NPASS Natural Product

Natural Product: NPC143799

Natural Product ID:	NPC143799
Common Name:	Rhamnocitrin
IUPAC Name:	3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
Synonyms:	Rhamnocitrin
Molecular Formula:	C16H12O6
Standard InCHIKey:	MQSZRBPYXNEFHF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3
Canonical SMILES:	COc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccc(cc1)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO18345	Phora velutina	Species	Phoridae	Eukaryota		UNPD*
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota		UNPD*
NPO18163	Aulosira fertilissima	Species	Fortieaceae	Bacteria		UNPD*
NPO19832	Gambierdiscus toxicus	Species	Goniodomataceae	Eukaryota		UNPD*
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota		TCMID*
NPO23961	Scytonema ocellatum	Species	Scytonemataceae	Bacteria		UNPD*
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota		UNPD*
NPO22455	Corydalis sewerzowi	Species	Papaveraceae	Eukaryota		UNPD*
NPO18422	Stizolobium deeringianum	NA	NA	NA		UNPD*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota		HerDing*
NPO23696	Solanum diflorum	Species	Solanaceae	Eukaryota		UNPD*
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria		UNPD*
NPO20998	Machaerium kuhlmannii	Species	Dolichopodidae	Eukaryota		UNPD*
NPO26532	Gmelina asiatica	Species	Lamiaceae	Eukaryota		UNPD*
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota		HerDing*
NPO23884	Hippobroma longiflora	Species	Campanulaceae	Eukaryota		UNPD*
NPO17222	Hesperis matronalis	Species	Brassicaceae	Eukaryota		UNPD*
NPO5782	Aniba rosaeodora	Species	Lauraceae	Eukaryota		UNPD*
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota		UNPD*
NPO12006	Apis mellifera	Species	Apidae	Eukaryota		HerDing*
NPO19766	Viguiera linearis	Species	Asteraceae	Eukaryota		UNPD*
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota		UNPD*
NPO23924	Psilotum nudum	Species	Psilotaceae	Eukaryota		UNPD*
NPO5946	Caryophylliflos	NA	NA	NA		TCMSP*
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota		TCMID*
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota		TCM_Taiwan*
NPO33456	inula viscosa	Species	Asteraceae	Eukaryota		PMID[10217718]
NPO22143	Genista sessilifolia	Species	Fabaceae	Eukaryota		UNPD*
NPO23545	Vellozia streptophylla	Species	Velloziaceae	Eukaryota		UNPD*
NPO10766	Alpiniae officinarum rhizome	NA	NA	NA		TCMSP*
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota		HerDing*
NPO5018	Nervilia fordii	Species	Orchidaceae	Eukaryota	Whole Plants	PMID[19422205]
NPO18260	Eremanthus seidelii	Species	Asteraceae	Eukaryota		UNPD*
NPO21625	Bidens tripartita	Species	Asteraceae	Eukaryota		UNPD*
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota		PMID[22494026]
NPO17350	Jatropha macrorhiza	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO8080	Sarcophyton elegans	Species	Alcyoniidae	Eukaryota		UNPD*
NPO17737	Lepidorhinus squamosus	NA	NA	NA		UNPD*
NPO5024	Alpinia japonica	Species	Zingiberaceae	Eukaryota		TCMID*
NPO22555	Alomia myriadenia	Species	Asteraceae	Eukaryota		TCMID*
NPO22595	Trapa bicornis	Species	Lythraceae	Eukaryota		UNPD*
NPO14249	Diplodia natalensis	Species	Botryosphaeriaceae	Eukaryota		UNPD*
NPO24445	Arbacia pustulosa	Species	Arbaciidae	Eukaryota		UNPD*
NPO22636	Sterculia foetida	Species	Malvaceae	Eukaryota		UNPD*
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota		TCM_Taiwan*
NPO24290	Claviceps microcephala	Species	Clavicipitaceae	Eukaryota		UNPD*
NPO23739	Staehelina fruticosa	Species	Asteraceae	Eukaryota		UNPD*
NPO20637	Piper acutifolium	Species	Piperaceae	Eukaryota		UNPD*
NPO9394	Herba artemisiae scopariae	NA	NA	NA		TCMID*
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota		HerDing*
NPO13344	Helichrysum cephaloideum	Species	Asteraceae	Eukaryota		UNPD*
NPO8593	Zygosaccharomyces rouxii	Species	Saccharomycetaceae	Eukaryota		UNPD*
NPO18839	Lilium umbellatum	Species	Liliaceae	Eukaryota		UNPD*
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota		TCMID*
NPO22555	Alomia myriadenia	Species	Asteraceae	Eukaryota		HerDing*
NPO19571	Oreopteris quelpaertensis	Species	Thelypteridaceae	Eukaryota		UNPD*
NPO18976	Centaurea arbutifolia	Species	Asteraceae	Eukaryota		UNPD*
NPO18672	Senecio adenophyllus	Species	Asteraceae	Eukaryota		UNPD*
NPO17698	Cirsium oligophyllum	Species	Asteraceae	Eukaryota		UNPD*
NPO8624	Artemisiae scopariae herba	NA	NA	NA		TCMSP*
NPO7528	Iris domestica	Species	Iridaceae	Eukaryota		TCMID*
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota		PMID[25757283]
NPO14715	Trollius chinensis	Species	Ranunculaceae	Eukaryota		UNPD*
NPO12860	Clione antarctica	Species	Clionidae	Eukaryota		UNPD*
NPO16043	Centaurea musimomum	Species	Asteraceae	Eukaryota		UNPD*
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota		UNPD*
NPO24886	Hedysarum multijugum maxim	Species	Fabaceae	Eukaryota		TCMSP*
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota		TCMID*
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota		HerDing*
NPO24408	Ariocarpus fissuratus	Species	Cactaceae	Eukaryota		UNPD*
NPO16132	Bryum argenteum	Species	Bryaceae	Eukaryota		UNPD*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota		TCMSP*
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota		TCMID*
NPO25176	Tamarix hispida	Species	Tamaricaceae	Eukaryota		HerDing*
NPO15786	Umbilicaria esculenta	Species	Umbilicariaceae	Eukaryota		UNPD*
NPO22324	Erium villosum	Species	Pseudococcidae	Eukaryota		UNPD*
NPO29650	Lysimachiae herba	NA	NA	NA		TCMSP*
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		TCMID*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota		TCM_Taiwan*
NPO18925	Artemisia rehan	Species	Asteraceae	Eukaryota		UNPD*
NPO4591	Neobellieria bullata	Species	Sarcophagidae	Eukaryota		UNPD*
NPO29634	Iridis tectori rhizoma	NA	NA	NA		TCMSP*
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota		TCMID*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota		HerDing*
NPO23413	Crematogaster africana	Species	Formicidae	Eukaryota		UNPD*
NPO19240	Ligularia cymbulifera	Species	Asteraceae	Eukaryota		UNPD*
NPO29643	Mume fructus	NA	NA	NA		TCMSP*
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota		TCMID*
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota		HerDing*
NPO15437	Aspergillus desertorum	Species	Aspergillaceae	Eukaryota		UNPD*
NPO14214	Sedum obtuso-lineare	Species	Crassulaceae	Eukaryota		UNPD*
NPO29546	Eriobotryae folium	NA	NA	NA		TCMSP*
NPO15538	Corymbia citriodora	Species	Myrtaceae	Eukaryota		TCMID*
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota		TCM_Taiwan*
NPO15119	Aphis graminum	Species	Aphididae	Eukaryota		UNPD*
NPO23043	Cryptolestes pusillus	Species	Laemophloeidae	Eukaryota		UNPD*
NPO21903	Belamcandae rhizome	NA	NA	NA		TCMSP*
NPO16309	Semen astragali complanati	NA	NA	NA		TCMID*
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota		HerDing*
NPO21827	Albatrellus caeruleoporus	Species	Albatrellaceae	Eukaryota		UNPD*
NPO19306	Cortinarius orellanus	Species	Cortinariaceae	Eukaryota		UNPD*
NPO23459	Onoseris alata	Species	Asteraceae	Eukaryota		UNPD*
NPO4499	Aglaia formosana	Species	Meliaceae	Eukaryota		UNPD*
NPO28357	Astragali cpmplanatisemen	NA	NA	NA		TCMSP*
NPO19792	Populus tomentosa	Species	Salicaceae	Eukaryota		TCMID*
NPO31132	Eucalyptus citriodora	Species	Myrtaceae	Eukaryota		TCM_Taiwan*
NPO19168	Solidago flexicaulis	Species	Asteraceae	Eukaryota		UNPD*
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota		UNPD*
NPO17749	Jackiella javanica	Species	Jackiellaceae	Eukaryota		UNPD*
NPO11262	Alpinia katsumadai hayat	Species	Staphylinidae	Eukaryota		TCMSP*
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota		TCMID*
NPO31132	Eucalyptus citriodora	Species	Myrtaceae	Eukaryota		HerDing*
NPO738	Dahlstedtia pentaphylla	Species	Fabaceae	Eukaryota		UNPD*
NPO23114	Cacalia robusta	Species	Asteraceae	Eukaryota		UNPD*
NPO19370	Coprosma areolata	Species	Rubiaceae	Eukaryota		UNPD*
NPO29580	Tamaricis cacumen	NA	NA	NA		TCMSP*
NPO24005	Mytilus galloprovincialis	Species	Mytilidae	Eukaryota		UNPD*
NPO31579	Artemisia capillaries	Species	Asteraceae	Eukaryota		TCM_Taiwan*
NPO11083	Avrainvillea longicaulis	Species	Udoteaceae	Eukaryota		UNPD*
NPO13727	Hemionitis japonica	Species	Pteridaceae	Eukaryota		UNPD*
NPO23792	Gomphostemma parviflorum	Species	Lamiaceae	Eukaryota		UNPD*
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota		TM-MC*
NPO19010	Elephantopus hirtiflorus	Species	Asteraceae	Eukaryota		UNPD*
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		HerDing*
NPO2354	Rhizobium leguminosarum	Species	Rhizobiaceae	Bacteria		UNPD*
NPO16776	Euphorbia amygdaloides	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO23920	Amanita pseudoporphyria	Species	Amanitaceae	Eukaryota		UNPD*
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota		TM-MC*
NPO23318	Aconitum palmatum	Species	Ranunculaceae	Eukaryota		UNPD*
NPO5024	Alpinia japonica	Species	Zingiberaceae	Eukaryota		TCM_Taiwan*
NPO21660	Magnolia montana	Species	Magnoliaceae	Eukaryota		UNPD*
NPO16978	Entada phaseoloides	Species	Fabaceae	Eukaryota		UNPD*
NPO24219	Erylus nobilis	Species	Geodiidae	Eukaryota		UNPD*
NPO15715	Astragalus mongholicus	Species	Fabaceae	Eukaryota		TM-MC*
NPO19535	Senecio zoellneri	Species	Asteraceae	Eukaryota		UNPD*
NPO5024	Alpinia japonica	Species	Zingiberaceae	Eukaryota		HerDing*
NPO23610	Aconitum tianschanicum	Species	Ranunculaceae	Eukaryota		UNPD*
NPO18599	Pangium edule	Species	Achariaceae	Eukaryota		UNPD*
NPO24249	Codonopsis cordifolioidea	Species	Campanulaceae	Eukaryota		UNPD*
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		TM-MC*
NPO23281	Aplysinella rhax	Species	Aplysinellidae	Eukaryota		UNPD*
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota		HerDing*
NPO17894	Rhus vulgaris	Species	Anacardiaceae	Eukaryota		UNPD*
NPO12429	Acicarpha tribuloides	Species	Calyceraceae	Eukaryota		UNPD*
NPO13127	Vallaris heynei	Species	Apocynaceae	Eukaryota		UNPD*
NPO24048	Cladonia pityrea	Species	Cladoniaceae	Eukaryota		UNPD*
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota		HerDing*
NPO11059	Callicarpa japonica	Species	Lamiaceae	Eukaryota		UNPD*
NPO16725	Dalbergia hupeana	Species	Fabaceae	Eukaryota		UNPD*
NPO17490	Trichophyton mentagrophytes	Species	Arthrodermataceae	Eukaryota		UNPD*
NPO19706	Polyzonium rosalbum	Species	Polyzoniidae	Eukaryota		UNPD*
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota		TM-MC*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota		TCMID*
NPO24090	Aplysilla rosea	Species	Darwinellidae	Eukaryota		UNPD*
NPO16316	Cylindrospermum muscicola	Species	Nostocaceae	Bacteria		UNPD*
NPO19086	Nematolepis phebalioides	Species	Rutaceae	Eukaryota		UNPD*
NPO23834	Chlamydomonas allensworthii	Species	Chlamydomonadaceae	Eukaryota		UNPD*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota		TCMID*
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota		TCMID*
NPO23211	Xyris indica	Species	Xyridaceae	Eukaryota		UNPD*
NPO15538	Corymbia citriodora	Species	Myrtaceae	Eukaryota		UNPD*
NPO18041	Cladrastis platycarpa	Species	Fabaceae	Eukaryota		UNPD*
NPO23364	Lambertella corni	Species	Rutstroemiaceae	Eukaryota		UNPD*
NPO25176	Tamarix hispida	Species	Tamaricaceae	Eukaryota		TCMID*
NPO19631	Aphis pini	Species	Aphididae	Eukaryota		UNPD*
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota		UNPD*
NPO15481	Hypericum balearicum	Species	Hypericaceae	Eukaryota		UNPD*
NPO24132	Euphausia superba	Species	Euphausiidae	Eukaryota		UNPD*
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota		TCMID*

Biological Activity

Activity Type	# Activity
IC50	4
MIC	7
Others	2

Activity Type	# Activity
Individual Protein	4
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	625	ug/ml	8904847
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MIC	=	625	ug/ml	8904847
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	1250	ug/ml	8904847
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MIC	=	1250	ug/ml	8904847
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	78	%	10217718
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	6	%	10217718
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	51500	nM	18640042
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	83900	nM	18640042
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	62000	nM	18640042
NPT1602	Individual Protein	Neuraminidase	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	15.46	ug/ml	20116898
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	15.3	ug/ml	10.1007/s00044-013-0485-8
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	37.7	ug/ml	10.1007/s00044-013-0485-8
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	59.7	ug/ml	10.1007/s00044-013-0485-8

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 NPC143799 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	245
0.1-0.2	1243
0.2-0.3	2756
0.3-0.4	6919
0.4-0.5	6052
0.5-0.6	2556
0.6-0.7	4405
0.7-0.8	3553
0.8-0.85	1512
0.85-0.9	1049
0.9-0.95	546
0.95-1	53

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC152042
1.0	High Similarity	NPC241838
0.9925	High Similarity	NPC230285
0.9925	High Similarity	NPC184536
0.9925	High Similarity	NPC146679
0.9925	High Similarity	NPC59951
0.9925	High Similarity	NPC103342
0.9925	High Similarity	NPC281207
0.9925	High Similarity	NPC269652
0.9925	High Similarity	NPC103904
0.9852	High Similarity	NPC136840
0.9852	High Similarity	NPC90582
0.9852	High Similarity	NPC262094
0.9776	High Similarity	NPC276905
0.9774	High Similarity	NPC187432
0.9774	High Similarity	NPC127447
0.9774	High Similarity	NPC47815
0.9774	High Similarity	NPC473887
0.9774	High Similarity	NPC256042
0.9774	High Similarity	NPC216361
0.9774	High Similarity	NPC281917
0.9774	High Similarity	NPC124784
0.9774	High Similarity	NPC231772
0.9774	High Similarity	NPC29353
0.9774	High Similarity	NPC234133
0.9774	High Similarity	NPC194281
0.9774	High Similarity	NPC116775
0.9708	High Similarity	NPC470216
0.9701	High Similarity	NPC266597
0.9701	High Similarity	NPC299379
0.9701	High Similarity	NPC250266
0.9638	High Similarity	NPC273538
0.9638	High Similarity	NPC216538
0.9635	High Similarity	NPC473042
0.9635	High Similarity	NPC200694
0.9627	High Similarity	NPC13408
0.9624	High Similarity	NPC248872
0.9568	High Similarity	NPC5820
0.9568	High Similarity	NPC124729
0.9568	High Similarity	NPC178343
0.9568	High Similarity	NPC306488
0.9565	High Similarity	NPC9117
0.9565	High Similarity	NPC190637
0.9565	High Similarity	NPC24821
0.9565	High Similarity	NPC158874
0.9565	High Similarity	NPC293053
0.9565	High Similarity	NPC212932
0.9559	High Similarity	NPC18260
0.9559	High Similarity	NPC78913
0.9549	High Similarity	NPC274121
0.9549	High Similarity	NPC50898
0.9549	High Similarity	NPC78540
0.9549	High Similarity	NPC213216
0.9496	High Similarity	NPC326500
0.9489	High Similarity	NPC241100
0.9489	High Similarity	NPC159275
0.9485	High Similarity	NPC99333
0.9485	High Similarity	NPC188947
0.9485	High Similarity	NPC280284
0.9485	High Similarity	NPC201395
0.9481	High Similarity	NPC61546
0.9481	High Similarity	NPC72452
0.9478	High Similarity	NPC172262
0.9474	High Similarity	NPC128216
0.9433	High Similarity	NPC244407
0.9433	High Similarity	NPC296869
0.9429	High Similarity	NPC470458
0.9429	High Similarity	NPC153758
0.942	High Similarity	NPC110969
0.942	High Similarity	NPC282300
0.9416	High Similarity	NPC303633
0.9416	High Similarity	NPC217186
0.9416	High Similarity	NPC274784
0.9416	High Similarity	NPC150648
0.9416	High Similarity	NPC96565
0.9416	High Similarity	NPC329203
0.9416	High Similarity	NPC222342
0.9416	High Similarity	NPC220062
0.9416	High Similarity	NPC53181
0.9416	High Similarity	NPC55018
0.9416	High Similarity	NPC216978
0.9416	High Similarity	NPC310135
0.9416	High Similarity	NPC265871
0.9416	High Similarity	NPC225153
0.9416	High Similarity	NPC301217
0.9416	High Similarity	NPC20709
0.9412	High Similarity	NPC228661
0.9412	High Similarity	NPC290291
0.9412	High Similarity	NPC275055
0.9412	High Similarity	NPC188879
0.9403	High Similarity	NPC57601
0.9398	High Similarity	NPC113006
0.9398	High Similarity	NPC475589
0.9398	High Similarity	NPC278556
0.9398	High Similarity	NPC31872
0.9398	High Similarity	NPC473584
0.9366	High Similarity	NPC470461
0.9366	High Similarity	NPC159103
0.9366	High Similarity	NPC270465
0.9366	High Similarity	NPC87125
0.9362	High Similarity	NPC259632
0.9362	High Similarity	NPC176869
0.9362	High Similarity	NPC44721
0.9362	High Similarity	NPC40086
0.9362	High Similarity	NPC122828
0.9362	High Similarity	NPC476182
0.9362	High Similarity	NPC14001
0.9362	High Similarity	NPC3779
0.9362	High Similarity	NPC166757
0.9362	High Similarity	NPC472918
0.9362	High Similarity	NPC211466
0.9357	High Similarity	NPC71210
0.9353	High Similarity	NPC11561
0.9353	High Similarity	NPC226636
0.9348	High Similarity	NPC188243
0.9348	High Similarity	NPC270883
0.9348	High Similarity	NPC172986
0.9348	High Similarity	NPC284550
0.9348	High Similarity	NPC76445
0.9348	High Similarity	NPC110228
0.9348	High Similarity	NPC261227
0.9348	High Similarity	NPC6407
0.9348	High Similarity	NPC129853
0.9348	High Similarity	NPC150522
0.9343	High Similarity	NPC124269
0.9343	High Similarity	NPC118813
0.9338	High Similarity	NPC121243
0.9338	High Similarity	NPC240147
0.9338	High Similarity	NPC240593
0.9328	High Similarity	NPC257756
0.9328	High Similarity	NPC212631
0.9328	High Similarity	NPC473655
0.9328	High Similarity	NPC10971
0.9328	High Similarity	NPC205468
0.9328	High Similarity	NPC25937
0.9328	High Similarity	NPC129132
0.9328	High Similarity	NPC87231
0.9328	High Similarity	NPC101294
0.9323	High Similarity	NPC5515
0.9323	High Similarity	NPC270369
0.9323	High Similarity	NPC137264
0.9301	High Similarity	NPC188871
0.9301	High Similarity	NPC61258
0.9301	High Similarity	NPC166753
0.9301	High Similarity	NPC50728
0.9301	High Similarity	NPC149127
0.9301	High Similarity	NPC286342
0.9296	High Similarity	NPC470460
0.9291	High Similarity	NPC229190
0.9291	High Similarity	NPC220418
0.9286	High Similarity	NPC113770
0.9281	High Similarity	NPC324386
0.9281	High Similarity	NPC4743
0.9281	High Similarity	NPC147688
0.9281	High Similarity	NPC64908
0.9281	High Similarity	NPC3188
0.9281	High Similarity	NPC213322
0.9281	High Similarity	NPC103362
0.9281	High Similarity	NPC205006
0.9281	High Similarity	NPC156590
0.9281	High Similarity	NPC118840
0.9281	High Similarity	NPC312391
0.9275	High Similarity	NPC140890
0.9275	High Similarity	NPC261234
0.927	High Similarity	NPC294409
0.927	High Similarity	NPC243083
0.927	High Similarity	NPC287246
0.927	High Similarity	NPC7013
0.927	High Similarity	NPC254841
0.927	High Similarity	NPC181124
0.927	High Similarity	NPC116632
0.927	High Similarity	NPC79943
0.927	High Similarity	NPC303644
0.927	High Similarity	NPC209560
0.927	High Similarity	NPC12296
0.927	High Similarity	NPC296490
0.927	High Similarity	NPC32441
0.927	High Similarity	NPC162680
0.927	High Similarity	NPC295261
0.927	High Similarity	NPC13768
0.927	High Similarity	NPC107586
0.9265	High Similarity	NPC9985
0.9265	High Similarity	NPC239495
0.9259	High Similarity	NPC242294
0.9259	High Similarity	NPC144051
0.9259	High Similarity	NPC82225
0.9259	High Similarity	NPC175098
0.9259	High Similarity	NPC56031
0.9259	High Similarity	NPC18877
0.9259	High Similarity	NPC263670
0.9259	High Similarity	NPC192304
0.9259	High Similarity	NPC188646
0.9259	High Similarity	NPC139813
0.9259	High Similarity	NPC294593
0.9259	High Similarity	NPC337373
0.9259	High Similarity	NPC159623
0.9259	High Similarity	NPC28753
0.9259	High Similarity	NPC312318
0.9259	High Similarity	NPC204960
0.9259	High Similarity	NPC223457

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC143799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	896
0.2-0.3	1483
0.3-0.4	2484
0.4-0.5	2052
0.5-0.6	1284
0.6-0.7	479
0.7-0.8	138
0.8-0.85	35
0.85-0.9	19
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9638	High Similarity	NPD4378	Clinical (unspecified phase)
0.927	High Similarity	NPD1550	Clinical (unspecified phase)
0.927	High Similarity	NPD1552	Clinical (unspecified phase)
0.9203	High Similarity	NPD1549	Phase 2
0.9155	High Similarity	NPD1512	Approved
0.9124	High Similarity	NPD1510	Phase 2
0.9111	High Similarity	NPD1240	Approved
0.9014	High Similarity	NPD1511	Approved
0.8978	High Similarity	NPD1607	Approved
0.8951	High Similarity	NPD7410	Clinical (unspecified phase)
0.8921	High Similarity	NPD2796	Approved
0.8881	High Similarity	NPD6799	Approved
0.8851	High Similarity	NPD2801	Approved
0.8784	High Similarity	NPD1934	Approved
0.8725	High Similarity	NPD2393	Clinical (unspecified phase)
0.8675	High Similarity	NPD7075	Discontinued
0.8667	High Similarity	NPD3817	Phase 2
0.8658	High Similarity	NPD6801	Discontinued
0.8649	High Similarity	NPD4380	Phase 2
0.8609	High Similarity	NPD3882	Suspended
0.86	High Similarity	NPD7096	Clinical (unspecified phase)
0.8591	High Similarity	NPD7411	Suspended
0.8553	High Similarity	NPD4381	Clinical (unspecified phase)
0.8543	High Similarity	NPD8443	Clinical (unspecified phase)
0.8542	High Similarity	NPD3750	Approved
0.8531	High Similarity	NPD970	Clinical (unspecified phase)
0.8523	High Similarity	NPD6599	Discontinued
0.8462	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6166	Phase 2
0.8446	Intermediate Similarity	NPD5403	Approved
0.8435	Intermediate Similarity	NPD5401	Approved
0.8418	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1551	Phase 2
0.8355	Intermediate Similarity	NPD7819	Suspended
0.8345	Intermediate Similarity	NPD2800	Approved
0.8313	Intermediate Similarity	NPD6797	Phase 2
0.8261	Intermediate Similarity	NPD7251	Discontinued
0.8219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7808	Phase 3
0.8194	Intermediate Similarity	NPD3749	Approved
0.8194	Intermediate Similarity	NPD3748	Approved
0.8188	Intermediate Similarity	NPD1203	Approved
0.8187	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD5402	Approved
0.8163	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6959	Discontinued
0.8137	Intermediate Similarity	NPD7472	Approved
0.8134	Intermediate Similarity	NPD1548	Phase 1
0.8129	Intermediate Similarity	NPD7768	Phase 2
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8113	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1243	Approved
0.8082	Intermediate Similarity	NPD2344	Approved
0.8079	Intermediate Similarity	NPD920	Approved
0.8056	Intermediate Similarity	NPD6651	Approved
0.8029	Intermediate Similarity	NPD422	Phase 1
0.8028	Intermediate Similarity	NPD2313	Discontinued
0.8025	Intermediate Similarity	NPD7074	Phase 3
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.7971	Intermediate Similarity	NPD9717	Approved
0.7947	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD3268	Approved
0.7899	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD6832	Phase 2
0.7879	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6232	Discontinued
0.7867	Intermediate Similarity	NPD2309	Approved
0.7862	Intermediate Similarity	NPD5494	Approved
0.7857	Intermediate Similarity	NPD3225	Approved
0.7853	Intermediate Similarity	NPD7286	Phase 2
0.784	Intermediate Similarity	NPD7473	Discontinued
0.7829	Intermediate Similarity	NPD2533	Approved
0.7829	Intermediate Similarity	NPD2532	Approved
0.7829	Intermediate Similarity	NPD2534	Approved
0.7823	Intermediate Similarity	NPD2799	Discontinued
0.7823	Intermediate Similarity	NPD7033	Discontinued
0.7812	Intermediate Similarity	NPD1247	Approved
0.7801	Intermediate Similarity	NPD2797	Approved
0.7799	Intermediate Similarity	NPD919	Approved
0.7793	Intermediate Similarity	NPD943	Approved
0.777	Intermediate Similarity	NPD1610	Phase 2
0.777	Intermediate Similarity	NPD6099	Approved
0.777	Intermediate Similarity	NPD6100	Approved
0.7762	Intermediate Similarity	NPD4908	Phase 1
0.7758	Intermediate Similarity	NPD5953	Discontinued
0.7746	Intermediate Similarity	NPD2798	Approved
0.7742	Intermediate Similarity	NPD3226	Approved
0.7733	Intermediate Similarity	NPD2654	Approved
0.7716	Intermediate Similarity	NPD3926	Phase 2
0.7711	Intermediate Similarity	NPD6559	Discontinued
0.7703	Intermediate Similarity	NPD4308	Phase 3
0.7703	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4628	Phase 3
0.7676	Intermediate Similarity	NPD3266	Approved
0.7676	Intermediate Similarity	NPD3267	Approved
0.7655	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1933	Approved
0.7619	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD9545	Approved
0.76	Intermediate Similarity	NPD2346	Discontinued
0.7591	Intermediate Similarity	NPD9493	Approved
0.7584	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1465	Phase 2
0.7543	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1296	Phase 2
0.7534	Intermediate Similarity	NPD6798	Discontinued
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7529	Intermediate Similarity	NPD4360	Phase 2
0.7529	Intermediate Similarity	NPD4363	Phase 3
0.7517	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD4288	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD6233	Phase 2
0.747	Intermediate Similarity	NPD3751	Discontinued
0.7465	Intermediate Similarity	NPD1608	Approved
0.7465	Intermediate Similarity	NPD1481	Phase 2
0.7465	Intermediate Similarity	NPD3972	Approved
0.7455	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1613	Approved
0.7432	Intermediate Similarity	NPD4307	Phase 2
0.7432	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD411	Approved
0.7403	Intermediate Similarity	NPD2354	Approved
0.7394	Intermediate Similarity	NPD1535	Discovery
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4361	Phase 2
0.7383	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD2403	Approved
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.7297	Intermediate Similarity	NPD3764	Approved
0.7284	Intermediate Similarity	NPD2296	Approved
0.7279	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1729	Discontinued
0.7273	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2353	Approved
0.7254	Intermediate Similarity	NPD17	Approved
0.7234	Intermediate Similarity	NPD1894	Discontinued
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7229	Intermediate Similarity	NPD5710	Approved
0.7229	Intermediate Similarity	NPD5711	Approved
0.7216	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4287	Approved
0.7197	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6104	Discontinued
0.7192	Intermediate Similarity	NPD1470	Approved
0.7186	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3887	Approved
0.7172	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD4340	Discontinued
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7440	Discontinued
0.7133	Intermediate Similarity	NPD4062	Phase 3
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7123	Intermediate Similarity	NPD1876	Approved
0.7114	Intermediate Similarity	NPD3027	Phase 3
0.7107	Intermediate Similarity	NPD5049	Phase 3
0.7099	Intermediate Similarity	NPD5890	Approved
0.7099	Intermediate Similarity	NPD5889	Approved
0.7095	Intermediate Similarity	NPD2861	Phase 2
0.7091	Intermediate Similarity	NPD6971	Discontinued
0.7089	Intermediate Similarity	NPD7212	Phase 2
0.7089	Intermediate Similarity	NPD7213	Phase 3
0.7086	Intermediate Similarity	NPD3142	Approved
0.7086	Intermediate Similarity	NPD3140	Approved
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD7584	Approved
0.7081	Intermediate Similarity	NPD7458	Discontinued
0.7075	Intermediate Similarity	NPD1164	Approved
0.707	Intermediate Similarity	NPD6190	Approved
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7059	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4661	Approved
0.7044	Intermediate Similarity	NPD4662	Approved
0.7044	Intermediate Similarity	NPD7447	Phase 1
0.7037	Intermediate Similarity	NPD6585	Discontinued
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD74	Approved
0.7007	Intermediate Similarity	NPD9266	Approved
0.7006	Intermediate Similarity	NPD7003	Approved

Structure

CID143799 OpenBabel06191715502D 22 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 4 1 0 0 0 0 2 8 2 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 12 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5320946
ChEMBL	CHEMBL442289
ZINC

Physicochemical Properties

Molecular Weight:	300.06
ALogP:	-1.9324
MLogP:	2.56
XLogP:	2.434
# Rotatable Bonds:	6
Polar Surface Area:	96.22
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	22

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