NPASS Compound

Structure

CID253662 OpenBabel06191716052D 33 36 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 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 -2.5981 1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -2.5981 2.5000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 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 22 1 0 0 0 0 7 19 1 0 0 0 0 8 23 1 0 0 0 0 9 10 2 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 14 2 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 31 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 1 0 0 0 16 20 1 0 0 0 0 16 28 2 0 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 21 1 0 0 0 0 18 30 1 1 0 0 0 19 20 2 0 0 0 0 19 31 1 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 21 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.1
Volume:	421.937
LogP:	0.264
LogD:	-0.013
LogS:	-3.564
# Rotatable Bonds:	4
TPSA:	210.51
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	4.008
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.265
MDCK Permeability:	6.821358510933351e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.432
Human Intestinal Absorption (HIA):	0.733
20% Bioavailability (F20%):	0.86
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	89.1961898803711%
Volume Distribution (VD):	0.845
Pgp-substrate:	13.478715896606445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.325
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.252
CYP2D6-inhibitor:	0.165
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.104
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	6.828
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.126
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.832
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.829
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.756
Respiratory Toxicity:	0.022

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC253662

Natural Product ID:	NPC253662
*Common Name:**	Miquelianin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	Miquelianin
Standard InCHIKey:	OVSQVDMCBVZWGM-DHALZPNHSA-N
Standard InCHI:	InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21-/m1/s1
SMILES:	OC[C@H]1O[C@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098724
PubChem CID:	12304323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2008.09.013]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479328]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785416]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11223086]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520228]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11524125]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11524125]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14559084]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730255]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[15730255]
NPO6742	Knema elegans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309311]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724861]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315967]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17341114]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	leaf	n.a.	n.a.	PMID[20035557]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	atlantic-forest-soil	n.a.	PMID[20450206]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302965]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22080044]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25050371]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607351]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27684202]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32031812]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	Flowers	São Paulo, Brazil.		PMID[32156350]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33170684]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288445]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	Bay of Naples, Italy	n.a.	PMID[7714539]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16353	Gynocardia odorata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16353	Gynocardia odorata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21520	Corydalis thalictrifolia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16353	Gynocardia odorata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21520	Corydalis thalictrifolia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8437	Encyothalia cliftonii	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2723	Artemisia carvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13579	Euthyroides episcopalis	Species	Euthyroididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5064	Derris uliginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9598	Psorospermum adamauense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14279.1	Ficus sarmentosa var. thunbergii	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5102	Ircinia wistarii	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8909	Pteris radiata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15448	Chrysothamnus parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21075	Phytolacca thyrsiflora	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22144	Daphne lancifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22225	Calliandra eriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8941	Salacia longipes	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23698	Gardneria insularis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21967	Astragalus asper	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16353	Gynocardia odorata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3119	Cephalaria uralensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3579	Lucilia sericata	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7013	Dicoma capensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21397	Venus mercenaria	Species	Veneridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2174	Polysiphonia elongata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26170	Haliclona mucosa	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8773	Sonchus ortunoi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24605	Monochaetia compta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5301	Haplophyllum ferganicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13351	Buxus malayana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6157	Dahlstedtia araripensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20575	Penicillium puberulum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10165	Haematomma porphyrium	Species	Haematommataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4073	Geranium sylvaticum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21520	Corydalis thalictrifolia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23975	Osteophloeum platyspermum	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5859	Bacterium sa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20008	Odontocline hollickii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4663	Kopsia profunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13825	Echinops dagestanicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8167	Astragalus mucidus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29226.1	Ficus cordata subsp. salicifolia	Subspecies	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO199	Dryopteris aitoniana	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25862	Lafoensia glyptocarpa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26287	Spodoptera eridania	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5541	Crotalaria aegyptiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO762	Digitalis isabelliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24230	Petriella sordida	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17768	Heliabravoa chende	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4351	Hedyosmum arborescens	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO550	Callicarpa maingayi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9233	Plexaura homomalla	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7625	Scopolia hladnikiana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25647	Taraxacum bicorne	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17531	Rosa portlandica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9139	Madhuca neriifolia	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6742	Knema elegans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Ki	1
Others	4

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT224	Individual Protein	Alpha-2c adrenergic receptor	Homo sapiens	Ki	=	4063.0	nM	PMID[529381]
NPT71	Cell Line	HEK293	Homo sapiens	Inhibition	=	-1.86	%	PMID[529382]
NPT1606	Individual Protein	NADPH oxidase 4	Homo sapiens	IC50	=	830.0	nM	PMID[529382]
NPT1606	Individual Protein	NADPH oxidase 4	Homo sapiens	Inhibition	=	105.0	%	PMID[529382]
NPT1606	Individual Protein	NADPH oxidase 4	Homo sapiens	Inhibition	=	104.63	%	PMID[529382]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	TIME	=	0.02483	hr	PMID[529381]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC253662 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	463
0.1-0.2	1895
0.2-0.3	4423
0.3-0.4	10023
0.4-0.5	7901
0.5-0.6	4220
0.6-0.7	5307
0.7-0.8	5185
0.8-0.85	1550
0.85-0.9	1099
0.9-0.95	438
0.95-1	193

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179950
1.0	High Similarity	NPC88789
1.0	High Similarity	NPC145038
1.0	High Similarity	NPC281131
1.0	High Similarity	NPC274618
1.0	High Similarity	NPC118284
1.0	High Similarity	NPC308404
1.0	High Similarity	NPC276222
1.0	High Similarity	NPC56077
0.9936	High Similarity	NPC127546
0.9936	High Similarity	NPC52550
0.9936	High Similarity	NPC19388
0.9936	High Similarity	NPC223424
0.9936	High Similarity	NPC84362
0.9936	High Similarity	NPC173637
0.9936	High Similarity	NPC277205
0.9936	High Similarity	NPC240431
0.9936	High Similarity	NPC317489
0.9936	High Similarity	NPC55786
0.9873	High Similarity	NPC328940
0.9873	High Similarity	NPC73855
0.9873	High Similarity	NPC219904
0.9873	High Similarity	NPC120099
0.9873	High Similarity	NPC203050
0.9873	High Similarity	NPC21100
0.9873	High Similarity	NPC223747
0.9873	High Similarity	NPC135599
0.9873	High Similarity	NPC113968
0.9873	High Similarity	NPC277174
0.9873	High Similarity	NPC197285
0.9873	High Similarity	NPC225434
0.9811	High Similarity	NPC136042
0.9811	High Similarity	NPC155763
0.9811	High Similarity	NPC20505
0.9811	High Similarity	NPC95866
0.9811	High Similarity	NPC254855
0.9811	High Similarity	NPC259896
0.9811	High Similarity	NPC156869
0.9811	High Similarity	NPC235260
0.9811	High Similarity	NPC244776
0.9811	High Similarity	NPC29958
0.9811	High Similarity	NPC255157
0.9811	High Similarity	NPC67326
0.9811	High Similarity	NPC206123
0.9811	High Similarity	NPC116864
0.981	High Similarity	NPC226304
0.981	High Similarity	NPC325555
0.981	High Similarity	NPC160156
0.981	High Similarity	NPC92565
0.981	High Similarity	NPC265530
0.9808	High Similarity	NPC77660
0.9808	High Similarity	NPC189142
0.975	High Similarity	NPC176740
0.975	High Similarity	NPC203259
0.975	High Similarity	NPC471748
0.975	High Similarity	NPC190003
0.975	High Similarity	NPC33054
0.975	High Similarity	NPC471725
0.975	High Similarity	NPC153755
0.975	High Similarity	NPC245452
0.975	High Similarity	NPC26230
0.975	High Similarity	NPC134532
0.975	High Similarity	NPC60735
0.975	High Similarity	NPC155877
0.975	High Similarity	NPC175107
0.9748	High Similarity	NPC52382
0.9748	High Similarity	NPC138927
0.9748	High Similarity	NPC270578
0.9747	High Similarity	NPC67037
0.9747	High Similarity	NPC255615
0.9745	High Similarity	NPC168822
0.9745	High Similarity	NPC270335
0.9745	High Similarity	NPC191306
0.9745	High Similarity	NPC19709
0.9689	High Similarity	NPC101026
0.9689	High Similarity	NPC24043
0.9689	High Similarity	NPC4390
0.9689	High Similarity	NPC45522
0.9689	High Similarity	NPC21666
0.9689	High Similarity	NPC42773
0.9689	High Similarity	NPC169977
0.9688	High Similarity	NPC285197
0.9688	High Similarity	NPC67105
0.9688	High Similarity	NPC245014
0.9688	High Similarity	NPC282987
0.9688	High Similarity	NPC84265
0.9686	High Similarity	NPC149244
0.9686	High Similarity	NPC275454
0.9686	High Similarity	NPC48640
0.9684	High Similarity	NPC311830
0.9684	High Similarity	NPC34531
0.9684	High Similarity	NPC22832
0.9682	High Similarity	NPC473043
0.963	High Similarity	NPC214621
0.963	High Similarity	NPC294815
0.963	High Similarity	NPC237435
0.963	High Similarity	NPC473327
0.963	High Similarity	NPC115760
0.963	High Similarity	NPC220173
0.963	High Similarity	NPC253685
0.963	High Similarity	NPC81042
0.963	High Similarity	NPC19108
0.963	High Similarity	NPC101191
0.963	High Similarity	NPC476472
0.963	High Similarity	NPC135277
0.963	High Similarity	NPC294629
0.963	High Similarity	NPC223426
0.963	High Similarity	NPC16194
0.963	High Similarity	NPC49344
0.963	High Similarity	NPC34267
0.963	High Similarity	NPC210094
0.963	High Similarity	NPC43211
0.9627	High Similarity	NPC117260
0.9627	High Similarity	NPC476405
0.9625	High Similarity	NPC227508
0.9623	High Similarity	NPC210073
0.9623	High Similarity	NPC8856
0.9623	High Similarity	NPC115674
0.9623	High Similarity	NPC254306
0.962	High Similarity	NPC284960
0.962	High Similarity	NPC243930
0.962	High Similarity	NPC222936
0.962	High Similarity	NPC309025
0.962	High Similarity	NPC29830
0.962	High Similarity	NPC88023
0.9571	High Similarity	NPC198324
0.9571	High Similarity	NPC202908
0.9571	High Similarity	NPC122467
0.9571	High Similarity	NPC89127
0.9571	High Similarity	NPC292019
0.9571	High Similarity	NPC65563
0.9571	High Similarity	NPC144097
0.9571	High Similarity	NPC8573
0.9571	High Similarity	NPC61904
0.9571	High Similarity	NPC219043
0.9571	High Similarity	NPC470949
0.9571	High Similarity	NPC472385
0.9571	High Similarity	NPC14187
0.9571	High Similarity	NPC471669
0.9565	High Similarity	NPC72249
0.9563	High Similarity	NPC229729
0.9563	High Similarity	NPC58716
0.9563	High Similarity	NPC146792
0.9563	High Similarity	NPC45618
0.9557	High Similarity	NPC300537
0.9557	High Similarity	NPC127782
0.9551	High Similarity	NPC133671
0.9551	High Similarity	NPC135391
0.9551	High Similarity	NPC197304
0.9551	High Similarity	NPC77672
0.9551	High Similarity	NPC54802
0.9551	High Similarity	NPC78263
0.9512	High Similarity	NPC217520
0.9512	High Similarity	NPC251417
0.9512	High Similarity	NPC113836
0.9512	High Similarity	NPC139571
0.9512	High Similarity	NPC35167
0.9512	High Similarity	NPC89052
0.9512	High Similarity	NPC253521
0.9512	High Similarity	NPC168584
0.9512	High Similarity	NPC173837
0.9512	High Similarity	NPC37668
0.9509	High Similarity	NPC264735
0.9509	High Similarity	NPC477848
0.9503	High Similarity	NPC86008
0.9503	High Similarity	NPC45638
0.9503	High Similarity	NPC201292
0.9503	High Similarity	NPC58053
0.9503	High Similarity	NPC105025
0.9503	High Similarity	NPC209296
0.9503	High Similarity	NPC475942
0.9503	High Similarity	NPC476771
0.9503	High Similarity	NPC186807
0.9503	High Similarity	NPC93337
0.9503	High Similarity	NPC195257
0.9503	High Similarity	NPC226294
0.9503	High Similarity	NPC469931
0.95	High Similarity	NPC5778
0.95	High Similarity	NPC236934
0.9497	High Similarity	NPC88043
0.9494	High Similarity	NPC182045
0.949	High Similarity	NPC41121
0.949	High Similarity	NPC472459
0.949	High Similarity	NPC111929
0.949	High Similarity	NPC320283
0.9487	High Similarity	NPC261866
0.9487	High Similarity	NPC307938
0.9487	High Similarity	NPC323593
0.9487	High Similarity	NPC203500
0.9455	High Similarity	NPC470443
0.9455	High Similarity	NPC470444
0.9455	High Similarity	NPC110941
0.9455	High Similarity	NPC241423
0.9455	High Similarity	NPC473571
0.9455	High Similarity	NPC192539
0.9455	High Similarity	NPC473682
0.9455	High Similarity	NPC126784
0.9451	High Similarity	NPC473862
0.9451	High Similarity	NPC154741
0.9451	High Similarity	NPC233994

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC253662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	956
0.2-0.3	2010
0.3-0.4	2681
0.4-0.5	1740
0.5-0.6	889
0.6-0.7	294
0.7-0.8	122
0.8-0.85	9
0.85-0.9	17
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.975	High Similarity	NPD6797	Phase 2
0.9689	High Similarity	NPD7251	Discontinued
0.963	High Similarity	NPD4338	Clinical (unspecified phase)
0.9509	High Similarity	NPD7808	Phase 3
0.9503	High Similarity	NPD7054	Approved
0.9444	High Similarity	NPD7472	Approved
0.9325	High Similarity	NPD7074	Phase 3
0.9321	High Similarity	NPD3818	Discontinued
0.9304	High Similarity	NPD4381	Clinical (unspecified phase)
0.9146	High Similarity	NPD7804	Clinical (unspecified phase)
0.908	High Similarity	NPD6167	Clinical (unspecified phase)
0.908	High Similarity	NPD6166	Phase 2
0.908	High Similarity	NPD6168	Clinical (unspecified phase)
0.8938	High Similarity	NPD3817	Phase 2
0.8931	High Similarity	NPD1934	Approved
0.891	High Similarity	NPD1512	Approved
0.8875	High Similarity	NPD2393	Clinical (unspecified phase)
0.8782	High Similarity	NPD1511	Approved
0.8765	High Similarity	NPD3882	Suspended
0.8758	High Similarity	NPD2801	Approved
0.8688	High Similarity	NPD4380	Phase 2
0.865	High Similarity	NPD4868	Clinical (unspecified phase)
0.8598	High Similarity	NPD7075	Discontinued
0.8589	High Similarity	NPD5402	Approved
0.85	High Similarity	NPD5403	Approved
0.848	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6801	Discontinued
0.843	Intermediate Similarity	NPD6559	Discontinued
0.8415	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD5401	Approved
0.8313	Intermediate Similarity	NPD6799	Approved
0.828	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1549	Phase 2
0.8221	Intermediate Similarity	NPD1653	Approved
0.8198	Intermediate Similarity	NPD3751	Discontinued
0.8176	Intermediate Similarity	NPD3787	Discontinued
0.8111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD5494	Approved
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8036	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD2796	Approved
0.7976	Intermediate Similarity	NPD7819	Suspended
0.7976	Intermediate Similarity	NPD1465	Phase 2
0.7964	Intermediate Similarity	NPD7411	Suspended
0.7943	Intermediate Similarity	NPD5844	Phase 1
0.7927	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7685	Pre-registration
0.7907	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1613	Approved
0.7861	Intermediate Similarity	NPD6232	Discontinued
0.7853	Intermediate Similarity	NPD6190	Approved
0.7831	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7473	Discontinued
0.7821	Intermediate Similarity	NPD8313	Approved
0.7821	Intermediate Similarity	NPD8312	Approved
0.7803	Intermediate Similarity	NPD7199	Phase 2
0.7791	Intermediate Similarity	NPD919	Approved
0.7784	Intermediate Similarity	NPD7228	Approved
0.7735	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7266	Discontinued
0.7713	Intermediate Similarity	NPD6776	Approved
0.7713	Intermediate Similarity	NPD6779	Approved
0.7713	Intermediate Similarity	NPD6780	Approved
0.7713	Intermediate Similarity	NPD6781	Approved
0.7713	Intermediate Similarity	NPD6782	Approved
0.7713	Intermediate Similarity	NPD6777	Approved
0.7713	Intermediate Similarity	NPD6778	Approved
0.7701	Intermediate Similarity	NPD1247	Approved
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD7435	Discontinued
0.7683	Intermediate Similarity	NPD3750	Approved
0.7683	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD943	Approved
0.7673	Intermediate Similarity	NPD1240	Approved
0.767	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7584	Approved
0.7643	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3926	Phase 2
0.7609	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD37	Approved
0.758	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1607	Approved
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD8455	Phase 2
0.7553	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3749	Approved
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD7696	Phase 3
0.75	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD7698	Approved
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7485	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3027	Phase 3
0.7471	Intermediate Similarity	NPD7768	Phase 2
0.747	Intermediate Similarity	NPD4628	Phase 3
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7449	Intermediate Similarity	NPD7874	Approved
0.7449	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6534	Approved
0.7447	Intermediate Similarity	NPD6535	Approved
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.7378	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.733	Intermediate Similarity	NPD7699	Phase 2
0.733	Intermediate Similarity	NPD7700	Phase 2
0.7323	Intermediate Similarity	NPD7783	Phase 2
0.7323	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7801	Approved
0.7322	Intermediate Similarity	NPD7240	Approved
0.7308	Intermediate Similarity	NPD1091	Approved
0.7305	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD447	Suspended
0.7294	Intermediate Similarity	NPD2533	Approved
0.7294	Intermediate Similarity	NPD2534	Approved
0.7294	Intermediate Similarity	NPD2532	Approved
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8319	Approved
0.7282	Intermediate Similarity	NPD8320	Phase 1
0.7278	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7259	Intermediate Similarity	NPD7585	Approved
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7219	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD8150	Discontinued
0.7209	Intermediate Similarity	NPD920	Approved
0.7208	Intermediate Similarity	NPD7583	Approved
0.7202	Intermediate Similarity	NPD2800	Approved
0.7193	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6233	Phase 2
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5953	Discontinued
0.7173	Intermediate Similarity	NPD4363	Phase 3
0.7173	Intermediate Similarity	NPD4360	Phase 2
0.7169	Intermediate Similarity	NPD7033	Discontinued
0.7165	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6099	Approved
0.7126	Intermediate Similarity	NPD3226	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7126	Intermediate Similarity	NPD6100	Approved
0.7125	Intermediate Similarity	NPD1203	Approved
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.7102	Intermediate Similarity	NPD6844	Discontinued
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7101	Intermediate Similarity	NPD1652	Phase 2
0.7101	Intermediate Similarity	NPD1243	Approved
0.7099	Intermediate Similarity	NPD4908	Phase 1
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7091	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2798	Approved
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
0.7035	Intermediate Similarity	NPD7390	Discontinued
0.7031	Intermediate Similarity	NPD6213	Phase 3
0.7031	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6212	Phase 3
0.7029	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5124	Phase 1
0.6988	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2346	Discontinued
0.6982	Remote Similarity	NPD2344	Approved
0.6981	Remote Similarity	NPD1610	Phase 2
0.697	Remote Similarity	NPD7680	Approved
0.6964	Remote Similarity	NPD2799	Discontinued
0.6959	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3225	Approved
0.6937	Remote Similarity	NPD9269	Phase 2
0.6928	Remote Similarity	NPD4060	Phase 1
0.6927	Remote Similarity	NPD5353	Approved
0.6919	Remote Similarity	NPD2163	Approved
0.6909	Remote Similarity	NPD3268	Approved
0.6902	Remote Similarity	NPD2403	Approved
0.69	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4340	Discontinued
0.6885	Remote Similarity	NPD5710	Approved
0.6885	Remote Similarity	NPD5711	Approved
0.6878	Remote Similarity	NPD7930	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data