	High Similarity	NPC201451
0.98	High Similarity	NPC183597
0.98	High Similarity	NPC146165
0.98	High Similarity	NPC227325
0.9735	High Similarity	NPC265511
0.9733	High Similarity	NPC276409
0.9733	High Similarity	NPC86485
0.9733	High Similarity	NPC250822
0.9733	High Similarity	NPC69394
0.9733	High Similarity	NPC162351
0.9733	High Similarity	NPC270620
0.9733	High Similarity	NPC78326
0.9733	High Similarity	NPC75279
0.9733	High Similarity	NPC183878
0.9733	High Similarity	NPC160951
0.9733	High Similarity	NPC22519
0.9733	High Similarity	NPC246204
0.9733	High Similarity	NPC231018
0.9733	High Similarity	NPC179126
0.9733	High Similarity	NPC274327
0.9733	High Similarity	NPC145379
0.9733	High Similarity	NPC236223
0.9733	High Similarity	NPC58382
0.9733	High Similarity	NPC176775
0.9733	High Similarity	NPC255350
0.9733	High Similarity	NPC47781
0.9673	High Similarity	NPC246478
0.9669	High Similarity	NPC256612
0.9669	High Similarity	NPC20830
0.9669	High Similarity	NPC208197
0.9669	High Similarity	NPC213622
0.9667	High Similarity	NPC57030
0.9667	High Similarity	NPC301123
0.9667	High Similarity	NPC83508
0.9667	High Similarity	NPC275722
0.9667	High Similarity	NPC120163
0.9667	High Similarity	NPC301323
0.9667	High Similarity	NPC82325
0.9667	High Similarity	NPC25270
0.9667	High Similarity	NPC279989
0.9667	High Similarity	NPC156222
0.9667	High Similarity	NPC198826
0.9667	High Similarity	NPC123886
0.9667	High Similarity	NPC27208
0.9667	High Similarity	NPC100887
0.9667	High Similarity	NPC256283
0.9667	High Similarity	NPC222830
0.9667	High Similarity	NPC293183
0.9667	High Similarity	NPC239128
0.9667	High Similarity	NPC187498
0.9667	High Similarity	NPC188203
0.9667	High Similarity	NPC142540
0.9667	High Similarity	NPC241498
0.9667	High Similarity	NPC162313
0.9667	High Similarity	NPC134677
0.9667	High Similarity	NPC275836
0.9667	High Similarity	NPC131624
0.9667	High Similarity	NPC212678
0.9667	High Similarity	NPC71334
0.9613	High Similarity	NPC470459
0.9608	High Similarity	NPC195832
0.96	High Similarity	NPC76376
0.96	High Similarity	NPC208043
0.96	High Similarity	NPC252933
0.96	High Similarity	NPC226973
0.96	High Similarity	NPC133953
0.96	High Similarity	NPC225731
0.96	High Similarity	NPC50403
0.96	High Similarity	NPC125062
0.96	High Similarity	NPC236769
0.96	High Similarity	NPC28274
0.96	High Similarity	NPC200740
0.96	High Similarity	NPC54394
0.9554	High Similarity	NPC76482
0.9551	High Similarity	NPC470457
0.9542	High Similarity	NPC470402
0.9536	High Similarity	NPC55205
0.9536	High Similarity	NPC39732
0.9536	High Similarity	NPC60972
0.9533	High Similarity	NPC201547
0.9533	High Similarity	NPC77858
0.9533	High Similarity	NPC219330
0.9533	High Similarity	NPC188871
0.9533	High Similarity	NPC50728
0.9533	High Similarity	NPC166753
0.9533	High Similarity	NPC286342
0.9533	High Similarity	NPC259058
0.9533	High Similarity	NPC306821
0.9533	High Similarity	NPC184136
0.9533	High Similarity	NPC149127
0.9494	High Similarity	NPC280493
0.949	High Similarity	NPC470462
0.9481	High Similarity	NPC152904
0.9477	High Similarity	NPC472916
0.947	High Similarity	NPC260895
0.947	High Similarity	NPC308451
0.9467	High Similarity	NPC328119
0.9467	High Similarity	NPC52005
0.9467	High Similarity	NPC48479
0.9467	High Similarity	NPC181250
0.9467	High Similarity	NPC177298
0.9467	High Similarity	NPC216318
0.9467	High Similarity	NPC259713
0.9467	High Similarity	NPC69752
0.9467	High Similarity	NPC183950
0.9467	High Similarity	NPC195351
0.9467	High Similarity	NPC87125
0.9467	High Similarity	NPC17286
0.9467	High Similarity	NPC270465
0.9467	High Similarity	NPC137062
0.9467	High Similarity	NPC159103
0.9467	High Similarity	NPC223579
0.9467	High Similarity	NPC296197
0.9467	High Similarity	NPC287101
0.943	High Similarity	NPC295082
0.943	High Similarity	NPC158761
0.943	High Similarity	NPC470456
0.9419	High Similarity	NPC263449
0.9419	High Similarity	NPC476980
0.9416	High Similarity	NPC471479
0.9416	High Similarity	NPC78225
0.9416	High Similarity	NPC474836
0.9416	High Similarity	NPC472910
0.9416	High Similarity	NPC471515
0.9416	High Similarity	NPC222814
0.9416	High Similarity	NPC174908
0.9416	High Similarity	NPC472913
0.9416	High Similarity	NPC48208
0.9416	High Similarity	NPC472914
0.9416	High Similarity	NPC96167
0.9416	High Similarity	NPC156057
0.9416	High Similarity	NPC162869
0.9416	High Similarity	NPC472911
0.9416	High Similarity	NPC245758

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC152166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	898
0.2-0.3	1745
0.3-0.4	2667
0.4-0.5	1817
0.5-0.6	1038
0.6-0.7	468
0.7-0.8	135
0.8-0.85	27
0.85-0.9	13
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9733	High Similarity	NPD2801	Approved
0.9351	High Similarity	NPD3882	Suspended
0.9286	High Similarity	NPD3817	Phase 2
0.9267	High Similarity	NPD1512	Approved
0.9156	High Similarity	NPD1934	Approved
0.9141	High Similarity	NPD4338	Clinical (unspecified phase)
0.9133	High Similarity	NPD1511	Approved
0.9062	High Similarity	NPD6166	Phase 2
0.9062	High Similarity	NPD6168	Clinical (unspecified phase)
0.9062	High Similarity	NPD6167	Clinical (unspecified phase)
0.8974	High Similarity	NPD2393	Clinical (unspecified phase)
0.8902	High Similarity	NPD6797	Phase 2
0.8848	High Similarity	NPD7251	Discontinued
0.8834	High Similarity	NPD3818	Discontinued
0.8824	High Similarity	NPD4378	Clinical (unspecified phase)
0.8795	High Similarity	NPD7808	Phase 3
0.878	High Similarity	NPD7054	Approved
0.8727	High Similarity	NPD7472	Approved
0.8679	High Similarity	NPD5402	Approved
0.8614	High Similarity	NPD7074	Phase 3
0.8571	High Similarity	NPD7075	Discontinued
0.8516	High Similarity	NPD6799	Approved
0.8509	High Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD5494	Approved
0.8438	Intermediate Similarity	NPD6801	Discontinued
0.8428	Intermediate Similarity	NPD4380	Phase 2
0.8415	Intermediate Similarity	NPD1247	Approved
0.8385	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8247	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD5403	Approved
0.8235	Intermediate Similarity	NPD1510	Phase 2
0.8235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD3926	Phase 2
0.8199	Intermediate Similarity	NPD6599	Discontinued
0.8194	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD2796	Approved
0.816	Intermediate Similarity	NPD1465	Phase 2
0.8113	Intermediate Similarity	NPD5401	Approved
0.8092	Intermediate Similarity	NPD943	Approved
0.8092	Intermediate Similarity	NPD1240	Approved
0.8072	Intermediate Similarity	NPD919	Approved
0.8049	Intermediate Similarity	NPD7819	Suspended
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1607	Approved
0.7962	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7411	Suspended
0.7925	Intermediate Similarity	NPD6190	Approved
0.7885	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6959	Discontinued
0.7834	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD230	Phase 1
0.7806	Intermediate Similarity	NPD447	Suspended
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3750	Approved
0.7746	Intermediate Similarity	NPD3751	Discontinued
0.7744	Intermediate Similarity	NPD1653	Approved
0.7742	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1613	Approved
0.7719	Intermediate Similarity	NPD3787	Discontinued
0.7688	Intermediate Similarity	NPD2800	Approved
0.768	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3027	Phase 3
0.763	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1551	Phase 2
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3749	Approved
0.7561	Intermediate Similarity	NPD2534	Approved
0.7561	Intermediate Similarity	NPD2532	Approved
0.7561	Intermediate Similarity	NPD2533	Approved
0.7558	Intermediate Similarity	NPD7199	Phase 2
0.7544	Intermediate Similarity	NPD6234	Discontinued
0.7532	Intermediate Similarity	NPD9494	Approved
0.7531	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3226	Approved
0.747	Intermediate Similarity	NPD920	Approved
0.7469	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1933	Approved
0.7453	Intermediate Similarity	NPD2344	Approved
0.7452	Intermediate Similarity	NPD6233	Phase 2
0.7438	Intermediate Similarity	NPD3748	Approved
0.7423	Intermediate Similarity	NPD4628	Phase 3
0.7421	Intermediate Similarity	NPD6651	Approved
0.7419	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5953	Discontinued
0.7391	Intermediate Similarity	NPD6100	Approved
0.7391	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD2313	Discontinued
0.7374	Intermediate Similarity	NPD7685	Pre-registration
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7362	Intermediate Similarity	NPD1243	Approved
0.7353	Intermediate Similarity	NPD37	Approved
0.7349	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2403	Approved
0.7329	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4966	Approved
0.7326	Intermediate Similarity	NPD4965	Approved
0.7326	Intermediate Similarity	NPD4967	Phase 2
0.7303	Intermediate Similarity	NPD7286	Phase 2
0.7302	Intermediate Similarity	NPD6779	Approved
0.7302	Intermediate Similarity	NPD6782	Approved
0.7302	Intermediate Similarity	NPD6777	Approved
0.7302	Intermediate Similarity	NPD6776	Approved
0.7302	Intermediate Similarity	NPD6780	Approved
0.7302	Intermediate Similarity	NPD6778	Approved
0.7302	Intermediate Similarity	NPD6781	Approved
0.729	Intermediate Similarity	NPD1203	Approved
0.7289	Intermediate Similarity	NPD7390	Discontinued
0.7278	Intermediate Similarity	NPD6798	Discontinued
0.7277	Intermediate Similarity	NPD7435	Discontinued
0.7273	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD6832	Phase 2
0.7251	Intermediate Similarity	NPD6844	Discontinued
0.7247	Intermediate Similarity	NPD7228	Approved
0.7239	Intermediate Similarity	NPD2346	Discontinued
0.7232	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7208	Intermediate Similarity	NPD9269	Phase 2
0.7197	Intermediate Similarity	NPD3018	Phase 2
0.7175	Intermediate Similarity	NPD5242	Approved
0.7174	Intermediate Similarity	NPD8150	Discontinued
0.717	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7134	Intermediate Similarity	NPD2798	Approved
0.7117	Intermediate Similarity	NPD7033	Discontinued
0.7108	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD8313	Approved
0.7104	Intermediate Similarity	NPD8312	Approved
0.7098	Intermediate Similarity	NPD7697	Approved
0.7098	Intermediate Similarity	NPD7698	Approved
0.7098	Intermediate Similarity	NPD7696	Phase 3
0.7097	Intermediate Similarity	NPD9717	Approved
0.7093	Intermediate Similarity	NPD6385	Approved
0.7093	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD4357	Discontinued
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.707	Intermediate Similarity	NPD2797	Approved
0.7069	Intermediate Similarity	NPD5353	Approved
0.7066	Intermediate Similarity	NPD2354	Approved
0.7063	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7871	Phase 2
0.7062	Intermediate Similarity	NPD7870	Phase 2
0.7056	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2163	Approved
0.7056	Intermediate Similarity	NPD7874	Approved
0.7051	Intermediate Similarity	NPD2982	Phase 2
0.7051	Intermediate Similarity	NPD2983	Phase 2
0.7048	Intermediate Similarity	NPD2654	Approved
0.7041	Intermediate Similarity	NPD7701	Phase 2
0.7039	Intermediate Similarity	NPD5536	Phase 2
0.7037	Intermediate Similarity	NPD4363	Phase 3
0.7037	Intermediate Similarity	NPD4360	Phase 2
0.7037	Intermediate Similarity	NPD6534	Approved
0.7037	Intermediate Similarity	NPD6535	Approved
0.7032	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1610	Phase 2
0.703	Intermediate Similarity	NPD1471	Phase 3
0.7022	Intermediate Similarity	NPD5710	Approved
0.7022	Intermediate Similarity	NPD5711	Approved
0.7012	Intermediate Similarity	NPD4308	Phase 3
0.7006	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD7095	Approved
0.699	Remote Similarity	NPD7584	Approved
0.6987	Remote Similarity	NPD1608	Approved
0.6987	Remote Similarity	NPD2981	Phase 2
0.6981	Remote Similarity	NPD2861	Phase 2
0.6961	Remote Similarity	NPD7907	Approved
0.6957	Remote Similarity	NPD411	Approved
0.6957	Remote Similarity	NPD7549	Discontinued
0.6948	Remote Similarity	NPD9268	Approved
0.6946	Remote Similarity	NPD2899	Discontinued
0.6946	Remote Similarity	NPD1652	Phase 2
0.6941	Remote Similarity	NPD3146	Approved
0.6941	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7801	Approved

Structure

CID152166 OpenBabel06191715522D 27 29 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 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 2.5981 1.5000 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 -2.5981 -0.5000 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 -1.7321 1.0000 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 -1.7321 -0.0000 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 -2.0000 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 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 -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 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 19 1 0 0 0 0 15 22 2 0 0 0 0 16 19 2 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5459184
ChEMBL	CHEMBL73991
ZINC

Physicochemical Properties

Molecular Weight:	374.10
ALogP:	-1.9715
MLogP:	2.67
XLogP:	1.438
# Rotatable Bonds:	11
Polar Surface Area:	103.68
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	27

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