NPASS Compound

Structure

CID266389 OpenBabel06191716072D 32 34 0 0 1 0 0 0 0 0999 V2000 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 4.3301 1.5000 0.0000 C 0 0 1 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 3.4641 1.0000 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 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 2.5981 1.5000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 9 2 0 0 0 0 5 9 1 0 0 0 0 6 21 3 0 0 0 0 7 22 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 10 6 1 1 0 0 0 10 30 1 0 0 0 0 11 7 1 1 0 0 0 11 13 1 0 0 0 0 11 31 1 0 0 0 0 12 8 1 6 0 0 0 12 14 1 0 0 0 0 12 32 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 6 0 0 0 14 16 1 0 0 0 0 14 24 1 1 0 0 0 15 17 1 0 0 0 0 15 25 1 1 0 0 0 16 18 1 0 0 0 0 16 26 1 6 0 0 0 17 19 1 0 0 0 0 17 27 1 6 0 0 0 18 20 1 0 0 0 0 18 28 1 1 0 0 0 19 29 1 1 0 0 0 19 31 1 0 0 0 0 20 30 1 6 0 0 0 20 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	457.16
Volume:	423.314
LogP:	-1.127
LogD:	-1.332
LogS:	-1.126
# Rotatable Bonds:	7
TPSA:	202.32
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.218
Synthetic Accessibility Score:	4.512
Fsp3:	0.65
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.895
MDCK Permeability:	9.804490400711074e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.77
Human Intestinal Absorption (HIA):	0.985
20% Bioavailability (F20%):	0.785
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	28.92198371887207%
Volume Distribution (VD):	0.412
Pgp-substrate:	50.65781021118164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	0.999
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.529
Rat Oral Acute Toxicity:	0.471
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.822
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.322
Respiratory Toxicity:	0.876

Download Data

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

Natural Product: NPC266389

Natural Product ID:	NPC266389
*Common Name:**	Amygdalin
IUPAC Name:	(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
Synonyms:	Amygdalin
Standard InCHIKey:	XUCIJNAGGSZNQT-JHSLDZJXSA-N
Standard InCHI:	InChI=1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10-,11+,12+,13+,14+,15-,16-,17+,18+,19+,20+/m0/s1
SMILES:	c1ccc(cc1)[C@H](C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461727
PubChem CID:	656516
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:0002365] Cyanogenic 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
NPO22761	Gentiana cruciata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)88887-1]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO14117	Diplodia sapinea	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075753]
NPO24512	Xestospongia testudinaria	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543913]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[12232058]
NPO25046	Aplidium meridianum	Species	Polyclinidae	Eukaryota	n.a.	South Georgia Islands, South Atlantic	n.a.	PMID[15026054]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038554]
NPO13854	Prunus serotina	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[16652960]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[17226159]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17237222]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044840]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25391	Vitex glabrata	Species	Lamiaceae	Eukaryota	leaves	Chantaburi Province, Thailand	2007-Nov	PMID[19943620]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2045817]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21381684]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21381684]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	stem	n.a.	PMID[21381684]
NPO28887	Eupomatia laurina	Species	Eupomatiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504145]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21648406]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22187429]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23784883]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	seeds	n.a.	n.a.	PMID[23985009]
NPO24745	Salvia cavaleriei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256484]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24400858]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26934105]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128898]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[27133212]
NPO22780	Sphaeranthus africanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30074787]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[7092570]
NPO10029.1	Prunus dulcis var. amara	Varieties	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[7092570]
NPO25046	Aplidium meridianum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748381]
NPO13854	Prunus serotina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13767	Woodfordia fruticosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13854	Prunus serotina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24077	Astragalus pterocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24077	Astragalus pterocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13854	Prunus serotina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13767	Woodfordia fruticosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13854	Prunus serotina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25099	Prunus mandshurica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29018	Prunus humillis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24449	Prunus pedunculata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12951	Talaromyces coalescens	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14117	Diplodia sapinea	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15178	Psychotria bahiensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11644	Prosopis ruscifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15434	Rhodomicrobium vannielii	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22056.1	Streptomyces fervens	Subspecies	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14914	Esox saurus	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18842	Gnaphalium gaudichaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22293	Bryobium hyacinthoides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5027	Peniophora polygonia	Species	Peniophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2607	Ophiorrhiza blumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23568	Guatteria pogonopus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25091	Samadera bidwillii	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13740	Aconitum kamtschaticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11962	Garcinia macrophylla	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12457	Siphocampylus verticillatus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28887	Eupomatia laurina	Species	Eupomatiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14604	Dipteronia dyeriana	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25700	Psiadia punctulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15679	Amyris marshii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25625	Hymenophyllum recurvum	Species	Hymenophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1723	Sideritis syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15570	Plectranthus mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14442	Gouania microcarpa	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16625	Phalaenopsis aphrodite	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13273	Maytenus loeseneri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24745	Salvia cavaleriei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16541	Veratrum stenophyllum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3697	Ongokea klaineana	Species	Aptandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25391	Vitex glabrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9386	Ectropis bicolor	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24512	Xestospongia testudinaria	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15312	Coelogorgia palmosa	Species	Coelogorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15159	Podocarpus salignus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26256	Zanthoxylum chiriquinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10452	Odontites rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14747	Usnea florida	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5750	Monomorium floricola	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24077	Astragalus pterocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8671	Physalis solanaceus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22053	Vepris pilosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25364	Didemnum candidum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7077	Canarium strictum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13767	Woodfordia fruticosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22761	Gentiana cruciata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16311	Rusavskia elegans	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7792	Coreopsis grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12547	Viburnum chingii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22780	Sphaeranthus africanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16109	Actinidia kolomikta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13854	Prunus serotina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11376	Schistostephium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12470	Brachyspira hyodysenteriae	Species	Brachyspiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25046	Aplidium meridianum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13582	Leucopaxillus giganteus	Species	Tricholomataceae	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
EC50	2
Others	30
Potency	1

Activity Type	# Activity
Individual Protein	7
NON-MOLECULAR	5
ORGANISM	5
Others	10
SINGLE PROTEIN	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1112	Individual Protein	T-cell surface antigen CD4	Homo sapiens	Chemotactic index	=	0.63	n.a.	PMID[555984]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[555987]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	0.78	%	PMID[555989]
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	=	50.44	%	PMID[555994]
NPT27	Others	Unspecified		log10(%HIA +10)	=	1.176	n.a.	PMID[555986]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	5.7	%	PMID[555989]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	103.64	%	PMID[555990]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	118.13	%	PMID[555990]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	0.0	n.a.	PMID[555991]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	0.0	%	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (acute)	=	0.0	n.a.	PMID[555991]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (acute)	=	0.0	%	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (cytolytic)	=	0.0	n.a.	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (choleostasis)	=	0.0	n.a.	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (severe hepatitis)	=	1.0	n.a.	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (chronic liver disease)	=	0.0	n.a.	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (cirrhosis)	=	0.0	n.a.	PMID[555991]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (granulomatous hepatitis)	=	0.0	n.a.	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (association with vascular disease)	=	0.0	n.a.	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (steatosis)	=	0.0	n.a.	PMID[555991]
NPT2	Others	Unspecified		Hepatotoxicity (malignant tumour)	=	0.0	n.a.	PMID[555991]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (benign tumour)	=	0.0	n.a.	PMID[555991]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-4.61	%	PMID[555992]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	29.86	%	PMID[555995]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-3.957	%	PMID[555996]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.12	%	PMID[555997]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.09	%	PMID[555998]
NPT27193	SINGLE PROTEIN	Taste receptor type 2 member 16	Homo sapiens	Activity	=	2.3	mM	PMID[555993]
NPT27193	SINGLE PROTEIN	Taste receptor type 2 member 16	Homo sapiens	EC50	=	20000000.0	nM	PMID[555993]

☑ 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 NPC266389 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	218
0.1-0.2	1101
0.2-0.3	3014
0.3-0.4	9689
0.4-0.5	13130
0.5-0.6	12226
0.6-0.7	2937
0.7-0.8	361
0.8-0.85	8
0.85-0.9	6
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC122245
1.0	High Similarity	NPC216605
0.9633	High Similarity	NPC120217
0.9266	High Similarity	NPC276061
0.9266	High Similarity	NPC474148
0.9182	High Similarity	NPC30563
0.8899	High Similarity	NPC37714
0.8899	High Similarity	NPC152384
0.8839	High Similarity	NPC264784
0.875	High Similarity	NPC212176
0.8716	High Similarity	NPC469527
0.8487	Intermediate Similarity	NPC14950
0.8468	Intermediate Similarity	NPC148060
0.8349	Intermediate Similarity	NPC262826
0.832	Intermediate Similarity	NPC198798
0.8304	Intermediate Similarity	NPC47286
0.8226	Intermediate Similarity	NPC57607
0.8211	Intermediate Similarity	NPC476142
0.8197	Intermediate Similarity	NPC229600
0.812	Intermediate Similarity	NPC470825
0.8083	Intermediate Similarity	NPC175771
0.8017	Intermediate Similarity	NPC184633
0.7984	Intermediate Similarity	NPC55608
0.7953	Intermediate Similarity	NPC114096
0.7934	Intermediate Similarity	NPC148055
0.7917	Intermediate Similarity	NPC157338
0.7917	Intermediate Similarity	NPC313193
0.7903	Intermediate Similarity	NPC160854
0.7903	Intermediate Similarity	NPC201402
0.7903	Intermediate Similarity	NPC198734
0.7903	Intermediate Similarity	NPC469703
0.7903	Intermediate Similarity	NPC469704
0.7903	Intermediate Similarity	NPC469412
0.7891	Intermediate Similarity	NPC148026
0.784	Intermediate Similarity	NPC469686
0.7833	Intermediate Similarity	NPC474641
0.7829	Intermediate Similarity	NPC301857
0.7823	Intermediate Similarity	NPC469702
0.7823	Intermediate Similarity	NPC469708
0.7823	Intermediate Similarity	NPC60589
0.7823	Intermediate Similarity	NPC282409
0.7795	Intermediate Similarity	NPC287429
0.7786	Intermediate Similarity	NPC9912
0.7778	Intermediate Similarity	NPC471067
0.776	Intermediate Similarity	NPC469548
0.776	Intermediate Similarity	NPC476448
0.776	Intermediate Similarity	NPC476445
0.776	Intermediate Similarity	NPC269242
0.7752	Intermediate Similarity	NPC288416
0.7734	Intermediate Similarity	NPC470510
0.7731	Intermediate Similarity	NPC43584
0.7727	Intermediate Similarity	NPC254275
0.7717	Intermediate Similarity	NPC232454
0.7717	Intermediate Similarity	NPC178449
0.7717	Intermediate Similarity	NPC470907
0.7698	Intermediate Similarity	NPC226712
0.7652	Intermediate Similarity	NPC235294
0.7652	Intermediate Similarity	NPC46137
0.7652	Intermediate Similarity	NPC475067
0.7652	Intermediate Similarity	NPC138777
0.7652	Intermediate Similarity	NPC246869
0.7652	Intermediate Similarity	NPC225384
0.7642	Intermediate Similarity	NPC473556
0.7642	Intermediate Similarity	NPC301651
0.7638	Intermediate Similarity	NPC52097
0.7638	Intermediate Similarity	NPC140561
0.7638	Intermediate Similarity	NPC141970
0.7634	Intermediate Similarity	NPC27712
0.7623	Intermediate Similarity	NPC29607
0.7615	Intermediate Similarity	NPC106677
0.7612	Intermediate Similarity	NPC35731
0.7597	Intermediate Similarity	NPC126991
0.7597	Intermediate Similarity	NPC83218
0.7578	Intermediate Similarity	NPC138798
0.7576	Intermediate Similarity	NPC472024
0.7576	Intermediate Similarity	NPC80600
0.7559	Intermediate Similarity	NPC266045
0.7559	Intermediate Similarity	NPC11724
0.7538	Intermediate Similarity	NPC471157
0.7538	Intermediate Similarity	NPC252114
0.7519	Intermediate Similarity	NPC478255
0.7519	Intermediate Similarity	NPC87153
0.7519	Intermediate Similarity	NPC162925
0.7519	Intermediate Similarity	NPC248307
0.7519	Intermediate Similarity	NPC65942
0.75	Intermediate Similarity	NPC270849
0.75	Intermediate Similarity	NPC97326
0.75	Intermediate Similarity	NPC26653
0.75	Intermediate Similarity	NPC295970
0.75	Intermediate Similarity	NPC184092
0.7482	Intermediate Similarity	NPC63628
0.7482	Intermediate Similarity	NPC178466
0.7481	Intermediate Similarity	NPC476411
0.7481	Intermediate Similarity	NPC87696
0.7481	Intermediate Similarity	NPC79715
0.7481	Intermediate Similarity	NPC264900
0.7481	Intermediate Similarity	NPC108659
0.7481	Intermediate Similarity	NPC187194
0.7481	Intermediate Similarity	NPC231607
0.7481	Intermediate Similarity	NPC469687
0.748	Intermediate Similarity	NPC476872
0.7462	Intermediate Similarity	NPC77651
0.7462	Intermediate Similarity	NPC28069
0.7462	Intermediate Similarity	NPC90318
0.7459	Intermediate Similarity	NPC265002
0.7445	Intermediate Similarity	NPC87777
0.7445	Intermediate Similarity	NPC78363
0.7445	Intermediate Similarity	NPC262328
0.7445	Intermediate Similarity	NPC304152
0.7444	Intermediate Similarity	NPC319995
0.7444	Intermediate Similarity	NPC289415
0.7426	Intermediate Similarity	NPC79957
0.7426	Intermediate Similarity	NPC263829
0.7424	Intermediate Similarity	NPC146540
0.7424	Intermediate Similarity	NPC225307
0.7424	Intermediate Similarity	NPC302378
0.7424	Intermediate Similarity	NPC148982
0.7424	Intermediate Similarity	NPC40377
0.7405	Intermediate Similarity	NPC124878
0.7405	Intermediate Similarity	NPC231888
0.7405	Intermediate Similarity	NPC290276
0.7405	Intermediate Similarity	NPC10121
0.7405	Intermediate Similarity	NPC198918
0.7405	Intermediate Similarity	NPC10883
0.7405	Intermediate Similarity	NPC204214
0.7405	Intermediate Similarity	NPC63404
0.7405	Intermediate Similarity	NPC92283
0.7405	Intermediate Similarity	NPC94179
0.7405	Intermediate Similarity	NPC35338
0.7402	Intermediate Similarity	NPC146673
0.7402	Intermediate Similarity	NPC233923
0.7398	Intermediate Similarity	NPC172525
0.7395	Intermediate Similarity	NPC472316
0.7395	Intermediate Similarity	NPC472315
0.7395	Intermediate Similarity	NPC474376
0.7395	Intermediate Similarity	NPC475203
0.7385	Intermediate Similarity	NPC145287
0.7385	Intermediate Similarity	NPC244454
0.7381	Intermediate Similarity	NPC228907
0.7377	Intermediate Similarity	NPC234376
0.7377	Intermediate Similarity	NPC185840
0.7372	Intermediate Similarity	NPC52277
0.7372	Intermediate Similarity	NPC177035
0.7372	Intermediate Similarity	NPC471345
0.7372	Intermediate Similarity	NPC199459
0.7372	Intermediate Similarity	NPC469383
0.7368	Intermediate Similarity	NPC307110
0.7368	Intermediate Similarity	NPC218003
0.7368	Intermediate Similarity	NPC166040
0.7368	Intermediate Similarity	NPC253595
0.7368	Intermediate Similarity	NPC248355
0.7353	Intermediate Similarity	NPC34293
0.7353	Intermediate Similarity	NPC188555
0.7353	Intermediate Similarity	NPC470881
0.7353	Intermediate Similarity	NPC130496
0.7353	Intermediate Similarity	NPC34456
0.7353	Intermediate Similarity	NPC287597
0.7353	Intermediate Similarity	NPC169398
0.7353	Intermediate Similarity	NPC886
0.7348	Intermediate Similarity	NPC173150
0.7348	Intermediate Similarity	NPC231627
0.7348	Intermediate Similarity	NPC45224
0.7348	Intermediate Similarity	NPC471881
0.7348	Intermediate Similarity	NPC471882
0.7348	Intermediate Similarity	NPC471025
0.7348	Intermediate Similarity	NPC35288
0.7348	Intermediate Similarity	NPC156692
0.7338	Intermediate Similarity	NPC106944
0.7333	Intermediate Similarity	NPC473285
0.7333	Intermediate Similarity	NPC269421
0.7333	Intermediate Similarity	NPC303422
0.7333	Intermediate Similarity	NPC85799
0.7333	Intermediate Similarity	NPC165686
0.7333	Intermediate Similarity	NPC26080
0.7328	Intermediate Similarity	NPC123704
0.7319	Intermediate Similarity	NPC65262
0.7319	Intermediate Similarity	NPC101686
0.7319	Intermediate Similarity	NPC470413
0.7319	Intermediate Similarity	NPC260425
0.7319	Intermediate Similarity	NPC469364
0.7319	Intermediate Similarity	NPC138738
0.7317	Intermediate Similarity	NPC153795
0.7317	Intermediate Similarity	NPC290353
0.7317	Intermediate Similarity	NPC42911
0.7313	Intermediate Similarity	NPC17567
0.7313	Intermediate Similarity	NPC469705
0.7313	Intermediate Similarity	NPC470122
0.7313	Intermediate Similarity	NPC17968
0.7313	Intermediate Similarity	NPC262606
0.7299	Intermediate Similarity	NPC470236
0.7299	Intermediate Similarity	NPC238243
0.7293	Intermediate Similarity	NPC471024
0.7293	Intermediate Similarity	NPC237182
0.7293	Intermediate Similarity	NPC226101
0.7293	Intermediate Similarity	NPC158673
0.7286	Intermediate Similarity	NPC108674
0.7286	Intermediate Similarity	NPC476385
0.7286	Intermediate Similarity	NPC134405
0.7279	Intermediate Similarity	NPC25821
0.7279	Intermediate Similarity	NPC215833

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 NPC266389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	715
0.2-0.3	1307
0.3-0.4	3233
0.4-0.5	2290
0.5-0.6	1270
0.6-0.7	156
0.7-0.8	7
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
0.7967	Intermediate Similarity	NPD5125	Phase 3
0.7967	Intermediate Similarity	NPD5126	Approved
0.7698	Intermediate Similarity	NPD1091	Approved
0.7394	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD969	Suspended
0.7266	Intermediate Similarity	NPD7266	Discontinued
0.687	Remote Similarity	NPD5723	Approved
0.6846	Remote Similarity	NPD7741	Discontinued
0.6774	Remote Similarity	NPD9532	Phase 3
0.6744	Remote Similarity	NPD4198	Discontinued
0.6736	Remote Similarity	NPD2424	Discontinued
0.6694	Remote Similarity	NPD2558	Approved
0.6694	Remote Similarity	NPD3524	Approved
0.6694	Remote Similarity	NPD2549	Approved
0.6694	Remote Similarity	NPD2552	Approved
0.6694	Remote Similarity	NPD2555	Approved
0.6694	Remote Similarity	NPD2550	Approved
0.6694	Remote Similarity	NPD2553	Approved
0.6694	Remote Similarity	NPD3526	Approved
0.669	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9713	Approved
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD7876	Discontinued
0.6667	Remote Similarity	NPD5058	Phase 3
0.6643	Remote Similarity	NPD4404	Approved
0.6641	Remote Similarity	NPD7843	Approved
0.664	Remote Similarity	NPD290	Approved
0.6639	Remote Similarity	NPD4188	Approved
0.6639	Remote Similarity	NPD4189	Approved
0.6596	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2684	Approved
0.6575	Remote Similarity	NPD6674	Discontinued
0.6567	Remote Similarity	NPD3847	Discontinued
0.6556	Remote Similarity	NPD1653	Approved
0.6554	Remote Similarity	NPD5756	Phase 2
0.6544	Remote Similarity	NPD3685	Discontinued
0.6532	Remote Similarity	NPD3048	Approved
0.6532	Remote Similarity	NPD3047	Approved
0.6532	Remote Similarity	NPD3046	Approved
0.6519	Remote Similarity	NPD3705	Approved
0.6508	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3027	Phase 3
0.6489	Remote Similarity	NPD7157	Approved
0.648	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD1613	Approved
0.6479	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD531	Approved
0.6458	Remote Similarity	NPD4536	Approved
0.6458	Remote Similarity	NPD5886	Approved
0.6458	Remote Similarity	NPD4538	Approved
0.6458	Remote Similarity	NPD41	Approved
0.6458	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD3122	Phase 3
0.6439	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD5292	Approved
0.6439	Remote Similarity	NPD5291	Approved
0.6434	Remote Similarity	NPD4572	Approved
0.6434	Remote Similarity	NPD4573	Approved
0.6434	Remote Similarity	NPD4571	Approved
0.6433	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD811	Approved
0.6429	Remote Similarity	NPD2559	Approved
0.6429	Remote Similarity	NPD810	Approved
0.6429	Remote Similarity	NPD2551	Approved
0.6429	Remote Similarity	NPD812	Approved
0.6414	Remote Similarity	NPD5588	Approved
0.6414	Remote Similarity	NPD5960	Phase 3
0.6414	Remote Similarity	NPD4108	Discontinued
0.6412	Remote Similarity	NPD2629	Approved
0.6403	Remote Similarity	NPD7247	Discontinued
0.6402	Remote Similarity	NPD7007	Discovery
0.6393	Remote Similarity	NPD9495	Approved
0.6393	Remote Similarity	NPD5926	Approved
0.6383	Remote Similarity	NPD3180	Approved
0.6383	Remote Similarity	NPD3179	Approved
0.638	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9294	Approved
0.6357	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD1652	Phase 2
0.635	Remote Similarity	NPD2235	Phase 2
0.635	Remote Similarity	NPD7249	Approved
0.635	Remote Similarity	NPD2231	Phase 2
0.635	Remote Similarity	NPD7250	Approved
0.6349	Remote Similarity	NPD5048	Discontinued
0.6345	Remote Similarity	NPD7097	Phase 1
0.6333	Remote Similarity	NPD5295	Discontinued
0.6331	Remote Similarity	NPD2626	Approved
0.6331	Remote Similarity	NPD2627	Approved
0.6331	Remote Similarity	NPD2625	Approved
0.6331	Remote Similarity	NPD2159	Approved
0.6331	Remote Similarity	NPD2628	Approved
0.6331	Remote Similarity	NPD2160	Approved
0.6327	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD2575	Approved
0.6296	Remote Similarity	NPD1357	Approved
0.6296	Remote Similarity	NPD770	Discontinued
0.6294	Remote Similarity	NPD6233	Phase 2
0.6282	Remote Similarity	NPD4433	Discontinued
0.6271	Remote Similarity	NPD689	Discontinued
0.6268	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2677	Approved
0.626	Remote Similarity	NPD9609	Approved
0.626	Remote Similarity	NPD9611	Approved
0.626	Remote Similarity	NPD9612	Approved
0.626	Remote Similarity	NPD821	Approved
0.6259	Remote Similarity	NPD8651	Approved
0.6259	Remote Similarity	NPD5667	Approved
0.625	Remote Similarity	NPD5305	Approved
0.625	Remote Similarity	NPD6406	Approved
0.625	Remote Similarity	NPD6516	Phase 2
0.625	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5846	Approved
0.625	Remote Similarity	NPD5306	Approved
0.6242	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD5062	Approved
0.6242	Remote Similarity	NPD5289	Phase 2
0.6242	Remote Similarity	NPD5061	Approved
0.6241	Remote Similarity	NPD2861	Phase 2
0.624	Remote Similarity	NPD854	Approved
0.624	Remote Similarity	NPD855	Approved
0.6232	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD2201	Approved
0.6222	Remote Similarity	NPD1182	Approved
0.6222	Remote Similarity	NPD1548	Phase 1
0.6212	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4136	Approved
0.6204	Remote Similarity	NPD4135	Approved
0.6204	Remote Similarity	NPD4106	Approved
0.6203	Remote Similarity	NPD2415	Discontinued
0.62	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4110	Phase 3
0.6197	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD4620	Approved
0.6197	Remote Similarity	NPD5201	Approved
0.6197	Remote Similarity	NPD4908	Phase 1
0.6197	Remote Similarity	NPD4617	Approved
0.6197	Remote Similarity	NPD5203	Approved
0.619	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4656	Approved
0.619	Remote Similarity	NPD4229	Approved
0.619	Remote Similarity	NPD4658	Approved
0.619	Remote Similarity	NPD4231	Approved
0.6183	Remote Similarity	NPD6912	Phase 3
0.6182	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7054	Approved
0.6172	Remote Similarity	NPD6685	Approved
0.6172	Remote Similarity	NPD968	Approved
0.617	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.617	Remote Similarity	NPD558	Phase 2
0.6159	Remote Similarity	NPD4480	Approved
0.6159	Remote Similarity	NPD4806	Approved
0.6159	Remote Similarity	NPD1610	Phase 2
0.6159	Remote Similarity	NPD6190	Approved
0.6159	Remote Similarity	NPD4807	Approved
0.6154	Remote Similarity	NPD550	Approved
0.6154	Remote Similarity	NPD556	Approved
0.6154	Remote Similarity	NPD2067	Discontinued
0.6154	Remote Similarity	NPD5240	Approved
0.6154	Remote Similarity	NPD551	Approved
0.6154	Remote Similarity	NPD5236	Approved
0.6154	Remote Similarity	NPD5237	Approved
0.6154	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5239	Approved
0.6154	Remote Similarity	NPD5235	Approved
0.6145	Remote Similarity	NPD7472	Approved
0.6145	Remote Similarity	NPD7074	Phase 3
0.6144	Remote Similarity	NPD3985	Discontinued
0.6139	Remote Similarity	NPD2978	Approved
0.6139	Remote Similarity	NPD2977	Approved
0.6139	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD2238	Phase 2
0.6138	Remote Similarity	NPD5120	Approved
0.6138	Remote Similarity	NPD5121	Approved
0.6138	Remote Similarity	NPD5119	Approved
0.6138	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2497	Approved
0.6136	Remote Similarity	NPD2496	Approved
0.6133	Remote Similarity	NPD4236	Phase 3
0.6133	Remote Similarity	NPD4237	Approved
0.6127	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7228	Approved
0.6115	Remote Similarity	NPD1840	Phase 2
0.6111	Remote Similarity	NPD6798	Discontinued
0.6111	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6797	Phase 2
0.6107	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD1375	Discontinued
0.6103	Remote Similarity	NPD7042	Phase 3
0.6103	Remote Similarity	NPD4016	Approved
0.6103	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD1817	Approved
0.6099	Remote Similarity	NPD1794	Approved
0.6099	Remote Similarity	NPD1818	Approved
0.6099	Remote Similarity	NPD1819	Approved
0.6099	Remote Similarity	NPD1820	Approved
0.6096	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD4340	Discontinued
0.6096	Remote Similarity	NPD5124	Phase 1
0.6093	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.609	Remote Similarity	NPD6010	Discontinued

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