NPASS Compound

Structure

CID176775 OpenBabel06191715552D 26 28 0 0 0 0 0 0 0 0999 V2000 7.7942 1.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 7 1 0 0 0 0 5 10 2 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 13 2 0 0 0 0 10 13 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 26 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 26 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	351.951
LogP:	3.372
LogD:	2.776
LogS:	-4.436
# Rotatable Bonds:	5
TPSA:	87.36
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	2.386
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.595
MDCK Permeability:	2.7609112294157967e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	80.0037612915039%
Volume Distribution (VD):	0.915
Pgp-substrate:	20.70616912841797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.587
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.747
CYP2C19-substrate:	0.738
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.407
CYP3A4-substrate:	0.574

ADMET: Excretion

Clearance (CL):	3.092
Half-life (T1/2):	0.335

ADMET: Toxicity

hERG Blockers:	0.218
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.547
Rat Oral Acute Toxicity:	0.426
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.437
Carcinogencity:	0.106
Eye Corrosion:	0.003
Eye Irritation:	0.093
Respiratory Toxicity:	0.118

Download Data

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

Natural Product: NPC176775

Natural Product ID:	NPC176775
*Common Name:**	Gardenin B
IUPAC Name:	5-hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	LXEVSYZNYDZSOB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3
SMILES:	COc1ccc(cc1)c1cc(=O)c2c(o1)c(OC)c(c(c2O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226512
PubChem CID:	96539
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002593] 8-O-methylated flavonoids

*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
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)88710-5]
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075761]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096857]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO30669	Gnaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10820110]
NPO129	Biebersteinia orphanidis	Species	Biebersteiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11198823]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15128261]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18357995]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO24316	Salvia mirzayanii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20857430]
NPO9537	Bauhinia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22348826]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23186307]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507152]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25919052]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31836445]
NPO40480	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[521819]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30669	Gnaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24511	Dipterocarpus alatus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2387	Antennaria geyeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20823	Stenostomum lucidum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12094	Cyclamen balearicum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24291	Rhizobium phaseoli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29013	Annulohypoxylon cohaerens	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26540	Echinopsis spachiana	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24383	Ficus formosana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9537	Bauhinia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28974	Smilax ornata	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23567	Coccus fagi	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24877	Maianthemum stellatum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24675	Quercus aegilops	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7552	Alligator mississippiensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23453	Pheidole pallidula	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25144	Artemisia monogyna	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25529	Bursaria spinosa	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24556	Bassia butyracea	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23963	Odixia angusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25390	Pterocarpus grandiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23691	Pyrosoma giganteum	Species	Pyrosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25326	Dendrosenecio kilimanjari	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO129	Biebersteinia orphanidis	Species	Biebersteiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7445	Pteris prolifera	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29157	Reichardia gaditana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25187	Cladonia evansii	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25291	Lactarius scrobiculatus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25090	Araujia sericifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24929	Aria pallescens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25234	Epaltes gariepina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9312	Placopecten magellanicus	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18352	Anaxagorea clavata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23251	Polygala glomerata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24640	Echinops amplexicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24316	Salvia mirzayanii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25671	Gardenia fosbergii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25969	Aspergillus nomius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20833	Beyeria brevifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5904	Grindelia humilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29402	Launaea arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28870	Clausena lenis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24068	Prunus laurocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24830	Prosopis glandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28829	Pelvetia wrightii	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11524	Macrotomia ugamensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13643	Rhamnus japonica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25471	Chromolaena pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24218	Fusarium gibbosum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2962	Curvularia spicifera	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11978	Tanacetum argyrophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1794	Ilex affinis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24987	Simira eliezeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25699	Vitex madiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28808	Piptanthus mongolicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29194	Harziella entomophila	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26042	Agnorhiza bolanderi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23422	Tephrosia procumbens	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24599	Streptomyces althioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28665	Sesbania punicea	Species	Fabaceae	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
NPO17752	NPC176775	Dried Or Powder	n.a.	18.72214259	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO17752	NPC176775	n.a.	n.a.	18.72214	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

☑ 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
AC50	1
ED50	2
GI50	60
IC50	5
Ki	2
Others	7
Potency	11

Activity Type	# Activity
Cell Line	70
Individual Protein	13
NON-MOLECULAR	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[533338]
NPT116	Cell Line	HL-60	Homo sapiens	AC50	>	100000.0	nM	PMID[533338]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	6.0	ug ml-1	PMID[533341]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	28.0	%	PMID[533342]
NPT116	Cell Line	HL-60	Homo sapiens	FC	=	3.8	n.a.	PMID[533342]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	10000.0	nM	PMID[533343]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[533344]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	432.51	nM	PMID[533345]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	36307.81	nM	PMID[533345]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	27352.69	nM	PMID[533345]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	862.98	nM	PMID[533345]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	61659.5	nM	PMID[533345]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	5520.77	nM	PMID[533345]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	28575.91	nM	PMID[533345]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	497.74	nM	PMID[533345]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	10092.53	nM	PMID[533345]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	6471.43	nM	PMID[533345]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	24547.09	nM	PMID[533345]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	15523.87	nM	PMID[533345]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	98627.95	nM	PMID[533345]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	25351.29	nM	PMID[533345]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	389.94	nM	PMID[533345]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	12560.3	nM	PMID[533345]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	26181.83	nM	PMID[533345]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	2133.04	nM	PMID[533345]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	920.45	nM	PMID[533345]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	6576.58	nM	PMID[533345]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	16519.62	nM	PMID[533345]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	28119.01	nM	PMID[533345]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	16218.1	nM	PMID[533345]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	17619.76	nM	PMID[533345]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	12793.81	nM	PMID[533345]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	10069.32	nM	PMID[533345]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	10209.39	nM	PMID[533345]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	1713.96	nM	PMID[533345]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	2371.37	nM	PMID[533345]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	68391.16	nM	PMID[533345]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	13365.96	nM	PMID[533345]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	4864.07	nM	PMID[533345]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	29991.63	nM	PMID[533345]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	26853.44	nM	PMID[533345]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	8375.29	nM	PMID[533345]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	24888.57	nM	PMID[533345]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	45289.76	nM	PMID[533345]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	430.53	nM	PMID[533345]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	20749.14	nM	PMID[533345]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2333.46	nM	PMID[533345]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	26181.83	nM	PMID[533345]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	21527.82	nM	PMID[533345]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	4168.69	nM	PMID[533345]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[533345]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	10641.43	nM	PMID[533345]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	7834.3	nM	PMID[533345]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[533344]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	6.0	nM	PMID[533344]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	2511.9	nM	PMID[533344]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[533344]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	5173.5	nM	PMID[533343]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	8199.5	nM	PMID[533344]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	40000.0	nM	PMID[533347]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	85000.0	nM	PMID[533347]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	75000.0	nM	PMID[533347]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	30000.0	nM	PMID[533347]
NPT885	Cell Line	PBL		Activity	=	20.0	%	PMID[533347]
NPT1167	Individual Protein	Delta opioid receptor	Mus musculus	Ki	>	50000.0	nM	PMID[533348]
NPT1168	Individual Protein	Mu opioid receptor	Mus musculus	Ki	>	50000.0	nM	PMID[533348]
NPT140	Organism	Artemia	Artemia	LC50	>	700.0	ppm	PMID[533339]
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	CD	>	20.0	ug ml-1	PMID[533340]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	112.2	nM	PMID[533343]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	n.a.	630.9	nM	PMID[533343]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[533344]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	pED50	=	6.74	n.a.	PMID[533346]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	=	1.8	10'-7mol/cm2	PMID[533346]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	75.4	%	PMID[533347]

☑ 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 NPC176775 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	443
0.1-0.2	1941
0.2-0.3	5049
0.3-0.4	11261
0.4-0.5	6084
0.5-0.6	3859
0.6-0.7	5174
0.7-0.8	4793
0.8-0.85	1954
0.85-0.9	1181
0.9-0.95	684
0.95-1	274

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC274327
1.0	High Similarity	NPC22519
1.0	High Similarity	NPC69394
1.0	High Similarity	NPC231018
1.0	High Similarity	NPC255350
1.0	High Similarity	NPC145379
1.0	High Similarity	NPC160951
1.0	High Similarity	NPC47781
1.0	High Similarity	NPC183878
0.9932	High Similarity	NPC198826
0.9932	High Similarity	NPC162313
0.9932	High Similarity	NPC131624
0.9932	High Similarity	NPC71334
0.9932	High Similarity	NPC239128
0.9932	High Similarity	NPC213622
0.9932	High Similarity	NPC156222
0.9932	High Similarity	NPC138360
0.9932	High Similarity	NPC187498
0.9932	High Similarity	NPC20830
0.9932	High Similarity	NPC275722
0.9932	High Similarity	NPC4455
0.9932	High Similarity	NPC120163
0.9932	High Similarity	NPC92659
0.9932	High Similarity	NPC83508
0.9932	High Similarity	NPC100887
0.9932	High Similarity	NPC163780
0.9932	High Similarity	NPC183597
0.9932	High Similarity	NPC301323
0.9932	High Similarity	NPC256612
0.9932	High Similarity	NPC188203
0.9932	High Similarity	NPC201136
0.9932	High Similarity	NPC212678
0.9932	High Similarity	NPC275836
0.9932	High Similarity	NPC128863
0.9932	High Similarity	NPC293183
0.9932	High Similarity	NPC50715
0.9932	High Similarity	NPC227325
0.9932	High Similarity	NPC57030
0.9932	High Similarity	NPC222830
0.9932	High Similarity	NPC256283
0.9932	High Similarity	NPC25270
0.9932	High Similarity	NPC2476
0.9932	High Similarity	NPC196439
0.9932	High Similarity	NPC167815
0.9932	High Similarity	NPC280339
0.9932	High Similarity	NPC146165
0.9932	High Similarity	NPC241498
0.9865	High Similarity	NPC49824
0.9864	High Similarity	NPC250822
0.9864	High Similarity	NPC276409
0.9864	High Similarity	NPC75279
0.9863	High Similarity	NPC208043
0.9863	High Similarity	NPC226973
0.9799	High Similarity	NPC75215
0.9799	High Similarity	NPC93376
0.9799	High Similarity	NPC110070
0.9799	High Similarity	NPC227192
0.9799	High Similarity	NPC189179
0.9799	High Similarity	NPC470402
0.9799	High Similarity	NPC203891
0.9799	High Similarity	NPC224137
0.9799	High Similarity	NPC101830
0.9797	High Similarity	NPC44079
0.9797	High Similarity	NPC208197
0.9797	High Similarity	NPC201451
0.9797	High Similarity	NPC26227
0.9796	High Similarity	NPC60972
0.9796	High Similarity	NPC142540
0.9796	High Similarity	NPC39732
0.9795	High Similarity	NPC306821
0.9795	High Similarity	NPC184136
0.9733	High Similarity	NPC19687
0.9733	High Similarity	NPC25495
0.9733	High Similarity	NPC176300
0.9733	High Similarity	NPC261004
0.9733	High Similarity	NPC18772
0.9733	High Similarity	NPC105242
0.9733	High Similarity	NPC130894
0.9733	High Similarity	NPC204854
0.9733	High Similarity	NPC152166
0.9733	High Similarity	NPC115798
0.9733	High Similarity	NPC143828
0.9733	High Similarity	NPC300943
0.9733	High Similarity	NPC9609
0.9733	High Similarity	NPC191459
0.9733	High Similarity	NPC22472
0.9733	High Similarity	NPC18607
0.9733	High Similarity	NPC7846
0.9733	High Similarity	NPC4481
0.9733	High Similarity	NPC253634
0.9733	High Similarity	NPC288669
0.9732	High Similarity	NPC266960
0.9732	High Similarity	NPC98661
0.9732	High Similarity	NPC43243
0.9732	High Similarity	NPC247017
0.9732	High Similarity	NPC472916
0.9732	High Similarity	NPC292107
0.9732	High Similarity	NPC474520
0.9732	High Similarity	NPC245546
0.973	High Similarity	NPC86485
0.9728	High Similarity	NPC308451
0.9726	High Similarity	NPC223579
0.9726	High Similarity	NPC177298
0.9726	High Similarity	NPC328119
0.9726	High Similarity	NPC183950
0.9726	High Similarity	NPC48479
0.9726	High Similarity	NPC296197
0.9726	High Similarity	NPC216318
0.9726	High Similarity	NPC17286
0.9726	High Similarity	NPC259713
0.9726	High Similarity	NPC287101
0.9726	High Similarity	NPC52005
0.9726	High Similarity	NPC137062
0.9669	High Similarity	NPC476980
0.9667	High Similarity	NPC472914
0.9667	High Similarity	NPC176665
0.9667	High Similarity	NPC29841
0.9667	High Similarity	NPC472438
0.9667	High Similarity	NPC48208
0.9667	High Similarity	NPC96167
0.9667	High Similarity	NPC472913
0.9667	High Similarity	NPC475267
0.9667	High Similarity	NPC163524
0.9667	High Similarity	NPC474836
0.9667	High Similarity	NPC472911
0.9667	High Similarity	NPC472910
0.9667	High Similarity	NPC78302
0.9667	High Similarity	NPC235215
0.9667	High Similarity	NPC245758
0.9667	High Similarity	NPC287979
0.9667	High Similarity	NPC474208
0.9667	High Similarity	NPC222814
0.9667	High Similarity	NPC162869
0.9667	High Similarity	NPC78225
0.9667	High Similarity	NPC7973
0.9667	High Similarity	NPC156057
0.9667	High Similarity	NPC305663
0.9664	High Similarity	NPC2928
0.9664	High Similarity	NPC32557
0.9664	High Similarity	NPC189960
0.9662	High Similarity	NPC301123
0.9662	High Similarity	NPC120537
0.9662	High Similarity	NPC180234
0.9662	High Similarity	NPC199100
0.966	High Similarity	NPC45873
0.9658	High Similarity	NPC120464
0.9658	High Similarity	NPC195202
0.9605	High Similarity	NPC258331
0.9603	High Similarity	NPC193842
0.96	High Similarity	NPC200388
0.96	High Similarity	NPC68093
0.96	High Similarity	NPC178854
0.96	High Similarity	NPC191146
0.96	High Similarity	NPC55619
0.96	High Similarity	NPC268161
0.96	High Similarity	NPC100916
0.96	High Similarity	NPC235165
0.96	High Similarity	NPC265511
0.96	High Similarity	NPC255106
0.9597	High Similarity	NPC167091
0.9597	High Similarity	NPC124714
0.9597	High Similarity	NPC271779
0.9597	High Similarity	NPC292214
0.9597	High Similarity	NPC78326
0.9597	High Similarity	NPC270620
0.9597	High Similarity	NPC280937
0.9597	High Similarity	NPC206238
0.9597	High Similarity	NPC472915
0.9597	High Similarity	NPC88645
0.9597	High Similarity	NPC179126
0.9597	High Similarity	NPC236223
0.9595	High Similarity	NPC117579
0.9595	High Similarity	NPC225731
0.9595	High Similarity	NPC200740
0.9595	High Similarity	NPC125062
0.9595	High Similarity	NPC252933
0.9595	High Similarity	NPC54394
0.9592	High Similarity	NPC92722
0.9592	High Similarity	NPC102003
0.9589	High Similarity	NPC33265
0.9589	High Similarity	NPC130230
0.9589	High Similarity	NPC30647
0.9589	High Similarity	NPC61871
0.9589	High Similarity	NPC62536
0.9589	High Similarity	NPC55557
0.9589	High Similarity	NPC275772
0.9589	High Similarity	NPC108406
0.9589	High Similarity	NPC12200
0.9589	High Similarity	NPC239312
0.9542	High Similarity	NPC472448
0.9542	High Similarity	NPC83922
0.9539	High Similarity	NPC246478
0.9539	High Similarity	NPC204290
0.9536	High Similarity	NPC241904
0.9536	High Similarity	NPC476981
0.9536	High Similarity	NPC469584
0.9536	High Similarity	NPC262286
0.9536	High Similarity	NPC36852
0.9536	High Similarity	NPC210084
0.9536	High Similarity	NPC300727

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 NPC176775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	995
0.2-0.3	1855
0.3-0.4	2653
0.4-0.5	1746
0.5-0.6	972
0.6-0.7	353
0.7-0.8	110
0.8-0.85	32
0.85-0.9	13
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2801	Approved
0.94	High Similarity	NPD1934	Approved
0.9384	High Similarity	NPD1511	Approved
0.9257	High Similarity	NPD1512	Approved
0.9216	High Similarity	NPD3882	Suspended
0.9211	High Similarity	NPD2393	Clinical (unspecified phase)
0.9026	High Similarity	NPD3817	Phase 2
0.8938	High Similarity	NPD3818	Discontinued
0.8931	High Similarity	NPD6166	Phase 2
0.8931	High Similarity	NPD6167	Clinical (unspecified phase)
0.8931	High Similarity	NPD6168	Clinical (unspecified phase)
0.8896	High Similarity	NPD4338	Clinical (unspecified phase)
0.8882	High Similarity	NPD7054	Approved
0.8827	High Similarity	NPD7472	Approved
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.8712	High Similarity	NPD7074	Phase 3
0.8679	High Similarity	NPD5494	Approved
0.8659	High Similarity	NPD6797	Phase 2
0.8608	High Similarity	NPD4868	Clinical (unspecified phase)
0.8606	High Similarity	NPD7251	Discontinued
0.8554	High Similarity	NPD7808	Phase 3
0.8526	High Similarity	NPD4380	Phase 2
0.8467	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8456	Intermediate Similarity	NPD1510	Phase 2
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD5402	Approved
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8411	Intermediate Similarity	NPD1549	Phase 2
0.84	Intermediate Similarity	NPD2796	Approved
0.8377	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8311	Intermediate Similarity	NPD1240	Approved
0.8311	Intermediate Similarity	NPD943	Approved
0.8282	Intermediate Similarity	NPD1247	Approved
0.825	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD1465	Phase 2
0.8204	Intermediate Similarity	NPD5844	Phase 1
0.82	Intermediate Similarity	NPD1607	Approved
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.817	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7819	Suspended
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD3926	Phase 2
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8041	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8013	Intermediate Similarity	NPD447	Suspended
0.8013	Intermediate Similarity	NPD230	Phase 1
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7987	Intermediate Similarity	NPD5403	Approved
0.7973	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.7949	Intermediate Similarity	NPD3750	Approved
0.7947	Intermediate Similarity	NPD1613	Approved
0.7947	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD919	Approved
0.7885	Intermediate Similarity	NPD2800	Approved
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3027	Phase 3
0.7862	Intermediate Similarity	NPD5401	Approved
0.7857	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7826	Intermediate Similarity	NPD1653	Approved
0.7815	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1551	Phase 2
0.7771	Intermediate Similarity	NPD3749	Approved
0.775	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2532	Approved
0.775	Intermediate Similarity	NPD2533	Approved
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD9494	Approved
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7768	Phase 2
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6190	Approved
0.7662	Intermediate Similarity	NPD1933	Approved
0.7658	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD920	Approved
0.7643	Intermediate Similarity	NPD2344	Approved
0.7633	Intermediate Similarity	NPD7199	Phase 2
0.7628	Intermediate Similarity	NPD3748	Approved
0.7619	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD3751	Discontinued
0.761	Intermediate Similarity	NPD4628	Phase 3
0.7588	Intermediate Similarity	NPD3787	Discontinued
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.758	Intermediate Similarity	NPD6100	Approved
0.758	Intermediate Similarity	NPD6099	Approved
0.7561	Intermediate Similarity	NPD3226	Approved
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1243	Approved
0.7544	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7483	Intermediate Similarity	NPD1203	Approved
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7286	Phase 2
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2309	Approved
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.7425	Intermediate Similarity	NPD37	Approved
0.7425	Intermediate Similarity	NPD6844	Discontinued
0.7421	Intermediate Similarity	NPD2346	Discontinued
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7407	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9269	Phase 2
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7362	Intermediate Similarity	NPD7390	Discontinued
0.7355	Intermediate Similarity	NPD3268	Approved
0.7341	Intermediate Similarity	NPD5242	Approved
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7338	Intermediate Similarity	NPD4908	Phase 1
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2798	Approved
0.7314	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD6233	Phase 2
0.7296	Intermediate Similarity	NPD7033	Discontinued
0.7285	Intermediate Similarity	NPD9717	Approved
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7262	Intermediate Similarity	NPD6385	Approved
0.7262	Intermediate Similarity	NPD6386	Approved
0.7256	Intermediate Similarity	NPD4357	Discontinued
0.7255	Intermediate Similarity	NPD2797	Approved
0.7244	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7235	Intermediate Similarity	NPD5353	Approved
0.723	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.719	Intermediate Similarity	NPD3225	Approved
0.7189	Intermediate Similarity	NPD4360	Phase 2
0.7189	Intermediate Similarity	NPD4363	Phase 3
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7184	Intermediate Similarity	NPD5711	Approved
0.7184	Intermediate Similarity	NPD5710	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7171	Intermediate Similarity	NPD1608	Approved
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.7161	Intermediate Similarity	NPD2861	Phase 2
0.7134	Intermediate Similarity	NPD6798	Discontinued
0.7134	Intermediate Similarity	NPD411	Approved
0.7133	Intermediate Similarity	NPD9268	Approved
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7117	Intermediate Similarity	NPD1652	Phase 2
0.7111	Intermediate Similarity	NPD7549	Discontinued
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7229	Phase 3
0.7085	Intermediate Similarity	NPD2899	Discontinued
0.707	Intermediate Similarity	NPD4625	Phase 3
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7066	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1481	Phase 2
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4361	Phase 2
0.7059	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD228	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7047	Intermediate Similarity	NPD7584	Approved
0.7035	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD1470	Approved
0.7032	Intermediate Similarity	NPD3267	Approved
0.7032	Intermediate Similarity	NPD3266	Approved
0.7013	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6994	Remote Similarity	NPD7266	Discontinued
0.6993	Remote Similarity	NPD1535	Discovery
0.6993	Remote Similarity	NPD1201	Approved
0.699	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7696	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