NPASS Natural Product

Natural Product: NPC67037

Natural Product ID:	NPC67037
Common Name:	Avicularin
IUPAC Name:	3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:	Avicularin
Molecular Formula:	C20H18O11
Standard InCHIKey:	BDCDNTVZSILEOY-UXYNSRGZSA-N
Standard InCHI:	InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1
Canonical SMILES:	OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Reference
NPO13919	Agathis microstachya	Species	Araucariaceae	Eukaryota			UNPD*
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota			UNPD*
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	Leaves		DOI[10.1002/ardp.19542870405]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota			UNPD*
NPO20658	Lonicera caerulea	Species	Caprifoliaceae	Eukaryota			UNPD*
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota			UNPD*
NPO13854	Prunus serotina	Species	Rosaceae	Eukaryota			ACTA POLONIAE PHARMACEUTICA - DRUG RESEARCH,2005,62(2): 127
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota			TM-MC*
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota			UNPD*
NPO22730	Indigofera spicata	Species	Fabaceae	Eukaryota			UNPD*
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaves		CHINESE PHARMACEUTICAL JOURNAL,2009,44(7): 496
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota			TM-MC*
NPO26900	Vallota purpurea	NA	NA	NA			UNPD*
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota			UNPD*
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	Whole Plants		DOI[10.1007/BF02329610]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota			TM-MC*
NPO28241	Agelas conifera	Species	Agelasidae	Eukaryota			UNPD*
NPO3374	Pestalotiopsis guepinii	Species	Sporocadaceae	Eukaryota			UNPD*
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota			PMID[14600382]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota			TM-MC*
NPO28498	Fusarium roseum	Species	Nectriaceae	Eukaryota			UNPD*
NPO9097	Solanum hypomalacophyllum	Species	Solanaceae	Eukaryota			UNPD*
NPO2768	Berchemia floribunda	Species	Rhamnaceae	Eukaryota			DOI[10.1002/cbdv.200690067]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota			TM-MC*
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	Leaves		DOI[10.1016/S0031-9422(00)94055-X]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota			TM-MC*
NPO28834	Anabaena minutissima	Species	Nostocaceae	Bacteria			UNPD*
NPO28546	Entomophthora virulenta	Species	Entomophthoraceae	Eukaryota			UNPD*
NPO29847	Reynoutria sachalinensis	Species	Polygonaceae	Eukaryota	Flowers		DOI[10.1007/BF02975130]
NPO28815	Phycopsis terpnis	Species	Bubaridae	Eukaryota			UNPD*
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota			UNPD*
NPO11384	Tibouchina semidecandra	Species	Melastomataceae	Eukaryota			UNPD*
NPO30277	Hypericum hyssopifolium	Species	Hypericaceae	Eukaryota	Aerial parts		PMID[12787957]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota			TCMID*
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota			UNPD*
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota			UNPD*
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria			UNPD*
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	Whole Plants		DOI[10.1016/S1572-557X(05)02007-6]
NPO4425	Delphinium honanense	Species	Ranunculaceae	Eukaryota			UNPD*
NPO13415	Securigera coronilla	Species	Romaleidae	Eukaryota			UNPD*
NPO2679	Dictyota bartayresiana	Species	Dictyotaceae	Eukaryota			UNPD*
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota			UNPD*
NPO30630.1	Vaccinium vitisidaea var. minus	Varieties	Ericaceae	Eukaryota	Leaves		PMID[17177509]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota			UNPD*
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota			UNPD*
NPO5633	Osyris abyssinica	Species	Santalaceae	Eukaryota			UNPD*
NPO12771	Eucalyptus alba	Species	Myrtaceae	Eukaryota			UNPD*
NPO31296	Rhododendron brachycarpum	Species	Ericaceae	Eukaryota	Leaves		DOI[10.1007/BF02856638]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota			UNPD*
NPO12431	Cytospora rhizophorae	Species	Valsaceae	Eukaryota			UNPD*
NPO4165	Chrysocoma tenuifolia	Species	Asteraceae	Eukaryota			UNPD*
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Leaves		DOI[10.1016/j.foodchem.2010.03.088]
NPO4922	Asphodelus albus	Species	Xanthorrhoeaceae	Eukaryota			UNPD*
NPO9860.2	Pinus brutia var. pityusa	Varieties	Pinaceae	Eukaryota			UNPD*
NPO25482	Phyllogeiton zeyheri	NA	NA	NA			UNPD*
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota			UNPD*
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	Twigs		PMID[9179367]
NPO29081	Plantago bellardi	Species	Plantaginaceae	Eukaryota			UNPD*
NPO23780	Psoroma crassum	Species	Pannariaceae	Eukaryota			UNPD*
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota			UNPD*
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota			UNPD*
NPO8284	Pyrola elliptica	Species	Ericaceae	Eukaryota			DOI[10.1016/S0031-9422(97)00878-9]
NPO13625	Salacia beddomei	Species	Celastraceae	Eukaryota			UNPD*
NPO28041	Scaevola taccada	Species	Goodeniaceae	Eukaryota			UNPD*
NPO6238	Pseudo-nitzschia multiseries	Species	Bacillariaceae	Eukaryota			UNPD*
NPO1889	Panorpa japonica	Species	Panorpidae	Eukaryota			UNPD*
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota			UNPD*
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota			UNPD*
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota			UNPD*
NPO26828	Barbarea verna	Species	Brassicaceae	Eukaryota			UNPD*
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota			UNPD*
NPO11569	Hypsizygus ulmarius	Species	Lyophyllaceae	Eukaryota			UNPD*
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota			UNPD*
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota			UNPD*
NPO10049	Coleophoma empetri	Species	NA	Eukaryota			UNPD*
NPO24162	Erysimum canescens	Species	Brassicaceae	Eukaryota			UNPD*
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota			UNPD*
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota		Uzbekistan	PMID[15568778]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota			UNPD*
NPO2201	Orthocaulis attenuatus	Species	Anastrophyllaceae	Eukaryota			UNPD*
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota			UNPD*
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota			UNPD*
NPO25896	Bragantia wallichii	NA	NA	NA			UNPD*
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota			UNPD*
NPO969	Streptomyces setonensis	Species	Streptomycetaceae	Bacteria			UNPD*
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota			UNPD*
NPO10422	Penicillium thymicola	Species	Aspergillaceae	Eukaryota			UNPD*
NPO12926	Dendrospora tenella	Species	NA	Eukaryota			UNPD*
NPO6750	Kitaibelia vitifolia	NA	NA	NA			UNPD*
NPO3784	Saccharopolyspora spinosa	Species	Pseudonocardiaceae	Bacteria			UNPD*
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota			UNPD*
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota			UNPD*
NPO7310	Corchorus trilocularis	Species	Malvaceae	Eukaryota			UNPD*
NPO13091	Helianthus ciliaris	Species	Asteraceae	Eukaryota			UNPD*
NPO6594	Hypericum sikokumontanum	Species	Hypericaceae	Eukaryota			UNPD*
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota			UNPD*
NPO25532	Blitum virgatum	Species	Chenopodiaceae	Eukaryota			UNPD*
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota			UNPD*
NPO26183	Scabiosa pyrenaica	Species	Caprifoliaceae	Eukaryota			UNPD*
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota			UNPD*
NPO13518	Senecio stabianus	Species	Asteraceae	Eukaryota			UNPD*
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota			UNPD*
NPO673	Peyssonnelia caulifera	Species	Peyssonneliaceae	Eukaryota			UNPD*
NPO29573	Saururi herba	NA	NA	NA			TCMSP*
NPO12245	Lasiosiphon burchellii	Species	Thymelaeaceae	Eukaryota			UNPD*
NPO28199	Sargassum thunbergii	Species	Sargassaceae	Eukaryota			UNPD*
NPO29641	Rhododendri daurici folium	NA	NA	NA			TCMSP*
NPO40	Ostryopsis davidiana	Species	Betulaceae	Eukaryota			UNPD*
NPO28629	Hedeoma multiflora	Species	Lamiaceae	Eukaryota			UNPD*
NPO28357	Astragali cpmplanatisemen	NA	NA	NA			TCMSP*
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota			UNPD*
NPO24551	Sclerotinia fructicola	Species	Sclerotiniaceae	Eukaryota			UNPD*
NPO29616	Polygoni avicularis herba	NA	NA	NA			TCMSP*
NPO4698	Polymnia uvedalia	Species	Asteraceae	Eukaryota			UNPD*
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota			UNPD*
NPO29694	Mori cortex	NA	NA	NA			TCMSP*
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota			UNPD*
NPO10700	Filipendula ulmaria	Species	Rosaceae	Eukaryota	Leaves		DOI[10.1007/s10600-006-0064-z]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota			TM-MC*

Biological Activity

Activity Type	# Activity
IC50	10
Others	6

Activity Type	# Activity
Cell Line	2
Individual Protein	3
Organism	3
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	30.8	%	3379415
NPT2	Others	Unspecified		Activity	=	0		8882428
NPT1585	Organism	Microcystis aeruginosa	Microcystis aeruginosa	IC50	=	180000	nM	10.1021/np50066a004
NPT1586	Organism	Anabaena flos-aquae	Dolichospermum flos-aquae	IC50	=	28000	nM	10.1021/np50066a004
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	19050	nM	22261024
NPT3141	Individual Protein	Fatty acid synthase	Gallus gallus	IC50	=	6150	nM	21726077
NPT1724	Organism	Dengue virus	Dengue virus	IC50	=	1700	nM	25305334
NPT2	Others	Unspecified		IC50	>	10	ug/ml	25862199
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10	ug/ml	25862199
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10	ug/ml	25862199
NPT1	Others	Radical scavenging activity		IC50	=	16.13	ug/ml	25862199
NPT2	Others	Unspecified		IC50	=	6.9	ug/ml	25862199
NPT2	Others	Unspecified		Activity	=	123.88	umol/ml	25862199
NPT2	Others	Unspecified		Activity	=	0.269	umol/ml	25862199
NPT2	Others	Unspecified		Activity	=	291.63	umol/ml	25862199
NPT2	Others	Unspecified		Activity	=	324.58	umol/ml	25862199

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 NPC67037 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	325
0.1-0.2	1239
0.2-0.3	2668
0.3-0.4	6090
0.4-0.5	6536
0.5-0.6	3142
0.6-0.7	3455
0.7-0.8	4481
0.8-0.85	1631
0.85-0.9	863
0.9-0.95	378
0.95-1	81

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC255615
0.9936	High Similarity	NPC34531
0.9873	High Similarity	NPC254306
0.981	High Similarity	NPC149244
0.981	High Similarity	NPC48640
0.975	High Similarity	NPC245452
0.9748	High Similarity	NPC476771
0.9747	High Similarity	NPC118284
0.9747	High Similarity	NPC281131
0.9747	High Similarity	NPC88789
0.9747	High Similarity	NPC145038
0.9747	High Similarity	NPC274618
0.9747	High Similarity	NPC276222
0.9747	High Similarity	NPC253662
0.9747	High Similarity	NPC179950
0.9747	High Similarity	NPC56077
0.9747	High Similarity	NPC308404
0.9688	High Similarity	NPC72249
0.9686	High Similarity	NPC173637
0.9686	High Similarity	NPC127546
0.9686	High Similarity	NPC52550
0.9686	High Similarity	NPC84362
0.9686	High Similarity	NPC223424
0.9686	High Similarity	NPC317489
0.9684	High Similarity	NPC240431
0.9684	High Similarity	NPC277205
0.9684	High Similarity	NPC55786
0.9684	High Similarity	NPC19388
0.9627	High Similarity	NPC476772
0.9625	High Similarity	NPC219904
0.9625	High Similarity	NPC120099
0.9625	High Similarity	NPC223747
0.9625	High Similarity	NPC225434
0.9625	High Similarity	NPC203050
0.9623	High Similarity	NPC197285
0.9623	High Similarity	NPC21100
0.9623	High Similarity	NPC135599
0.9623	High Similarity	NPC113968
0.9623	High Similarity	NPC277174
0.9623	High Similarity	NPC328940
0.9623	High Similarity	NPC73855
0.9571	High Similarity	NPC154741
0.9571	High Similarity	NPC296018
0.9565	High Similarity	NPC235260
0.9565	High Similarity	NPC255157
0.9565	High Similarity	NPC20505
0.9565	High Similarity	NPC206123
0.9565	High Similarity	NPC155763
0.9565	High Similarity	NPC254855
0.9565	High Similarity	NPC67326
0.9565	High Similarity	NPC29958
0.9565	High Similarity	NPC156869
0.9565	High Similarity	NPC259896
0.9565	High Similarity	NPC244776
0.9565	High Similarity	NPC95866
0.9565	High Similarity	NPC116864
0.9565	High Similarity	NPC136042
0.9563	High Similarity	NPC160156
0.9563	High Similarity	NPC92565
0.9563	High Similarity	NPC265530
0.9563	High Similarity	NPC226304
0.9563	High Similarity	NPC325555
0.9557	High Similarity	NPC77660
0.9557	High Similarity	NPC189142
0.9551	High Similarity	NPC288084
0.9512	High Similarity	NPC476773
0.9506	High Similarity	NPC33054
0.9506	High Similarity	NPC176740
0.9506	High Similarity	NPC471748
0.9506	High Similarity	NPC26230
0.9506	High Similarity	NPC153755
0.9506	High Similarity	NPC203259
0.9506	High Similarity	NPC155877
0.9506	High Similarity	NPC190003
0.9506	High Similarity	NPC60735
0.9506	High Similarity	NPC175107
0.9506	High Similarity	NPC134532
0.9506	High Similarity	NPC471725
0.9503	High Similarity	NPC52382
0.9503	High Similarity	NPC138927
0.9503	High Similarity	NPC270578
0.9497	High Similarity	NPC168822
0.9497	High Similarity	NPC19709
0.9497	High Similarity	NPC270335
0.9497	High Similarity	NPC191306
0.9448	High Similarity	NPC45522
0.9448	High Similarity	NPC24043
0.9448	High Similarity	NPC169977
0.9448	High Similarity	NPC101026
0.9448	High Similarity	NPC4390
0.9448	High Similarity	NPC42773
0.9448	High Similarity	NPC21666
0.9444	High Similarity	NPC245014
0.9444	High Similarity	NPC67105
0.9444	High Similarity	NPC282987
0.9444	High Similarity	NPC84265
0.9444	High Similarity	NPC285197
0.9441	High Similarity	NPC76482
0.9441	High Similarity	NPC275454
0.9437	High Similarity	NPC311830
0.9437	High Similarity	NPC22832
0.9434	High Similarity	NPC127782
0.9434	High Similarity	NPC473043
0.9434	High Similarity	NPC300537
0.9398	High Similarity	NPC473071
0.9398	High Similarity	NPC473073
0.939	High Similarity	NPC294629
0.939	High Similarity	NPC135277
0.939	High Similarity	NPC16194
0.939	High Similarity	NPC49344
0.939	High Similarity	NPC34267
0.939	High Similarity	NPC294815
0.939	High Similarity	NPC214621
0.939	High Similarity	NPC223426
0.939	High Similarity	NPC19108
0.939	High Similarity	NPC210094
0.939	High Similarity	NPC220173
0.939	High Similarity	NPC237435
0.939	High Similarity	NPC253685
0.939	High Similarity	NPC43211
0.939	High Similarity	NPC81042
0.939	High Similarity	NPC476472
0.939	High Similarity	NPC473327
0.939	High Similarity	NPC115760
0.939	High Similarity	NPC101191
0.9387	High Similarity	NPC476405
0.9387	High Similarity	NPC117260
0.9387	High Similarity	NPC235575
0.9383	High Similarity	NPC227508
0.9379	High Similarity	NPC8856
0.9379	High Similarity	NPC115674
0.9379	High Similarity	NPC210073
0.9375	High Similarity	NPC29830
0.9375	High Similarity	NPC88043
0.9375	High Similarity	NPC284960
0.9375	High Similarity	NPC243930
0.9375	High Similarity	NPC88023
0.9375	High Similarity	NPC309025
0.9375	High Similarity	NPC222936
0.9341	High Similarity	NPC473072
0.9333	High Similarity	NPC65563
0.9333	High Similarity	NPC472385
0.9333	High Similarity	NPC471669
0.9333	High Similarity	NPC89127
0.9333	High Similarity	NPC292019
0.9333	High Similarity	NPC144097
0.9333	High Similarity	NPC219043
0.9333	High Similarity	NPC14187
0.9333	High Similarity	NPC198324
0.9333	High Similarity	NPC202908
0.9333	High Similarity	NPC470949
0.9333	High Similarity	NPC122467
0.9333	High Similarity	NPC8573
0.9333	High Similarity	NPC61904
0.9325	High Similarity	NPC212748
0.9321	High Similarity	NPC229729
0.9321	High Similarity	NPC42892
0.9321	High Similarity	NPC58716
0.9321	High Similarity	NPC45618
0.9321	High Similarity	NPC146792
0.9317	High Similarity	NPC165720
0.9313	High Similarity	NPC150164
0.9308	High Similarity	NPC269906
0.9304	High Similarity	NPC78263
0.9304	High Similarity	NPC133671
0.9304	High Similarity	NPC135391
0.9304	High Similarity	NPC197304
0.9304	High Similarity	NPC77672
0.9304	High Similarity	NPC54802
0.9277	High Similarity	NPC217520
0.9277	High Similarity	NPC139571
0.9277	High Similarity	NPC173837
0.9277	High Similarity	NPC35167
0.9277	High Similarity	NPC251417
0.9277	High Similarity	NPC113836
0.9277	High Similarity	NPC89052
0.9277	High Similarity	NPC37668
0.9277	High Similarity	NPC168584
0.9277	High Similarity	NPC253521
0.9273	High Similarity	NPC472607
0.9273	High Similarity	NPC264735
0.9273	High Similarity	NPC477848
0.9268	High Similarity	NPC261254
0.9264	High Similarity	NPC45638
0.9264	High Similarity	NPC195257
0.9264	High Similarity	NPC186807
0.9264	High Similarity	NPC469931
0.9264	High Similarity	NPC226294
0.9264	High Similarity	NPC475942
0.9264	High Similarity	NPC93337
0.9264	High Similarity	NPC201292
0.9264	High Similarity	NPC209296
0.9264	High Similarity	NPC105025
0.9264	High Similarity	NPC86008
0.9264	High Similarity	NPC58053
0.9259	High Similarity	NPC236934
0.9259	High Similarity	NPC5778
0.925	High Similarity	NPC182045
0.9245	High Similarity	NPC472459
0.9245	High Similarity	NPC41121

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC67037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	839
0.2-0.3	1827
0.3-0.4	2612
0.4-0.5	1919
0.5-0.6	1027
0.6-0.7	439
0.7-0.8	126
0.8-0.85	22
0.85-0.9	11
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9563	High Similarity	NPD3818	Discontinued
0.9506	High Similarity	NPD6797	Phase 2
0.9448	High Similarity	NPD7251	Discontinued
0.939	High Similarity	NPD4338	Clinical (unspecified phase)
0.9273	High Similarity	NPD7808	Phase 3
0.9264	High Similarity	NPD7054	Approved
0.9207	High Similarity	NPD7472	Approved
0.9091	High Similarity	NPD7074	Phase 3
0.9062	High Similarity	NPD4381	Clinical (unspecified phase)
0.9	High Similarity	NPD3882	Suspended
0.8938	High Similarity	NPD3817	Phase 2
0.8916	High Similarity	NPD7804	Clinical (unspecified phase)
0.891	High Similarity	NPD1512	Approved
0.8848	High Similarity	NPD6168	Clinical (unspecified phase)
0.8848	High Similarity	NPD6167	Clinical (unspecified phase)
0.8848	High Similarity	NPD6166	Phase 2
0.8812	High Similarity	NPD1934	Approved
0.8782	High Similarity	NPD1511	Approved
0.8758	High Similarity	NPD2801	Approved
0.8758	High Similarity	NPD2393	Clinical (unspecified phase)
0.8538	High Similarity	NPD6559	Discontinued
0.8485	Intermediate Similarity	NPD7075	Discontinued
0.8476	Intermediate Similarity	NPD5402	Approved
0.8466	Intermediate Similarity	NPD6801	Discontinued
0.8457	Intermediate Similarity	NPD4380	Phase 2
0.8424	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5403	Approved
0.8375	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6799	Approved
0.8303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5401	Approved
0.8165	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1549	Phase 2
0.811	Intermediate Similarity	NPD1653	Approved
0.8059	Intermediate Similarity	NPD5494	Approved
0.8049	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8012	Intermediate Similarity	NPD7199	Phase 2
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD919	Approved
0.7989	Intermediate Similarity	NPD3751	Discontinued
0.7987	Intermediate Similarity	NPD2796	Approved
0.7965	Intermediate Similarity	NPD3787	Discontinued
0.7912	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD1247	Approved
0.7895	Intermediate Similarity	NPD6234	Discontinued
0.787	Intermediate Similarity	NPD7819	Suspended
0.7861	Intermediate Similarity	NPD6232	Discontinued
0.7853	Intermediate Similarity	NPD6190	Approved
0.7829	Intermediate Similarity	NPD7473	Discontinued
0.7824	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD3926	Phase 2
0.7811	Intermediate Similarity	NPD37	Approved
0.7809	Intermediate Similarity	NPD7685	Pre-registration
0.7785	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1613	Approved
0.7784	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4965	Approved
0.7765	Intermediate Similarity	NPD1465	Phase 2
0.7758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7411	Suspended
0.774	Intermediate Similarity	NPD5844	Phase 1
0.7735	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6959	Discontinued
0.7683	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD943	Approved
0.7673	Intermediate Similarity	NPD1240	Approved
0.7669	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7578	Intermediate Similarity	NPD1607	Approved
0.7576	Intermediate Similarity	NPD3750	Approved
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3749	Approved
0.7526	Intermediate Similarity	NPD6779	Approved
0.7526	Intermediate Similarity	NPD6781	Approved
0.7526	Intermediate Similarity	NPD6778	Approved
0.7526	Intermediate Similarity	NPD6776	Approved
0.7526	Intermediate Similarity	NPD6782	Approved
0.7526	Intermediate Similarity	NPD6777	Approved
0.7526	Intermediate Similarity	NPD6780	Approved
0.7516	Intermediate Similarity	NPD230	Phase 1
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3027	Phase 3
0.7474	Intermediate Similarity	NPD7584	Approved
0.7472	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD920	Approved
0.741	Intermediate Similarity	NPD2800	Approved
0.7407	Intermediate Similarity	NPD1933	Approved
0.7405	Intermediate Similarity	NPD8434	Phase 2
0.7396	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7768	Phase 2
0.7356	Intermediate Similarity	NPD8455	Phase 2
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.7322	Intermediate Similarity	NPD7240	Approved
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7698	Approved
0.731	Intermediate Similarity	NPD8151	Discontinued
0.7305	Intermediate Similarity	NPD1243	Approved
0.7305	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD447	Suspended
0.7282	Intermediate Similarity	NPD7871	Phase 2
0.7282	Intermediate Similarity	NPD7870	Phase 2
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD3748	Approved
0.7263	Intermediate Similarity	NPD6535	Approved
0.7263	Intermediate Similarity	NPD6534	Approved
0.7259	Intermediate Similarity	NPD7701	Phase 2
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD1091	Approved
0.7195	Intermediate Similarity	NPD6355	Discontinued
0.7193	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2344	Approved
0.7182	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6233	Phase 2
0.7174	Intermediate Similarity	NPD5953	Discontinued
0.715	Intermediate Similarity	NPD7700	Phase 2
0.715	Intermediate Similarity	NPD7801	Approved
0.715	Intermediate Similarity	NPD7783	Phase 2
0.715	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7699	Phase 2
0.7126	Intermediate Similarity	NPD3226	Approved
0.7125	Intermediate Similarity	NPD1203	Approved
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.7107	Intermediate Similarity	NPD8319	Approved
0.7107	Intermediate Similarity	NPD8320	Phase 1
0.7104	Intermediate Similarity	NPD2163	Approved
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7092	Intermediate Similarity	NPD6823	Phase 2
0.7088	Intermediate Similarity	NPD2403	Approved
0.7085	Intermediate Similarity	NPD7585	Approved
0.7081	Intermediate Similarity	NPD2798	Approved
0.7077	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7286	Phase 2
0.7051	Intermediate Similarity	NPD1548	Phase 1
0.7048	Intermediate Similarity	NPD6651	Approved
0.7037	Intermediate Similarity	NPD9494	Approved
0.7037	Intermediate Similarity	NPD8150	Discontinued
0.7035	Intermediate Similarity	NPD7583	Approved
0.7029	Intermediate Similarity	NPD7458	Discontinued
0.7026	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6100	Approved
0.7024	Intermediate Similarity	NPD6099	Approved
0.7019	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2309	Approved
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1652	Phase 2
0.6995	Remote Similarity	NPD4363	Phase 3
0.6995	Remote Similarity	NPD4360	Phase 2
0.6988	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5710	Approved
0.6978	Remote Similarity	NPD5711	Approved
0.697	Remote Similarity	NPD7680	Approved
0.6964	Remote Similarity	NPD2799	Discontinued
0.6961	Remote Similarity	NPD7930	Approved
0.6959	Remote Similarity	NPD4361	Phase 2
0.6959	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD9269	Phase 2
0.6936	Remote Similarity	NPD7390	Discontinued
0.6931	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5006	Approved
0.6919	Remote Similarity	NPD5005	Approved
0.691	Remote Similarity	NPD6844	Discontinued
0.6909	Remote Similarity	NPD3268	Approved
0.6901	Remote Similarity	NPD2654	Approved
0.6901	Remote Similarity	NPD6674	Discontinued
0.689	Remote Similarity	NPD4908	Phase 1
0.6886	Remote Similarity	NPD4340	Discontinued
0.6885	Remote Similarity	NPD7229	Phase 3
0.6882	Remote Similarity	NPD2346	Discontinued
0.6875	Remote Similarity	NPD1610	Phase 2
0.6875	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD4062	Phase 3
0.6864	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6398	Clinical (unspecified phase)

Structure

CID67037 OpenBabel06191715402D 31 34 0 0 1 0 0 0 0 0999 V2000 -3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2514 1.4476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -5.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8185 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 2.5227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -2.5933 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 -1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 21 1 0 0 0 0 7 18 1 0 0 0 0 8 22 1 0 0 0 0 9 10 2 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 29 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 1 0 0 0 16 19 1 0 0 0 0 16 27 2 0 0 0 0 17 20 1 0 0 0 0 17 28 1 6 0 0 0 18 19 2 0 0 0 0 18 29 1 0 0 0 0 19 31 1 0 0 0 0 20 30 1 0 0 0 0 20 31 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	5490064
ChEMBL	CHEMBL471282
ZINC

Physicochemical Properties

Molecular Weight:	434.08
ALogP:	-4.3814
MLogP:	2.45
XLogP:	-0.111
# Rotatable Bonds:	11
Polar Surface Area:	186.37
# H-Bond Aceptor:	6
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	31

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