NPASS Natural Product

Natural Product: NPC91495

Natural Product ID:	NPC91495
Common Name:	Arachidonic Acid
IUPAC Name:	(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Synonyms:	Arachidonic Acid; Cis-5,8,11,14-Eicosatetraenoic Acid
Molecular Formula:	C20H32O2
Standard InCHIKey:	YZXBAPSDXZZRGB-DOFZRALJSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
Canonical SMILES:	CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO15983	Udotea cyathiformis	Species	Udoteaceae	Eukaryota		UNPD*
NPO14434	Alluaudia humbertii	Species	Didiereaceae	Eukaryota		UNPD*
NPO29621	Portulacae herba	NA	NA	NA		TCMSP*
NPO15428	Cheilanthes tenuifolia	Species	Pteridaceae	Eukaryota		UNPD*
NPO20404.1	Eruca vesicaria subsp. sativa	Subspecies	Brassicaceae	Eukaryota		UNPD*
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota		TCM_Taiwan*
NPO15674	Acanthosyris spinescens	Species	Cervantesiaceae	Eukaryota		UNPD*
NPO26988	Acinos thymoides	NA	NA	NA		UNPD*
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	urine	PMID[14643447]
NPO16740	Helipterum venustum	Species	Asteraceae	Eukaryota		UNPD*
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota		UNPD*
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	blood	PMID[20671299]
NPO16453	Lycium cestroides	Species	Solanaceae	Eukaryota		UNPD*
NPO14107	Teucrium montanum	Species	Lamiaceae	Eukaryota		UNPD*
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	cerebrospinal fluid	PMID[2835791]
NPO11982	Yucca faxoniana	Species	Asparagaceae	Eukaryota		UNPD*
NPO13264	Alstonia lanceolifera	Species	Apocynaceae	Eukaryota		UNPD*
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	saliva	PMID[22308371]
NPO12451	Dermocybe cinnabarina	Species	Cortinariaceae	Eukaryota		UNPD*
NPO10443	Sloanea zuliaensis	Species	Elaeocarpaceae	Eukaryota		UNPD*
NPO20338	Mus musculus	Species	Muridae	Eukaryota		PMID[25518943]
NPO14909	Artemisia caerulescens	Species	Asteraceae	Eukaryota		UNPD*
NPO13733	Saccharopolyspora erythraea	Species	Pseudonocardiaceae	Bacteria		UNPD*
NPO20338	Mus musculus	Species	Muridae	Eukaryota		PMID[19425150]
NPO26508	Uvariopsis tripetala	Species	Annonaceae	Eukaryota		UNPD*
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria		UNPD*
NPO30323	Daphnia galeata	Species	Daphniidae	Eukaryota		Freshwater Biology,1997,38:731-738
NPO12217	Buccinum undatum	Species	Buccinidae	Eukaryota		UNPD*
NPO7023	Tetracera rosiflora	Species	Dilleniaceae	Eukaryota		UNPD*
NPO11721	Litseae fructus	NA	NA	NA		TCMSP*
NPO14591	Rhabdodendron amazonicum	Species	Rhabdodendraceae	Eukaryota		UNPD*
NPO19018	Senecio provincialis	Species	Asteraceae	Eukaryota		UNPD*
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		TM-MC*
NPO16617	Paepalanthus hilairei	Species	Eriocaulaceae	Eukaryota		UNPD*
NPO12764	Tillandsia fragrans	Species	Bromeliaceae	Eukaryota		UNPD*
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota		TM-MC*
NPO25278	Cystofilobasidium infirmominiatum	Species	Cystofilobasidiaceae	Eukaryota		UNPD*
NPO11365	Lecidea lithophila	Species	Lecideaceae	Eukaryota		UNPD*
NPO13577	Pieris formosa	Species	Ericaceae	Eukaryota		UNPD*
NPO16206	Umbilicaria indica	Species	Umbilicariaceae	Eukaryota		UNPD*
NPO15879	Euphorbia nivulia	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO11762	Agrimonia eupatoria	Species	Rosaceae	Eukaryota		UNPD*
NPO12806	Bellendena montana	Species	Proteaceae	Eukaryota		UNPD*
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota		UNPD*
NPO13950	Goniothalamus donnaiensis	Species	Annonaceae	Eukaryota		UNPD*
NPO10877	Humboldtia laurifolia	Species	Fabaceae	Eukaryota		UNPD*
NPO10931	Epimedium rugosum	Species	Berberidaceae	Eukaryota		UNPD*
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota		UNPD*
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota		UNPD*
NPO5719	Hedyotis lawsoniae	Species	Rubiaceae	Eukaryota		UNPD*
NPO16301	Ilex macropoda	Species	Aquifoliaceae	Eukaryota		UNPD*
NPO6809	Cailliea cinerea	NA	NA	NA		UNPD*
NPO10782	Myroxylon balsamum	Species	Fabaceae	Eukaryota		UNPD*
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota		UNPD*
NPO639	Formica polyctena	Species	Formicidae	Eukaryota		UNPD*
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota		TCMSP*
NPO9314	Gouania ulmifolia	Species	Gobiesocidae	Eukaryota		UNPD*
NPO28680	Corayceps	NA	NA	NA		TCMSP*
NPO15773	Ecteinascidia thurstoni	Species	Perophoridae	Eukaryota		UNPD*
NPO27197	Platycladi semen	NA	NA	NA		TCMSP*
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota		UNPD*
NPO23624	Thalluslaminariae	NA	NA	NA		TCMSP*
NPO15037	Echinops spinosissimus	Species	Asteraceae	Eukaryota		UNPD*
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota		TCMSP*
NPO13931	Selaginella uncinata	Species	Selaginellaceae	Eukaryota		UNPD*
NPO21137	Combretum indicum	Species	Combretaceae	Eukaryota		TCMSP*
NPO1655	Corydendrium parasiticum	Species	Oceaniidae	Eukaryota		UNPD*
NPO13417	Campanula medium	Species	Campanulaceae	Eukaryota		UNPD*
NPO29690	Leonuri herba	NA	NA	NA		TCMSP*
NPO16774	Hermidium alipes	NA	NA	NA		UNPD*
NPO73	Pseudanabaena persicina	Species	Pseudanabaenaceae	Bacteria		UNPD*
NPO21889	Pollen typhae	NA	NA	NA		TCMSP*
NPO13036	Culicinomyces clavisporus	Species	Clavicipitaceae	Eukaryota		UNPD*
NPO2584	Monostroma fuscum	Species	Monostromataceae	Eukaryota		UNPD*
NPO29597	Perillae fructus	NA	NA	NA		TCMSP*
NPO5127	Cladocroce incurvata	Species	Chalinidae	Eukaryota		UNPD*
NPO16534	Pterocaulon alopecuroides	Species	Asteraceae	Eukaryota		UNPD*
NPO29582	Aloe	Genus	Asphodelaceae	Eukaryota		TCMSP*

Biological Activity

Activity Type	# Activity
EC50	2
IC50	28
Kd	2
Ki	2
Others	23
Potency	64

Activity Type	# Activity
Cell Line	5
Individual Protein	70
Organism	25
Others	19
Protein-Protein Interaction	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT142	Individual Protein	Fatty acid binding protein adipocyte	Homo sapiens	Kd	=	180	nM	12036355
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	0	%	10328303
NPT4038	Individual Protein	Cytosolic phospholipase A2 gamma	Homo sapiens	IC50	>	100000	nM	11229777
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	40000	nM	11229777
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	180	nM	11229777
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	4.7	nM	11229777
NPT605	Organism	Homo sapiens	Homo sapiens	IC50	>	10000	nM	11229777
NPT605	Organism	Homo sapiens	Homo sapiens	IC50	=	940	nM	11229777
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Inhibition	=	0	%	15876534
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Inhibition	=	6	%	15876534
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Inhibition	=	24	%	15876534
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Inhibition	=	61	%	15876534
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Inhibition	=	100	%	15876534
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	IC50	~	60000	nM	15876534
NPT2217	Individual Protein	Cytochrome P450 51	Homo sapiens	IC50	>	200000	nM	17194716
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	EC50	=	22100	nM	17420205
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	=	48		18003907
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	=	50	%	18003907
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	=	95	%	18003907
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	IC50	=	60000	nM	18003907
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	IC50	=	10000	nM	18003907
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	=	40	%	18003907
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	>	90	%	18003907
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Activity	=	8		18003907
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	IC50	=	105000	nM	9834151
NPT863	Individual Protein	Trypsin	Sus scrofa	IC50	>	200000	nM	9834151
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	IC50	>	100000	nM	18983142
NPT2	Others	Unspecified		Inhibition	<	20	%	18459759
NPT2	Others	Unspecified		IC50	=	300	nM	18459759
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Activity	=	11.5	%	16643058
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	28200	nM	16643058
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Activity	=	147.2	%	16643058
NPT2	Others	Unspecified		Activity	=	56	%	18793849
NPT2	Others	Unspecified		Activity	=	18	%	18793849
NPT2	Others	Unspecified		Activity	=	28	%	18793849
NPT2	Others	Unspecified		IC50	=	380000	nM	17954701
NPT2	Others	Unspecified		Kd	=	180000	nM	17954701
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	2238.7	nM	PubChem BioAssay data set
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	44668.4	nM	PubChem BioAssay data set
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	3981.1	nM	PubChem BioAssay data set
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	1995.3	nM	PubChem BioAssay data set
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	3981.1	nM	PubChem BioAssay data set
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	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
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	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
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	2818.4	nM	PubChem BioAssay data set
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	22387.2	nM	PubChem BioAssay data set
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	63095.7	nM	PubChem BioAssay data set
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	79.4	nM	PubChem BioAssay data set
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	316.2	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	35481.3	nM	PubChem BioAssay data set
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT277	Individual Protein	Caspase-1	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	31622.8	nM	PubChem BioAssay data set
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency		22387.2	nM	PubChem BioAssay data set
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency		39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		8199.5	nM	PubChem BioAssay data set
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency		15848.9	nM	PubChem BioAssay data set
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency		31622.8	nM	PubChem BioAssay data set
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency		5623.4	nM	PubChem BioAssay data set
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency		7943.3	nM	PubChem BioAssay data set
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency		33498.3	nM	PubChem BioAssay data set
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency		15848.9	nM	PubChem BioAssay data set
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency		12589.3	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency		18526	nM	PubChem BioAssay data set
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency		56234.1	nM	PubChem BioAssay data set
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency		50118.7	nM	PubChem BioAssay data set
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency		50118.7	nM	PubChem BioAssay data set
NPT784	Cell Line	MDA-MB-468	Homo sapiens	EC50	>	100000	nM	22822908
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	>	100000	nM	22822908
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	IC50	=	1200	nM	10.1007/s00044-008-9102-7
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	IC50	=	3100	nM	10.1007/s00044-012-0285-6
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	IC50	=	1600	nM	10.1007/s00044-012-0285-6
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	IC50	=	1200	nM	10.1007/s00044-012-0285-6
NPT2	Others	Unspecified		Potency		11582.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		23715	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		18356.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		29855.4	nM	PubChem BioAssay data set
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	5.402	%	23571415
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	IC50	=	1071.52	nM	23571415
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Ki	=	820	nM	23571415
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	23.4	%	23571415
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	IC50	=	602.56	nM	23571415
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Ki	=	330	nM	23571415
NPT2	Others	Unspecified		Potency		25118.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		12589.3	nM	PubChem BioAssay data set
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency		12589.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		22387.2	nM	PubChem BioAssay data set
NPT2719	Individual Protein	Voltage-gated L-type calcium channel alpha-1C subunit	Rattus norvegicus	IC50	=	5800	nM	22761000
NPT2719	Individual Protein	Voltage-gated L-type calcium channel alpha-1C subunit	Rattus norvegicus	IC50	=	8500	nM	22761000
NPT2	Others	Unspecified		Potency		14125.4	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 NPC91495 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	49
0.1-0.2	1947
0.2-0.3	13066
0.3-0.4	8267
0.4-0.5	5341
0.5-0.6	1764
0.6-0.7	317
0.7-0.8	87
0.8-0.85	23
0.85-0.9	21
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC59051
0.9545	High Similarity	NPC117572
0.9348	High Similarity	NPC149821
0.9348	High Similarity	NPC5413
0.9167	High Similarity	NPC92114
0.913	High Similarity	NPC207292
0.9091	High Similarity	NPC270796
0.898	High Similarity	NPC70387
0.898	High Similarity	NPC321062
0.8958	High Similarity	NPC48162
0.88	High Similarity	NPC87564
0.88	High Similarity	NPC290563
0.88	High Similarity	NPC85813
0.88	High Similarity	NPC6095
0.88	High Similarity	NPC281972
0.88	High Similarity	NPC424
0.88	High Similarity	NPC88966
0.88	High Similarity	NPC32467
0.88	High Similarity	NPC25417
0.88	High Similarity	NPC154245
0.88	High Similarity	NPC261831
0.86	High Similarity	NPC36061
0.86	High Similarity	NPC1813
0.86	High Similarity	NPC139029
0.86	High Similarity	NPC294548
0.8571	High Similarity	NPC28205
0.8571	High Similarity	NPC284212
0.8511	High Similarity	NPC42304
0.8462	Intermediate Similarity	NPC18951
0.8462	Intermediate Similarity	NPC477201
0.8431	Intermediate Similarity	NPC322461
0.84	Intermediate Similarity	NPC129458
0.84	Intermediate Similarity	NPC281245
0.8302	Intermediate Similarity	NPC323597
0.8302	Intermediate Similarity	NPC323498
0.8302	Intermediate Similarity	NPC323436
0.8302	Intermediate Similarity	NPC211752
0.8269	Intermediate Similarity	NPC274290
0.8269	Intermediate Similarity	NPC473863
0.8235	Intermediate Similarity	NPC10081
0.8235	Intermediate Similarity	NPC225066
0.82	Intermediate Similarity	NPC262968
0.8113	Intermediate Similarity	NPC179764
0.8113	Intermediate Similarity	NPC325977
0.8113	Intermediate Similarity	NPC187777
0.8113	Intermediate Similarity	NPC327388
0.8039	Intermediate Similarity	NPC303765
0.8	Intermediate Similarity	NPC224227
0.8	Intermediate Similarity	NPC106851
0.8	Intermediate Similarity	NPC274927
0.8	Intermediate Similarity	NPC329249
0.7963	Intermediate Similarity	NPC225929
0.7925	Intermediate Similarity	NPC54766
0.7925	Intermediate Similarity	NPC45626
0.7885	Intermediate Similarity	NPC139545
0.7885	Intermediate Similarity	NPC39633
0.7885	Intermediate Similarity	NPC309606
0.7857	Intermediate Similarity	NPC243532
0.7857	Intermediate Similarity	NPC328311
0.7857	Intermediate Similarity	NPC321919
0.7857	Intermediate Similarity	NPC327112
0.7857	Intermediate Similarity	NPC81896
0.7843	Intermediate Similarity	NPC178586
0.7818	Intermediate Similarity	NPC329819
0.7736	Intermediate Similarity	NPC137538
0.7719	Intermediate Similarity	NPC321838
0.7719	Intermediate Similarity	NPC320305
0.7719	Intermediate Similarity	NPC201939
0.7719	Intermediate Similarity	NPC328776
0.7679	Intermediate Similarity	NPC329550
0.7679	Intermediate Similarity	NPC322002
0.76	Intermediate Similarity	NPC180534
0.7593	Intermediate Similarity	NPC28779
0.7593	Intermediate Similarity	NPC223677
0.7593	Intermediate Similarity	NPC200845
0.7593	Intermediate Similarity	NPC228473
0.7593	Intermediate Similarity	NPC128061
0.7593	Intermediate Similarity	NPC10316
0.7593	Intermediate Similarity	NPC52264
0.7544	Intermediate Similarity	NPC235242
0.7544	Intermediate Similarity	NPC174447
0.7544	Intermediate Similarity	NPC122521
0.7544	Intermediate Similarity	NPC251042
0.75	Intermediate Similarity	NPC267817
0.7458	Intermediate Similarity	NPC328089
0.7458	Intermediate Similarity	NPC68343
0.7451	Intermediate Similarity	NPC163345
0.7414	Intermediate Similarity	NPC174560
0.7414	Intermediate Similarity	NPC40082
0.7414	Intermediate Similarity	NPC125312
0.7407	Intermediate Similarity	NPC87394
0.7358	Intermediate Similarity	NPC18357
0.7358	Intermediate Similarity	NPC477779
0.7333	Intermediate Similarity	NPC476654
0.7333	Intermediate Similarity	NPC476657
0.7333	Intermediate Similarity	NPC318420
0.7333	Intermediate Similarity	NPC326268
0.7333	Intermediate Similarity	NPC136164
0.7333	Intermediate Similarity	NPC317881
0.7333	Intermediate Similarity	NPC320642
0.7333	Intermediate Similarity	NPC323045
0.7333	Intermediate Similarity	NPC245947
0.7333	Intermediate Similarity	NPC255863
0.7333	Intermediate Similarity	NPC476655
0.7288	Intermediate Similarity	NPC322457
0.7273	Intermediate Similarity	NPC477984
0.7273	Intermediate Similarity	NPC67367
0.7273	Intermediate Similarity	NPC474672
0.7222	Intermediate Similarity	NPC71761
0.7213	Intermediate Similarity	NPC476656
0.7213	Intermediate Similarity	NPC476659
0.7193	Intermediate Similarity	NPC34416
0.7193	Intermediate Similarity	NPC325734
0.7174	Intermediate Similarity	NPC92863
0.7174	Intermediate Similarity	NPC155880
0.717	Intermediate Similarity	NPC477777
0.717	Intermediate Similarity	NPC470410
0.717	Intermediate Similarity	NPC477458
0.717	Intermediate Similarity	NPC470412
0.7167	Intermediate Similarity	NPC470320
0.7119	Intermediate Similarity	NPC113293
0.7115	Intermediate Similarity	NPC207815
0.7097	Intermediate Similarity	NPC104537
0.7097	Intermediate Similarity	NPC22101
0.7097	Intermediate Similarity	NPC49863
0.7097	Intermediate Similarity	NPC26500
0.7097	Intermediate Similarity	NPC330426
0.7097	Intermediate Similarity	NPC148192
0.7097	Intermediate Similarity	NPC478097
0.7097	Intermediate Similarity	NPC127091
0.7097	Intermediate Similarity	NPC478100
0.7097	Intermediate Similarity	NPC99619
0.7097	Intermediate Similarity	NPC271921
0.7069	Intermediate Similarity	NPC322186
0.7069	Intermediate Similarity	NPC318306
0.7059	Intermediate Similarity	NPC308331
0.7037	Intermediate Similarity	NPC216407
0.7018	Intermediate Similarity	NPC283502
0.6984	Remote Similarity	NPC273508
0.6984	Remote Similarity	NPC141481
0.6984	Remote Similarity	NPC48218
0.6984	Remote Similarity	NPC473559
0.6984	Remote Similarity	NPC209327
0.6984	Remote Similarity	NPC324981
0.6949	Remote Similarity	NPC229252
0.6949	Remote Similarity	NPC143857
0.6935	Remote Similarity	NPC478101
0.6935	Remote Similarity	NPC328653
0.6923	Remote Similarity	NPC216130
0.6909	Remote Similarity	NPC217188
0.6909	Remote Similarity	NPC284224
0.6885	Remote Similarity	NPC476658
0.6885	Remote Similarity	NPC226592
0.6875	Remote Similarity	NPC317583
0.6863	Remote Similarity	NPC76976
0.6852	Remote Similarity	NPC470411
0.6842	Remote Similarity	NPC324224
0.6842	Remote Similarity	NPC472808
0.6833	Remote Similarity	NPC477829
0.6825	Remote Similarity	NPC473829
0.6825	Remote Similarity	NPC475443
0.6809	Remote Similarity	NPC34873
0.6809	Remote Similarity	NPC40434
0.6786	Remote Similarity	NPC474127
0.678	Remote Similarity	NPC478095
0.6774	Remote Similarity	NPC478099
0.6774	Remote Similarity	NPC323477
0.6774	Remote Similarity	NPC478098
0.6769	Remote Similarity	NPC476660
0.6769	Remote Similarity	NPC42526
0.6731	Remote Similarity	NPC110234
0.6731	Remote Similarity	NPC163751
0.6731	Remote Similarity	NPC44363
0.6727	Remote Similarity	NPC161366
0.6727	Remote Similarity	NPC170167
0.6721	Remote Similarity	NPC54925
0.6721	Remote Similarity	NPC68110
0.6721	Remote Similarity	NPC477707
0.6721	Remote Similarity	NPC316674
0.6719	Remote Similarity	NPC476614
0.6667	Remote Similarity	NPC304079
0.6667	Remote Similarity	NPC477983
0.6667	Remote Similarity	NPC142423
0.6667	Remote Similarity	NPC225974
0.6667	Remote Similarity	NPC6963
0.6667	Remote Similarity	NPC477981
0.6667	Remote Similarity	NPC308294
0.6615	Remote Similarity	NPC143396
0.6615	Remote Similarity	NPC236208
0.6615	Remote Similarity	NPC470436
0.6615	Remote Similarity	NPC473772
0.6613	Remote Similarity	NPC234767
0.6613	Remote Similarity	NPC34883
0.661	Remote Similarity	NPC471619
0.661	Remote Similarity	NPC469373
0.661	Remote Similarity	NPC478096
0.661	Remote Similarity	NPC254095
0.6596	Remote Similarity	NPC158179
0.6567	Remote Similarity	NPC325627
0.6562	Remote Similarity	NPC60120

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC91495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	51
0.1-0.2	2686
0.2-0.3	4443
0.3-0.4	1443
0.4-0.5	421
0.5-0.6	81
0.6-0.7	16
0.7-0.8	7
0.8-0.85	3
0.85-0.9	6
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9545	High Similarity	NPD4222	Approved
0.9545	High Similarity	NPD39	Approved
0.9348	High Similarity	NPD3173	Approved
0.9091	High Similarity	NPD5326	Phase 3
0.88	High Similarity	NPD3195	Phase 2
0.88	High Similarity	NPD4266	Approved
0.88	High Similarity	NPD3196	Approved
0.88	High Similarity	NPD3194	Approved
0.8696	High Similarity	NPD3174	Discontinued
0.86	High Similarity	NPD3172	Approved
0.8333	Intermediate Similarity	NPD5343	Approved
0.82	Intermediate Similarity	NPD29	Approved
0.82	Intermediate Similarity	NPD28	Approved
0.7857	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6097	Approved
0.7708	Intermediate Similarity	NPD6096	Approved
0.76	Intermediate Similarity	NPD622	Approved
0.75	Intermediate Similarity	NPD6109	Phase 1
0.7458	Intermediate Similarity	NPD3197	Phase 1
0.7097	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6927	Phase 3
0.6792	Remote Similarity	NPD4220	Pre-registration
0.6667	Remote Similarity	NPD5783	Phase 3
0.6538	Remote Similarity	NPD4265	Approved
0.64	Remote Similarity	NPD2270	Approved
0.6154	Remote Similarity	NPD9411	Phase 1
0.6154	Remote Similarity	NPD7331	Phase 2
0.6111	Remote Similarity	NPD3732	Approved
0.6111	Remote Similarity	NPD4271	Approved
0.6111	Remote Similarity	NPD4268	Approved
0.6111	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9448	Phase 2
0.6	Remote Similarity	NPD77	Approved
0.6	Remote Similarity	NPD633	Phase 3
0.6	Remote Similarity	NPD9450	Approved
0.5946	Remote Similarity	NPD4252	Approved
0.5946	Remote Similarity	NPD4822	Approved
0.5946	Remote Similarity	NPD4819	Approved
0.5946	Remote Similarity	NPD4820	Approved
0.5946	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5368	Approved
0.5946	Remote Similarity	NPD4821	Approved
0.5938	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD8971	Approved
0.5867	Remote Similarity	NPD5369	Approved
0.58	Remote Similarity	NPD3206	Approved
0.5789	Remote Similarity	NPD4270	Approved
0.5789	Remote Similarity	NPD6435	Approved
0.5789	Remote Similarity	NPD4269	Approved
0.5781	Remote Similarity	NPD4192	Approved
0.5781	Remote Similarity	NPD4194	Approved
0.5781	Remote Similarity	NPD4191	Approved
0.5781	Remote Similarity	NPD4193	Approved
0.5753	Remote Similarity	NPD4756	Discovery
0.5714	Remote Similarity	NPD5332	Approved
0.5714	Remote Similarity	NPD5331	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD5362	Discontinued
0.5694	Remote Similarity	NPD8039	Approved
0.5686	Remote Similarity	NPD9655	Approved
0.5672	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD4790	Discontinued
0.5645	Remote Similarity	NPD8779	Phase 3
0.5625	Remote Similarity	NPD8857	Approved

Structure

CID91495 OpenBabel06191715432D 22 21 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 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 3.4641 2.0000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	444899
ChEMBL	CHEMBL15594
ZINC

Physicochemical Properties

Molecular Weight:	304.24
ALogP:	1.2639
MLogP:	3.44
XLogP:	8.349
# Rotatable Bonds:	16
Polar Surface Area:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	22

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