NPASS Compound

Structure

CID2003 OpenBabel06191715322D 26 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 -4.5000 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 -4.8301 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 -1.6340 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 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 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 11 2 1 6 0 0 0 11 25 1 0 0 0 0 12 21 2 0 0 0 0 13 6 1 1 0 0 0 13 19 1 0 0 0 0 14 9 1 6 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 1 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 25 1 6 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.2
Volume:	373.689
LogP:	0.95
LogD:	-0.284
LogS:	-1.482
# Rotatable Bonds:	5
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	4.596
Fsp3:	0.737
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:	-5.296
MDCK Permeability:	1.2196066563774366e-05
Pgp-inhibitor:	0.92
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.871
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.182
Plasma Protein Binding (PPB):	49.78227615356445%
Volume Distribution (VD):	0.95
Pgp-substrate:	46.06797409057617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.683
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.128
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	1.816
Half-life (T1/2):	0.859

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.316
AMES Toxicity:	0.68
Rat Oral Acute Toxicity:	0.272
Maximum Recommended Daily Dose:	0.32
Skin Sensitization:	0.516
Carcinogencity:	0.266
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.824

Download Data

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

Natural Product: NPC2003

Natural Product ID:	NPC2003
*Common Name:**	(6R,9R)-3-Oxo-Alpha-Ionol-Beta-D-Glucopyranoside
IUPAC Name:	(4R)-3,5,5-trimethyl-4-[(E,3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-1-enyl]cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	SZOPSAFLRCYJCX-ITEOXOHJSA-N
Standard InCHI:	InChI=1S/C19H30O7/c1-10-7-12(21)8-19(3,4)13(10)6-5-11(2)25-18-17(24)16(23)15(22)14(9-20)26-18/h5-7,11,13-18,20,22-24H,8-9H2,1-4H3/b6-5+/t11-,13+,14-,15-,16+,17-,18-/m1/s1
SMILES:	CC1=CC(=O)CC(C)(C)[C@H]1/C=C/[C@@H](C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3114752
PubChem CID:	9820702
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11087590]
NPO10304	Colletotrichum gloeosporioides	Species	Glomerellaceae	Eukaryota	Artemisia mongolica	n.a.	n.a.	PMID[11087599]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11421757]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO10729	Lechevalieria aerocolonigenes	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15620255]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15974621]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	Krachong waterfall area, Trang Province, Thailand	2001-APR	PMID[15974621]
NPO17799	Siraitia grosvenorii	Species	Cucurbitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16268506]
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17451272]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18844422]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO17799	Siraitia grosvenorii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21893415]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO22821.1	Chamaecyparis obtusa var. formosana	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25026733]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO17799	Siraitia grosvenorii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28448136]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28972755]
NPO10304	Colletotrichum gloeosporioides	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29035525]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5118	Zanthoxylum myriacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6724	Glycosmis stenocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5118	Zanthoxylum myriacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9231	Mikania mendocina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11452	Pterocarpus officinalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26396	Coprinopsis atramentaria	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17799	Siraitia grosvenorii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1581	Passiflora caerulea	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26719	Tetrapanax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1252	Aglaia grandis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8543	Meconopsis horridula	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6724	Glycosmis stenocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3280	Penicillium crustaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO477	Lepraria xanthina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9231	Mikania mendocina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15164	Jacobaea adonidifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6724	Glycosmis stenocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6802	Rothmannia wittii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10304	Colletotrichum gloeosporioides	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5118	Zanthoxylum myriacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29479	Epilobium rosmarinifolium	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO896	Streptomyces kanamyceticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10729	Lechevalieria aerocolonigenes	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26396	Coprinopsis atramentaria	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7087	Oxera splendida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9265	Jasonia candicans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26719	Tetrapanax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5344	Calodendrum capense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6330	Croton caudatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7968	Artemisia kurramensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO305	Vitex pinnata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7779	Impatiens edgeworthii	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6341	Magonia glabrata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8120	Episcia cupreata	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1252	Aglaia grandis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17799	Siraitia grosvenorii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7463	Ranzania japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8543	Meconopsis horridula	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10483	Chrysanthemum sinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO557	Bhesa nitidissima	Species	Centroplacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1581	Passiflora caerulea	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10798	Cis punctifer	Species	Ciidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29108	Strychnos pseudoquina	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12330	Pseudophryne coriacea	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9447	Tolypothrix tenuis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28621	Sepedonium ampullosporum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12613	Catunaregam tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10081	Othonna sedifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16285	Stachys byzantina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29431	Rhapis humilis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11544	Vernonia lanuginosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO540	Anaphalis araneosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22821.1	Chamaecyparis obtusa var. formosana	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10536	Rhabdonia verticillata	Species	Areschougiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12153	Adenia globosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11452	Pterocarpus officinalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5508	Stevia purpurea	Species	Asteraceae	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	2
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	IC50	>	1000000.0	nM	PMID[523075]
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	=	12.51	%	PMID[523075]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	16800.0	nM	PMID[523076]

☑ 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 NPC2003 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	194
0.1-0.2	1178
0.2-0.3	4647
0.3-0.4	9217
0.4-0.5	13676
0.5-0.6	7921
0.6-0.7	5221
0.7-0.8	601
0.8-0.85	21
0.85-0.9	9
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC25701
0.956	High Similarity	NPC40182
0.956	High Similarity	NPC198422
0.9348	High Similarity	NPC81483
0.9348	High Similarity	NPC307517
0.9348	High Similarity	NPC169468
0.9348	High Similarity	NPC61630
0.9032	High Similarity	NPC474194
0.8958	High Similarity	NPC151516
0.8817	High Similarity	NPC108141
0.8778	High Similarity	NPC471755
0.8778	High Similarity	NPC471756
0.8723	High Similarity	NPC256230
0.8557	High Similarity	NPC154127
0.8542	High Similarity	NPC70733
0.8542	High Similarity	NPC56071
0.8469	Intermediate Similarity	NPC223834
0.8316	Intermediate Similarity	NPC294293
0.8298	Intermediate Similarity	NPC477749
0.828	Intermediate Similarity	NPC477748
0.8247	Intermediate Similarity	NPC278506
0.8235	Intermediate Similarity	NPC392
0.8235	Intermediate Similarity	NPC177524
0.8235	Intermediate Similarity	NPC219900
0.8191	Intermediate Similarity	NPC202886
0.8182	Intermediate Similarity	NPC198992
0.8144	Intermediate Similarity	NPC143446
0.8132	Intermediate Similarity	NPC266718
0.8077	Intermediate Similarity	NPC83005
0.8061	Intermediate Similarity	NPC309503
0.8061	Intermediate Similarity	NPC96597
0.8061	Intermediate Similarity	NPC155319
0.8061	Intermediate Similarity	NPC125551
0.8061	Intermediate Similarity	NPC239547
0.8061	Intermediate Similarity	NPC91197
0.8039	Intermediate Similarity	NPC82251
0.8021	Intermediate Similarity	NPC61201
0.8021	Intermediate Similarity	NPC474792
0.8021	Intermediate Similarity	NPC91654
0.8021	Intermediate Similarity	NPC67398
0.8021	Intermediate Similarity	NPC320552
0.8	Intermediate Similarity	NPC327253
0.7944	Intermediate Similarity	NPC475163
0.7935	Intermediate Similarity	NPC475035
0.7921	Intermediate Similarity	NPC201191
0.7909	Intermediate Similarity	NPC48692
0.7895	Intermediate Similarity	NPC309310
0.7885	Intermediate Similarity	NPC272576
0.7885	Intermediate Similarity	NPC473288
0.7864	Intermediate Similarity	NPC239961
0.785	Intermediate Similarity	NPC311592
0.785	Intermediate Similarity	NPC75167
0.7849	Intermediate Similarity	NPC477747
0.7849	Intermediate Similarity	NPC477746
0.7822	Intermediate Similarity	NPC280991
0.7812	Intermediate Similarity	NPC6414
0.7812	Intermediate Similarity	NPC303451
0.781	Intermediate Similarity	NPC246205
0.7802	Intermediate Similarity	NPC280367
0.78	Intermediate Similarity	NPC472015
0.7778	Intermediate Similarity	NPC181145
0.7778	Intermediate Similarity	NPC54731
0.7778	Intermediate Similarity	NPC306041
0.7745	Intermediate Similarity	NPC13171
0.7745	Intermediate Similarity	NPC195510
0.7745	Intermediate Similarity	NPC121423
0.7736	Intermediate Similarity	NPC46407
0.7736	Intermediate Similarity	NPC119550
0.7736	Intermediate Similarity	NPC235014
0.7732	Intermediate Similarity	NPC302584
0.7727	Intermediate Similarity	NPC473828
0.7727	Intermediate Similarity	NPC234522
0.7727	Intermediate Similarity	NPC473617
0.7723	Intermediate Similarity	NPC306344
0.7723	Intermediate Similarity	NPC22149
0.7723	Intermediate Similarity	NPC255677
0.7714	Intermediate Similarity	NPC217921
0.7714	Intermediate Similarity	NPC135015
0.7714	Intermediate Similarity	NPC128795
0.7714	Intermediate Similarity	NPC48548
0.77	Intermediate Similarity	NPC266842
0.77	Intermediate Similarity	NPC472290
0.7692	Intermediate Similarity	NPC252296
0.7685	Intermediate Similarity	NPC473159
0.7685	Intermediate Similarity	NPC474410
0.7685	Intermediate Similarity	NPC293658
0.7684	Intermediate Similarity	NPC475037
0.766	Intermediate Similarity	NPC34581
0.7653	Intermediate Similarity	NPC474835
0.7653	Intermediate Similarity	NPC238090
0.7653	Intermediate Similarity	NPC472195
0.7653	Intermediate Similarity	NPC472196
0.7653	Intermediate Similarity	NPC320089
0.7647	Intermediate Similarity	NPC28304
0.7647	Intermediate Similarity	NPC285231
0.7647	Intermediate Similarity	NPC21568
0.7647	Intermediate Similarity	NPC298255
0.7642	Intermediate Similarity	NPC316974
0.7642	Intermediate Similarity	NPC40728
0.764	Intermediate Similarity	NPC229655
0.7636	Intermediate Similarity	NPC474483
0.7629	Intermediate Similarity	NPC117596
0.7624	Intermediate Similarity	NPC222303
0.7619	Intermediate Similarity	NPC184512
0.7619	Intermediate Similarity	NPC125423
0.7619	Intermediate Similarity	NPC474285
0.7619	Intermediate Similarity	NPC88013
0.7619	Intermediate Similarity	NPC254538
0.7604	Intermediate Similarity	NPC248312
0.7596	Intermediate Similarity	NPC100955
0.7596	Intermediate Similarity	NPC194941
0.7596	Intermediate Similarity	NPC121566
0.7593	Intermediate Similarity	NPC174836
0.7593	Intermediate Similarity	NPC471967
0.7582	Intermediate Similarity	NPC321728
0.7579	Intermediate Similarity	NPC478112
0.7576	Intermediate Similarity	NPC159698
0.7573	Intermediate Similarity	NPC238397
0.7573	Intermediate Similarity	NPC150463
0.7573	Intermediate Similarity	NPC471363
0.7573	Intermediate Similarity	NPC222062
0.7573	Intermediate Similarity	NPC214277
0.7573	Intermediate Similarity	NPC310804
0.7573	Intermediate Similarity	NPC261117
0.7568	Intermediate Similarity	NPC45475
0.7551	Intermediate Similarity	NPC472197
0.7551	Intermediate Similarity	NPC472126
0.7551	Intermediate Similarity	NPC9447
0.7551	Intermediate Similarity	NPC472125
0.7551	Intermediate Similarity	NPC324157
0.7551	Intermediate Similarity	NPC472124
0.7547	Intermediate Similarity	NPC311223
0.7545	Intermediate Similarity	NPC471816
0.7525	Intermediate Similarity	NPC240372
0.7525	Intermediate Similarity	NPC476613
0.7525	Intermediate Similarity	NPC476612
0.7524	Intermediate Similarity	NPC95243
0.7524	Intermediate Similarity	NPC476738
0.7524	Intermediate Similarity	NPC210178
0.7524	Intermediate Similarity	NPC85670
0.7524	Intermediate Similarity	NPC476740
0.7524	Intermediate Similarity	NPC63023
0.7524	Intermediate Similarity	NPC162033
0.7523	Intermediate Similarity	NPC62696
0.7523	Intermediate Similarity	NPC293038
0.7523	Intermediate Similarity	NPC260665
0.7523	Intermediate Similarity	NPC477944
0.7523	Intermediate Similarity	NPC264153
0.7522	Intermediate Similarity	NPC476204
0.7522	Intermediate Similarity	NPC170084
0.75	Intermediate Similarity	NPC469543
0.75	Intermediate Similarity	NPC127933
0.75	Intermediate Similarity	NPC197541
0.75	Intermediate Similarity	NPC234304
0.75	Intermediate Similarity	NPC134270
0.75	Intermediate Similarity	NPC475889
0.75	Intermediate Similarity	NPC170204
0.75	Intermediate Similarity	NPC99266
0.75	Intermediate Similarity	NPC475834
0.75	Intermediate Similarity	NPC284929
0.75	Intermediate Similarity	NPC474179
0.75	Intermediate Similarity	NPC267869
0.75	Intermediate Similarity	NPC472750
0.75	Intermediate Similarity	NPC118761
0.75	Intermediate Similarity	NPC309398
0.75	Intermediate Similarity	NPC100697
0.75	Intermediate Similarity	NPC472747
0.75	Intermediate Similarity	NPC7613
0.75	Intermediate Similarity	NPC7644
0.75	Intermediate Similarity	NPC473070
0.7478	Intermediate Similarity	NPC318135
0.7477	Intermediate Similarity	NPC23046
0.7477	Intermediate Similarity	NPC473405
0.7476	Intermediate Similarity	NPC476611
0.7474	Intermediate Similarity	NPC475034
0.7474	Intermediate Similarity	NPC470124
0.7455	Intermediate Similarity	NPC165439
0.7455	Intermediate Similarity	NPC102088
0.7455	Intermediate Similarity	NPC74727
0.7453	Intermediate Similarity	NPC293512
0.7451	Intermediate Similarity	NPC469565
0.7449	Intermediate Similarity	NPC231710
0.7449	Intermediate Similarity	NPC65665
0.7449	Intermediate Similarity	NPC270908
0.7449	Intermediate Similarity	NPC327183
0.7449	Intermediate Similarity	NPC307699
0.7449	Intermediate Similarity	NPC216826
0.7449	Intermediate Similarity	NPC470573
0.7449	Intermediate Similarity	NPC473311
0.7449	Intermediate Similarity	NPC328935
0.7449	Intermediate Similarity	NPC120021
0.7436	Intermediate Similarity	NPC245094
0.7434	Intermediate Similarity	NPC476127
0.7434	Intermediate Similarity	NPC476150
0.7434	Intermediate Similarity	NPC470312
0.7434	Intermediate Similarity	NPC473130
0.7431	Intermediate Similarity	NPC317460
0.7431	Intermediate Similarity	NPC328074
0.7431	Intermediate Similarity	NPC321272
0.7431	Intermediate Similarity	NPC470025

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 NPC2003 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1506
0.2-0.3	3986
0.3-0.4	2340
0.4-0.5	711
0.5-0.6	350
0.6-0.7	87
0.7-0.8	4
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
0.8235	Intermediate Similarity	NPD6686	Approved
0.7961	Intermediate Similarity	NPD6412	Phase 2
0.7449	Intermediate Similarity	NPD46	Approved
0.7449	Intermediate Similarity	NPD6698	Approved
0.7119	Intermediate Similarity	NPD7507	Approved
0.7115	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7503	Approved
0.701	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7328	Approved
0.6957	Remote Similarity	NPD7327	Approved
0.6949	Remote Similarity	NPD8328	Phase 3
0.6942	Remote Similarity	NPD7319	Approved
0.6907	Remote Similarity	NPD6110	Phase 1
0.6897	Remote Similarity	NPD7516	Approved
0.6864	Remote Similarity	NPD6370	Approved
0.6847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8294	Approved
0.6838	Remote Similarity	NPD8377	Approved
0.6792	Remote Similarity	NPD7638	Approved
0.6792	Remote Similarity	NPD4225	Approved
0.678	Remote Similarity	NPD8513	Phase 3
0.678	Remote Similarity	NPD8378	Approved
0.678	Remote Similarity	NPD8380	Approved
0.678	Remote Similarity	NPD8517	Approved
0.678	Remote Similarity	NPD8033	Approved
0.678	Remote Similarity	NPD8516	Approved
0.678	Remote Similarity	NPD8296	Approved
0.678	Remote Similarity	NPD8335	Approved
0.678	Remote Similarity	NPD8379	Approved
0.678	Remote Similarity	NPD8515	Approved
0.6765	Remote Similarity	NPD7838	Discovery
0.6754	Remote Similarity	NPD8133	Approved
0.6729	Remote Similarity	NPD7639	Approved
0.6729	Remote Similarity	NPD7640	Approved
0.6726	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6054	Approved
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6637	Remote Similarity	NPD6371	Approved
0.6585	Remote Similarity	NPD7736	Approved
0.6583	Remote Similarity	NPD5988	Approved
0.6581	Remote Similarity	NPD7115	Discovery
0.6581	Remote Similarity	NPD6009	Approved
0.6571	Remote Similarity	NPD5282	Discontinued
0.6555	Remote Similarity	NPD6059	Approved
0.6538	Remote Similarity	NPD7983	Approved
0.6529	Remote Similarity	NPD6067	Discontinued
0.6529	Remote Similarity	NPD7830	Approved
0.6529	Remote Similarity	NPD7829	Approved
0.6514	Remote Similarity	NPD5344	Discontinued
0.6504	Remote Similarity	NPD8293	Discontinued
0.6491	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5778	Approved
0.6476	Remote Similarity	NPD5779	Approved
0.6475	Remote Similarity	NPD7492	Approved
0.6466	Remote Similarity	NPD4632	Approved
0.6465	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6616	Approved
0.6417	Remote Similarity	NPD6319	Approved
0.6393	Remote Similarity	NPD7642	Approved
0.6387	Remote Similarity	NPD7641	Discontinued
0.6381	Remote Similarity	NPD7637	Suspended
0.6381	Remote Similarity	NPD6411	Approved
0.6379	Remote Similarity	NPD6053	Discontinued
0.6379	Remote Similarity	NPD6882	Approved
0.6371	Remote Similarity	NPD7078	Approved
0.6364	Remote Similarity	NPD8444	Approved
0.6355	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3666	Approved
0.6337	Remote Similarity	NPD3665	Phase 1
0.6337	Remote Similarity	NPD3133	Approved
0.63	Remote Similarity	NPD5209	Approved
0.6286	Remote Similarity	NPD5785	Approved
0.6275	Remote Similarity	NPD1694	Approved
0.6263	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7748	Approved
0.624	Remote Similarity	NPD8074	Phase 3
0.6239	Remote Similarity	NPD8297	Approved
0.6239	Remote Similarity	NPD7902	Approved
0.6239	Remote Similarity	NPD6084	Phase 2
0.6239	Remote Similarity	NPD6083	Phase 2
0.6228	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5697	Approved
0.6226	Remote Similarity	NPD7515	Phase 2
0.6224	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5956	Approved
0.6214	Remote Similarity	NPD5279	Phase 3
0.6214	Remote Similarity	NPD3618	Phase 1
0.6214	Remote Similarity	NPD4249	Approved
0.6207	Remote Similarity	NPD4634	Approved
0.6204	Remote Similarity	NPD5695	Phase 3
0.619	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4753	Phase 2
0.619	Remote Similarity	NPD6101	Approved
0.6174	Remote Similarity	NPD6899	Approved
0.6174	Remote Similarity	NPD6881	Approved
0.6172	Remote Similarity	NPD7260	Phase 2
0.6168	Remote Similarity	NPD6399	Phase 3
0.6161	Remote Similarity	NPD5211	Phase 2
0.6161	Remote Similarity	NPD7632	Discontinued
0.616	Remote Similarity	NPD8451	Approved
0.6154	Remote Similarity	NPD4250	Approved
0.6154	Remote Similarity	NPD4251	Approved
0.6147	Remote Similarity	NPD7839	Suspended
0.614	Remote Similarity	NPD7128	Approved
0.614	Remote Similarity	NPD6402	Approved
0.614	Remote Similarity	NPD6675	Approved
0.614	Remote Similarity	NPD5739	Approved
0.6139	Remote Similarity	NPD3667	Approved
0.6126	Remote Similarity	NPD4696	Approved
0.6126	Remote Similarity	NPD6648	Approved
0.6126	Remote Similarity	NPD5285	Approved
0.6126	Remote Similarity	NPD5286	Approved
0.6121	Remote Similarity	NPD6012	Approved
0.6121	Remote Similarity	NPD6014	Approved
0.6121	Remote Similarity	NPD6013	Approved
0.6111	Remote Similarity	NPD8448	Approved
0.61	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4695	Discontinued
0.6098	Remote Similarity	NPD5983	Phase 2
0.6094	Remote Similarity	NPD6914	Discontinued
0.6091	Remote Similarity	NPD4755	Approved
0.6087	Remote Similarity	NPD5701	Approved
0.6082	Remote Similarity	NPD8039	Approved
0.6075	Remote Similarity	NPD6079	Approved
0.6068	Remote Similarity	NPD7102	Approved
0.6068	Remote Similarity	NPD6883	Approved
0.6068	Remote Similarity	NPD7290	Approved
0.6063	Remote Similarity	NPD6033	Approved
0.6058	Remote Similarity	NPD4623	Approved
0.6058	Remote Similarity	NPD4519	Discontinued
0.6058	Remote Similarity	NPD7146	Approved
0.6058	Remote Similarity	NPD6409	Approved
0.6058	Remote Similarity	NPD7334	Approved
0.6058	Remote Similarity	NPD5330	Approved
0.6058	Remote Similarity	NPD6684	Approved
0.6058	Remote Similarity	NPD7521	Approved
0.6055	Remote Similarity	NPD5210	Approved
0.6055	Remote Similarity	NPD4629	Approved
0.6053	Remote Similarity	NPD5141	Approved
0.6038	Remote Similarity	NPD5328	Approved
0.6036	Remote Similarity	NPD5696	Approved
0.6034	Remote Similarity	NPD6011	Approved
0.6034	Remote Similarity	NPD7320	Approved
0.6033	Remote Similarity	NPD7500	Approved
0.6019	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD4786	Approved
0.6018	Remote Similarity	NPD5225	Approved
0.6018	Remote Similarity	NPD5226	Approved
0.6018	Remote Similarity	NPD4633	Approved
0.6018	Remote Similarity	NPD5224	Approved
0.6017	Remote Similarity	NPD6650	Approved
0.6017	Remote Similarity	NPD8130	Phase 1
0.6017	Remote Similarity	NPD6847	Approved
0.6017	Remote Similarity	NPD6649	Approved
0.6017	Remote Similarity	NPD6869	Approved
0.6017	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD5221	Approved
0.5983	Remote Similarity	NPD6372	Approved
0.5983	Remote Similarity	NPD6373	Approved
0.5982	Remote Similarity	NPD4700	Approved
0.598	Remote Similarity	NPD6435	Approved
0.5969	Remote Similarity	NPD8392	Approved
0.5969	Remote Similarity	NPD8390	Approved
0.5969	Remote Similarity	NPD8391	Approved
0.5965	Remote Similarity	NPD5175	Approved
0.5965	Remote Similarity	NPD5174	Approved
0.5963	Remote Similarity	NPD7900	Approved
0.5963	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD8299	Approved
0.5952	Remote Similarity	NPD8340	Approved
0.5952	Remote Similarity	NPD8341	Approved
0.5952	Remote Similarity	NPD8342	Approved
0.5946	Remote Similarity	NPD5173	Approved
0.5943	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6672	Approved
0.5943	Remote Similarity	NPD5737	Approved
0.5943	Remote Similarity	NPD6903	Approved
0.594	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5223	Approved
0.5926	Remote Similarity	NPD5284	Approved
0.5926	Remote Similarity	NPD5281	Approved
0.5926	Remote Similarity	NPD5693	Phase 1
0.5922	Remote Similarity	NPD7154	Phase 3
0.5918	Remote Similarity	NPD8264	Approved
0.5906	Remote Similarity	NPD6336	Discontinued
0.59	Remote Similarity	NPD4271	Approved
0.59	Remote Similarity	NPD4268	Approved
0.5865	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6008	Approved
0.5856	Remote Similarity	NPD4697	Phase 3

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