NPASS Compound

Structure

CID307699 OpenBabel06191716112D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 1.7321 -2.0000 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 -5.1962 -3.0000 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 -2.5981 -1.5000 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 3 4 1 0 0 0 0 4 22 1 0 0 0 0 5 17 1 0 0 0 0 6 9 2 0 0 0 0 6 23 1 0 0 0 0 7 2 1 1 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 3 1 1 0 0 0 8 9 1 0 0 0 0 9 14 1 0 0 0 0 10 5 1 6 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 16 1 0 0 0 0 13 20 1 1 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 25 1 6 0 0 0 16 24 1 0 0 0 0 16 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.13
Volume:	330.826
LogP:	0.255
LogD:	0.057
LogS:	-1.181
# Rotatable Bonds:	4
TPSA:	134.91
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	4.709
Fsp3:	0.688
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.753
MDCK Permeability:	0.00010122330422746018
Pgp-inhibitor:	0.001
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.933
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.267
Plasma Protein Binding (PPB):	27.317235946655273%
Volume Distribution (VD):	0.376
Pgp-substrate:	56.886165618896484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.25
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	1.605
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.303
AMES Toxicity:	0.117
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.237
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.2
Respiratory Toxicity:	0.823

Download Data

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

Natural Product: NPC307699

Natural Product ID:	NPC307699
*Common Name:**	Sweroside
IUPAC Name:	(3S,4R,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
Synonyms:	Sweroside
Standard InCHIKey:	VSJGJMKGNMDJCI-ZASXJUAOSA-N
Standard InCHI:	InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10-,11-,12+,13-,15+,16+/m1/s1
SMILES:	C=C[C@H]1[C@@H](OC=C2[C@H]1CCOC2=O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456137
PubChem CID:	161036
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.lwt.2014.11.023]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10705751]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11735581]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	seed	n.a.	PMID[12822897]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[16335823]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	roots	n.a.	n.a.	PMID[17375953]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17404979]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18064621]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[18064621]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1905	Fagraea fragrans	Species	Gentianaceae	Eukaryota	bark and leaves	Koh Kong Province, Cambodia	2005-DEC	PMID[19053508]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[20645211]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20813533]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21448706]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21856162]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[22233034]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[22822669]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23001436]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23002924]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO22355	Flacourtia indica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23354072]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23599008]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[24257774]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868877]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[24919480]
NPO11907	Streptomyces nitrosporeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25304895]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[26129938]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[29140705]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29799195]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141299]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33052051]
NPO4956	Celtis australis	Species	Cannabaceae	Eukaryota	Seeds	Nodeh, Nowdeh, Khalkhal, Ardebil, Iran		PMID[33055442]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO11907	Streptomyces nitrosporeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8609080]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[9397205]
NPO25228	Corollospora pulchella	Species	Halosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9666182]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16539	Viguiera puruana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20828	Swertia leducii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24661	Leontice leontopetalum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20828	Swertia leducii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22459	Impatiens capensis	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25070	Naranga aenescens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14921	Anisothrix integra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9983.1	Ambrosia artemisiifolia var. elatior	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11907	Streptomyces nitrosporeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6133	Cornus sericea	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22818	Acritopappus confertus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22475.1	Brachylaena discolor var. rotundata	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16965	Lyngbya aestuarii	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22424	Cetraria ornata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22085	Cercospora traversiana	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6543	Parachlorella kessleri	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8254	Melicope lasioneura	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11120	Brassica rapa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11200.1	Paenibacillus larvae subsp. pulvifaciens	Subspecies	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21220	Pulicaria uliginosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6207	Porthetria dispar	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24661	Leontice leontopetalum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25134	Cephalosporium chrysogenum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19646	Cynthia papillosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10942	Retama sphaerocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10429	Gentiana scabra	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22355	Flacourtia indica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4956	Celtis australis	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23166	Keteleeria evelyniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2825	Chiloscyphus pallescens	Species	Lophocoleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7360	Teucrium lamiifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21804	Dryopteris villarii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10458	Pithecollobium dulce	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1905	Fagraea fragrans	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10470	Pimpinella major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8082	Chelonanthus chelonoides	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5687	Comanthus parvicirrus	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO403	Gentiana lutea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6888	Pultenaea altissima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23799	Gentiana triflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23292	Andrographis macrobotrys	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25228	Corollospora pulchella	Species	Halosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24468	Zanthoxylum macrophyllum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13483	Silene praemixta	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24875	Lithocarpus litseifolius	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5155	Peritassa compta	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16539	Viguiera puruana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9660	Caiophora sepiaria	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20828	Swertia leducii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19759	Begonia fagifolia	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	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	4

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[447950]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	IC50	=	89500.0	nM	PMID[447952]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	50.0	ug.mL-1	PMID[447949]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11200.0	nM	PMID[447950]

☑ 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 NPC307699 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	229
0.1-0.2	1670
0.2-0.3	5477
0.3-0.4	12321
0.4-0.5	12171
0.5-0.6	8299
0.6-0.7	2249
0.7-0.8	225
0.8-0.85	30
0.85-0.9	10
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC472125
0.9882	High Similarity	NPC472124
0.9882	High Similarity	NPC472126
0.9545	High Similarity	NPC101051
0.9535	High Similarity	NPC117596
0.9318	High Similarity	NPC61201
0.931	High Similarity	NPC470573
0.931	High Similarity	NPC231710
0.931	High Similarity	NPC65665
0.931	High Similarity	NPC216826
0.931	High Similarity	NPC270908
0.931	High Similarity	NPC120021
0.8901	High Similarity	NPC170204
0.8737	High Similarity	NPC222062
0.8696	High Similarity	NPC469543
0.8667	High Similarity	NPC6414
0.8667	High Similarity	NPC303451
0.8646	High Similarity	NPC267869
0.8646	High Similarity	NPC197541
0.8646	High Similarity	NPC234304
0.8646	High Similarity	NPC284929
0.8646	High Similarity	NPC118761
0.8542	High Similarity	NPC195510
0.8542	High Similarity	NPC13171
0.8526	High Similarity	NPC306344
0.8526	High Similarity	NPC22149
0.8526	High Similarity	NPC255677
0.8438	Intermediate Similarity	NPC28304
0.8438	Intermediate Similarity	NPC298255
0.8404	Intermediate Similarity	NPC241911
0.8351	Intermediate Similarity	NPC310804
0.8351	Intermediate Similarity	NPC261117
0.8351	Intermediate Similarity	NPC250545
0.8211	Intermediate Similarity	NPC161293
0.8182	Intermediate Similarity	NPC86095
0.8081	Intermediate Similarity	NPC475928
0.8046	Intermediate Similarity	NPC323472
0.802	Intermediate Similarity	NPC474285
0.802	Intermediate Similarity	NPC254538
0.798	Intermediate Similarity	NPC106668
0.798	Intermediate Similarity	NPC4899
0.798	Intermediate Similarity	NPC474730
0.798	Intermediate Similarity	NPC35185
0.798	Intermediate Similarity	NPC177013
0.7921	Intermediate Similarity	NPC41681
0.7921	Intermediate Similarity	NPC170432
0.79	Intermediate Similarity	NPC27687
0.79	Intermediate Similarity	NPC37240
0.7895	Intermediate Similarity	NPC320552
0.7872	Intermediate Similarity	NPC327253
0.7843	Intermediate Similarity	NPC80338
0.7843	Intermediate Similarity	NPC197813
0.7843	Intermediate Similarity	NPC148270
0.7812	Intermediate Similarity	NPC294293
0.7802	Intermediate Similarity	NPC266718
0.7723	Intermediate Similarity	NPC197736
0.7717	Intermediate Similarity	NPC470124
0.7708	Intermediate Similarity	NPC280390
0.77	Intermediate Similarity	NPC3488
0.77	Intermediate Similarity	NPC287539
0.7677	Intermediate Similarity	NPC198422
0.7677	Intermediate Similarity	NPC40182
0.7653	Intermediate Similarity	NPC306041
0.7629	Intermediate Similarity	NPC63897
0.7619	Intermediate Similarity	NPC193741
0.7609	Intermediate Similarity	NPC475035
0.7604	Intermediate Similarity	NPC9447
0.7604	Intermediate Similarity	NPC477749
0.7596	Intermediate Similarity	NPC110701
0.7579	Intermediate Similarity	NPC50464
0.7573	Intermediate Similarity	NPC127235
0.7553	Intermediate Similarity	NPC475037
0.7526	Intermediate Similarity	NPC472196
0.7526	Intermediate Similarity	NPC238090
0.7526	Intermediate Similarity	NPC472195
0.75	Intermediate Similarity	NPC49833
0.75	Intermediate Similarity	NPC249171
0.7477	Intermediate Similarity	NPC475851
0.7477	Intermediate Similarity	NPC475924
0.7474	Intermediate Similarity	NPC137368
0.7451	Intermediate Similarity	NPC471599
0.7451	Intermediate Similarity	NPC201191
0.7451	Intermediate Similarity	NPC80144
0.7449	Intermediate Similarity	NPC159698
0.7449	Intermediate Similarity	NPC71589
0.7449	Intermediate Similarity	NPC2003
0.7449	Intermediate Similarity	NPC25701
0.7429	Intermediate Similarity	NPC473807
0.7426	Intermediate Similarity	NPC244878
0.7423	Intermediate Similarity	NPC473150
0.7423	Intermediate Similarity	NPC294643
0.7423	Intermediate Similarity	NPC274274
0.7419	Intermediate Similarity	NPC136699
0.7419	Intermediate Similarity	NPC220167
0.74	Intermediate Similarity	NPC472290
0.7396	Intermediate Similarity	NPC285588
0.7396	Intermediate Similarity	NPC477748
0.7396	Intermediate Similarity	NPC93190
0.7374	Intermediate Similarity	NPC6765
0.7374	Intermediate Similarity	NPC93869
0.7368	Intermediate Similarity	NPC475186
0.7368	Intermediate Similarity	NPC118077
0.7363	Intermediate Similarity	NPC127295
0.7363	Intermediate Similarity	NPC163362
0.7353	Intermediate Similarity	NPC2313
0.7353	Intermediate Similarity	NPC154132
0.7353	Intermediate Similarity	NPC20673
0.7353	Intermediate Similarity	NPC475157
0.7353	Intermediate Similarity	NPC219038
0.7353	Intermediate Similarity	NPC475655
0.7353	Intermediate Similarity	NPC471637
0.7353	Intermediate Similarity	NPC57586
0.7347	Intermediate Similarity	NPC474835
0.734	Intermediate Similarity	NPC475034
0.734	Intermediate Similarity	NPC477746
0.734	Intermediate Similarity	NPC477747
0.7327	Intermediate Similarity	NPC151093
0.7327	Intermediate Similarity	NPC472015
0.732	Intermediate Similarity	NPC202886
0.73	Intermediate Similarity	NPC54731
0.7292	Intermediate Similarity	NPC473151
0.7282	Intermediate Similarity	NPC304163
0.7273	Intermediate Similarity	NPC477348
0.7273	Intermediate Similarity	NPC477345
0.7273	Intermediate Similarity	NPC238264
0.7273	Intermediate Similarity	NPC256368
0.7273	Intermediate Similarity	NPC274588
0.7264	Intermediate Similarity	NPC219900
0.7264	Intermediate Similarity	NPC177524
0.7264	Intermediate Similarity	NPC392
0.7245	Intermediate Similarity	NPC470379
0.7245	Intermediate Similarity	NPC110072
0.7245	Intermediate Similarity	NPC470373
0.7245	Intermediate Similarity	NPC472199
0.7245	Intermediate Similarity	NPC472197
0.7238	Intermediate Similarity	NPC476738
0.7238	Intermediate Similarity	NPC476740
0.7228	Intermediate Similarity	NPC236580
0.7228	Intermediate Similarity	NPC304445
0.7228	Intermediate Similarity	NPC278506
0.7212	Intermediate Similarity	NPC473148
0.7212	Intermediate Similarity	NPC309398
0.7204	Intermediate Similarity	NPC251026
0.7196	Intermediate Similarity	NPC133625
0.7188	Intermediate Similarity	NPC142583
0.7188	Intermediate Similarity	NPC74139
0.7184	Intermediate Similarity	NPC4637
0.7184	Intermediate Similarity	NPC98859
0.7184	Intermediate Similarity	NPC476611
0.7184	Intermediate Similarity	NPC67296
0.7184	Intermediate Similarity	NPC198992
0.7172	Intermediate Similarity	NPC320089
0.7157	Intermediate Similarity	NPC61630
0.7157	Intermediate Similarity	NPC37866
0.7157	Intermediate Similarity	NPC169468
0.7157	Intermediate Similarity	NPC307517
0.7157	Intermediate Similarity	NPC81483
0.7143	Intermediate Similarity	NPC473311
0.7143	Intermediate Similarity	NPC133377
0.7143	Intermediate Similarity	NPC469869
0.713	Intermediate Similarity	NPC83005
0.713	Intermediate Similarity	NPC472508
0.7129	Intermediate Similarity	NPC475164
0.7129	Intermediate Similarity	NPC473605
0.7129	Intermediate Similarity	NPC143446
0.7129	Intermediate Similarity	NPC476066
0.7129	Intermediate Similarity	NPC475375
0.7129	Intermediate Similarity	NPC475593
0.7129	Intermediate Similarity	NPC475525
0.7129	Intermediate Similarity	NPC473765
0.7129	Intermediate Similarity	NPC475241
0.7129	Intermediate Similarity	NPC170527
0.7129	Intermediate Similarity	NPC475540
0.7129	Intermediate Similarity	NPC256230
0.7128	Intermediate Similarity	NPC142111
0.7128	Intermediate Similarity	NPC473315
0.7126	Intermediate Similarity	NPC474078
0.7113	Intermediate Similarity	NPC470137
0.7113	Intermediate Similarity	NPC248312
0.7103	Intermediate Similarity	NPC193765
0.7103	Intermediate Similarity	NPC472507
0.71	Intermediate Similarity	NPC472198
0.7097	Intermediate Similarity	NPC469469
0.7075	Intermediate Similarity	NPC82251
0.7075	Intermediate Similarity	NPC315070
0.7071	Intermediate Similarity	NPC477349
0.7071	Intermediate Similarity	NPC276298
0.7065	Intermediate Similarity	NPC321728
0.7059	Intermediate Similarity	NPC309503
0.7059	Intermediate Similarity	NPC91197
0.7059	Intermediate Similarity	NPC96597
0.7059	Intermediate Similarity	NPC475332
0.7059	Intermediate Similarity	NPC155319
0.7059	Intermediate Similarity	NPC474194
0.7059	Intermediate Similarity	NPC476612
0.7059	Intermediate Similarity	NPC125551
0.7059	Intermediate Similarity	NPC239547
0.7059	Intermediate Similarity	NPC476613
0.7053	Intermediate Similarity	NPC473308
0.7053	Intermediate Similarity	NPC98276

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 NPC307699 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1974
0.2-0.3	4095
0.3-0.4	1940
0.4-0.5	663
0.5-0.6	233
0.6-0.7	37
0.7-0.8	2
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
0.7264	Intermediate Similarity	NPD6686	Approved
0.7157	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.697	Remote Similarity	NPD46	Approved
0.697	Remote Similarity	NPD6698	Approved
0.6957	Remote Similarity	NPD8513	Phase 3
0.6909	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8516	Approved
0.681	Remote Similarity	NPD8515	Approved
0.681	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6637	Remote Similarity	NPD8133	Approved
0.6634	Remote Similarity	NPD7838	Discovery
0.6555	Remote Similarity	NPD7830	Approved
0.6555	Remote Similarity	NPD7829	Approved
0.6408	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD7507	Approved
0.6271	Remote Similarity	NPD7641	Discontinued
0.6263	Remote Similarity	NPD6110	Phase 1
0.626	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD6412	Phase 2
0.6238	Remote Similarity	NPD4249	Approved
0.6179	Remote Similarity	NPD8451	Approved
0.6176	Remote Similarity	NPD4251	Approved
0.6176	Remote Similarity	NPD4250	Approved
0.6167	Remote Similarity	NPD8294	Approved
0.6167	Remote Similarity	NPD8377	Approved
0.616	Remote Similarity	NPD7319	Approved
0.6148	Remote Similarity	NPD8328	Phase 3
0.6148	Remote Similarity	NPD7642	Approved
0.6134	Remote Similarity	NPD7327	Approved
0.6134	Remote Similarity	NPD7328	Approved
0.6129	Remote Similarity	NPD8448	Approved
0.6121	Remote Similarity	NPD6053	Discontinued
0.6116	Remote Similarity	NPD8378	Approved
0.6116	Remote Similarity	NPD8444	Approved
0.6116	Remote Similarity	NPD8296	Approved
0.6116	Remote Similarity	NPD8380	Approved
0.6116	Remote Similarity	NPD8335	Approved
0.6116	Remote Similarity	NPD8379	Approved
0.6111	Remote Similarity	NPD8392	Approved
0.6111	Remote Similarity	NPD8390	Approved
0.6111	Remote Similarity	NPD8391	Approved
0.6091	Remote Similarity	NPD5344	Discontinued
0.6083	Remote Similarity	NPD7516	Approved
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.605	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD898	Approved
0.6044	Remote Similarity	NPD897	Approved
0.6044	Remote Similarity	NPD896	Approved
0.604	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7329	Approved
0.6019	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8342	Approved
0.5968	Remote Similarity	NPD8341	Approved
0.5968	Remote Similarity	NPD8299	Approved
0.5968	Remote Similarity	NPD8340	Approved
0.5965	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8080	Discontinued
0.5909	Remote Similarity	NPD4225	Approved
0.5905	Remote Similarity	NPD6101	Approved
0.5905	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3181	Approved
0.5888	Remote Similarity	NPD5779	Approved
0.5888	Remote Similarity	NPD5778	Approved
0.5854	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD888	Phase 3
0.5833	Remote Similarity	NPD893	Approved
0.5833	Remote Similarity	NPD892	Phase 3
0.5833	Remote Similarity	NPD891	Phase 3
0.5825	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6371	Approved
0.58	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6411	Approved
0.5784	Remote Similarity	NPD7154	Phase 3
0.5784	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD3669	Approved
0.578	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7638	Approved
0.573	Remote Similarity	NPD6123	Approved
0.5726	Remote Similarity	NPD8266	Approved
0.5726	Remote Similarity	NPD8268	Approved
0.5726	Remote Similarity	NPD8267	Approved
0.5726	Remote Similarity	NPD8269	Approved
0.5714	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD7640	Approved
0.5714	Remote Similarity	NPD6648	Approved
0.5703	Remote Similarity	NPD7736	Approved
0.5702	Remote Similarity	NPD1407	Approved
0.5688	Remote Similarity	NPD5282	Discontinued
0.568	Remote Similarity	NPD6370	Approved
0.5656	Remote Similarity	NPD7115	Discovery
0.5656	Remote Similarity	NPD6009	Approved
0.5648	Remote Similarity	NPD7637	Suspended
0.5645	Remote Similarity	NPD6319	Approved
0.56	Remote Similarity	NPD4271	Approved
0.56	Remote Similarity	NPD4268	Approved
0.56	Remote Similarity	NPD6921	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