NPASS Natural Product

Natural Product: NPC136699

Natural Product ID:	NPC136699
Common Name:	Aucubin
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Aucubin
Molecular Formula:	C15H22O9
Standard InCHIKey:	RJWJHRPNHPHBRN-FKVJWERZSA-N
Standard InCHI:	InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
Canonical SMILES:	OCC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO11243	Exochorda giraldii	Species	Rosaceae	Eukaryota	UNPD*
NPO13955	Lippia javanica	Species	Verbenaceae	Eukaryota	UNPD*
NPO9299.3	Hordeum vulgare var. distichon	Varieties	Poaceae	Eukaryota	UNPD*
NPO15806	Rhododendron campylocarpum	Species	Ericaceae	Eukaryota	UNPD*
NPO10511	Lycopodium confertum	Species	Lycopodiaceae	Eukaryota	UNPD*
NPO2289	Vicia hirsuta	Species	Fabaceae	Eukaryota	UNPD*
NPO4856	Trichothecium crotocinigenum	Species	NA	Eukaryota	UNPD*
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	UNPD*
NPO16178	Aster maximus	Species	Asteraceae	Eukaryota	UNPD*
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	UNPD*
NPO15093	Carpinus laxiflora	Species	Betulaceae	Eukaryota	UNPD*
NPO12241	Hypericum reflexum	Species	Hypericaceae	Eukaryota	UNPD*
NPO15456	Sideritis soluta	Species	Lamiaceae	Eukaryota	UNPD*
NPO14065	Artemisia koidzumii	Species	Asteraceae	Eukaryota	UNPD*
NPO12492	Dictyophora indusiata	Species	Phallaceae	Eukaryota	UNPD*
NPO1350	Danaus plexippus	Species	Nymphalidae	Eukaryota	UNPD*
NPO2580	Globularia vulgaris	Species	Plantaginaceae	Eukaryota	UNPD*
NPO3681	Eucalyptus incrassata	Species	Myrtaceae	Eukaryota	UNPD*
NPO26510	Gentianopsis ciliata	Species	Gentianaceae	Eukaryota	UNPD*
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	UNPD*
NPO10109	Haemanthus natalensis	Species	Amaryllidaceae	Eukaryota	UNPD*
NPO4313	Corynebacterium poinsettiae	Species	Corynebacteriaceae	Bacteria	UNPD*
NPO14776	Petrosia weinbergi	Species	Petrosiidae	Eukaryota	UNPD*
NPO944	Senecio sandersonii	Species	Asteraceae	Eukaryota	UNPD*
NPO6413	Viguiera stenoloba	Species	Asteraceae	Eukaryota	UNPD*
NPO24674	Trichoderma album	Species	Hypocreaceae	Eukaryota	UNPD*
NPO9162	Nicotiana affinis	Species	Solanaceae	Eukaryota	UNPD*
NPO11255	Veronica thomsonii	Species	Plantaginaceae	Eukaryota	UNPD*
NPO9254	Scutellaria racemosa	Species	Lamiaceae	Eukaryota	UNPD*
NPO21851	Chaetomella raphigera	Species	Chaetomellaceae	Eukaryota	UNPD*
NPO4315	Fagara tessmannii	NA	NA	NA	UNPD*
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	UNPD*
NPO6853	Ostracion cubicus	Species	Ostraciidae	Eukaryota	UNPD*
NPO18375	Bauhinia tomentosa	Species	Fabaceae	Eukaryota	UNPD*
NPO21689	Titanotrichum oldhamii	Species	Gesneriaceae	Eukaryota	UNPD*
NPO8687	Chaerophyllum temulum	Species	Apiaceae	Eukaryota	UNPD*
NPO12175	Iostephane heterophylla	Species	Asteraceae	Eukaryota	UNPD*
NPO10011	Myrsine capitellata	Species	Primulaceae	Eukaryota	UNPD*
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	UNPD*
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	UNPD*
NPO14719	Tephrosia noctiflora	Species	Geometridae	Eukaryota	UNPD*
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	UNPD*
NPO12653	Diacarnus levii	Species	Podospongiidae	Eukaryota	UNPD*
NPO9908	Adenium somalense	Species	Apocynaceae	Eukaryota	UNPD*
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	UNPD*
NPO1790	Plectranthus comosus	Species	Lamiaceae	Eukaryota	UNPD*
NPO8446	Alnus mandshurica	Species	Betulaceae	Eukaryota	UNPD*
NPO11397	Cladophora rupestris	Species	Cladophoraceae	Eukaryota	UNPD*
NPO20733	Neonauclea calycina	Species	Rubiaceae	Eukaryota	UNPD*
NPO8556	Eucalyptus kitsoniana	Species	Myrtaceae	Eukaryota	UNPD*
NPO5598	Caesalpinia brevifolia	Species	Fabaceae	Eukaryota	UNPD*
NPO5173	Antidesma pentandrum	Species	Phyllanthaceae	Eukaryota	UNPD*
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	PMID[26351040]
NPO2576	Eusideroxylon zwageri	Species	Lauraceae	Eukaryota	UNPD*
NPO2667	Acacia lasiopetala	Species	Fabaceae	Eukaryota	UNPD*
NPO4039	Verbascum pseudonobile	Species	Scrophulariaceae	Eukaryota	UNPD*
NPO9561	Preussia australis	Species	Sporormiaceae	Eukaryota	UNPD*
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	PMID[26351040]
NPO14207	Euphorbia neriifolia	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	UNPD*
NPO24096	Furcraea macrophylla	Species	Asparagaceae	Eukaryota	UNPD*
NPO12373	Vinca minor	Species	Apocynaceae	Eukaryota	UNPD*
NPO33328	cresentia alata	Species	NA	NA	PMID[26351040]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	UNPD*
NPO13315	Alpinia kumatake	Species	Staphylinidae	Eukaryota	UNPD*
NPO17590	Usnea bayleyi	Species	Parmeliaceae	Eukaryota	UNPD*
NPO14980	Scrophularia nodosa	Species	Scrophulariaceae	Eukaryota	TCMSP*
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	PMID[26351040]
NPO10527	Cyathula tomentosa	Species	Amaranthaceae	Eukaryota	UNPD*
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	UNPD*
NPO12598	Osteospermum fruticosum	Species	Asteraceae	Eukaryota	UNPD*
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	TCM_Taiwan*
NPO10000	Rehmanniae radix praeparata	NA	NA	NA	TCMSP*
NPO3211	Liatris microcephala	Species	Asteraceae	Eukaryota	UNPD*
NPO1777	Toddalia aculeata	Species	Rutaceae	Eukaryota	UNPD*
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	UNPD*
NPO13244	Pomacea canaliculata	Species	Ampullariidae	Eukaryota	UNPD*
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	TCM_Taiwan*
NPO29619	Plantaginis semen	NA	NA	NA	TCMSP*
NPO18170	Aconitum miyabei	Species	Ranunculaceae	Eukaryota	UNPD*
NPO13460	Asphodeline damascena	Species	Asphodelaceae	Eukaryota	UNPD*
NPO4923	Ononis hircina	Species	Fabaceae	Eukaryota	UNPD*
NPO7179	Diospyros leucomelas	Species	Ebenaceae	Eukaryota	UNPD*
NPO30110	Veronica lavaudiana	Species	Plantaginaceae	Eukaryota	PMID[21568305]
NPO29666	Plantaginis herba	NA	NA	NA	TCMSP*
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	UNPD*
NPO11625	Markhamia stipulata	Species	Bignoniaceae	Eukaryota	UNPD*
NPO11946	Cleistanthus gracilis	Species	Phyllanthaceae	Eukaryota	UNPD*
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	UNPD*
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	TCM_Taiwan*
NPO29684	Buddlejae flos	NA	NA	NA	TCMSP*
NPO7648	Geigeria plumosa	Species	Asteraceae	Eukaryota	UNPD*
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	UNPD*
NPO27134	Euphrasia rubra	Species	Orobanchaceae	Eukaryota	UNPD*
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	UNPD*
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	TCM_Taiwan*
NPO18744	Verbenae herb	NA	NA	NA	TCMSP*
NPO13327	Phomopsis leptostromiformis	Species	Valsaceae	Eukaryota	UNPD*
NPO16962	Dipsacus laciniatus	Species	Caprifoliaceae	Eukaryota	UNPD*
NPO13466	Atroxima afzeliana	Species	Polygalaceae	Eukaryota	UNPD*
NPO16938	Limnodynastes salmini	Species	Myobatrachidae	Eukaryota	UNPD*
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	TCM_Taiwan*
NPO29685	Eucommiae folium	NA	NA	NA	TCMSP*
NPO29635	Eucommiae cortex	NA	NA	NA	TCMSP*
NPO20400	Physcia caesia	Species	Physciaceae	Eukaryota	UNPD*
NPO25931	Psammogeton canescens	Species	Apiaceae	Eukaryota	UNPD*
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	UNPD*
NPO15144	Combretum molle	Species	Combretaceae	Eukaryota	UNPD*
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	TCM_Taiwan*
NPO3599	Rheum maximowiczii	Species	Polygonaceae	Eukaryota	UNPD*
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	TM-MC*
NPO13225	Spergula japonica	Species	Caryophyllaceae	Eukaryota	UNPD*
NPO29322	Rhodanthe maryonii	Species	Asteraceae	Eukaryota	UNPD*
NPO20867	Parmelinopsis bonariensis	Species	Parmeliaceae	Eukaryota	UNPD*
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	UNPD*
NPO255	Solanum pseudopersicum	Species	Solanaceae	Eukaryota	UNPD*
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	TM-MC*
NPO3040	Acanthella carteri	Species	Melastomataceae	Eukaryota	UNPD*
NPO14404	Agave kerchovei	Species	Asparagaceae	Eukaryota	UNPD*
NPO8142	Pinus pumilio	Species	Pinaceae	Eukaryota	UNPD*
NPO14462	Jasonia tuberosa	Species	Asteraceae	Eukaryota	UNPD*
NPO19265	Metarhizium viride	Species	Clavicipitaceae	Eukaryota	UNPD*
NPO396	Ventilago goughii	Species	Rhamnaceae	Eukaryota	UNPD*
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	TM-MC*
NPO15718	Lindera sericea	Species	Tineidae	Eukaryota	UNPD*
NPO5311	Isertia haenkeana	Species	Rubiaceae	Eukaryota	UNPD*
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	UNPD*
NPO5805	Chlorociboria aeruginascens	Species	NA	Eukaryota	UNPD*
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	UNPD*
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	TM-MC*
NPO26381	Bombus pascuorum	Species	Apidae	Eukaryota	UNPD*
NPO1455	Aspergillus caelatus	Species	Aspergillaceae	Eukaryota	UNPD*
NPO9550	Eritrichium incanum	Species	Boraginaceae	Eukaryota	UNPD*
NPO793	Pestalotiopsis microspora	Species	Sporocadaceae	Eukaryota	UNPD*
NPO10102	Pithecellobium albicans	Species	Fabaceae	Eukaryota	UNPD*
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	TM-MC*
NPO409	Inga brenesii	Species	Oecophoridae	Eukaryota	UNPD*
NPO20033	Arcopilus cupreus	Species	Chaetomiaceae	Eukaryota	UNPD*
NPO10035	Ficus pantoniana	Species	Moraceae	Eukaryota	UNPD*
NPO6864	Lactarius spinosulus	Species	Russulaceae	Eukaryota	UNPD*
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	UNPD*
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	TM-MC*
NPO151	Pedicularis striata	Species	Orobanchaceae	Eukaryota	UNPD*
NPO10003	Veronica cymbalaria	Species	Plantaginaceae	Eukaryota	UNPD*
NPO2471	Axinyssa variabilis	Species	Halichondriidae	Eukaryota	UNPD*
NPO22101	Himantoglossum hircinum	Species	Orchidaceae	Eukaryota	UNPD*
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	UNPD*
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	TM-MC*
NPO26951	Gymnopus androsaceus	Species	Omphalotaceae	Eukaryota	UNPD*
NPO13581	Daphnandra repandula	Species	Atherospermataceae	Eukaryota	UNPD*
NPO19124	Guevaria sodiroi	NA	NA	NA	UNPD*
NPO3671	Rhodiola coccinea	Species	Crassulaceae	Eukaryota	UNPD*
NPO26737	Solanum mauritianum	Species	Solanaceae	Eukaryota	UNPD*
NPO11342	Sideritis trojana	Species	Lamiaceae	Eukaryota	UNPD*
NPO3432	Tovomita brasiliensis	Species	Clusiaceae	Eukaryota	UNPD*
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	TM-MC*
NPO12762	Elattostachys apetala	Species	Sapindaceae	Eukaryota	UNPD*
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	UNPD*
NPO7323	Lindera pipericarpa	Species	Tineidae	Eukaryota	UNPD*
NPO12047	Solanum unguiculatum	Species	Solanaceae	Eukaryota	UNPD*
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO3618	Pinus pinea	Species	Pinaceae	Eukaryota	UNPD*
NPO15513	Pseudocyphellaria rubella	Species	Lobariaceae	Eukaryota	UNPD*
NPO1314	Goodenia strophiolata	Species	Goodeniaceae	Eukaryota	UNPD*
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	UNPD*
NPO11674	Viburnum lantanoides	Species	Adoxaceae	Eukaryota	UNPD*
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	UNPD*
NPO17497	Bohadschia koellikeri	Species	Holothuriidae	Eukaryota	UNPD*
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	UNPD*
NPO18057	Chlorobium phaeobacteroides	Species	Chlorobiaceae	Bacteria	UNPD*
NPO10553	Heterophyllaea pustulata	Species	Rubiaceae	Eukaryota	UNPD*
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	UNPD*
NPO10871	Arisaema triphyllum	Species	Araceae	Eukaryota	UNPD*
NPO4005	Andrachne rotundifolia	Species	Phyllanthaceae	Eukaryota	UNPD*
NPO15078	Suckleya suckleyana	Species	Chenopodiaceae	Eukaryota	UNPD*
NPO27353	Tovomita brevistaminea	Species	Clusiaceae	Eukaryota	UNPD*
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	UNPD*
NPO7135	Mollugo spergula	Species	Molluginaceae	Eukaryota	UNPD*
NPO20607	Boussingaultia baselloides	NA	NA	NA	UNPD*
NPO11491	Vellozia declinans	Species	Velloziaceae	Eukaryota	UNPD*
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	UNPD*
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	UNPD*
NPO12526	Veronica turrilliana	Species	Plantaginaceae	Eukaryota	UNPD*
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	UNPD*
NPO214	Platycodon grandiflorus	Species	Campanulaceae	Eukaryota	UNPD*
NPO22168	Scutellaria rivularis	Species	Lamiaceae	Eukaryota	UNPD*
NPO19003	Isodon pleiophyllus	Species	Lamiaceae	Eukaryota	UNPD*
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	UNPD*
NPO5908	Dianella tasmanica	Species	Asphodelaceae	Eukaryota	UNPD*
NPO13951	Phialophora alba	Species	Herpotrichiellaceae	Eukaryota	UNPD*
NPO13096	Lecidea kochiana	Species	Lecideaceae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
IC50	5
Others	12
Potency	2

Activity Type	# Activity
Cell Line	3
Individual Protein	12
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	21.7	%	12542353
NPT2	Others	Unspecified		Inhibition	=	89.3	%	12542353
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	63.1	nM	PubChem BioAssay data set
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	81.25	%	22137340
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	99.1	%	22137340
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		183.6	nM	PubChem BioAssay data set
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-1.28	%	23062825
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-12.67	%	23062825
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	49.9	%	26351040
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	48.2	%	26351040
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	50.2	%	26351040
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<=	30	%	26351040
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000	nM	26859776
NPT2	Others	Unspecified		IC50	>	10000	nM	26859776
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000	nM	26859776
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	26859776

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 NPC136699 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	114
0.1-0.2	1071
0.2-0.3	3757
0.3-0.4	10125
0.4-0.5	9554
0.5-0.6	5018
0.6-0.7	1125
0.7-0.8	104
0.8-0.85	18
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC220167
0.907	High Similarity	NPC280390
0.8556	High Similarity	NPC241911
0.828	Intermediate Similarity	NPC255677
0.828	Intermediate Similarity	NPC22149
0.828	Intermediate Similarity	NPC306344
0.8256	Intermediate Similarity	NPC470658
0.8191	Intermediate Similarity	NPC298255
0.8191	Intermediate Similarity	NPC28304
0.8161	Intermediate Similarity	NPC171484
0.8161	Intermediate Similarity	NPC149018
0.814	Intermediate Similarity	NPC259296
0.814	Intermediate Similarity	NPC98276
0.8105	Intermediate Similarity	NPC250545
0.809	Intermediate Similarity	NPC104129
0.809	Intermediate Similarity	NPC249408
0.8021	Intermediate Similarity	NPC118761
0.8021	Intermediate Similarity	NPC284929
0.8021	Intermediate Similarity	NPC267869
0.8021	Intermediate Similarity	NPC197541
0.8021	Intermediate Similarity	NPC234304
0.7938	Intermediate Similarity	NPC86095
0.7917	Intermediate Similarity	NPC13171
0.7917	Intermediate Similarity	NPC195510
0.7917	Intermediate Similarity	NPC310804
0.7917	Intermediate Similarity	NPC261117
0.7917	Intermediate Similarity	NPC222062
0.7901	Intermediate Similarity	NPC132938
0.7865	Intermediate Similarity	NPC258501
0.7831	Intermediate Similarity	NPC229655
0.7826	Intermediate Similarity	NPC61201
0.7812	Intermediate Similarity	NPC20673
0.7802	Intermediate Similarity	NPC327253
0.7778	Intermediate Similarity	NPC148534
0.7717	Intermediate Similarity	NPC294643
0.7717	Intermediate Similarity	NPC473150
0.7717	Intermediate Similarity	NPC274274
0.7708	Intermediate Similarity	NPC244878
0.7692	Intermediate Similarity	NPC93190
0.7692	Intermediate Similarity	NPC22918
0.7692	Intermediate Similarity	NPC50464
0.7634	Intermediate Similarity	NPC320552
0.7604	Intermediate Similarity	NPC151093
0.7527	Intermediate Similarity	NPC276298
0.75	Intermediate Similarity	NPC20072
0.7474	Intermediate Similarity	NPC170204
0.7471	Intermediate Similarity	NPC100697
0.7449	Intermediate Similarity	NPC4637
0.7449	Intermediate Similarity	NPC219038
0.7449	Intermediate Similarity	NPC98859
0.7426	Intermediate Similarity	NPC254538
0.7426	Intermediate Similarity	NPC474285
0.7419	Intermediate Similarity	NPC303451
0.7419	Intermediate Similarity	NPC307699
0.7419	Intermediate Similarity	NPC117596
0.7419	Intermediate Similarity	NPC6414
0.7391	Intermediate Similarity	NPC137368
0.7391	Intermediate Similarity	NPC248312
0.7381	Intermediate Similarity	NPC472174
0.7374	Intermediate Similarity	NPC471599
0.7347	Intermediate Similarity	NPC469942
0.7342	Intermediate Similarity	NPC294813
0.7342	Intermediate Similarity	NPC13143
0.734	Intermediate Similarity	NPC472124
0.734	Intermediate Similarity	NPC472125
0.734	Intermediate Similarity	NPC472126
0.7333	Intermediate Similarity	NPC266718
0.7312	Intermediate Similarity	NPC299527
0.7292	Intermediate Similarity	NPC101051
0.7273	Intermediate Similarity	NPC470434
0.7228	Intermediate Similarity	NPC75608
0.7216	Intermediate Similarity	NPC161293
0.7172	Intermediate Similarity	NPC473146
0.7158	Intermediate Similarity	NPC302584
0.7158	Intermediate Similarity	NPC472199
0.7158	Intermediate Similarity	NPC9447
0.7158	Intermediate Similarity	NPC472197
0.7157	Intermediate Similarity	NPC472899
0.7157	Intermediate Similarity	NPC472898
0.7157	Intermediate Similarity	NPC472900
0.7143	Intermediate Similarity	NPC240372
0.7143	Intermediate Similarity	NPC475035
0.7143	Intermediate Similarity	NPC474194
0.7143	Intermediate Similarity	NPC470683
0.7143	Intermediate Similarity	NPC470684
0.7129	Intermediate Similarity	NPC473198
0.7128	Intermediate Similarity	NPC477748
0.7113	Intermediate Similarity	NPC469543
0.7113	Intermediate Similarity	NPC291709
0.7113	Intermediate Similarity	NPC241407
0.71	Intermediate Similarity	NPC285231
0.71	Intermediate Similarity	NPC21568
0.7097	Intermediate Similarity	NPC475037
0.7097	Intermediate Similarity	NPC125142
0.7097	Intermediate Similarity	NPC142583
0.7087	Intermediate Similarity	NPC33053
0.7083	Intermediate Similarity	NPC472195
0.7083	Intermediate Similarity	NPC472196
0.7083	Intermediate Similarity	NPC238090
0.7079	Intermediate Similarity	NPC163362
0.7079	Intermediate Similarity	NPC127295
0.7073	Intermediate Similarity	NPC59442
0.7071	Intermediate Similarity	NPC158088
0.7065	Intermediate Similarity	NPC477746
0.7065	Intermediate Similarity	NPC73166
0.7065	Intermediate Similarity	NPC477747
0.7065	Intermediate Similarity	NPC470124
0.7059	Intermediate Similarity	NPC93352
0.7053	Intermediate Similarity	NPC202886
0.7041	Intermediate Similarity	NPC90583
0.7041	Intermediate Similarity	NPC207617
0.7037	Intermediate Similarity	NPC147292
0.703	Intermediate Similarity	NPC272015
0.7019	Intermediate Similarity	NPC472897
0.7019	Intermediate Similarity	NPC472896
0.7011	Intermediate Similarity	NPC326661
0.701	Intermediate Similarity	NPC2003
0.701	Intermediate Similarity	NPC25701
0.701	Intermediate Similarity	NPC256368
0.701	Intermediate Similarity	NPC63897
0.701	Intermediate Similarity	NPC472198
0.701	Intermediate Similarity	NPC159698
0.7	Intermediate Similarity	NPC280367
0.7	Intermediate Similarity	NPC64348
0.7	Intermediate Similarity	NPC219656
0.6989	Remote Similarity	NPC470836
0.6979	Remote Similarity	NPC477749
0.6977	Remote Similarity	NPC472173
0.697	Remote Similarity	NPC153559
0.697	Remote Similarity	NPC472290
0.697	Remote Similarity	NPC473890
0.697	Remote Similarity	NPC243728
0.6962	Remote Similarity	NPC155457
0.6961	Remote Similarity	NPC197736
0.6947	Remote Similarity	NPC309310
0.6931	Remote Similarity	NPC267510
0.6931	Remote Similarity	NPC287539
0.6931	Remote Similarity	NPC3488
0.6931	Remote Similarity	NPC198992
0.6923	Remote Similarity	NPC231340
0.6923	Remote Similarity	NPC477390
0.6923	Remote Similarity	NPC477385
0.6907	Remote Similarity	NPC91654
0.6907	Remote Similarity	NPC474792
0.6907	Remote Similarity	NPC67398
0.69	Remote Similarity	NPC198422
0.69	Remote Similarity	NPC81483
0.69	Remote Similarity	NPC124181
0.69	Remote Similarity	NPC473307
0.69	Remote Similarity	NPC307517
0.69	Remote Similarity	NPC61630
0.69	Remote Similarity	NPC169468
0.69	Remote Similarity	NPC40182
0.69	Remote Similarity	NPC90819
0.6887	Remote Similarity	NPC141433
0.6882	Remote Similarity	NPC475034
0.6875	Remote Similarity	NPC231710
0.6875	Remote Similarity	NPC470573
0.6875	Remote Similarity	NPC65665
0.6875	Remote Similarity	NPC120021
0.6875	Remote Similarity	NPC159876
0.6875	Remote Similarity	NPC216826
0.6875	Remote Similarity	NPC233500
0.6875	Remote Similarity	NPC270908
0.6869	Remote Similarity	NPC54731
0.6869	Remote Similarity	NPC306041
0.6869	Remote Similarity	NPC256230
0.6863	Remote Similarity	NPC154452
0.6863	Remote Similarity	NPC304163
0.6863	Remote Similarity	NPC201191
0.6863	Remote Similarity	NPC136816
0.686	Remote Similarity	NPC55652
0.6857	Remote Similarity	NPC235824
0.6852	Remote Similarity	NPC307642
0.6848	Remote Similarity	NPC188717
0.6848	Remote Similarity	NPC211455
0.6848	Remote Similarity	NPC473315
0.6848	Remote Similarity	NPC142111
0.6842	Remote Similarity	NPC475991
0.6837	Remote Similarity	NPC477927
0.6837	Remote Similarity	NPC72817
0.6837	Remote Similarity	NPC315059
0.6832	Remote Similarity	NPC473200
0.6832	Remote Similarity	NPC7341
0.6832	Remote Similarity	NPC282669
0.6827	Remote Similarity	NPC127235
0.6824	Remote Similarity	NPC474078
0.6814	Remote Similarity	NPC196130
0.6813	Remote Similarity	NPC15978
0.6809	Remote Similarity	NPC472379
0.6809	Remote Similarity	NPC278283
0.6804	Remote Similarity	NPC235051
0.6796	Remote Similarity	NPC475928
0.6792	Remote Similarity	NPC472901
0.6778	Remote Similarity	NPC179933
0.6774	Remote Similarity	NPC116613
0.6774	Remote Similarity	NPC473308
0.6774	Remote Similarity	NPC32676
0.6771	Remote Similarity	NPC478110
0.6771	Remote Similarity	NPC473058

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC136699 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	127
0.1-0.2	1611
0.2-0.3	4278
0.3-0.4	2315
0.4-0.5	615
0.5-0.6	162
0.6-0.7	53
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6579	Remote Similarity	NPD7503	Approved
0.6458	Remote Similarity	NPD4249	Approved
0.6408	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4250	Approved
0.6392	Remote Similarity	NPD7524	Approved
0.6392	Remote Similarity	NPD4251	Approved
0.6389	Remote Similarity	NPD6686	Approved
0.6364	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7332	Phase 2
0.6293	Remote Similarity	NPD8513	Phase 3
0.625	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6698	Approved
0.62	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.62	Remote Similarity	NPD46	Approved
0.6174	Remote Similarity	NPD7328	Approved
0.6174	Remote Similarity	NPD7327	Approved
0.617	Remote Similarity	NPD7514	Phase 3
0.6154	Remote Similarity	NPD8517	Approved
0.6154	Remote Similarity	NPD8516	Approved
0.6154	Remote Similarity	NPD8515	Approved
0.6154	Remote Similarity	NPD8033	Approved
0.6147	Remote Similarity	NPD6412	Phase 2
0.6146	Remote Similarity	NPD7154	Phase 3
0.6146	Remote Similarity	NPD6695	Phase 3
0.6146	Remote Similarity	NPD6110	Phase 1
0.6139	Remote Similarity	NPD7983	Approved
0.6139	Remote Similarity	NPD7637	Suspended
0.6129	Remote Similarity	NPD7145	Approved
0.6121	Remote Similarity	NPD7516	Approved
0.6105	Remote Similarity	NPD6902	Approved
0.6082	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD895	Approved
0.6076	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD894	Approved
0.6076	Remote Similarity	NPD893	Approved
0.6076	Remote Similarity	NPD889	Approved
0.6076	Remote Similarity	NPD891	Phase 3
0.6076	Remote Similarity	NPD887	Approved
0.6076	Remote Similarity	NPD892	Phase 3
0.6076	Remote Similarity	NPD888	Phase 3
0.6068	Remote Similarity	NPD8377	Approved
0.6068	Remote Similarity	NPD8294	Approved
0.604	Remote Similarity	NPD7838	Discovery
0.6026	Remote Similarity	NPD904	Phase 3
0.6026	Remote Similarity	NPD905	Approved
0.6022	Remote Similarity	NPD6925	Approved
0.6022	Remote Similarity	NPD5776	Phase 2
0.6017	Remote Similarity	NPD8296	Approved
0.6017	Remote Similarity	NPD8335	Approved
0.6017	Remote Similarity	NPD8379	Approved
0.6017	Remote Similarity	NPD8380	Approved
0.6017	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6898	Phase 1
0.59	Remote Similarity	NPD7750	Discontinued
0.5895	Remote Similarity	NPD6929	Approved
0.5882	Remote Similarity	NPD368	Approved
0.5872	Remote Similarity	NPD1407	Approved
0.5851	Remote Similarity	NPD6932	Approved
0.5833	Remote Similarity	NPD6931	Approved
0.5833	Remote Similarity	NPD5344	Discontinued
0.5833	Remote Similarity	NPD6930	Phase 2
0.582	Remote Similarity	NPD7507	Approved
0.5816	Remote Similarity	NPD5362	Discontinued
0.5789	Remote Similarity	NPD4271	Approved
0.5789	Remote Similarity	NPD4268	Approved
0.5766	Remote Similarity	NPD6640	Phase 3
0.5755	Remote Similarity	NPD7839	Suspended
0.575	Remote Similarity	NPD2269	Approved
0.5738	Remote Similarity	NPD1091	Approved
0.5728	Remote Similarity	NPD7136	Phase 2
0.5714	Remote Similarity	NPD5282	Discontinued
0.568	Remote Similarity	NPD7319	Approved
0.5673	Remote Similarity	NPD7087	Discontinued
0.567	Remote Similarity	NPD4822	Approved
0.567	Remote Similarity	NPD4820	Approved
0.567	Remote Similarity	NPD4819	Approved
0.567	Remote Similarity	NPD4821	Approved
0.5645	Remote Similarity	NPD8074	Phase 3
0.5619	Remote Similarity	NPD5778	Approved
0.5619	Remote Similarity	NPD5779	Approved
0.5612	Remote Similarity	NPD4790	Discontinued
0.561	Remote Similarity	NPD8342	Approved
0.561	Remote Similarity	NPD8299	Approved
0.561	Remote Similarity	NPD8340	Approved
0.561	Remote Similarity	NPD8341	Approved
0.5603	Remote Similarity	NPD6429	Approved
0.5603	Remote Similarity	NPD6430	Approved
0.5603	Remote Similarity	NPD6053	Discontinued

Structure

CID136699 OpenBabel06191715492D 24 26 0 0 1 0 0 0 0 0999 V2000 -3.4641 -0.0000 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 -3.8005 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1369 3.2213 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 -2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2072 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4459 4.1723 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 -5.1854 1.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 22 1 0 0 0 0 3 6 2 0 0 0 0 3 8 1 0 0 0 0 4 6 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 7 1 1 1 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 18 1 6 0 0 0 9 5 1 1 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 6 1 1 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 6 0 0 0 12 13 1 0 0 0 0 12 20 1 1 0 0 0 13 15 1 0 0 0 0 13 21 1 6 0 0 0 14 22 1 0 0 0 0 14 24 1 6 0 0 0 15 23 1 0 0 0 0 15 24 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	91458
ChEMBL	CHEMBL514882
ZINC

Physicochemical Properties

Molecular Weight:	346.13
ALogP:	-3.5817
MLogP:	2.12
XLogP:	-2.39
# Rotatable Bonds:	10
Polar Surface Area:	149.07
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	24

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General Info & Identifiers & Properties
Structure MOL file
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Biological Activities
Similar NPs/Drugs