NPASS Natural Product

Natural Product: NPC22481

Natural Product ID:	NPC22481
Common Name:	Atherospermidine
IUPAC Name:
Synonyms:	Atherospermidine; Lanuginosine; Oxoxylopine
Molecular Formula:	C18H11NO4
Standard InCHIKey:	WLXLLQQGGGHOMA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H11NO4/c1-21-10-2-3-11-12(7-10)17(20)16-14-9(4-5-19-16)6-13-18(15(11)14)23-8-22-13/h2-7H,8H2,1H3
Canonical SMILES:	COc1ccc2c(c1)C(=O)c1c3c2c2OCOc2cc3ccn1
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria		UNPD*
NPO10905	Baccharis truncata	Species	Asteraceae	Eukaryota		UNPD*
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota		UNPD*
NPO273	Phyllobates bicolor	Species	Dendrobatidae	Eukaryota		UNPD*
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria		UNPD*
NPO3482	Alpinia flabellata	Species	Zingiberaceae	Eukaryota		UNPD*
NPO22452	Leucanthemum vulgare	Species	Asteraceae	Eukaryota		UNPD*
NPO14329	Sigillina signifera	Species	Polycitoridae	Eukaryota		UNPD*
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota		UNPD*
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria		UNPD*
NPO15514	Pedicularis rex	Species	Orobanchaceae	Eukaryota		UNPD*
NPO9133	Lathyrus latifolius	Species	Fabaceae	Eukaryota		UNPD*
NPO25431	Anthemis cotula	Species	Asteraceae	Eukaryota		UNPD*
NPO1168	Euphorbia sikkimensis	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO8172	Emericellopsis minima	Species	NA	Eukaryota		UNPD*
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota		UNPD*
NPO13617	Eria rigida	Species	Orchidaceae	Eukaryota		UNPD*
NPO1514	Myxine glutinosa	Species	Myxinidae	Eukaryota		UNPD*
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota		UNPD*
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota		UNPD*
NPO20581	Sargassum fulvellum	Species	Sargassaceae	Eukaryota		UNPD*
NPO2043	Pseudocyphellaria coronata	Species	Lobariaceae	Eukaryota		UNPD*
NPO20704	Conus gladiator	Species	Conidae	Eukaryota		UNPD*
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota		UNPD*
NPO20965	Oxytropis lanata	Species	Fabaceae	Eukaryota		UNPD*
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota		UNPD*
NPO20325	Dictyodendrilla cavernosa	Species	Dictyodendrillidae	Eukaryota		UNPD*
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota		UNPD*
NPO4041	Guatteria multivenia	Species	Annonaceae	Eukaryota		UNPD*
NPO25457	Anemone anhuiensis	Species	Ranunculaceae	Eukaryota		UNPD*
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota		UNPD*
NPO6236	Polymastia boletiformis	Species	Polymastiidae	Eukaryota		UNPD*
NPO16788	Syzygium formosanum	Species	Myrtaceae	Eukaryota		UNPD*
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	Stems	PMID[17081761]
NPO2292	Teclea verdoorniana	Species	Rutaceae	Eukaryota		UNPD*
NPO17630	Helenium integrifolium	Species	Asteraceae	Eukaryota		UNPD*
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota		UNPD*
NPO6090	Caulerpa prolifera	Species	Caulerpaceae	Eukaryota		UNPD*
NPO5998	Echinoclathria subhispida	Species	Microcionidae	Eukaryota		UNPD*
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota		UNPD*
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota		UNPD*
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota		UNPD*
NPO13745	Gynoxys verrucosa	Species	Asteraceae	Eukaryota		UNPD*
NPO18026	Bipolaris sacchari	Species	Pleosporaceae	Eukaryota		UNPD*
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota		UNPD*
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota		UNPD*
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota		UNPD*
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota		UNPD*
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota		UNPD*
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota		UNPD*
NPO2680	Holothuria squamifera	Species	Holothuriidae	Eukaryota		UNPD*
NPO25403	Alstonia villosa	Species	Apocynaceae	Eukaryota		UNPD*
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota		UNPD*
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota		UNPD*
NPO4282	Fouquieria diguetii	Species	Fouquieriaceae	Eukaryota		UNPD*
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota		UNPD*
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota		UNPD*
NPO19668.1	Euphorbia characias subsp. wulfenii	Subspecies	Euphorbiaceae	Eukaryota		UNPD*
NPO25612	Polyalthia microtus	Species	Annonaceae	Eukaryota		UNPD*
NPO10358	Bupleurum gerardi	Species	Apiaceae	Eukaryota		UNPD*
NPO17166	Euphorbia palustris	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO11592	Cuphea hyssopifolia	Species	Lythraceae	Eukaryota		UNPD*
NPO19888	Doronicum grandiflorum	Species	Asteraceae	Eukaryota		UNPD*
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota		TCMID*
NPO25346	Eucalyptus cneorifolia	Species	Myrtaceae	Eukaryota		UNPD*
NPO12018	Alternaria bataticola	Species	Pleosporaceae	Eukaryota		UNPD*
NPO8126	Ustilago virens	Species	Ustilaginaceae	Eukaryota		UNPD*
NPO16279	Croptilon divaricatum	Species	Asteraceae	Eukaryota		UNPD*
NPO5725	Stephania dinklagei	Species	Menispermaceae	Eukaryota		TCMID*
NPO5150	Mephitis mephitis	Species	Mephitidae	Eukaryota		UNPD*
NPO25118	Centaurea benedicta	Species	Asteraceae	Eukaryota		UNPD*
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota		UNPD*
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota		UNPD*
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		TCMID*
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota		UNPD*
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota		UNPD*
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota		UNPD*
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota		UNPD*
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota		TCMID*
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota		UNPD*
NPO21780	Strychnos gossweileri	Species	Loganiaceae	Eukaryota		UNPD*
NPO13018	Thelephora aurantiotincta	Species	Thelephoraceae	Eukaryota		UNPD*
NPO21468	Dilophus guineensis	Species	Dictyotaceae	Eukaryota		UNPD*
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota		TCMID*
NPO3371	Podocarpus nubigenus	Species	Podocarpaceae	Eukaryota		UNPD*
NPO7993	Euclea pseudebenus	Species	Ebenaceae	Eukaryota		UNPD*
NPO14455	Triunia erythrocarpa	Species	Proteaceae	Eukaryota		UNPD*
NPO18533	Delisea elegans	Species	Bonnemaisoniaceae	Eukaryota		UNPD*
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota		TCMID*
NPO13730	Magnolia liliiflora	Species	Magnoliaceae	Eukaryota		TCMID*
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota		HerDing*
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota		UNPD*
NPO1798	Duguetia obovata	Species	Annonaceae	Eukaryota		UNPD*
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota		UNPD*
NPO13380	Atherosperma moschatum	Species	Atherospermataceae	Eukaryota		TCMID*
NPO22942	Moesziomyces antarcticus	Species	Ustilaginaceae	Eukaryota		UNPD*
NPO13380	Atherosperma moschatum	Species	Atherospermataceae	Eukaryota		HerDing*
NPO7009	Callyspongia spinosissima	Species	Callyspongiidae	Eukaryota		UNPD*
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota		UNPD*
NPO12223	Stellaria media	Species	Caryophyllaceae	Eukaryota		UNPD*
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota		UNPD*
NPO17358	Sorbus torminalis	Species	Rosaceae	Eukaryota		UNPD*
NPO5725	Stephania dinklagei	Species	Menispermaceae	Eukaryota		HerDing*
NPO15127	Senecio congestus	Species	Asteraceae	Eukaryota		UNPD*
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	Eukaryota		UNPD*
NPO10562	Aglaia archboldiana	Species	Meliaceae	Eukaryota		UNPD*
NPO22436	Lora quadra	NA	NA	NA		UNPD*
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota		UNPD*
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota		UNPD*
NPO22181	Leibnitzia anandria	Species	Asteraceae	Eukaryota		UNPD*
NPO2070	Thioalkalivibrio versutus	Species	Ectothiorhodospiraceae	Bacteria		UNPD*
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota		UNPD*
NPO8721	Parectatosoma mocquerysi	Species	Anisacanthidae	Eukaryota		UNPD*
NPO19709	Pseudocyphellaria australiensis	Species	Lobariaceae	Eukaryota		UNPD*
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota		UNPD*
NPO4563	Clinopodium acinos	Species	Lamiaceae	Eukaryota		UNPD*
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	Eukaryota		UNPD*
NPO3800	Indigofera arrecta	Species	Fabaceae	Eukaryota		UNPD*
NPO18333	Sphaerophysa salsula	Species	Fabaceae	Eukaryota		UNPD*
NPO10048	Pyrus bourgaeana	Species	Rosaceae	Eukaryota		UNPD*
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota		UNPD*
NPO15992	Hypogymnia vittata	Species	Parmeliaceae	Eukaryota		UNPD*
NPO27148	Chuquiraga erinacea	Species	Asteraceae	Eukaryota		UNPD*
NPO2568	Posidonia oceanica	Species	Posidoniaceae	Eukaryota		UNPD*
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota		UNPD*
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota		UNPD*
NPO22545	Plectranthus crassus	Species	Lamiaceae	Eukaryota		UNPD*
NPO22629	Spongia vaginalis	Species	Spongiidae	Eukaryota		UNPD*
NPO13101	Passiflora hybrid	Species	Passifloraceae	Eukaryota		UNPD*
NPO11246	Ononis viscosa	Species	Fabaceae	Eukaryota		UNPD*
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota		UNPD*
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota		UNPD*
NPO17499	Bursera kerberi	Species	Burseraceae	Eukaryota		UNPD*
NPO14194	Mamestra brassicae	Species	Noctuidae	Eukaryota		UNPD*
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota		UNPD*
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota		UNPD*
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota		UNPD*
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota		UNPD*
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota		UNPD*
NPO9538	Pterocarpus erinaceus	Species	Fabaceae	Eukaryota		UNPD*
NPO1909	Michelia lanuginosa	Species	Magnoliaceae	Eukaryota		UNPD*
NPO4973	Cirsium rivulare	Species	Asteraceae	Eukaryota		UNPD*
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota		UNPD*
NPO22498	Lithocarpus haipinii	Species	Fagaceae	Eukaryota		UNPD*
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota		UNPD*
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota		UNPD*
NPO4717	Laserpitium siler	Species	Apiaceae	Eukaryota		UNPD*
NPO23743	Camoensia maxima	Species	Fabaceae	Eukaryota		UNPD*
NPO7002	Ardisia hortorum	Species	Primulaceae	Eukaryota		UNPD*
NPO12769	Hosta sieboldii	Species	Asparagaceae	Eukaryota		UNPD*
NPO15405	Suaeda maritima	Species	Chenopodiaceae	Eukaryota		UNPD*
NPO6698	Euphorbia pithyusa	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO16325	Sideritis dasygnaphala	Species	Lamiaceae	Eukaryota		UNPD*
NPO23897	Lobophytum strictum	Species	Alcyoniidae	Eukaryota		UNPD*
NPO19170	Lasianthaea podocephala	Species	Asteraceae	Eukaryota		UNPD*
NPO10532	Pinus edulis	Species	Pinaceae	Eukaryota		UNPD*
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota		UNPD*
NPO3436	Taraxacum linearisquameum	Species	Asteraceae	Eukaryota		UNPD*

Biological Activity

Activity Type	# Activity
IC50	5
Others	2

Activity Type	# Activity
Cell Line	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	4160	nM	17081761
NPT1076	Cell Line	B-cells		IC50	=	7290	nM	17081761
NPT2	Others	Unspecified		Ratio CC50/IC50	=	3		17081761
NPT2	Others	Unspecified		Ratio CC50/IC50	=	2		17081761
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.8	ug/ml	11575948
NPT2	Others	Unspecified		IC50	=	2.2	ug/ml	11575948
NPT2	Others	Unspecified		IC50	=	45	ug/ml	12088427

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 NPC22481 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	429
0.1-0.2	1928
0.2-0.3	7152
0.3-0.4	5393
0.4-0.5	7538
0.5-0.6	6733
0.6-0.7	1421
0.7-0.8	239
0.8-0.85	33
0.85-0.9	5
0.9-0.95	8
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC189903
0.9856	High Similarity	NPC182907
0.9854	High Similarity	NPC278525
0.9809	High Similarity	NPC108342
0.9623	High Similarity	NPC166722
0.9581	High Similarity	NPC124313
0.9579	High Similarity	NPC207283
0.9579	High Similarity	NPC84164
0.9563	High Similarity	NPC210434
0.9533	High Similarity	NPC210296
0.9476	High Similarity	NPC24019
0.9364	High Similarity	NPC183537
0.9276	High Similarity	NPC77878
0.9209	High Similarity	NPC90875
0.9206	High Similarity	NPC233334
0.913	High Similarity	NPC146976
0.9082	High Similarity	NPC236668
0.9005	High Similarity	NPC15406
0.8852	High Similarity	NPC251160
0.8773	High Similarity	NPC253675
0.8756	High Similarity	NPC470020
0.8596	High Similarity	NPC270515
0.8505	High Similarity	NPC235076
0.8491	Intermediate Similarity	NPC188420
0.8447	Intermediate Similarity	NPC322482
0.8414	Intermediate Similarity	NPC119134
0.8413	Intermediate Similarity	NPC477019
0.8387	Intermediate Similarity	NPC23614
0.8387	Intermediate Similarity	NPC100079
0.8372	Intermediate Similarity	NPC271215
0.8372	Intermediate Similarity	NPC149471
0.8349	Intermediate Similarity	NPC46451
0.8326	Intermediate Similarity	NPC296482
0.8326	Intermediate Similarity	NPC53069
0.8326	Intermediate Similarity	NPC202768
0.8325	Intermediate Similarity	NPC234197
0.8288	Intermediate Similarity	NPC470018
0.8263	Intermediate Similarity	NPC313189
0.8251	Intermediate Similarity	NPC74575
0.8241	Intermediate Similarity	NPC171409
0.8241	Intermediate Similarity	NPC96405
0.8235	Intermediate Similarity	NPC118121
0.8219	Intermediate Similarity	NPC204446
0.8178	Intermediate Similarity	NPC135549
0.8167	Intermediate Similarity	NPC132385
0.8164	Intermediate Similarity	NPC133140
0.8164	Intermediate Similarity	NPC195268
0.8106	Intermediate Similarity	NPC49547
0.8101	Intermediate Similarity	NPC478045
0.8082	Intermediate Similarity	NPC55470
0.8079	Intermediate Similarity	NPC470017
0.8072	Intermediate Similarity	NPC216612
0.8043	Intermediate Similarity	NPC470022
0.8	Intermediate Similarity	NPC476581
0.8	Intermediate Similarity	NPC36229
0.8	Intermediate Similarity	NPC16452
0.7991	Intermediate Similarity	NPC122463
0.7974	Intermediate Similarity	NPC246381
0.7934	Intermediate Similarity	NPC476582
0.7934	Intermediate Similarity	NPC476578
0.7934	Intermediate Similarity	NPC4071
0.786	Intermediate Similarity	NPC31930
0.7839	Intermediate Similarity	NPC208522
0.7824	Intermediate Similarity	NPC137353
0.7783	Intermediate Similarity	NPC220337
0.7763	Intermediate Similarity	NPC308943
0.7754	Intermediate Similarity	NPC72905
0.7748	Intermediate Similarity	NPC202605
0.7748	Intermediate Similarity	NPC112206
0.7738	Intermediate Similarity	NPC290689
0.7722	Intermediate Similarity	NPC142385
0.7721	Intermediate Similarity	NPC23080
0.7721	Intermediate Similarity	NPC193906
0.7685	Intermediate Similarity	NPC5374
0.7669	Intermediate Similarity	NPC41501
0.7665	Intermediate Similarity	NPC174049
0.7642	Intermediate Similarity	NPC94842
0.7635	Intermediate Similarity	NPC134637
0.7602	Intermediate Similarity	NPC193238
0.7602	Intermediate Similarity	NPC222561
0.7588	Intermediate Similarity	NPC54066
0.7564	Intermediate Similarity	NPC471004
0.756	Intermediate Similarity	NPC206201
0.7558	Intermediate Similarity	NPC71124
0.7551	Intermediate Similarity	NPC318068
0.7535	Intermediate Similarity	NPC254957
0.751	Intermediate Similarity	NPC107123
0.751	Intermediate Similarity	NPC303374
0.75	Intermediate Similarity	NPC204385
0.75	Intermediate Similarity	NPC473822
0.749	Intermediate Similarity	NPC129897
0.7489	Intermediate Similarity	NPC122436
0.7478	Intermediate Similarity	NPC232225
0.7466	Intermediate Similarity	NPC207971
0.746	Intermediate Similarity	NPC191489
0.7453	Intermediate Similarity	NPC249405
0.7437	Intermediate Similarity	NPC235685
0.7432	Intermediate Similarity	NPC268077
0.7419	Intermediate Similarity	NPC146724
0.7406	Intermediate Similarity	NPC101350
0.7403	Intermediate Similarity	NPC280799
0.7389	Intermediate Similarity	NPC208284
0.7388	Intermediate Similarity	NPC302807
0.7373	Intermediate Similarity	NPC474688
0.7368	Intermediate Similarity	NPC298449
0.7364	Intermediate Similarity	NPC472061
0.7344	Intermediate Similarity	NPC475844
0.7341	Intermediate Similarity	NPC100734
0.7341	Intermediate Similarity	NPC88923
0.7341	Intermediate Similarity	NPC315634
0.7333	Intermediate Similarity	NPC100573
0.7333	Intermediate Similarity	NPC207873
0.7324	Intermediate Similarity	NPC179704
0.7321	Intermediate Similarity	NPC300156
0.7315	Intermediate Similarity	NPC312531
0.7311	Intermediate Similarity	NPC329631
0.7311	Intermediate Similarity	NPC96584
0.7311	Intermediate Similarity	NPC255800
0.7304	Intermediate Similarity	NPC246658
0.73	Intermediate Similarity	NPC201508
0.73	Intermediate Similarity	NPC260434
0.7296	Intermediate Similarity	NPC477788
0.7296	Intermediate Similarity	NPC144452
0.7273	Intermediate Similarity	NPC148889
0.7269	Intermediate Similarity	NPC124086
0.7269	Intermediate Similarity	NPC13603
0.7269	Intermediate Similarity	NPC478083
0.7265	Intermediate Similarity	NPC1608
0.7264	Intermediate Similarity	NPC287588
0.7257	Intermediate Similarity	NPC82548
0.7257	Intermediate Similarity	NPC90185
0.7251	Intermediate Similarity	NPC473833
0.7249	Intermediate Similarity	NPC162530
0.7249	Intermediate Similarity	NPC266931
0.7249	Intermediate Similarity	NPC324361
0.7246	Intermediate Similarity	NPC478078
0.7244	Intermediate Similarity	NPC45190
0.7238	Intermediate Similarity	NPC312872
0.7238	Intermediate Similarity	NPC172222
0.7231	Intermediate Similarity	NPC253482
0.7229	Intermediate Similarity	NPC475301
0.7229	Intermediate Similarity	NPC169402
0.7229	Intermediate Similarity	NPC85879
0.7229	Intermediate Similarity	NPC53255
0.7229	Intermediate Similarity	NPC473513
0.7229	Intermediate Similarity	NPC326930
0.7217	Intermediate Similarity	NPC207721
0.7217	Intermediate Similarity	NPC237740
0.7215	Intermediate Similarity	NPC274640
0.7213	Intermediate Similarity	NPC475648
0.7212	Intermediate Similarity	NPC4687
0.721	Intermediate Similarity	NPC225279
0.7207	Intermediate Similarity	NPC287437
0.7205	Intermediate Similarity	NPC474428
0.7203	Intermediate Similarity	NPC473506
0.7198	Intermediate Similarity	NPC46561
0.7195	Intermediate Similarity	NPC224928
0.7194	Intermediate Similarity	NPC328928
0.7189	Intermediate Similarity	NPC474009
0.7183	Intermediate Similarity	NPC89549
0.7179	Intermediate Similarity	NPC121069
0.7176	Intermediate Similarity	NPC470042
0.7173	Intermediate Similarity	NPC476110
0.7173	Intermediate Similarity	NPC122968
0.7173	Intermediate Similarity	NPC228377
0.7173	Intermediate Similarity	NPC475600
0.7173	Intermediate Similarity	NPC475631
0.7173	Intermediate Similarity	NPC328186
0.7173	Intermediate Similarity	NPC87152
0.7173	Intermediate Similarity	NPC477787
0.7169	Intermediate Similarity	NPC141915
0.7169	Intermediate Similarity	NPC280964
0.7169	Intermediate Similarity	NPC114335
0.7166	Intermediate Similarity	NPC91868
0.7166	Intermediate Similarity	NPC63971
0.7162	Intermediate Similarity	NPC17677
0.7162	Intermediate Similarity	NPC127085
0.716	Intermediate Similarity	NPC168922
0.7156	Intermediate Similarity	NPC474904
0.7155	Intermediate Similarity	NPC475303
0.7155	Intermediate Similarity	NPC292416
0.7155	Intermediate Similarity	NPC475596
0.7155	Intermediate Similarity	NPC473689
0.7155	Intermediate Similarity	NPC316841
0.7149	Intermediate Similarity	NPC174758
0.7149	Intermediate Similarity	NPC174672
0.7143	Intermediate Similarity	NPC239763
0.7143	Intermediate Similarity	NPC4421
0.7143	Intermediate Similarity	NPC116238
0.7143	Intermediate Similarity	NPC475644
0.7143	Intermediate Similarity	NPC470486
0.7143	Intermediate Similarity	NPC471977
0.7143	Intermediate Similarity	NPC190401
0.7143	Intermediate Similarity	NPC471190
0.7143	Intermediate Similarity	NPC284685
0.7137	Intermediate Similarity	NPC39370
0.7137	Intermediate Similarity	NPC249583
0.7137	Intermediate Similarity	NPC469439
0.7137	Intermediate Similarity	NPC475406
0.7137	Intermediate Similarity	NPC208898

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC22481 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	689
0.2-0.3	960
0.3-0.4	1456
0.4-0.5	2630
0.5-0.6	2238
0.6-0.7	805
0.7-0.8	76
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
0.8349	Intermediate Similarity	NPD3763	Approved
0.8326	Intermediate Similarity	NPD3816	Phase 1
0.8326	Intermediate Similarity	NPD3815	Phase 1
0.8164	Intermediate Similarity	NPD3921	Approved
0.8164	Intermediate Similarity	NPD3923	Approved
0.8164	Intermediate Similarity	NPD3924	Approved
0.8164	Intermediate Similarity	NPD3922	Approved
0.8136	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD8091	Phase 3
0.7713	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6790	Phase 1
0.7668	Intermediate Similarity	NPD7069	Discontinued
0.7639	Intermediate Similarity	NPD4885	Approved
0.7633	Intermediate Similarity	NPD3920	Phase 2
0.7629	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7886	Phase 2
0.7595	Intermediate Similarity	NPD7885	Phase 2
0.7511	Intermediate Similarity	NPD6242	Discontinued
0.746	Intermediate Similarity	NPD7708	Approved
0.7449	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5866	Approved
0.7424	Intermediate Similarity	NPD6568	Discontinued
0.7424	Intermediate Similarity	NPD7395	Discontinued
0.7418	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1483	Discontinued
0.7383	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5805	Approved
0.7341	Intermediate Similarity	NPD7803	Approved
0.7333	Intermediate Similarity	NPD6727	Phase 2
0.7311	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6494	Phase 2
0.7311	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD5488	Discontinued
0.7291	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4889	Approved
0.7276	Intermediate Similarity	NPD5482	Discontinued
0.7273	Intermediate Similarity	NPD4429	Discontinued
0.7265	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4952	Phase 3
0.7243	Intermediate Similarity	NPD6716	Phase 1
0.7231	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5429	Discontinued
0.7185	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4373	Phase 2
0.7162	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4989	Phase 2
0.7143	Intermediate Similarity	NPD7955	Approved
0.7143	Intermediate Similarity	NPD7956	Approved
0.7137	Intermediate Similarity	NPD8479	Phase 2
0.7137	Intermediate Similarity	NPD6964	Approved
0.7137	Intermediate Similarity	NPD7588	Discontinued
0.7137	Intermediate Similarity	NPD6963	Approved
0.7124	Intermediate Similarity	NPD3354	Phase 2
0.7118	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5914	Approved
0.7115	Intermediate Similarity	NPD6228	Discontinued
0.7113	Intermediate Similarity	NPD5022	Discontinued
0.7105	Intermediate Similarity	NPD5658	Approved
0.7104	Intermediate Similarity	NPD4418	Discontinued
0.7102	Intermediate Similarity	NPD6517	Phase 3
0.7101	Intermediate Similarity	NPD3259	Approved
0.708	Intermediate Similarity	NPD5513	Phase 2
0.7076	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7417	Discontinued
0.7059	Intermediate Similarity	NPD7426	Phase 1
0.7048	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6531	Approved
0.7047	Intermediate Similarity	NPD6530	Approved
0.7046	Intermediate Similarity	NPD7278	Phase 2
0.7046	Intermediate Similarity	NPD7279	Phase 2
0.7045	Intermediate Similarity	NPD6230	Discontinued
0.7031	Intermediate Similarity	NPD4859	Phase 1
0.7027	Intermediate Similarity	NPD5459	Phase 2
0.7023	Intermediate Similarity	NPD3217	Phase 2
0.7022	Intermediate Similarity	NPD6219	Discontinued
0.7021	Intermediate Similarity	NPD5519	Discontinued
0.7018	Intermediate Similarity	NPD7010	Phase 3
0.7016	Intermediate Similarity	NPD6460	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6962	Phase 2
0.6996	Remote Similarity	NPD3257	Approved
0.6979	Remote Similarity	NPD5632	Approved
0.6967	Remote Similarity	NPD5891	Approved
0.6966	Remote Similarity	NPD8149	Discontinued
0.6962	Remote Similarity	NPD4923	Phase 1
0.696	Remote Similarity	NPD4558	Phase 2
0.6958	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7994	Phase 2
0.6957	Remote Similarity	NPD7467	Discontinued
0.6951	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8016	Phase 3
0.6943	Remote Similarity	NPD5530	Phase 1
0.6938	Remote Similarity	NPD5450	Discontinued
0.6937	Remote Similarity	NPD6569	Phase 2
0.6933	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6281	Approved
0.692	Remote Similarity	NPD7180	Phase 3
0.692	Remote Similarity	NPD5850	Phase 3
0.6913	Remote Similarity	NPD7222	Phase 2
0.691	Remote Similarity	NPD7225	Discontinued
0.6902	Remote Similarity	NPD7169	Suspended
0.6901	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3006	Discontinued
0.6892	Remote Similarity	NPD2334	Discontinued
0.6885	Remote Similarity	NPD7925	Phase 2
0.6885	Remote Similarity	NPD7924	Phase 2
0.688	Remote Similarity	NPD8100	Phase 3
0.6878	Remote Similarity	NPD3258	Approved
0.6878	Remote Similarity	NPD7233	Approved
0.6878	Remote Similarity	NPD7234	Approved
0.6875	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5601	Phase 2
0.686	Remote Similarity	NPD7555	Discontinued
0.6851	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3263	Phase 3
0.6844	Remote Similarity	NPD5512	Phase 3
0.6835	Remote Similarity	NPD3386	Phase 2
0.6833	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7567	Approved
0.683	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.683	Remote Similarity	NPD1038	Approved
0.6829	Remote Similarity	NPD7853	Phase 2
0.6822	Remote Similarity	NPD5612	Discontinued
0.6818	Remote Similarity	NPD4328	Approved
0.6818	Remote Similarity	NPD4845	Discontinued
0.6816	Remote Similarity	NPD7558	Phase 2
0.6813	Remote Similarity	NPD8468	Phase 2
0.6808	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8101	Phase 3
0.6797	Remote Similarity	NPD2060	Approved
0.6795	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2780	Approved
0.6792	Remote Similarity	NPD2782	Approved
0.6789	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3328	Phase 2
0.6786	Remote Similarity	NPD8358	Approved
0.6784	Remote Similarity	NPD8463	Approved
0.6784	Remote Similarity	NPD5532	Phase 2
0.678	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5479	Discontinued
0.6759	Remote Similarity	NPD8102	Discontinued
0.6754	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6987	Phase 1
0.6753	Remote Similarity	NPD3947	Discontinued
0.6753	Remote Similarity	NPD4795	Phase 2
0.6753	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD3394	Approved
0.6751	Remote Similarity	NPD3393	Approved
0.6751	Remote Similarity	NPD3389	Approved
0.675	Remote Similarity	NPD6298	Discontinued
0.6745	Remote Similarity	NPD7859	Phase 2
0.6742	Remote Similarity	NPD7689	Approved
0.6738	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3945	Discontinued
0.6736	Remote Similarity	NPD3925	Approved
0.6735	Remote Similarity	NPD1505	Phase 2
0.6729	Remote Similarity	NPD2781	Approved
0.6725	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7673	Phase 3
0.6712	Remote Similarity	NPD4375	Approved
0.6711	Remote Similarity	NPD5071	Phase 2
0.6709	Remote Similarity	NPD5902	Approved
0.6709	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5903	Approved
0.6709	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5930	Phase 3
0.6708	Remote Similarity	NPD5640	Discontinued
0.6707	Remote Similarity	NPD6825	Phase 1
0.6706	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7453	Approved
0.6695	Remote Similarity	NPD7452	Approved
0.6694	Remote Similarity	NPD1659	Phase 1
0.6692	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4035	Approved
0.6681	Remote Similarity	NPD4122	Approved
0.6681	Remote Similarity	NPD2778	Approved
0.6681	Remote Similarity	NPD4038	Approved
0.6681	Remote Similarity	NPD4034	Approved
0.6681	Remote Similarity	NPD4033	Approved
0.6681	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD31	Approved
0.6681	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4037	Approved
0.6681	Remote Similarity	NPD32	Approved
0.6681	Remote Similarity	NPD5901	Discontinued
0.6681	Remote Similarity	NPD4039	Approved

Structure

CID22481 OpenBabel06191715352D 23 27 0 0 0 0 0 0 0 0999 V2000 -4.2358 1.3926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 0.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8084 0.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1973 -3.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9926 -4.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6056 -2.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4061 -0.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9139 0.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1925 -2.7392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4184 0.0189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7961 -0.8894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5950 -1.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6048 -1.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9883 -2.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9955 -1.3516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7984 -2.7423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5990 -2.2801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1911 -0.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7885 -3.6657 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3999 -2.7401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2237 0.4697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2877 -0.7434 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 19 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	97622
ChEMBL	CHEMBL389400
ZINC

Physicochemical Properties

Molecular Weight:	305.07
ALogP:	-0.6183
MLogP:	2.89
XLogP:	2.198
# Rotatable Bonds:	2
Polar Surface Area:	57.65
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	23

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