NPASS Natural Product

Natural Product: NPC209364

Natural Product ID:	NPC209364
Common Name:	Gedunin
IUPAC Name:
Synonyms:	Gedunin
Molecular Formula:	C28H34O7
Standard InCHIKey:	YJXDGWUNRYLINJ-BHAPSIHVSA-N
Standard InCHI:	InChI=1S/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
Canonical SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@@]2([C@@H]2[C@]1(C)[C@@]13O[C@@H]1C(=O)O[C@H]([C@@]3(CC2)C)c1ccoc1)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO13287	Cedrela odorata	Species	Meliaceae	Eukaryota	xylem	PMID[9134742]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota		HerDing*
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	bark	PMID[17450509]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	Seeds	PMID[10661881]
NPO29947	Cedrela sinensis	Species	Meliaceae	Eukaryota	cortex	PMID[16989525]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruit	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	bark	PMID[9134742]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota		HerDing*
NPO1469	Cyperus compressus	Species	Cyperaceae	Eukaryota		UNPD*
NPO8937	Ferreirea spectabilis	NA	NA	NA		UNPD*
NPO7417	Pieris melete	Species	Pieridae	Eukaryota		UNPD*
NPO10266	Alaria nana	Species	Alariaceae	Eukaryota		UNPD*
NPO9736	Artemisia arctica	Species	Asteraceae	Eukaryota		UNPD*
NPO4899	Streptomyces fungicidicus	Species	Streptomycetaceae	Bacteria		UNPD*
NPO29699	Meliae cortex	NA	NA	NA		TCMSP*
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota		TCMID*
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota		TCMID*
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota		PMID[9134742]
NPO29947	Cedrela sinensis	Species	Meliaceae	Eukaryota		PMID[16989525]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	PMID[21381696]
NPO32938	cedrela spp.	Species	Meliaceae	Eukaryota		PMID[10820113]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota		PMID[18816111]

Biological Activity

Activity Type	# Activity
AC50	2
EC50	3
IC50	20
LD50	1
Others	88
Potency	28

Activity Type	# Activity
Cell Line	13
Individual Protein	19
Organism	96
Others	12
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.8	ug/ml	9134742
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.72	ug/ml	9134742
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.039	ug/ml	9134742
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.02	ug/ml	9134742
NPT91	Cell Line	KB	Homo sapiens	Activity	=	32	%	9134742
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.3	ug/ml	9134742
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8840	nM	18816111
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	3220	nM	18816111
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1000	nM	2607354
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	300	nM	2607354
NPT168	Cell Line	P388	Mus musculus	IC50	=	3.3	ug/ml	16989525
NPT519	Cell Line	SH-SY5Y	Homo sapiens	EC50	=	38.95	nM	19138859
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1660	nM	20669933
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1310	nM	20669933
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	26121.6	nM	PubChem BioAssay data set
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	10000	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	22230	nM	PubChem BioAssay data set
NPT1416	Individual Protein	Neuropeptide S receptor	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		29092.9	nM	PubChem BioAssay data set
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency		20596.2	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5900	nM	21381696
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	8300	nM	21381696
NPT2	Others	Unspecified		IC50	=	16900	nM	21381696
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000	nM	21381696
NPT2	Others	Unspecified		IC50	>	20000	nM	21381696
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency		3294.4	nM	PubChem BioAssay data set
NPT2866	Individual Protein	Replicative DNA helicase	Mycobacterium tuberculosis	AC50	=	4566	nM	PubChem BioAssay data set
NPT2867	Individual Protein	Protein RecA	Mycobacterium tuberculosis	EC50	=	16100	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		31622.8	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency		1651.1	nM	PubChem BioAssay data set
NPT2866	Individual Protein	Replicative DNA helicase	Mycobacterium tuberculosis	AC50	=	44530	nM	PubChem BioAssay data set
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency		251.2	nM	PubChem BioAssay data set
NPT71	Cell Line	HEK293	Homo sapiens	Potency		18356.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		2059.6	nM	PubChem BioAssay data set
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000	nM	22586124
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	=	760	nM	22586124
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		5173.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		22387.2	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		4109.5	nM	PubChem BioAssay data set
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency		31622.8	nM	PubChem BioAssay data set
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency		5623.4	nM	PubChem BioAssay data set
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	43.16	%	10.1016/j.cropro.2005.01.009
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	46.46	%	10.1016/j.cropro.2005.01.009
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	1.007	mg/kg/day	10.1016/j.cropro.2005.01.009
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	0.4707	mg/kg/day	10.1016/j.cropro.2005.01.009
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	2.357	mg/kg/day	10.1016/j.cropro.2005.01.009
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	5	ug	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	6.8	ug	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	10.5	ug	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	11	ug	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	9	ug	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	8.5	ug	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	13.3	%	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	23.3	%	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	49.3	%	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	39.3	%	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	51.3	%	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	82	%	10.1271/bbb.56.1835
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	80	%	10.1271/bbb.56.1835
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Ratio	=	0.11		10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Ratio	=	0.55		10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Ratio	=	0.71		10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	13	%	10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0	%	10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	15	%	10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	41.7	%	10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	54.2	%	10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	1.35	%	10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.05	%	10.1016/j.indcrop.2012.05.014
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LC50	=	11.93	ug/ml	10.1016/j.indcrop.2012.05.014
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	30	%	10.1016/j.indcrop.2012.12.038
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LC50	=	11.93	ug/ml	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Inhibition	=	0	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	LD50	=	10.78	ug/ml	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	14.1	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	54.7	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	11.6	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.05	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	20	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	16.7	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	32.5	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.3	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	1.9	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	7.1	%	10.1016/j.indcrop.2012.12.038
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	4.17	%	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	16.7	%	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	17.9	%	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	20.8	%	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.052	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	122.4	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	147.9	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.1	mm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2	mm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.6	mm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.9	mm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.2	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.8	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.45	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.61	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	4.95	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	16.12	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	LC50	=	39	ppm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.2	cm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.25	cm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.3	cm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.35	cm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.4	cm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.5	cm	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	1.9	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.3	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.4	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.6	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	4.9	ug	10820113
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	6.12	ug	10820113
NPT2	Others	Unspecified		Potency		20596.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		29092.9	nM	PubChem BioAssay data set
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency		10322.5	nM	PubChem BioAssay data set
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	65.45	%	23571415
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	105.39	%	23571415
NPT2	Others	Unspecified		Potency		7943.3	nM	PubChem BioAssay data set
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency		44668.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		10000	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		15848.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		EC50		895	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	10900	nM	25756299

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 NPC209364 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	285
0.1-0.2	1138
0.2-0.3	2114
0.3-0.4	4133
0.4-0.5	6857
0.5-0.6	7458
0.6-0.7	6489
0.7-0.8	2059
0.8-0.85	174
0.85-0.9	97
0.9-0.95	72
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC286722
0.9866	High Similarity	NPC473473
0.9866	High Similarity	NPC475295
0.9865	High Similarity	NPC107646
0.9735	High Similarity	NPC5079
0.9732	High Similarity	NPC60973
0.9671	High Similarity	NPC234660
0.9671	High Similarity	NPC51568
0.9669	High Similarity	NPC475381
0.9605	High Similarity	NPC470939
0.96	High Similarity	NPC126723
0.9539	High Similarity	NPC335761
0.9536	High Similarity	NPC472283
0.9484	High Similarity	NPC473766
0.9484	High Similarity	NPC473753
0.9474	High Similarity	NPC237155
0.947	High Similarity	NPC263265
0.9416	High Similarity	NPC39986
0.9416	High Similarity	NPC469846
0.9416	High Similarity	NPC134254
0.9416	High Similarity	NPC302369
0.9412	High Similarity	NPC25255
0.9412	High Similarity	NPC305016
0.9412	High Similarity	NPC472653
0.9404	High Similarity	NPC469850
0.9363	High Similarity	NPC302392
0.9359	High Similarity	NPC173516
0.9355	High Similarity	NPC476856
0.9355	High Similarity	NPC476857
0.9355	High Similarity	NPC476858
0.9351	High Similarity	NPC290400
0.9351	High Similarity	NPC193798
0.9351	High Similarity	NPC96443
0.9299	High Similarity	NPC471397
0.929	High Similarity	NPC292389
0.929	High Similarity	NPC469338
0.9272	High Similarity	NPC476201
0.9267	High Similarity	NPC196864
0.9267	High Similarity	NPC159927
0.9267	High Similarity	NPC469335
0.9267	High Similarity	NPC477404
0.9252	High Similarity	NPC86935
0.9236	High Similarity	NPC472282
0.9236	High Similarity	NPC476853
0.9236	High Similarity	NPC476850
0.9236	High Similarity	NPC476861
0.9231	High Similarity	NPC476860
0.9231	High Similarity	NPC469849
0.9231	High Similarity	NPC123088
0.9231	High Similarity	NPC276551
0.9231	High Similarity	NPC470940
0.9226	High Similarity	NPC117986
0.9226	High Similarity	NPC82851
0.9226	High Similarity	NPC69028
0.9226	High Similarity	NPC149896
0.9221	High Similarity	NPC477403
0.9221	High Similarity	NPC473368
0.9205	High Similarity	NPC18135
0.9177	High Similarity	NPC271235
0.9177	High Similarity	NPC160651
0.9172	High Similarity	NPC470875
0.9172	High Similarity	NPC23387
0.9167	High Similarity	NPC476197
0.9167	High Similarity	NPC477405
0.9156	High Similarity	NPC249021
0.9156	High Similarity	NPC187149
0.915	High Similarity	NPC44675
0.915	High Similarity	NPC214541
0.915	High Similarity	NPC476262
0.9139	High Similarity	NPC476122
0.9139	High Similarity	NPC46551
0.9114	High Similarity	NPC472651
0.9103	High Similarity	NPC18347
0.9103	High Similarity	NPC197596
0.9085	High Similarity	NPC178932
0.9067	High Similarity	NPC221809
0.9057	High Similarity	NPC472652
0.9038	High Similarity	NPC477402
0.9038	High Similarity	NPC191828
0.9032	High Similarity	NPC167142
0.9032	High Similarity	NPC261597
0.9032	High Similarity	NPC299038
0.9026	High Similarity	NPC469336
0.902	High Similarity	NPC469503
0.9	High Similarity	NPC262198
0.8987	High Similarity	NPC271657
0.8981	High Similarity	NPC329938
0.8981	High Similarity	NPC263432
0.8974	High Similarity	NPC307383
0.8974	High Similarity	NPC475967
0.8961	High Similarity	NPC282445
0.8961	High Similarity	NPC30222
0.8961	High Similarity	NPC57998
0.894	High Similarity	NPC470941
0.891	High Similarity	NPC45101
0.891	High Similarity	NPC36655
0.8903	High Similarity	NPC264943
0.8903	High Similarity	NPC35000
0.8896	High Similarity	NPC44577
0.8882	High Similarity	NPC470995
0.8875	High Similarity	NPC472775
0.8875	High Similarity	NPC472774
0.8868	High Similarity	NPC470182
0.8867	High Similarity	NPC142113
0.8861	High Similarity	NPC472771
0.8861	High Similarity	NPC200782
0.8846	High Similarity	NPC469485
0.8844	High Similarity	NPC476943
0.8827	High Similarity	NPC160818
0.8827	High Similarity	NPC169299
0.882	High Similarity	NPC327922
0.8812	High Similarity	NPC478178
0.8812	High Similarity	NPC475779
0.8805	High Similarity	NPC472773
0.8805	High Similarity	NPC224394
0.8805	High Similarity	NPC663
0.879	High Similarity	NPC472772
0.879	High Similarity	NPC173544
0.8782	High Similarity	NPC281258
0.878	High Similarity	NPC262386
0.8776	High Similarity	NPC310830
0.8774	High Similarity	NPC75906
0.8773	High Similarity	NPC469848
0.8766	High Similarity	NPC156189
0.8765	High Similarity	NPC82602
0.8758	High Similarity	NPC19747
0.8742	High Similarity	NPC211777
0.8742	High Similarity	NPC472668
0.8742	High Similarity	NPC207978
0.8734	High Similarity	NPC474932
0.872	High Similarity	NPC236004
0.8716	High Similarity	NPC220094
0.8712	High Similarity	NPC159232
0.8701	High Similarity	NPC471001
0.8693	High Similarity	NPC255414
0.8688	High Similarity	NPC472669
0.8688	High Similarity	NPC198047
0.8675	High Similarity	NPC223415
0.8667	High Similarity	NPC167340
0.8654	High Similarity	NPC268905
0.8642	High Similarity	NPC476224
0.8642	High Similarity	NPC478179
0.8627	High Similarity	NPC346
0.8625	High Similarity	NPC188649
0.8625	High Similarity	NPC471167
0.8625	High Similarity	NPC6326
0.8625	High Similarity	NPC471166
0.8618	High Similarity	NPC476944
0.8616	High Similarity	NPC474611
0.8616	High Similarity	NPC262872
0.8614	High Similarity	NPC478177
0.8609	High Similarity	NPC121158
0.8606	High Similarity	NPC94763
0.8589	High Similarity	NPC296558
0.8581	High Similarity	NPC125182
0.8581	High Similarity	NPC195325
0.8581	High Similarity	NPC470790
0.8581	High Similarity	NPC69647
0.8581	High Similarity	NPC472654
0.8581	High Similarity	NPC470791
0.858	High Similarity	NPC93172
0.858	High Similarity	NPC97574
0.8571	High Similarity	NPC88841
0.8571	High Similarity	NPC419
0.8571	High Similarity	NPC250228
0.8571	High Similarity	NPC71821
0.8571	High Similarity	NPC165218
0.8571	High Similarity	NPC288602
0.8571	High Similarity	NPC471168
0.8562	High Similarity	NPC470789
0.8562	High Similarity	NPC41182
0.8553	High Similarity	NPC472776
0.8553	High Similarity	NPC243577
0.8553	High Similarity	NPC472777
0.8553	High Similarity	NPC472778
0.8553	High Similarity	NPC470741
0.8535	High Similarity	NPC246164
0.8528	High Similarity	NPC100333
0.8523	High Similarity	NPC310043
0.8519	High Similarity	NPC146991
0.8506	High Similarity	NPC470999
0.8506	High Similarity	NPC62799
0.8497	Intermediate Similarity	NPC251865
0.8497	Intermediate Similarity	NPC137295
0.8491	Intermediate Similarity	NPC204663
0.8487	Intermediate Similarity	NPC473152
0.8481	Intermediate Similarity	NPC114880
0.8477	Intermediate Similarity	NPC90296
0.8477	Intermediate Similarity	NPC56197
0.8471	Intermediate Similarity	NPC247563
0.8471	Intermediate Similarity	NPC116717
0.8471	Intermediate Similarity	NPC272590
0.8471	Intermediate Similarity	NPC242068
0.8466	Intermediate Similarity	NPC472141
0.8462	Intermediate Similarity	NPC211625
0.8457	Intermediate Similarity	NPC475039
0.8457	Intermediate Similarity	NPC476035
0.8457	Intermediate Similarity	NPC472139
0.8457	Intermediate Similarity	NPC14499
0.8456	Intermediate Similarity	NPC214572

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC209364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	940
0.2-0.3	1950
0.3-0.4	2682
0.4-0.5	1909
0.5-0.6	1016
0.6-0.7	330
0.7-0.8	43
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5760	Phase 2
0.8313	Intermediate Similarity	NPD5761	Phase 2
0.8198	Intermediate Similarity	NPD8434	Phase 2
0.7803	Intermediate Similarity	NPD6764	Approved
0.7803	Intermediate Similarity	NPD6765	Approved
0.7651	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6785	Approved
0.7627	Intermediate Similarity	NPD6784	Approved
0.7576	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD5494	Approved
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD920	Approved
0.7375	Intermediate Similarity	NPD1471	Phase 3
0.7337	Intermediate Similarity	NPD7819	Suspended
0.7317	Intermediate Similarity	NPD6799	Approved
0.7283	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD6801	Discontinued
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7228	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3749	Approved
0.7207	Intermediate Similarity	NPD6559	Discontinued
0.7193	Intermediate Similarity	NPD5402	Approved
0.7193	Intermediate Similarity	NPD3817	Phase 2
0.7175	Intermediate Similarity	NPD3751	Discontinued
0.7152	Intermediate Similarity	NPD7236	Approved
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8404	Phase 2
0.7099	Intermediate Similarity	NPD2796	Approved
0.7083	Intermediate Similarity	NPD5403	Approved
0.7079	Intermediate Similarity	NPD7799	Discontinued
0.7066	Intermediate Similarity	NPD5401	Approved
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4107	Approved
0.7052	Intermediate Similarity	NPD3882	Suspended
0.7045	Intermediate Similarity	NPD3787	Discontinued
0.7039	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5844	Phase 1
0.7037	Intermediate Similarity	NPD3748	Approved
0.703	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7411	Suspended
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1243	Approved
0.6964	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4380	Phase 2
0.6954	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2346	Discontinued
0.6941	Remote Similarity	NPD7239	Suspended
0.694	Remote Similarity	NPD8313	Approved
0.694	Remote Similarity	NPD8312	Approved
0.6936	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4482	Phase 3
0.6927	Remote Similarity	NPD7473	Discontinued
0.6923	Remote Similarity	NPD6273	Approved
0.6914	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8285	Discontinued
0.6901	Remote Similarity	NPD7458	Discontinued
0.6901	Remote Similarity	NPD3226	Approved
0.6893	Remote Similarity	NPD8127	Discontinued
0.6886	Remote Similarity	NPD3887	Approved
0.6885	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1934	Approved
0.6872	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6166	Phase 2
0.6872	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.6856	Remote Similarity	NPD7435	Discontinued
0.6855	Remote Similarity	NPD6832	Phase 2
0.6852	Remote Similarity	NPD6355	Discontinued
0.6831	Remote Similarity	NPD7251	Discontinued
0.6829	Remote Similarity	NPD2799	Discontinued
0.6826	Remote Similarity	NPD3750	Approved
0.6811	Remote Similarity	NPD8407	Phase 2
0.6807	Remote Similarity	NPD1549	Phase 2
0.6802	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6959	Discontinued
0.6796	Remote Similarity	NPD3818	Discontinued
0.6793	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD6099	Approved
0.6788	Remote Similarity	NPD6100	Approved
0.6784	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2403	Approved
0.6778	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6797	Phase 2
0.6776	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2800	Approved
0.6761	Remote Similarity	NPD7768	Phase 2
0.676	Remote Similarity	NPD6232	Discontinued
0.6747	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7685	Pre-registration
0.6739	Remote Similarity	NPD8368	Discontinued
0.6732	Remote Similarity	NPD7907	Approved
0.6728	Remote Similarity	NPD8032	Phase 2
0.6725	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7074	Phase 3
0.6716	Remote Similarity	NPD4111	Phase 1
0.6687	Remote Similarity	NPD1551	Phase 2
0.6685	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6808	Phase 2
0.665	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7874	Approved
0.6648	Remote Similarity	NPD2801	Approved
0.6647	Remote Similarity	NPD5763	Approved
0.6647	Remote Similarity	NPD2344	Approved
0.6647	Remote Similarity	NPD5762	Approved
0.6647	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2353	Approved
0.6646	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1933	Approved
0.6634	Remote Similarity	NPD4665	Approved
0.6633	Remote Similarity	NPD3057	Approved
0.663	Remote Similarity	NPD7472	Approved
0.663	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7033	Discontinued
0.6624	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5980	Discovery
0.6615	Remote Similarity	NPD6778	Approved
0.6615	Remote Similarity	NPD6780	Approved
0.6615	Remote Similarity	NPD6776	Approved
0.6615	Remote Similarity	NPD6782	Approved
0.6615	Remote Similarity	NPD6781	Approved
0.6615	Remote Similarity	NPD6777	Approved
0.6615	Remote Similarity	NPD6779	Approved
0.6607	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7095	Approved
0.6603	Remote Similarity	NPD17	Approved
0.6599	Remote Similarity	NPD7696	Phase 3
0.6599	Remote Similarity	NPD7697	Approved
0.6599	Remote Similarity	NPD7698	Approved
0.6591	Remote Similarity	NPD37	Approved
0.6587	Remote Similarity	NPD2935	Discontinued
0.6585	Remote Similarity	NPD4307	Phase 2
0.6582	Remote Similarity	NPD3972	Approved
0.6579	Remote Similarity	NPD8435	Approved
0.6575	Remote Similarity	NPD7229	Phase 3
0.6573	Remote Similarity	NPD7058	Phase 2
0.6573	Remote Similarity	NPD7057	Phase 3
0.6573	Remote Similarity	NPD4967	Phase 2
0.6573	Remote Similarity	NPD4966	Approved
0.6573	Remote Similarity	NPD4965	Approved
0.6566	Remote Similarity	NPD8320	Phase 1
0.6566	Remote Similarity	NPD7097	Phase 1
0.6566	Remote Similarity	NPD8319	Approved
0.6566	Remote Similarity	NPD7870	Phase 2
0.6566	Remote Similarity	NPD7871	Phase 2
0.6564	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6798	Discontinued
0.6562	Remote Similarity	NPD3266	Approved
0.6562	Remote Similarity	NPD3267	Approved
0.6561	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1465	Phase 2
0.6548	Remote Similarity	NPD3533	Approved
0.6548	Remote Similarity	NPD2972	Approved
0.6532	Remote Similarity	NPD1512	Approved
0.6531	Remote Similarity	NPD4580	Approved
0.6529	Remote Similarity	NPD7003	Approved
0.6527	Remote Similarity	NPD1510	Phase 2
0.6524	Remote Similarity	NPD6233	Phase 2
0.6522	Remote Similarity	NPD7228	Approved
0.6517	Remote Similarity	NPD5353	Approved
0.6517	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7497	Discontinued
0.6509	Remote Similarity	NPD2897	Discontinued
0.65	Remote Similarity	NPD6234	Discontinued
0.6497	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD8361	Approved
0.6492	Remote Similarity	NPD8360	Approved
0.6491	Remote Similarity	NPD2354	Approved
0.6491	Remote Similarity	NPD2309	Approved
0.6489	Remote Similarity	NPD2968	Approved
0.6489	Remote Similarity	NPD2971	Approved
0.6488	Remote Similarity	NPD2438	Suspended
0.6485	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5710	Approved
0.6484	Remote Similarity	NPD5711	Approved
0.6478	Remote Similarity	NPD1608	Approved
0.6468	Remote Similarity	NPD7701	Phase 2
0.6463	Remote Similarity	NPD3268	Approved
0.6463	Remote Similarity	NPD3764	Approved
0.6462	Remote Similarity	NPD2974	Approved
0.6462	Remote Similarity	NPD2973	Approved
0.6462	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD2975	Approved

Structure

CID209364 OpenBabel06191716002D 35 40 0 0 1 0 0 0 0 0999 V2000 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 -1.5941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -0.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9237 -1.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4816 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 -1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4359 -2.1487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 0.4878 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 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 32 1 0 0 0 0 15 29 2 0 0 0 0 15 33 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 6 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 6 0 0 0 19 24 1 0 0 0 0 19 30 2 0 0 0 0 20 27 1 1 0 0 0 20 33 1 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 35 1 0 0 0 0 23 31 2 0 0 0 0 23 34 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 1 0 0 0 27 28 1 1 0 0 0 28 35 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	12004512
ChEMBL	CHEMBL465226
ZINC

Physicochemical Properties

Molecular Weight:	482.23
ALogP:	1.1166
MLogP:	3.77
XLogP:	3.636
# Rotatable Bonds:	9
Polar Surface Area:	95.34
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	35

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