NPASS Natural Product

Natural Product: NPC188646

Natural Product ID:	NPC188646
Common Name:	Flavokawain B
IUPAC Name:	(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
Synonyms:
Molecular Formula:	C17H16O4
Standard InCHIKey:	QKQLSQLKXBHUSO-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+
Canonical SMILES:	COc1cc(O)c(c(c1)OC)C(=O)/C=C/c1ccccc1
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO17249	Lespedeza capitata	Species	Fabaceae	Eukaryota		UNPD*
NPO28771	Clematis delavayi	Species	Ranunculaceae	Eukaryota		UNPD*
NPO21344	Fadogia agrestis	Species	Rubiaceae	Eukaryota		UNPD*
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota		UNPD*
NPO8943	Juniperus californica	Species	Cupressaceae	Eukaryota		UNPD*
NPO19008	Mentha cablin	Species	Lamiaceae	Eukaryota		UNPD*
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota		UNPD*
NPO18596	Melia dubia	Species	Meliaceae	Eukaryota		UNPD*
NPO18259	Chaetanthera chilensis	Species	Asteraceae	Eukaryota		UNPD*
NPO25321	Acantholimon glumaceum	Species	Plumbaginaceae	Eukaryota		UNPD*
NPO21534	Ostrya carpinifolia	Species	Betulaceae	Eukaryota		UNPD*
NPO19721	Impatiens roylei	Species	Balsaminaceae	Eukaryota		UNPD*
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota		UNPD*
NPO27620.1	Pteris cretica var. nervosa	Varieties	Pteridaceae	Eukaryota		TCMID*
NPO18529	Salvia broussoneti	Species	Lamiaceae	Eukaryota		UNPD*
NPO23489	Stachys anisochila	Species	Lamiaceae	Eukaryota		UNPD*
NPO5676	Annulohypoxylon multiforme	Species	Xylariaceae	Eukaryota		UNPD*
NPO24591	Trichosanthes dioica	Species	Cucurbitaceae	Eukaryota		UNPD*
NPO16772	Piper rusbyi	Species	Piperaceae	Eukaryota	Leaves	PMID[17354169]
NPO24549	Scutellaria cordifrons	Species	Lamiaceae	Eukaryota		UNPD*
NPO20691	Echinocereus merkeri	Species	Cactaceae	Eukaryota		UNPD*
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota		PMID[11830162]
NPO8788	Renealmia nicolaioides	Species	Zingiberaceae	Eukaryota		PMID[12444686]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	Root	PMID[25597012]
NPO24821	Nidorella resedifolia	Species	Asteraceae	Eukaryota		UNPD*
NPO16885	Phonus arborescens	Species	Asteraceae	Eukaryota		UNPD*
NPO24735	Cupania latifolia	Species	Sapindaceae	Eukaryota		UNPD*
NPO18762	Ilex microdonta	Species	Aquifoliaceae	Eukaryota		UNPD*
NPO25468	Tabernaemontana amygdalifolia	Species	Apocynaceae	Eukaryota		UNPD*
NPO20584	Cheilanthes fragrans	Species	Pteridaceae	Eukaryota		UNPD*
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota		UNPD*
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota		UNPD*
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota		UNPD*
NPO25557	Alternaria porri	Species	Pleosporaceae	Eukaryota		UNPD*
NPO10407	Petromyzon marinus	Species	Petromyzontidae	Eukaryota		UNPD*
NPO19082	Creolophus cirrhatus	Species	Hericiaceae	Eukaryota		UNPD*
NPO25410	Manilkara bidentata	Species	Sapotaceae	Eukaryota		UNPD*
NPO24866	Smilax aspera	Species	Smilacaceae	Eukaryota		UNPD*
NPO22637	Kunzea ambigua	Species	Myrtaceae	Eukaryota		UNPD*

Biological Activity

Activity Type	# Activity
GI50	58
IC50	7
Others	10
Potency	44

Activity Type	# Activity
Cell Line	63
Individual Protein	36
Organism	2
Others	18

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	20000	nM	11720850
NPT111	Cell Line	K562	Homo sapiens	Activity	=	28	%	18293907
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	1.7	ug/ml	12444686
NPT2	Others	Unspecified		IC50	>	20000	nM	19883086
NPT2	Others	Unspecified		IC50	=	8	ug/ml	19716299
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT1038	Individual Protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	10000	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	31622.8	nM	PubChem BioAssay data set
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	3300	nM	21112783
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency		31622.8	nM	PubChem BioAssay data set
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency		22387.2	nM	PubChem BioAssay data set
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency		14125.4	nM	PubChem BioAssay data set
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency		20587.8	nM	PubChem BioAssay data set
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency		14125.4	nM	PubChem BioAssay data set
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency		63095.7	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency		18526	nM	PubChem BioAssay data set
NPT65	Cell Line	HepG2	Homo sapiens	Potency		10000	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		8912.5	nM	PubChem BioAssay data set
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency		28183.8	nM	PubChem BioAssay data set
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency		10691	nM	PubChem BioAssay data set
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency		56234.1	nM	PubChem BioAssay data set
NPT367	Cell Line	MDA-N	Homo sapiens	GI50		3784.43	nM	PubChem BioAssay data set
NPT368	Cell Line	SN12C	Homo sapiens	GI50		3288.52	nM	PubChem BioAssay data set
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50		5970.35	nM	PubChem BioAssay data set
NPT369	Cell Line	ACHN	Homo sapiens	GI50		8729.71	nM	PubChem BioAssay data set
NPT371	Cell Line	UO-31	Homo sapiens	GI50		5834.45	nM	PubChem BioAssay data set
NPT372	Cell Line	HOP-92	Homo sapiens	GI50		3723.92	nM	PubChem BioAssay data set
NPT90	Cell Line	DU-145	Homo sapiens	GI50		7726.81	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		1207.81	nM	PubChem BioAssay data set
NPT374	Cell Line	SF-539	Homo sapiens	GI50		3784.43	nM	PubChem BioAssay data set
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50		9268.3	nM	PubChem BioAssay data set
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50		4613.18	nM	PubChem BioAssay data set
NPT376	Cell Line	A498	Homo sapiens	GI50		4425.88	nM	PubChem BioAssay data set
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50		7095.78	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		5370.32	nM	PubChem BioAssay data set
NPT379	Cell Line	HOP-62	Homo sapiens	GI50		12022.64	nM	PubChem BioAssay data set
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50		3801.89	nM	PubChem BioAssay data set
NPT380	Cell Line	U-251	Homo sapiens	GI50		4602.57	nM	PubChem BioAssay data set
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50		3639.15	nM	PubChem BioAssay data set
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50		23878.11	nM	PubChem BioAssay data set
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50		7638.36	nM	PubChem BioAssay data set
NPT383	Cell Line	SNB-19	Homo sapiens	GI50		3467.37	nM	PubChem BioAssay data set
NPT385	Cell Line	SR	Homo sapiens	GI50		1849.27	nM	PubChem BioAssay data set
NPT384	Cell Line	TK-10	Homo sapiens	GI50		6546.36	nM	PubChem BioAssay data set
NPT323	Cell Line	SW-620	Homo sapiens	GI50		3845.92	nM	PubChem BioAssay data set
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50		2421.03	nM	PubChem BioAssay data set
NPT386	Cell Line	KM12	Homo sapiens	GI50		3515.6	nM	PubChem BioAssay data set
NPT387	Cell Line	M14	Homo sapiens	GI50		7943.28	nM	PubChem BioAssay data set
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50		5164.16	nM	PubChem BioAssay data set
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50		3854.78	nM	PubChem BioAssay data set
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50		7998.34	nM	PubChem BioAssay data set
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50		2290.87	nM	PubChem BioAssay data set
NPT457	Cell Line	BT-549	Homo sapiens	GI50		4466.84	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		4623.81	nM	PubChem BioAssay data set
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50		2971.67	nM	PubChem BioAssay data set
NPT81	Cell Line	A549	Homo sapiens	GI50		10327.61	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		4508.17	nM	PubChem BioAssay data set
NPT393	Cell Line	HCT-116	Homo sapiens	GI50		5636.38	nM	PubChem BioAssay data set
NPT395	Cell Line	SF-268	Homo sapiens	GI50		4977.37	nM	PubChem BioAssay data set
NPT394	Cell Line	EKVX	Homo sapiens	GI50		10399.2	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50		6095.37	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	GI50		7798.3	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		11614.49	nM	PubChem BioAssay data set
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency		22387.2	nM	PubChem BioAssay data set
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency		10000	nM	PubChem BioAssay data set
NPT396	Cell Line	T47D	Homo sapiens	GI50		6823.39	nM	PubChem BioAssay data set
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50		3539.97	nM	PubChem BioAssay data set
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50		5284.45	nM	PubChem BioAssay data set
NPT398	Cell Line	UACC-62	Homo sapiens	GI50		4140	nM	PubChem BioAssay data set
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50		4709.77	nM	PubChem BioAssay data set
NPT399	Cell Line	SF-295	Homo sapiens	GI50		13031.67	nM	PubChem BioAssay data set
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50		4528.98	nM	PubChem BioAssay data set
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50		3198.9	nM	PubChem BioAssay data set
NPT401	Cell Line	786-0	Homo sapiens	GI50		4623.81	nM	PubChem BioAssay data set
NPT403	Cell Line	UACC-257	Homo sapiens	GI50		10789.47	nM	PubChem BioAssay data set
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50		2269.86	nM	PubChem BioAssay data set
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50		4149.54	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		7655.97	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		3341.95	nM	PubChem BioAssay data set
NPT406	Cell Line	RXF 393	Homo sapiens	GI50		12502.59	nM	PubChem BioAssay data set
NPT407	Cell Line	COLO 205	Homo sapiens	GI50		14521.12	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	101	%	22239485
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	191	%	22239485
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Inhibition	=	67.9	%	22449016
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Inhibition	=	60.4	%	22449016
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		14125.4	nM	PubChem BioAssay data set
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency		35481.3	nM	PubChem BioAssay data set
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency		25118.9	nM	PubChem BioAssay data set
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	27.15	%	23062825
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	4.56	%	23062825
NPT2	Others	Unspecified		Potency		18356.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		25929	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		14581	nM	PubChem BioAssay data set
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency		29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	1220000	nM	23567958
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	141.41	%	23571415
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	125.2	%	23571415
NPT2	Others	Unspecified		Potency		12589.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		22387.2	nM	PubChem BioAssay data set
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency		50118.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		11220.2	nM	PubChem BioAssay data set
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency		19952.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	4.9	ug/ml	25137491
NPT2	Others	Unspecified		IC50	=	7700	nM	25597012

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 NPC188646 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	222
0.1-0.2	1150
0.2-0.3	2523
0.3-0.4	6320
0.4-0.5	6800
0.5-0.6	2400
0.6-0.7	4448
0.7-0.8	4141
0.8-0.85	1501
0.85-0.9	881
0.9-0.95	419
0.95-1	84

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263670
1.0	High Similarity	NPC56031
1.0	High Similarity	NPC175098
1.0	High Similarity	NPC242294
1.0	High Similarity	NPC337373
1.0	High Similarity	NPC139813
1.0	High Similarity	NPC312318
1.0	High Similarity	NPC472365
1.0	High Similarity	NPC192304
0.9922	High Similarity	NPC286336
0.9921	High Similarity	NPC257756
0.9921	High Similarity	NPC212631
0.9921	High Similarity	NPC205468
0.9921	High Similarity	NPC87231
0.9921	High Similarity	NPC129132
0.9844	High Similarity	NPC18877
0.9844	High Similarity	NPC20560
0.9844	High Similarity	NPC159623
0.9844	High Similarity	NPC144051
0.9844	High Similarity	NPC28753
0.9844	High Similarity	NPC294593
0.9844	High Similarity	NPC204960
0.9844	High Similarity	NPC82225
0.9843	High Similarity	NPC64359
0.9843	High Similarity	NPC308037
0.9843	High Similarity	NPC262359
0.9769	High Similarity	NPC168105
0.9769	High Similarity	NPC477242
0.9769	High Similarity	NPC66349
0.9769	High Similarity	NPC472367
0.9769	High Similarity	NPC476333
0.9769	High Similarity	NPC473391
0.9769	High Similarity	NPC98115
0.9769	High Similarity	NPC472364
0.9769	High Similarity	NPC150399
0.9769	High Similarity	NPC249606
0.9769	High Similarity	NPC12165
0.9769	High Similarity	NPC186838
0.9769	High Similarity	NPC41461
0.9769	High Similarity	NPC25287
0.9769	High Similarity	NPC477243
0.9769	High Similarity	NPC1486
0.9769	High Similarity	NPC274109
0.9769	High Similarity	NPC477244
0.9695	High Similarity	NPC472419
0.9695	High Similarity	NPC153979
0.9695	High Similarity	NPC188879
0.9695	High Similarity	NPC317119
0.9692	High Similarity	NPC131039
0.9692	High Similarity	NPC13575
0.9692	High Similarity	NPC156092
0.9688	High Similarity	NPC475008
0.9688	High Similarity	NPC309717
0.9688	High Similarity	NPC186097
0.9688	High Similarity	NPC128348
0.9688	High Similarity	NPC313618
0.9688	High Similarity	NPC66384
0.9688	High Similarity	NPC112192
0.9688	High Similarity	NPC164236
0.9688	High Similarity	NPC189106
0.9688	High Similarity	NPC475009
0.9685	High Similarity	NPC247779
0.9621	High Similarity	NPC21350
0.9621	High Similarity	NPC124269
0.9621	High Similarity	NPC472368
0.9618	High Similarity	NPC240593
0.9618	High Similarity	NPC213603
0.9615	High Similarity	NPC103842
0.9606	High Similarity	NPC211120
0.9549	High Similarity	NPC470211
0.9549	High Similarity	NPC472366
0.9549	High Similarity	NPC477956
0.9545	High Similarity	NPC266597
0.9545	High Similarity	NPC116632
0.9545	High Similarity	NPC303644
0.9545	High Similarity	NPC162680
0.9545	High Similarity	NPC7013
0.9545	High Similarity	NPC209560
0.9545	High Similarity	NPC250266
0.9545	High Similarity	NPC181124
0.9545	High Similarity	NPC294409
0.9538	High Similarity	NPC27643
0.9528	High Similarity	NPC80694
0.9528	High Similarity	NPC186098
0.9478	High Similarity	NPC172250
0.9478	High Similarity	NPC215311
0.9478	High Similarity	NPC213659
0.9478	High Similarity	NPC48624
0.9478	High Similarity	NPC11056
0.9478	High Similarity	NPC259166
0.9478	High Similarity	NPC219917
0.9478	High Similarity	NPC326109
0.9478	High Similarity	NPC204985
0.9478	High Similarity	NPC144118
0.9478	High Similarity	NPC80962
0.9474	High Similarity	NPC471620
0.9474	High Similarity	NPC90665
0.9474	High Similarity	NPC251681
0.9474	High Similarity	NPC279668
0.9474	High Similarity	NPC278323
0.9474	High Similarity	NPC99333
0.9474	High Similarity	NPC309154
0.9474	High Similarity	NPC243528
0.9474	High Similarity	NPC55162
0.9474	High Similarity	NPC12175
0.9474	High Similarity	NPC188947
0.9474	High Similarity	NPC280284
0.947	High Similarity	NPC473887
0.947	High Similarity	NPC231772
0.947	High Similarity	NPC29353
0.947	High Similarity	NPC124784
0.947	High Similarity	NPC127447
0.947	High Similarity	NPC13408
0.947	High Similarity	NPC194281
0.947	High Similarity	NPC234133
0.947	High Similarity	NPC47815
0.9449	High Similarity	NPC305518
0.9449	High Similarity	NPC128428
0.9407	High Similarity	NPC55832
0.9407	High Similarity	NPC26051
0.9407	High Similarity	NPC268204
0.9407	High Similarity	NPC469404
0.9407	High Similarity	NPC470087
0.9407	High Similarity	NPC470089
0.9407	High Similarity	NPC321980
0.9407	High Similarity	NPC52789
0.9407	High Similarity	NPC110969
0.9407	High Similarity	NPC49108
0.9403	High Similarity	NPC109232
0.9403	High Similarity	NPC283429
0.9403	High Similarity	NPC295384
0.9398	High Similarity	NPC290291
0.9398	High Similarity	NPC275055
0.9394	High Similarity	NPC39426
0.9394	High Similarity	NPC234560
0.938	High Similarity	NPC185497
0.9338	High Similarity	NPC11561
0.9338	High Similarity	NPC471417
0.9338	High Similarity	NPC119663
0.9338	High Similarity	NPC226636
0.9333	High Similarity	NPC129853
0.9333	High Similarity	NPC253822
0.9333	High Similarity	NPC188243
0.9333	High Similarity	NPC110228
0.9333	High Similarity	NPC6407
0.9333	High Similarity	NPC76445
0.9333	High Similarity	NPC159275
0.9333	High Similarity	NPC69769
0.9333	High Similarity	NPC269652
0.9333	High Similarity	NPC172986
0.9333	High Similarity	NPC270883
0.9333	High Similarity	NPC241100
0.9333	High Similarity	NPC101366
0.9333	High Similarity	NPC265178
0.9333	High Similarity	NPC284550
0.9333	High Similarity	NPC281207
0.9333	High Similarity	NPC261227
0.9323	High Similarity	NPC24394
0.9323	High Similarity	NPC87545
0.9323	High Similarity	NPC235428
0.9318	High Similarity	NPC172262
0.9318	High Similarity	NPC164136
0.9313	High Similarity	NPC15834
0.9313	High Similarity	NPC203817
0.9313	High Similarity	NPC215875
0.9313	High Similarity	NPC10971
0.9302	High Similarity	NPC69235
0.9302	High Similarity	NPC212379
0.9302	High Similarity	NPC60558
0.9291	High Similarity	NPC65041
0.927	High Similarity	NPC149026
0.927	High Similarity	NPC18585
0.927	High Similarity	NPC475705
0.927	High Similarity	NPC117836
0.927	High Similarity	NPC301751
0.927	High Similarity	NPC166138
0.927	High Similarity	NPC175504
0.927	High Similarity	NPC91560
0.927	High Similarity	NPC39329
0.927	High Similarity	NPC75049
0.927	High Similarity	NPC106985
0.927	High Similarity	NPC143896
0.927	High Similarity	NPC257097
0.927	High Similarity	NPC245482
0.927	High Similarity	NPC169591
0.927	High Similarity	NPC51887
0.927	High Similarity	NPC68104
0.927	High Similarity	NPC150408
0.927	High Similarity	NPC310130
0.927	High Similarity	NPC164980
0.927	High Similarity	NPC476178
0.927	High Similarity	NPC221432
0.9265	High Similarity	NPC126534
0.9265	High Similarity	NPC90582
0.9265	High Similarity	NPC3188
0.9265	High Similarity	NPC262094
0.9265	High Similarity	NPC147688
0.9265	High Similarity	NPC232021
0.9265	High Similarity	NPC64908
0.9265	High Similarity	NPC26238

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC188646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	936
0.2-0.3	1316
0.3-0.4	2389
0.4-0.5	2192
0.5-0.6	1352
0.6-0.7	512
0.7-0.8	156
0.8-0.85	39
0.85-0.9	16
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9688	High Similarity	NPD1240	Approved
0.9538	High Similarity	NPD1607	Approved
0.9394	High Similarity	NPD1510	Phase 2
0.9185	High Similarity	NPD1549	Phase 2
0.9111	High Similarity	NPD1550	Clinical (unspecified phase)
0.9111	High Similarity	NPD1552	Clinical (unspecified phase)
0.9065	High Similarity	NPD4378	Clinical (unspecified phase)
0.8929	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD2796	Approved
0.8857	High Similarity	NPD6799	Approved
0.875	High Similarity	NPD4380	Phase 2
0.869	High Similarity	NPD7411	Suspended
0.8633	High Similarity	NPD970	Clinical (unspecified phase)
0.8592	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD3882	Suspended
0.8571	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD2393	Clinical (unspecified phase)
0.854	High Similarity	NPD6651	Approved
0.8523	High Similarity	NPD7075	Discontinued
0.8519	High Similarity	NPD6859	Clinical (unspecified phase)
0.8514	High Similarity	NPD8443	Clinical (unspecified phase)
0.8511	High Similarity	NPD1878	Clinical (unspecified phase)
0.8503	High Similarity	NPD1934	Approved
0.8493	Intermediate Similarity	NPD6599	Discontinued
0.8489	Intermediate Similarity	NPD1551	Phase 2
0.8489	Intermediate Similarity	NPD2935	Discontinued
0.8472	Intermediate Similarity	NPD1512	Approved
0.8446	Intermediate Similarity	NPD7819	Suspended
0.8446	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD3750	Approved
0.8378	Intermediate Similarity	NPD6801	Discontinued
0.831	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1203	Approved
0.8261	Intermediate Similarity	NPD943	Approved
0.8212	Intermediate Similarity	NPD7768	Phase 2
0.8194	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD2654	Approved
0.8169	Intermediate Similarity	NPD2344	Approved
0.8163	Intermediate Similarity	NPD5403	Approved
0.8158	Intermediate Similarity	NPD3749	Approved
0.8146	Intermediate Similarity	NPD3817	Phase 2
0.8102	Intermediate Similarity	NPD6832	Phase 2
0.8088	Intermediate Similarity	NPD2798	Approved
0.8077	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6166	Phase 2
0.8077	Intermediate Similarity	NPD9493	Approved
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.806	Intermediate Similarity	NPD3972	Approved
0.806	Intermediate Similarity	NPD9717	Approved
0.8056	Intermediate Similarity	NPD1243	Approved
0.8028	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3748	Approved
0.8028	Intermediate Similarity	NPD2799	Discontinued
0.8027	Intermediate Similarity	NPD5401	Approved
0.8027	Intermediate Similarity	NPD2532	Approved
0.8027	Intermediate Similarity	NPD2534	Approved
0.8027	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7955	Intermediate Similarity	NPD9545	Approved
0.7945	Intermediate Similarity	NPD2309	Approved
0.7937	Intermediate Similarity	NPD5953	Discontinued
0.7925	Intermediate Similarity	NPD7286	Phase 2
0.7925	Intermediate Similarity	NPD7054	Approved
0.7925	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD920	Approved
0.7891	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4628	Phase 3
0.7875	Intermediate Similarity	NPD7074	Phase 3
0.7875	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD422	Phase 1
0.7852	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6797	Phase 2
0.7821	Intermediate Similarity	NPD5494	Approved
0.782	Intermediate Similarity	NPD1548	Phase 1
0.78	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.773	Intermediate Similarity	NPD7808	Phase 3
0.773	Intermediate Similarity	NPD3268	Approved
0.773	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2313	Discontinued
0.7724	Intermediate Similarity	NPD6100	Approved
0.7724	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD7390	Discontinued
0.7714	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD230	Phase 1
0.7673	Intermediate Similarity	NPD3926	Phase 2
0.7669	Intermediate Similarity	NPD6559	Discontinued
0.7655	Intermediate Similarity	NPD7033	Discontinued
0.7655	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2797	Approved
0.7622	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1610	Phase 2
0.7582	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD1241	Discontinued
0.7569	Intermediate Similarity	NPD1933	Approved
0.7569	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3225	Approved
0.7554	Intermediate Similarity	NPD1876	Approved
0.7534	Intermediate Similarity	NPD4308	Phase 3
0.7532	Intermediate Similarity	NPD919	Approved
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD1164	Approved
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7482	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7464	Intermediate Similarity	NPD1201	Approved
0.7462	Intermediate Similarity	NPD9266	Approved
0.7462	Intermediate Similarity	NPD74	Approved
0.7448	Intermediate Similarity	NPD447	Suspended
0.7447	Intermediate Similarity	NPD1019	Discontinued
0.7439	Intermediate Similarity	NPD1729	Discontinued
0.7438	Intermediate Similarity	NPD1247	Approved
0.7432	Intermediate Similarity	NPD2346	Discontinued
0.7413	Intermediate Similarity	NPD3027	Phase 3
0.741	Intermediate Similarity	NPD1608	Approved
0.74	Intermediate Similarity	NPD7003	Approved
0.7394	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD9494	Approved
0.7391	Intermediate Similarity	NPD5711	Approved
0.7391	Intermediate Similarity	NPD5710	Approved
0.7389	Intermediate Similarity	NPD1465	Phase 2
0.7385	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD9263	Approved
0.7385	Intermediate Similarity	NPD9264	Approved
0.7385	Intermediate Similarity	NPD9267	Approved
0.7376	Intermediate Similarity	NPD3267	Approved
0.7376	Intermediate Similarity	NPD3266	Approved
0.7372	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5408	Approved
0.7365	Intermediate Similarity	NPD5404	Approved
0.7365	Intermediate Similarity	NPD5405	Approved
0.7365	Intermediate Similarity	NPD5406	Approved
0.7361	Intermediate Similarity	NPD1296	Phase 2
0.7349	Intermediate Similarity	NPD6104	Discontinued
0.7342	Intermediate Similarity	NPD4288	Approved
0.7342	Intermediate Similarity	NPD2296	Approved
0.7299	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1481	Phase 2
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7279	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD940	Approved
0.7266	Intermediate Similarity	NPD3847	Discontinued
0.7261	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3140	Approved
0.726	Intermediate Similarity	NPD4307	Phase 2
0.726	Intermediate Similarity	NPD3142	Approved
0.7241	Intermediate Similarity	NPD4361	Phase 2
0.7241	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6798	Discontinued
0.7237	Intermediate Similarity	NPD2354	Approved
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1535	Discovery
0.7211	Intermediate Similarity	NPD5124	Phase 1
0.7211	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4662	Approved
0.7208	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4661	Approved
0.72	Intermediate Similarity	NPD1471	Phase 3
0.7195	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD17	Approved
0.7174	Intermediate Similarity	NPD1894	Discontinued
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7168	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9269	Phase 2
0.7153	Intermediate Similarity	NPD3018	Phase 2
0.7153	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD6971	Discontinued
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7132	Intermediate Similarity	NPD9281	Approved
0.7124	Intermediate Similarity	NPD3887	Approved
0.7122	Intermediate Similarity	NPD9268	Approved
0.7122	Intermediate Similarity	NPD1651	Approved
0.7113	Intermediate Similarity	NPD4749	Approved
0.7108	Intermediate Similarity	NPD3751	Discontinued
0.7107	Intermediate Similarity	NPD6844	Discontinued
0.7107	Intermediate Similarity	NPD6280	Approved
0.7107	Intermediate Similarity	NPD6279	Approved
0.7103	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6355	Discontinued
0.7091	Intermediate Similarity	NPD2403	Approved
0.7086	Intermediate Similarity	NPD2355	Clinical (unspecified phase)

Structure

CID188646 OpenBabel06191715572D 21 22 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 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 5.1962 -0.0000 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 4.3301 -0.5000 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 2.5981 -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 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 -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 0.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5356121
ChEMBL	CHEMBL104255
ZINC

Physicochemical Properties

Molecular Weight:	284.10
ALogP:	-0.4666
MLogP:	2.89
XLogP:	4.857
# Rotatable Bonds:	8
Polar Surface Area:	55.76
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	21

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