NPASS Natural Product

Natural Product: NPC189470

Natural Product ID:	NPC189470
Common Name:	Anonaine
IUPAC Name:
Synonyms:	(-)-Anonaine; Anonaine
Molecular Formula:	C17H15NO2
Standard InCHIKey:	VZTUKBKUWSHDFM-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C17H15NO2/c1-2-4-12-10(3-1)7-13-15-11(5-6-18-13)8-14-17(16(12)15)20-9-19-14/h1-4,8,13,18H,5-7,9H2/t13-/m1/s1
Canonical SMILES:	c1ccc2c(c1)C[C@@H]1c3c2c2OCOc2cc3CCN1
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO4282	Fouquieria diguetii	Species	Fouquieriaceae	Eukaryota		UNPD*
NPO17964	Aspergillus subolivaceus	Species	Aspergillaceae	Eukaryota		UNPD*
NPO10532	Pinus edulis	Species	Pinaceae	Eukaryota		UNPD*
NPO8721	Parectatosoma mocquerysi	Species	Anisacanthidae	Eukaryota		UNPD*
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota		UNPD*
NPO18026	Bipolaris sacchari	Species	Pleosporaceae	Eukaryota		UNPD*
NPO8172	Emericellopsis minima	Species	NA	Eukaryota		UNPD*
NPO14194	Mamestra brassicae	Species	Noctuidae	Eukaryota		UNPD*
NPO17630	Helenium integrifolium	Species	Asteraceae	Eukaryota		UNPD*
NPO11592	Cuphea hyssopifolia	Species	Lythraceae	Eukaryota		UNPD*
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota		UNPD*
NPO15127	Senecio congestus	Species	Asteraceae	Eukaryota		UNPD*
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		TCM_Taiwan*
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota		UNPD*
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria		UNPD*
NPO2043	Pseudocyphellaria coronata	Species	Lobariaceae	Eukaryota		UNPD*
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		TCM_Taiwan*
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota		UNPD*
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria		UNPD*
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota		UNPD*
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota		TCM_Taiwan*
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota		UNPD*
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota		UNPD*
NPO18533	Delisea elegans	Species	Bonnemaisoniaceae	Eukaryota		UNPD*
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		TCM_Taiwan*
NPO14455	Triunia erythrocarpa	Species	Proteaceae	Eukaryota		UNPD*
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota		UNPD*
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	tubers	PMID[8254346]
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota		UNPD*
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota		UNPD*
NPO32838	artabottys maingayi	Species	NA	NA		PMID[8676127]
NPO11246	Ononis viscosa	Species	Fabaceae	Eukaryota		UNPD*
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota		UNPD*
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota		PMID[11087586]
NPO15887	Absidia orchidis	Species	Cunninghamellaceae	Eukaryota		UNPD*
NPO25118	Centaurea benedicta	Species	Asteraceae	Eukaryota		UNPD*
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota		UNPD*
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	Eukaryota		UNPD*
NPO12223	Stellaria media	Species	Caryophyllaceae	Eukaryota		UNPD*
NPO2568	Posidonia oceanica	Species	Posidoniaceae	Eukaryota		UNPD*
NPO17499	Bursera kerberi	Species	Burseraceae	Eukaryota		UNPD*
NPO15992	Hypogymnia vittata	Species	Parmeliaceae	Eukaryota		UNPD*
NPO12018	Alternaria bataticola	Species	Pleosporaceae	Eukaryota		UNPD*
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota		UNPD*
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota		UNPD*
NPO11373	Nonomuraea spiralis	Species	Streptosporangiaceae	Bacteria		UNPD*
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota		UNPD*
NPO3482	Alpinia flabellata	Species	Zingiberaceae	Eukaryota		UNPD*
NPO15405	Suaeda maritima	Species	Chenopodiaceae	Eukaryota		UNPD*
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota		UNPD*
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria		UNPD*
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota		UNPD*
NPO13018	Thelephora aurantiotincta	Species	Thelephoraceae	Eukaryota		UNPD*
NPO9133	Lathyrus latifolius	Species	Fabaceae	Eukaryota		UNPD*
NPO29675	Nelumbinis plumula	NA	NA	NA		TCMSP*
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota		UNPD*
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota		UNPD*
NPO28184	Folium nelumbinis	NA	NA	NA		TCMSP*
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota		UNPD*
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota		UNPD*
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota		TM-MC*
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota		UNPD*
NPO6698	Euphorbia pithyusa	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota		TM-MC*
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota		UNPD*
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota		UNPD*
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		TCMID*
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota		UNPD*
NPO5998	Echinoclathria subhispida	Species	Microcionidae	Eukaryota		UNPD*
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota		UNPD*
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota		UNPD*
NPO10048	Pyrus bourgaeana	Species	Rosaceae	Eukaryota		UNPD*
NPO19170	Lasianthaea podocephala	Species	Asteraceae	Eukaryota		UNPD*
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota		UNPD*
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota		UNPD*
NPO16325	Sideritis dasygnaphala	Species	Lamiaceae	Eukaryota		UNPD*
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota		UNPD*
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota		UNPD*
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota		UNPD*
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota		UNPD*
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota		UNPD*
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota		UNPD*
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota		UNPD*
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota		UNPD*
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota		UNPD*
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	Eukaryota		UNPD*
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota		UNPD*
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota		UNPD*
NPO13646	Phlebia strigosozonata	Species	Meruliaceae	Eukaryota		UNPD*
NPO10905	Baccharis truncata	Species	Asteraceae	Eukaryota		UNPD*
NPO13617	Eria rigida	Species	Orchidaceae	Eukaryota		UNPD*
NPO2070	Thioalkalivibrio versutus	Species	Ectothiorhodospiraceae	Bacteria		UNPD*
NPO2680	Holothuria squamifera	Species	Holothuriidae	Eukaryota		UNPD*
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota		UNPD*
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota		UNPD*
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota		UNPD*
NPO19709	Pseudocyphellaria australiensis	Species	Lobariaceae	Eukaryota		UNPD*
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota		UNPD*
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota		UNPD*
NPO17166	Euphorbia palustris	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO7009	Callyspongia spinosissima	Species	Callyspongiidae	Eukaryota		UNPD*
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota		UNPD*
NPO17358	Sorbus torminalis	Species	Rosaceae	Eukaryota		UNPD*
NPO12992	Shigella boydii	Species	Enterobacteriaceae	Bacteria		UNPD*
NPO15514	Pedicularis rex	Species	Orobanchaceae	Eukaryota		UNPD*
NPO9538	Pterocarpus erinaceus	Species	Fabaceae	Eukaryota		UNPD*
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota		UNPD*
NPO27148	Chuquiraga erinacea	Species	Asteraceae	Eukaryota		UNPD*
NPO273	Phyllobates bicolor	Species	Dendrobatidae	Eukaryota		UNPD*
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota		UNPD*
NPO14329	Sigillina signifera	Species	Polycitoridae	Eukaryota		UNPD*
NPO13745	Gynoxys verrucosa	Species	Asteraceae	Eukaryota		UNPD*

Biological Activity

Activity Type	# Activity
ED50	14
IC50	12
Others	11

Activity Type	# Activity
Cell Line	13
Individual Protein	6
Organism	8
Others	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4163	Individual Protein	Protein tyrosine phosphatase receptor type C-associated protein	Homo sapiens	IC50	=	17000	nM	10.1016/0960-894X(95)00250-W
NPT4163	Individual Protein	Protein tyrosine phosphatase receptor type C-associated protein	Homo sapiens	Inhibition	=	96	%	10.1016/0960-894X(95)00250-W
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	IC50	=	68000	nM	17228858
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	IC50	=	19000	nM	17228858
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	800	nM	17228858
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	8600	nM	11087586
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	28900	nM	11087586
NPT2	Others	Unspecified		IC50	=	16400	nM	11087586
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	20800	nM	11087586
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	IC50	=	70.3	ug/ml	18295494
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	33.5	ug/ml	18295494
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	24.8	ug/ml	18295494
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	99	%	8699188
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	Activity	=	50	ug/ml	8699188
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	25	ug/ml	8699188
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	90	%	8699188
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	100	ug/ml	8699188
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	90	%	8699188
NPT2	Others	Unspecified		ED50	=	3.3	ug/ml	8254346
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	2.4	ug/ml	8254346
NPT2	Others	Unspecified		ED50	=	1.8	ug/ml	8254346
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	15.8	ug/ml	8254346
NPT2	Others	Unspecified		ED50	=	4	ug/ml	8254346
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.6	ug/ml	8254346
NPT168	Cell Line	P388	Mus musculus	ED50	>	5	ug/ml	8254346
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	4.2	ug/ml	8254346
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	2.9	ug/ml	8254346
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	2.7	ug/ml	8254346
NPT2	Others	Unspecified		ED50	=	1.5	ug/ml	8254346
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	1.29	ug/ml	8254346
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	1.9	ug/ml	8254346
NPT2	Others	Unspecified		Ratio ED50	=	5		8254346
NPT2	Others	Unspecified		Ratio ED50	=	3		8254346
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	800	nM	8676127
NPT2	Others	Unspecified		Ratio IC50	=	85		8676127
NPT2	Others	Unspecified		Ratio IC50	=	23.5		8676127

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 NPC189470 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	310
0.1-0.2	1481
0.2-0.3	5933
0.3-0.4	6712
0.4-0.5	5344
0.5-0.6	8924
0.6-0.7	1583
0.7-0.8	406
0.8-0.85	109
0.85-0.9	44
0.9-0.95	39
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9869	High Similarity	NPC304659
0.9869	High Similarity	NPC86144
0.9679	High Similarity	NPC152212
0.9554	High Similarity	NPC6152
0.9497	High Similarity	NPC477558
0.9481	High Similarity	NPC477559
0.9481	High Similarity	NPC266753
0.9481	High Similarity	NPC160298
0.9481	High Similarity	NPC306902
0.9481	High Similarity	NPC232924
0.9412	High Similarity	NPC170503
0.9412	High Similarity	NPC203784
0.9412	High Similarity	NPC126519
0.9321	High Similarity	NPC267408
0.9317	High Similarity	NPC112575
0.9299	High Similarity	NPC225774
0.9299	High Similarity	NPC168409
0.9264	High Similarity	NPC474506
0.9264	High Similarity	NPC32413
0.9259	High Similarity	NPC23219
0.9241	High Similarity	NPC24264
0.9241	High Similarity	NPC476432
0.9241	High Similarity	NPC219341
0.9207	High Similarity	NPC476575
0.9202	High Similarity	NPC258695
0.9202	High Similarity	NPC470879
0.9182	High Similarity	NPC247389
0.9182	High Similarity	NPC298979
0.9177	High Similarity	NPC16805
0.9177	High Similarity	NPC302527
0.9177	High Similarity	NPC167546
0.9152	High Similarity	NPC135772
0.9146	High Similarity	NPC476574
0.9146	High Similarity	NPC312918
0.9146	High Similarity	NPC477561
0.9146	High Similarity	NPC155442
0.9125	High Similarity	NPC241055
0.9062	High Similarity	NPC210918
0.9026	High Similarity	NPC81733
0.9026	High Similarity	NPC326316
0.9	High Similarity	NPC476573
0.9	High Similarity	NPC35627
0.9	High Similarity	NPC81247
0.8929	High Similarity	NPC57036
0.8896	High Similarity	NPC149090
0.8896	High Similarity	NPC19520
0.8876	High Similarity	NPC476576
0.8876	High Similarity	NPC186546
0.8862	High Similarity	NPC275132
0.8827	High Similarity	NPC204947
0.8795	High Similarity	NPC114364
0.8795	High Similarity	NPC320223
0.8788	High Similarity	NPC229166
0.8788	High Similarity	NPC199465
0.8788	High Similarity	NPC128560
0.8743	High Similarity	NPC126284
0.8742	High Similarity	NPC476572
0.8734	High Similarity	NPC99659
0.8734	High Similarity	NPC41178
0.8734	High Similarity	NPC216459
0.8734	High Similarity	NPC138487
0.8734	High Similarity	NPC325871
0.8727	High Similarity	NPC66341
0.8727	High Similarity	NPC192135
0.8727	High Similarity	NPC477020
0.8721	High Similarity	NPC117717
0.872	High Similarity	NPC26240
0.872	High Similarity	NPC477562
0.872	High Similarity	NPC69712
0.871	High Similarity	NPC475959
0.8679	High Similarity	NPC31311
0.8679	High Similarity	NPC146288
0.8679	High Similarity	NPC234392
0.8663	High Similarity	NPC475754
0.8639	High Similarity	NPC248642
0.8634	High Similarity	NPC166014
0.8634	High Similarity	NPC27410
0.8616	High Similarity	NPC76079
0.8588	High Similarity	NPC156576
0.8571	High Similarity	NPC477080
0.8535	High Similarity	NPC219162
0.8529	High Similarity	NPC116284
0.8529	High Similarity	NPC249405
0.8521	High Similarity	NPC474507
0.8512	High Similarity	NPC148709
0.8512	High Similarity	NPC476577
0.8512	High Similarity	NPC173416
0.8491	Intermediate Similarity	NPC210148
0.8491	Intermediate Similarity	NPC233029
0.8475	Intermediate Similarity	NPC212163
0.8471	Intermediate Similarity	NPC179704
0.8462	Intermediate Similarity	NPC118633
0.8462	Intermediate Similarity	NPC294790
0.8462	Intermediate Similarity	NPC148693
0.8439	Intermediate Similarity	NPC237579
0.8418	Intermediate Similarity	NPC60538
0.8418	Intermediate Similarity	NPC207824
0.8415	Intermediate Similarity	NPC324144
0.8408	Intermediate Similarity	NPC253883
0.8408	Intermediate Similarity	NPC90844
0.8408	Intermediate Similarity	NPC95075
0.8402	Intermediate Similarity	NPC287588
0.8397	Intermediate Similarity	NPC145304
0.8385	Intermediate Similarity	NPC93593
0.8385	Intermediate Similarity	NPC244112
0.8382	Intermediate Similarity	NPC214116
0.838	Intermediate Similarity	NPC295676
0.8377	Intermediate Similarity	NPC470925
0.8373	Intermediate Similarity	NPC145832
0.8373	Intermediate Similarity	NPC117188
0.8373	Intermediate Similarity	NPC205421
0.8373	Intermediate Similarity	NPC474931
0.8373	Intermediate Similarity	NPC12053
0.8373	Intermediate Similarity	NPC81218
0.8373	Intermediate Similarity	NPC158376
0.8373	Intermediate Similarity	NPC306555
0.8364	Intermediate Similarity	NPC232514
0.8364	Intermediate Similarity	NPC477563
0.8364	Intermediate Similarity	NPC306843
0.8364	Intermediate Similarity	NPC136508
0.8364	Intermediate Similarity	NPC238530
0.8364	Intermediate Similarity	NPC96603
0.8364	Intermediate Similarity	NPC276944
0.8364	Intermediate Similarity	NPC13504
0.8364	Intermediate Similarity	NPC196447
0.8364	Intermediate Similarity	NPC78222
0.8364	Intermediate Similarity	NPC212794
0.8364	Intermediate Similarity	NPC253043
0.8354	Intermediate Similarity	NPC130941
0.8333	Intermediate Similarity	NPC474904
0.8323	Intermediate Similarity	NPC477564
0.8323	Intermediate Similarity	NPC2295
0.8313	Intermediate Similarity	NPC277669
0.8313	Intermediate Similarity	NPC76213
0.8312	Intermediate Similarity	NPC314682
0.8303	Intermediate Similarity	NPC1229
0.8302	Intermediate Similarity	NPC92541
0.8301	Intermediate Similarity	NPC253429
0.8291	Intermediate Similarity	NPC210437
0.8291	Intermediate Similarity	NPC476144
0.8291	Intermediate Similarity	NPC16107
0.8291	Intermediate Similarity	NPC106295
0.8291	Intermediate Similarity	NPC51957
0.8286	Intermediate Similarity	NPC82763
0.8261	Intermediate Similarity	NPC470924
0.8258	Intermediate Similarity	NPC213206
0.8258	Intermediate Similarity	NPC474915
0.8258	Intermediate Similarity	NPC188163
0.8258	Intermediate Similarity	NPC328750
0.8242	Intermediate Similarity	NPC244606
0.8242	Intermediate Similarity	NPC156728
0.8239	Intermediate Similarity	NPC7467
0.8235	Intermediate Similarity	NPC7018
0.8232	Intermediate Similarity	NPC111485
0.8229	Intermediate Similarity	NPC312531
0.8187	Intermediate Similarity	NPC211296
0.8182	Intermediate Similarity	NPC281581
0.8176	Intermediate Similarity	NPC144863
0.8171	Intermediate Similarity	NPC79328
0.8166	Intermediate Similarity	NPC118274
0.8166	Intermediate Similarity	NPC168753
0.8162	Intermediate Similarity	NPC46990
0.816	Intermediate Similarity	NPC78733
0.816	Intermediate Similarity	NPC187022
0.816	Intermediate Similarity	NPC80129
0.8158	Intermediate Similarity	NPC160692
0.8153	Intermediate Similarity	NPC476567
0.8153	Intermediate Similarity	NPC136860
0.8153	Intermediate Similarity	NPC128019
0.8148	Intermediate Similarity	NPC148898
0.8148	Intermediate Similarity	NPC26601
0.8144	Intermediate Similarity	NPC2770
0.8144	Intermediate Similarity	NPC39103
0.8137	Intermediate Similarity	NPC223125
0.8133	Intermediate Similarity	NPC24954
0.8121	Intermediate Similarity	NPC7393
0.8118	Intermediate Similarity	NPC239775
0.8092	Intermediate Similarity	NPC220961
0.809	Intermediate Similarity	NPC302001
0.8084	Intermediate Similarity	NPC475393
0.8084	Intermediate Similarity	NPC233650
0.807	Intermediate Similarity	NPC285941
0.807	Intermediate Similarity	NPC2314
0.8063	Intermediate Similarity	NPC476151
0.805	Intermediate Similarity	NPC185838
0.8037	Intermediate Similarity	NPC223124
0.8036	Intermediate Similarity	NPC134858
0.8035	Intermediate Similarity	NPC477560
0.8012	Intermediate Similarity	NPC106786
0.8011	Intermediate Similarity	NPC193906
0.8011	Intermediate Similarity	NPC23080
0.8	Intermediate Similarity	NPC162653
0.8	Intermediate Similarity	NPC180756
0.8	Intermediate Similarity	NPC29647
0.8	Intermediate Similarity	NPC323443
0.8	Intermediate Similarity	NPC186063
0.7987	Intermediate Similarity	NPC294249
0.7976	Intermediate Similarity	NPC320104
0.7964	Intermediate Similarity	NPC215829
0.7964	Intermediate Similarity	NPC97072

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC189470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	749
0.2-0.3	1001
0.3-0.4	1723
0.4-0.5	2878
0.5-0.6	1843
0.6-0.7	625
0.7-0.8	121
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8291	Intermediate Similarity	NPD4584	Approved
0.8258	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7298	Approved
0.8092	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6030	Approved
0.8075	Intermediate Similarity	NPD4727	Phase 1
0.8075	Intermediate Similarity	NPD6031	Approved
0.7937	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3845	Phase 1
0.7937	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD2420	Approved
0.7888	Intermediate Similarity	NPD2421	Approved
0.7882	Intermediate Similarity	NPD3051	Approved
0.7791	Intermediate Similarity	NPD4481	Phase 3
0.7758	Intermediate Similarity	NPD4017	Approved
0.7733	Intermediate Similarity	NPD2969	Approved
0.7733	Intermediate Similarity	NPD2970	Approved
0.7692	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD27	Approved
0.7688	Intermediate Similarity	NPD2489	Approved
0.7683	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3110	Approved
0.758	Intermediate Similarity	NPD3109	Approved
0.7574	Intermediate Similarity	NPD2977	Approved
0.7574	Intermediate Similarity	NPD2978	Approved
0.7572	Intermediate Similarity	NPD4166	Phase 2
0.7561	Intermediate Similarity	NPD7598	Phase 2
0.7546	Intermediate Similarity	NPD5241	Discontinued
0.7539	Intermediate Similarity	NPD4859	Phase 1
0.753	Intermediate Similarity	NPD3639	Approved
0.753	Intermediate Similarity	NPD3640	Phase 3
0.753	Intermediate Similarity	NPD3641	Approved
0.753	Intermediate Similarity	NPD5976	Discontinued
0.7514	Intermediate Similarity	NPD6107	Approved
0.75	Intermediate Similarity	NPD8252	Approved
0.75	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8251	Approved
0.75	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8099	Discontinued
0.7486	Intermediate Similarity	NPD2898	Approved
0.7485	Intermediate Similarity	NPD6788	Approved
0.7472	Intermediate Similarity	NPD6297	Approved
0.7458	Intermediate Similarity	NPD8156	Discontinued
0.7453	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2968	Approved
0.7444	Intermediate Similarity	NPD4577	Approved
0.7444	Intermediate Similarity	NPD2971	Approved
0.7444	Intermediate Similarity	NPD4578	Approved
0.7442	Intermediate Similarity	NPD7833	Phase 2
0.7442	Intermediate Similarity	NPD7831	Phase 2
0.7442	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5160	Discontinued
0.741	Intermediate Similarity	NPD1424	Approved
0.7389	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5754	Discontinued
0.7377	Intermediate Similarity	NPD7906	Approved
0.7353	Intermediate Similarity	NPD4773	Phase 2
0.7353	Intermediate Similarity	NPD4772	Phase 2
0.7342	Intermediate Similarity	NPD5718	Phase 2
0.7322	Intermediate Similarity	NPD4663	Approved
0.7308	Intermediate Similarity	NPD6851	Approved
0.7308	Intermediate Similarity	NPD6853	Approved
0.7283	Intermediate Similarity	NPD3349	Phase 2
0.7267	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5457	Discontinued
0.7256	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7310	Approved
0.7253	Intermediate Similarity	NPD7312	Approved
0.7253	Intermediate Similarity	NPD7311	Approved
0.7253	Intermediate Similarity	NPD7313	Approved
0.7249	Intermediate Similarity	NPD4420	Approved
0.7216	Intermediate Similarity	NPD7802	Discontinued
0.7213	Intermediate Similarity	NPD7309	Approved
0.7213	Intermediate Similarity	NPD8054	Approved
0.7213	Intermediate Similarity	NPD8053	Approved
0.7209	Intermediate Similarity	NPD3383	Approved
0.7209	Intermediate Similarity	NPD3382	Approved
0.7209	Intermediate Similarity	NPD3384	Approved
0.7204	Intermediate Similarity	NPD2490	Approved
0.7204	Intermediate Similarity	NPD2488	Approved
0.72	Intermediate Similarity	NPD7400	Phase 3
0.7188	Intermediate Similarity	NPD4474	Approved
0.7188	Intermediate Similarity	NPD4475	Approved
0.7175	Intermediate Similarity	NPD6071	Discontinued
0.7175	Intermediate Similarity	NPD4010	Discontinued
0.7164	Intermediate Similarity	NPD3763	Approved
0.716	Intermediate Similarity	NPD2492	Phase 1
0.7159	Intermediate Similarity	NPD6037	Discontinued
0.7151	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3124	Discontinued
0.7126	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2560	Approved
0.7126	Intermediate Similarity	NPD2563	Approved
0.7121	Intermediate Similarity	NPD7827	Phase 1
0.711	Intermediate Similarity	NPD5720	Discontinued
0.7108	Intermediate Similarity	NPD4162	Approved
0.7108	Intermediate Similarity	NPD3060	Approved
0.7107	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5006	Approved
0.7098	Intermediate Similarity	NPD5005	Approved
0.7072	Intermediate Similarity	NPD4873	Discontinued
0.7066	Intermediate Similarity	NPD6748	Discontinued
0.7065	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7280	Phase 3
0.7065	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7281	Phase 3
0.7048	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5604	Discontinued
0.7035	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7479	Phase 2
0.7029	Intermediate Similarity	NPD5977	Approved
0.7029	Intermediate Similarity	NPD5978	Approved
0.7027	Intermediate Similarity	NPD6618	Phase 2
0.7026	Intermediate Similarity	NPD4040	Phase 1
0.7017	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2973	Approved
0.7016	Intermediate Similarity	NPD2974	Approved
0.7016	Intermediate Similarity	NPD2975	Approved
0.7012	Intermediate Similarity	NPD6895	Approved
0.7012	Intermediate Similarity	NPD6896	Approved
0.7006	Intermediate Similarity	NPD5709	Phase 3
0.7	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2874	Phase 2
0.6995	Remote Similarity	NPD6612	Phase 2
0.6995	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2120	Phase 2
0.6978	Remote Similarity	NPD6042	Phase 2
0.6978	Remote Similarity	NPD42	Phase 2
0.6975	Remote Similarity	NPD3532	Approved
0.6975	Remote Similarity	NPD3531	Approved
0.6975	Remote Similarity	NPD3530	Approved
0.6971	Remote Similarity	NPD4585	Approved
0.697	Remote Similarity	NPD2155	Approved
0.697	Remote Similarity	NPD4108	Discontinued
0.697	Remote Similarity	NPD2156	Approved
0.697	Remote Similarity	NPD2154	Approved
0.6966	Remote Similarity	NPD4666	Phase 3
0.6963	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3450	Approved
0.6959	Remote Similarity	NPD3452	Approved
0.6951	Remote Similarity	NPD2989	Phase 2
0.6951	Remote Similarity	NPD2653	Approved
0.6951	Remote Similarity	NPD2986	Phase 2
0.6949	Remote Similarity	NPD4055	Discovery
0.6946	Remote Similarity	NPD4256	Phase 2
0.6946	Remote Similarity	NPD4257	Approved
0.6919	Remote Similarity	NPD1914	Approved
0.6919	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1336	Approved
0.6914	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4580	Approved
0.6905	Remote Similarity	NPD5177	Phase 3
0.6901	Remote Similarity	NPD7020	Approved
0.6901	Remote Similarity	NPD7019	Approved
0.6894	Remote Similarity	NPD3595	Approved
0.6894	Remote Similarity	NPD3594	Approved
0.6885	Remote Similarity	NPD5312	Approved
0.6885	Remote Similarity	NPD5313	Approved
0.6878	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7247	Discontinued
0.6872	Remote Similarity	NPD2494	Approved
0.6872	Remote Similarity	NPD2493	Approved
0.6866	Remote Similarity	NPD3816	Phase 1
0.6866	Remote Similarity	NPD3815	Phase 1
0.686	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5156	Approved
0.6852	Remote Similarity	NPD5155	Approved
0.6851	Remote Similarity	NPD4083	Discontinued
0.6851	Remote Similarity	NPD6688	Approved
0.6851	Remote Similarity	NPD6687	Approved
0.6848	Remote Similarity	NPD3885	Approved
0.6848	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6723	Discontinued
0.6839	Remote Similarity	NPD7034	Discontinued
0.6825	Remote Similarity	NPD7291	Discontinued
0.6824	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4107	Approved
0.6818	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3055	Approved
0.6813	Remote Similarity	NPD3053	Approved
0.681	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4002	Approved
0.6802	Remote Similarity	NPD4004	Approved
0.6797	Remote Similarity	NPD595	Approved
0.6797	Remote Similarity	NPD593	Approved
0.6793	Remote Similarity	NPD5095	Phase 3
0.6793	Remote Similarity	NPD3933	Discontinued
0.6793	Remote Similarity	NPD5096	Phase 3
0.6792	Remote Similarity	NPD1669	Approved
0.679	Remote Similarity	NPD2606	Approved
0.679	Remote Similarity	NPD2605	Approved
0.6786	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7262	Phase 1

Structure

CID189470 OpenBabel06191715572D 20 24 0 0 1 0 0 0 0 0999 V2000 3.3828 -0.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5923 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3707 0.9012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7896 -0.0397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1952 3.6286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9823 4.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5720 2.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5993 2.2524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9044 -0.0951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5680 1.3506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1905 2.7107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7774 0.8802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7797 2.7138 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5985 1.3442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9780 2.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9852 1.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1891 0.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7699 3.6275 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2743 0.7357 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 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 10 2 0 0 0 0 4 12 2 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 7 1 6 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	160597
ChEMBL	CHEMBL401798
ZINC

Physicochemical Properties

Molecular Weight:	265.11
ALogP:	-0.4439
MLogP:	3
XLogP:	3.657
# Rotatable Bonds:	0
Polar Surface Area:	30.49
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	20

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