NPASS Compound

Structure

CID35185 OpenBabel06191715362D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.0029 -1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -0.1691 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 -3.6720 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 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 -4.6665 -1.0827 0.0000 C 0 0 1 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 -3.4641 -0.0000 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 -5.1665 -1.9487 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 2 24 1 0 0 0 0 3 9 1 0 0 0 0 4 18 1 0 0 0 0 5 8 2 0 0 0 0 5 25 1 0 0 0 0 6 1 1 1 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 3 1 6 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 1 0 0 0 10 4 1 1 0 0 0 10 12 1 0 0 0 0 10 26 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 16 27 1 0 0 0 0 17 26 1 0 0 0 0 17 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.15
Volume:	359.548
LogP:	0.014
LogD:	0.131
LogS:	-1.009
# Rotatable Bonds:	5
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	4.69
Fsp3:	0.824
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:	-5.918
MDCK Permeability:	0.00011366309627192095
Pgp-inhibitor:	0.002
Pgp-substrate:	0.555
Human Intestinal Absorption (HIA):	0.9
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233
Plasma Protein Binding (PPB):	21.85498046875%
Volume Distribution (VD):	0.337
Pgp-substrate:	49.13771438598633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.56
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.644
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	1.904
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.562
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.237
Carcinogencity:	0.901
Eye Corrosion:	0.004
Eye Irritation:	0.069
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC35185

Natural Product ID:	NPC35185
*Common Name:**	Loganin
IUPAC Name:	methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:	Loganin
Standard InCHIKey:	AMBQHHVBBHTQBF-UOUCRYGSSA-N
Standard InCHI:	InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1
SMILES:	C[C@H]1[C@H](C[C@@H]2C(=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081584
PubChem CID:	87691
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid 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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.tet.2012.03.006]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[10.1016/j.tet.2012.03.006]
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]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713409]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[16317898]
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]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[17449162]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[19235686]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555121]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19555121]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19666019]
NPO23142	Lamium album	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19904996]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[20645211]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
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]
NPO30658	Lamiophlomis rotata	n.a.	n.a.	n.a.	aerial parts	Jiangzi County, Tibet, China	2007-Sep	PMID[22664131]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[22707864]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[22822669]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23088673]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[2393954]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO11907	Streptomyces nitrosporeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25304895]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[25594733]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128898]
NPO29943	Strychnos nux-blanda	Species	Loganiaceae	Eukaryota	n.a.	root	n.a.	PMID[27534097]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[29140705]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33052051]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[7912074]
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]
NPO20352	Gentiana straminea	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]
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]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30658	Lamiophlomis rotata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO362	Gentiana crassicaulis	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]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22686	Gentiana macrophylla	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]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20352	Gentiana straminea	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]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	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]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	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]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30658	Lamiophlomis rotata	n.a.	n.a.	n.a.	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]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	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]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	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]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	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]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14338	Pterocephalus hookeri	Species	Caprifoliaceae	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]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6067	Strychnos ignatii	Species	Loganiaceae	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]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	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]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8031	Portulaca okinawensis	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9492	Maesopsis eminii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1480	Dimocarpus fumatus	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28192	Xenia puertogalerae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21220	Pulicaria uliginosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22818	Acritopappus confertus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20352	Gentiana straminea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6354	Trypetheliopsis boninensis	Species	Monoblastiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14338	Pterocephalus hookeri	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11907	Streptomyces nitrosporeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	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]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5155	Peritassa compta	Species	Celastraceae	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]
NPO8254	Melicope lasioneura	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	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]
NPO7427	Fagara ailanthoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4907	Torulopsis magnoliae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO362	Gentiana crassicaulis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23142	Lamium album	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	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	12
Ki	1
Others	17

Activity Type	# Activity
Cell Line	10
Individual Protein	9
Organism	7
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6.45	ug.mL-1	PMID[486348]
NPT2400	Cell Line	PA-1	Homo sapiens	IC50	=	4.85	ug.mL-1	PMID[486348]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4.85	ug.mL-1	PMID[486348]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	=	3.45	ug.mL-1	PMID[486348]
NPT1527	Cell Line	WRL68	Homo sapiens	IC50	=	3.2	ug.mL-1	PMID[486348]
NPT2641	Cell Line	COLO 320	Homo sapiens	IC50	=	2.2	ug.mL-1	PMID[486348]
NPT1527	Cell Line	WRL68	Homo sapiens	IC50	=	1.86	ug.mL-1	PMID[486348]
NPT2400	Cell Line	PA-1	Homo sapiens	IC50	=	1.45	ug.mL-1	PMID[486348]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	=	1.28	ug.mL-1	PMID[486348]
NPT2641	Cell Line	COLO 320	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[486348]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	51.2	%	PMID[486350]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	51.5	%	PMID[486350]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	50.5	%	PMID[486350]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	33.0	%	PMID[486350]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	33.5	%	PMID[486350]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	34.2	%	PMID[486350]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	IC50	=	14000.0	nM	PMID[486351]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	24.8	%	PMID[486346]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	41.4	%	PMID[486346]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	IC50	=	16.0	ug.mL-1	PMID[486346]
NPT2	Others	Unspecified		RLU	=	0.56	n.a.	PMID[486347]
NPT2	Others	Unspecified		RLU	=	0.66	n.a.	PMID[486347]
NPT2640	Organism	Bacopa monnieri	Bacopa monnieri	Activity	=	6.0	n.a.	PMID[486348]
NPT2640	Organism	Bacopa monnieri	Bacopa monnieri	Activity	=	2.0	n.a.	PMID[486348]
NPT2640	Organism	Bacopa monnieri	Bacopa monnieri	Activity	=	0.4	cm	PMID[486348]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	98.87	%	PMID[486349]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	87.42	%	PMID[486349]
NPT2	Others	Unspecified		Ki	=	55000.0	nM	PMID[486352]

☑ 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 NPC35185 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	221
0.1-0.2	1477
0.2-0.3	5364
0.3-0.4	10214
0.4-0.5	11851
0.5-0.6	7473
0.6-0.7	5431
0.7-0.8	597
0.8-0.85	36
0.85-0.9	14
0.9-0.95	7
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474730
1.0	High Similarity	NPC177013
1.0	High Similarity	NPC4899
0.9895	High Similarity	NPC37240
0.9691	High Similarity	NPC170432
0.9688	High Similarity	NPC475928
0.9684	High Similarity	NPC3488
0.9684	High Similarity	NPC287539
0.9592	High Similarity	NPC197813
0.9592	High Similarity	NPC80338
0.9592	High Similarity	NPC148270
0.9381	High Similarity	NPC106668
0.9307	High Similarity	NPC193741
0.9293	High Similarity	NPC127235
0.9286	High Similarity	NPC27687
0.9126	High Similarity	NPC475924
0.9126	High Similarity	NPC475851
0.9109	High Similarity	NPC110701
0.9062	High Similarity	NPC161293
0.8854	High Similarity	NPC63897
0.88	High Similarity	NPC304163
0.8763	High Similarity	NPC93869
0.8763	High Similarity	NPC6765
0.866	High Similarity	NPC274588
0.8614	High Similarity	NPC80144
0.8544	High Similarity	NPC41681
0.8542	High Similarity	NPC65665
0.8542	High Similarity	NPC216826
0.8542	High Similarity	NPC231710
0.8542	High Similarity	NPC270908
0.8542	High Similarity	NPC470573
0.8542	High Similarity	NPC120021
0.8515	High Similarity	NPC67296
0.85	High Similarity	NPC49833
0.85	High Similarity	NPC249171
0.85	High Similarity	NPC37866
0.8485	Intermediate Similarity	NPC170527
0.84	Intermediate Similarity	NPC304445
0.84	Intermediate Similarity	NPC472290
0.84	Intermediate Similarity	NPC236580
0.835	Intermediate Similarity	NPC473148
0.8333	Intermediate Similarity	NPC216911
0.83	Intermediate Similarity	NPC284063
0.8265	Intermediate Similarity	NPC235051
0.8235	Intermediate Similarity	NPC476320
0.8235	Intermediate Similarity	NPC306344
0.8235	Intermediate Similarity	NPC476211
0.8235	Intermediate Similarity	NPC255677
0.8235	Intermediate Similarity	NPC22149
0.8218	Intermediate Similarity	NPC261372
0.8218	Intermediate Similarity	NPC263674
0.8218	Intermediate Similarity	NPC86843
0.8218	Intermediate Similarity	NPC58267
0.8173	Intermediate Similarity	NPC329834
0.8163	Intermediate Similarity	NPC117596
0.8155	Intermediate Similarity	NPC298255
0.8155	Intermediate Similarity	NPC27474
0.8155	Intermediate Similarity	NPC476230
0.8155	Intermediate Similarity	NPC28304
0.8137	Intermediate Similarity	NPC472015
0.8125	Intermediate Similarity	NPC470657
0.8119	Intermediate Similarity	NPC474297
0.8081	Intermediate Similarity	NPC66504
0.8081	Intermediate Similarity	NPC472124
0.8081	Intermediate Similarity	NPC472126
0.8081	Intermediate Similarity	NPC472125
0.8077	Intermediate Similarity	NPC261117
0.8077	Intermediate Similarity	NPC310804
0.8077	Intermediate Similarity	NPC195510
0.8077	Intermediate Similarity	NPC222062
0.8077	Intermediate Similarity	NPC13171
0.8041	Intermediate Similarity	NPC31349
0.8036	Intermediate Similarity	NPC13710
0.802	Intermediate Similarity	NPC167893
0.8	Intermediate Similarity	NPC329704
0.8	Intermediate Similarity	NPC118761
0.8	Intermediate Similarity	NPC197541
0.8	Intermediate Similarity	NPC267869
0.8	Intermediate Similarity	NPC61201
0.8	Intermediate Similarity	NPC284929
0.8	Intermediate Similarity	NPC234304
0.7981	Intermediate Similarity	NPC476228
0.798	Intermediate Similarity	NPC307699
0.798	Intermediate Similarity	NPC246173
0.7941	Intermediate Similarity	NPC241911
0.7925	Intermediate Similarity	NPC86095
0.7905	Intermediate Similarity	NPC250545
0.7885	Intermediate Similarity	NPC473146
0.7879	Intermediate Similarity	NPC50464
0.7879	Intermediate Similarity	NPC93190
0.7864	Intermediate Similarity	NPC471150
0.7833	Intermediate Similarity	NPC155529
0.7826	Intermediate Similarity	NPC470829
0.7826	Intermediate Similarity	NPC473228
0.78	Intermediate Similarity	NPC303451
0.78	Intermediate Similarity	NPC6414
0.7778	Intermediate Similarity	NPC254538
0.7778	Intermediate Similarity	NPC474285
0.775	Intermediate Similarity	NPC213634
0.7745	Intermediate Similarity	NPC71589
0.7736	Intermediate Similarity	NPC94919
0.7736	Intermediate Similarity	NPC471599
0.7723	Intermediate Similarity	NPC274274
0.7723	Intermediate Similarity	NPC294643
0.7723	Intermediate Similarity	NPC473150
0.7714	Intermediate Similarity	NPC186861
0.7714	Intermediate Similarity	NPC244878
0.7714	Intermediate Similarity	NPC471381
0.7706	Intermediate Similarity	NPC219900
0.7706	Intermediate Similarity	NPC392
0.7706	Intermediate Similarity	NPC177524
0.7699	Intermediate Similarity	NPC277583
0.7692	Intermediate Similarity	NPC27363
0.767	Intermediate Similarity	NPC101051
0.767	Intermediate Similarity	NPC472873
0.7658	Intermediate Similarity	NPC471251
0.7642	Intermediate Similarity	NPC158350
0.7642	Intermediate Similarity	NPC219038
0.7642	Intermediate Similarity	NPC20673
0.7636	Intermediate Similarity	NPC208307
0.7636	Intermediate Similarity	NPC471250
0.7636	Intermediate Similarity	NPC118225
0.7619	Intermediate Similarity	NPC151093
0.7596	Intermediate Similarity	NPC54731
0.7596	Intermediate Similarity	NPC306041
0.7586	Intermediate Similarity	NPC281840
0.7581	Intermediate Similarity	NPC289700
0.7581	Intermediate Similarity	NPC62172
0.7581	Intermediate Similarity	NPC127656
0.7576	Intermediate Similarity	NPC474949
0.7576	Intermediate Similarity	NPC476015
0.7576	Intermediate Similarity	NPC475019
0.7576	Intermediate Similarity	NPC474762
0.7568	Intermediate Similarity	NPC124053
0.7568	Intermediate Similarity	NPC106760
0.7568	Intermediate Similarity	NPC114961
0.7568	Intermediate Similarity	NPC50223
0.7568	Intermediate Similarity	NPC27551
0.7565	Intermediate Similarity	NPC475309
0.7563	Intermediate Similarity	NPC469750
0.7563	Intermediate Similarity	NPC250556
0.7551	Intermediate Similarity	NPC3464
0.7551	Intermediate Similarity	NPC474780
0.7551	Intermediate Similarity	NPC475963
0.7551	Intermediate Similarity	NPC151176
0.7549	Intermediate Similarity	NPC470379
0.7549	Intermediate Similarity	NPC470373
0.7544	Intermediate Similarity	NPC106228
0.7544	Intermediate Similarity	NPC88945
0.7544	Intermediate Similarity	NPC138372
0.7525	Intermediate Similarity	NPC215556
0.7525	Intermediate Similarity	NPC92974
0.7523	Intermediate Similarity	NPC85670
0.7523	Intermediate Similarity	NPC54737
0.7522	Intermediate Similarity	NPC132668
0.7521	Intermediate Similarity	NPC42675
0.75	Intermediate Similarity	NPC469543
0.75	Intermediate Similarity	NPC186148
0.75	Intermediate Similarity	NPC74139
0.75	Intermediate Similarity	NPC117702
0.75	Intermediate Similarity	NPC240070
0.75	Intermediate Similarity	NPC19028
0.75	Intermediate Similarity	NPC163228
0.75	Intermediate Similarity	NPC329784
0.75	Intermediate Similarity	NPC179412
0.75	Intermediate Similarity	NPC146456
0.75	Intermediate Similarity	NPC471356
0.75	Intermediate Similarity	NPC471357
0.75	Intermediate Similarity	NPC9674
0.75	Intermediate Similarity	NPC469757
0.7479	Intermediate Similarity	NPC318135
0.7478	Intermediate Similarity	NPC473304
0.7477	Intermediate Similarity	NPC59489
0.7477	Intermediate Similarity	NPC139838
0.7477	Intermediate Similarity	NPC98859
0.7477	Intermediate Similarity	NPC4637
0.7477	Intermediate Similarity	NPC471401
0.7476	Intermediate Similarity	NPC320089
0.7475	Intermediate Similarity	NPC149725
0.7475	Intermediate Similarity	NPC47958
0.7475	Intermediate Similarity	NPC304509
0.7475	Intermediate Similarity	NPC329749
0.746	Intermediate Similarity	NPC322503
0.746	Intermediate Similarity	NPC75616
0.746	Intermediate Similarity	NPC470143
0.7459	Intermediate Similarity	NPC173347
0.7458	Intermediate Similarity	NPC216866
0.7456	Intermediate Similarity	NPC106446
0.7456	Intermediate Similarity	NPC178289
0.7455	Intermediate Similarity	NPC287269
0.7451	Intermediate Similarity	NPC297474
0.7451	Intermediate Similarity	NPC216284
0.7451	Intermediate Similarity	NPC54065
0.7451	Intermediate Similarity	NPC206614
0.7451	Intermediate Similarity	NPC474323
0.7438	Intermediate Similarity	NPC245094
0.7438	Intermediate Similarity	NPC311534
0.7436	Intermediate Similarity	NPC470312
0.7436	Intermediate Similarity	NPC108072
0.7434	Intermediate Similarity	NPC243572

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 NPC35185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	2085
0.2-0.3	3879
0.3-0.4	1945
0.4-0.5	598
0.5-0.6	295
0.6-0.7	133
0.7-0.8	6
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
0.7706	Intermediate Similarity	NPD6686	Approved
0.7563	Intermediate Similarity	NPD7507	Approved
0.7522	Intermediate Similarity	NPD8133	Approved
0.7377	Intermediate Similarity	NPD7319	Approved
0.7373	Intermediate Similarity	NPD7503	Approved
0.7297	Intermediate Similarity	NPD6412	Phase 2
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7115	Intermediate Similarity	NPD46	Approved
0.7115	Intermediate Similarity	NPD6698	Approved
0.6975	Remote Similarity	NPD7328	Approved
0.6975	Remote Similarity	NPD7327	Approved
0.6942	Remote Similarity	NPD8513	Phase 3
0.6917	Remote Similarity	NPD7516	Approved
0.6897	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8294	Approved
0.686	Remote Similarity	NPD8377	Approved
0.6842	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8379	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.6803	Remote Similarity	NPD8296	Approved
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8335	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8378	Approved
0.6803	Remote Similarity	NPD8033	Approved
0.6803	Remote Similarity	NPD8380	Approved
0.675	Remote Similarity	NPD6009	Approved
0.6748	Remote Similarity	NPD6370	Approved
0.6746	Remote Similarity	NPD7736	Approved
0.6721	Remote Similarity	NPD6319	Approved
0.6695	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6371	Approved
0.664	Remote Similarity	NPD7492	Approved
0.6639	Remote Similarity	NPD4632	Approved
0.6612	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6616	Approved
0.6585	Remote Similarity	NPD6054	Approved
0.6574	Remote Similarity	NPD7983	Approved
0.6571	Remote Similarity	NPD4249	Approved
0.656	Remote Similarity	NPD7829	Approved
0.656	Remote Similarity	NPD7830	Approved
0.6555	Remote Similarity	NPD8297	Approved
0.6535	Remote Similarity	NPD7078	Approved
0.6532	Remote Similarity	NPD6015	Approved
0.6532	Remote Similarity	NPD6016	Approved
0.6522	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4250	Approved
0.6509	Remote Similarity	NPD4251	Approved
0.6481	Remote Similarity	NPD7838	Discovery
0.648	Remote Similarity	NPD8080	Discontinued
0.648	Remote Similarity	NPD5988	Approved
0.6471	Remote Similarity	NPD5368	Approved
0.6452	Remote Similarity	NPD6059	Approved
0.6441	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8328	Phase 3
0.6423	Remote Similarity	NPD7641	Discontinued
0.641	Remote Similarity	NPD5697	Approved
0.64	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1695	Approved
0.6372	Remote Similarity	NPD7638	Approved
0.6356	Remote Similarity	NPD6881	Approved
0.6356	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6899	Approved
0.6341	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6650	Approved
0.6333	Remote Similarity	NPD6649	Approved
0.6328	Remote Similarity	NPD8451	Approved
0.6325	Remote Similarity	NPD7128	Approved
0.6325	Remote Similarity	NPD5739	Approved
0.6325	Remote Similarity	NPD6402	Approved
0.6325	Remote Similarity	NPD6675	Approved
0.6321	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7640	Approved
0.6316	Remote Similarity	NPD7639	Approved
0.6303	Remote Similarity	NPD6012	Approved
0.6303	Remote Similarity	NPD6013	Approved
0.6303	Remote Similarity	NPD6372	Approved
0.6303	Remote Similarity	NPD6373	Approved
0.6303	Remote Similarity	NPD6014	Approved
0.6299	Remote Similarity	NPD7642	Approved
0.6286	Remote Similarity	NPD7154	Phase 3
0.6286	Remote Similarity	NPD5362	Discontinued
0.6279	Remote Similarity	NPD8074	Phase 3
0.6279	Remote Similarity	NPD8448	Approved
0.6271	Remote Similarity	NPD5701	Approved
0.627	Remote Similarity	NPD8444	Approved
0.627	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD8337	Approved
0.6231	Remote Similarity	NPD8336	Approved
0.6222	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7320	Approved
0.6218	Remote Similarity	NPD6011	Approved
0.6216	Remote Similarity	NPD5778	Approved
0.6216	Remote Similarity	NPD5779	Approved
0.621	Remote Similarity	NPD7115	Discovery
0.6198	Remote Similarity	NPD6847	Approved
0.6198	Remote Similarity	NPD6869	Approved
0.6198	Remote Similarity	NPD8130	Phase 1
0.6198	Remote Similarity	NPD6617	Approved
0.6195	Remote Similarity	NPD7839	Suspended
0.6182	Remote Similarity	NPD5785	Approved
0.6172	Remote Similarity	NPD7604	Phase 2
0.6167	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD8269	Approved
0.6142	Remote Similarity	NPD8267	Approved
0.6142	Remote Similarity	NPD8268	Approved
0.6142	Remote Similarity	NPD8266	Approved
0.614	Remote Similarity	NPD6083	Phase 2
0.614	Remote Similarity	NPD6084	Phase 2
0.6136	Remote Similarity	NPD8392	Approved
0.6136	Remote Similarity	NPD8391	Approved
0.6136	Remote Similarity	NPD8390	Approved
0.6132	Remote Similarity	NPD4788	Approved
0.6124	Remote Similarity	NPD8341	Approved
0.6124	Remote Similarity	NPD8299	Approved
0.6124	Remote Similarity	NPD8342	Approved
0.6124	Remote Similarity	NPD8340	Approved
0.6117	Remote Similarity	NPD4238	Approved
0.6117	Remote Similarity	NPD4802	Phase 2
0.6116	Remote Similarity	NPD4634	Approved
0.6111	Remote Similarity	NPD5786	Approved
0.6106	Remote Similarity	NPD5695	Phase 3
0.6091	Remote Similarity	NPD6101	Approved
0.6091	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.609	Remote Similarity	NPD7260	Phase 2
0.6087	Remote Similarity	NPD4225	Approved
0.6077	Remote Similarity	NPD6336	Discontinued
0.6068	Remote Similarity	NPD8083	Approved
0.6068	Remote Similarity	NPD8139	Approved
0.6068	Remote Similarity	NPD8084	Approved
0.6068	Remote Similarity	NPD8085	Approved
0.6068	Remote Similarity	NPD8086	Approved
0.6068	Remote Similarity	NPD5211	Phase 2
0.6068	Remote Similarity	NPD8082	Approved
0.6068	Remote Similarity	NPD8138	Approved
0.605	Remote Similarity	NPD6008	Approved
0.6047	Remote Similarity	NPD6067	Discontinued
0.6045	Remote Similarity	NPD8338	Approved
0.6034	Remote Similarity	NPD4696	Approved
0.6034	Remote Similarity	NPD5285	Approved
0.6034	Remote Similarity	NPD5286	Approved
0.6019	Remote Similarity	NPD5363	Approved
0.6018	Remote Similarity	NPD5282	Discontinued
0.6017	Remote Similarity	NPD8276	Approved
0.6017	Remote Similarity	NPD8275	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD4820	Approved
0.6	Remote Similarity	NPD4755	Approved
0.5985	Remote Similarity	NPD6033	Approved
0.5984	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5344	Discontinued
0.5982	Remote Similarity	NPD8035	Phase 2
0.5982	Remote Similarity	NPD6411	Approved
0.5982	Remote Similarity	NPD8034	Phase 2
0.5966	Remote Similarity	NPD8081	Approved
0.5966	Remote Similarity	NPD5141	Approved
0.5962	Remote Similarity	NPD4268	Approved
0.5962	Remote Similarity	NPD4271	Approved
0.5948	Remote Similarity	NPD5696	Approved
0.5943	Remote Similarity	NPD5369	Approved
0.5935	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5226	Approved
0.5932	Remote Similarity	NPD5224	Approved
0.5932	Remote Similarity	NPD7632	Discontinued
0.5932	Remote Similarity	NPD5225	Approved
0.5932	Remote Similarity	NPD4633	Approved
0.5929	Remote Similarity	NPD8171	Discontinued
0.5929	Remote Similarity	NPD6399	Phase 3
0.5926	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6845	Suspended
0.5917	Remote Similarity	NPD8393	Approved
0.5897	Remote Similarity	NPD4700	Approved
0.5896	Remote Similarity	NPD5956	Approved
0.5891	Remote Similarity	NPD6921	Approved
0.5888	Remote Similarity	NPD4269	Approved
0.5888	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4270	Approved
0.5882	Remote Similarity	NPD5175	Approved
0.5882	Remote Similarity	NPD5174	Approved
0.5872	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD8307	Discontinued
0.5868	Remote Similarity	NPD8140	Approved
0.5859	Remote Similarity	NPD7100	Approved
0.5859	Remote Similarity	NPD7101	Approved
0.5847	Remote Similarity	NPD5223	Approved
0.5841	Remote Similarity	NPD7637	Suspended

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