NPASS Compound

Structure

CID205522 OpenBabel06191715592D 27 29 0 0 0 0 0 0 0 0999 V2000 6.9282 1.0000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 4.3301 -0.5000 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 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 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 26 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 21 2 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 27 1 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.12
Volume:	369.247
LogP:	3.022
LogD:	2.864
LogS:	-4.755
# Rotatable Bonds:	6
TPSA:	76.36
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	2.248
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.549
MDCK Permeability:	5.254281495581381e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	70.28067016601562%
Volume Distribution (VD):	0.852
Pgp-substrate:	24.533279418945312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.335
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.525
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.515
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.701
CYP3A4-substrate:	0.73

ADMET: Excretion

Clearance (CL):	6.619
Half-life (T1/2):	0.449

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.285
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.241
Carcinogencity:	0.057
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.264

Download Data

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

Natural Product: NPC205522

Natural Product ID:	NPC205522
*Common Name:**	3',4',6,7,8-Pentamethoxyflavone
IUPAC Name:	2-(3,4-dimethoxyphenyl)-6,7,8-trimethoxychromen-4-one
Synonyms:	3',4',6,7,8-Pentamethoxyflavone
Standard InCHIKey:	MNQMRHVEXBTNRO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O7/c1-22-14-7-6-11(8-16(14)23-2)15-10-13(21)12-9-17(24-3)19(25-4)20(26-5)18(12)27-15/h6-10H,1-5H3
SMILES:	COc1ccc(cc1OC)c1cc(=O)c2cc(c(c(c2o1)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478762
PubChem CID:	44584772
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]
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]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654417]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374950]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[12467611]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	aerial parts	Bangdung, Indonesia	2000-Aug	PMID[12608860]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15104497]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15128261]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
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]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19691312]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
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]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25919052]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26473275]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28898076]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31836445]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	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	Stem	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	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]
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]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO23226	Satureja montana	Species	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]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8981	Senecio integerrimus	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]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25045	Senecio squalidus	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]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	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]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24987	Simira eliezeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22137	Vernonia serratuloides	Species	Asteraceae	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]
NPO23691	Pyrosoma giganteum	Species	Pyrosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23963	Odixia angusta	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]
NPO25699	Vitex madiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14887	Handroanthus guayacan	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1408	Cirsium helenioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7445	Pteris prolifera	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20833	Beyeria brevifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO592	Chroogomphus rutilus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1638	Ulmus laciniata	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5890	Astragalus inopinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24830	Prosopis glandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23453	Pheidole pallidula	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24929	Aria pallescens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24511	Dipterocarpus alatus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25144	Artemisia monogyna	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24068	Prunus laurocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25471	Chromolaena pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1794	Ilex affinis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26042	Agnorhiza bolanderi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14797	Orthosiphon aristatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24556	Bassia butyracea	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25258	Seriphidium cinum	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]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25326	Dendrosenecio kilimanjari	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24599	Streptomyces althioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20823	Stenostomum lucidum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25187	Cladonia evansii	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24291	Rhizobium phaseoli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25390	Pterocarpus grandiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25234	Epaltes gariepina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24383	Ficus formosana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25529	Bursaria spinosa	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24218	Fusarium gibbosum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2499	Celmisia petriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28665	Sesbania punicea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23567	Coccus fagi	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25090	Araujia sericifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24675	Quercus aegilops	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7552	Alligator mississippiensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18352	Anaxagorea clavata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24640	Echinops amplexicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25291	Lactarius scrobiculatus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25671	Gardenia fosbergii	Species	Rubiaceae	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
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	74.8	ug ml-1	PMID[560296]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	31.4	ug ml-1	PMID[560296]

☑ 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 NPC205522 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	528
0.1-0.2	2097
0.2-0.3	5467
0.3-0.4	11796
0.4-0.5	5241
0.5-0.6	4175
0.6-0.7	5648
0.7-0.8	4705
0.8-0.85	1755
0.85-0.9	851
0.9-0.95	365
0.95-1	69

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC106461
0.9929	High Similarity	NPC110639
0.9929	High Similarity	NPC215932
0.9929	High Similarity	NPC14958
0.9929	High Similarity	NPC40818
0.9858	High Similarity	NPC85233
0.9857	High Similarity	NPC136278
0.9789	High Similarity	NPC63256
0.9789	High Similarity	NPC10304
0.9787	High Similarity	NPC302408
0.9787	High Similarity	NPC283002
0.9786	High Similarity	NPC23955
0.9786	High Similarity	NPC113089
0.972	High Similarity	NPC69752
0.9716	High Similarity	NPC165512
0.9714	High Similarity	NPC9966
0.9714	High Similarity	NPC70853
0.9653	High Similarity	NPC259058
0.9653	High Similarity	NPC201547
0.9648	High Similarity	NPC216314
0.9648	High Similarity	NPC195919
0.9648	High Similarity	NPC231013
0.9648	High Similarity	NPC120924
0.9643	High Similarity	NPC214919
0.9643	High Similarity	NPC124467
0.9643	High Similarity	NPC29536
0.9589	High Similarity	NPC186507
0.9589	High Similarity	NPC472408
0.9586	High Similarity	NPC226973
0.9586	High Similarity	NPC308451
0.9586	High Similarity	NPC208043
0.9583	High Similarity	NPC181250
0.9583	High Similarity	NPC238366
0.958	High Similarity	NPC299923
0.9577	High Similarity	NPC471590
0.9571	High Similarity	NPC58229
0.9524	High Similarity	NPC20830
0.9524	High Similarity	NPC256612
0.9521	High Similarity	NPC166201
0.9521	High Similarity	NPC134677
0.9517	High Similarity	NPC306821
0.951	High Similarity	NPC310259
0.9507	High Similarity	NPC293201
0.9507	High Similarity	NPC182842
0.9456	High Similarity	NPC145379
0.9456	High Similarity	NPC472915
0.9456	High Similarity	NPC69394
0.9456	High Similarity	NPC255350
0.9456	High Similarity	NPC183878
0.9456	High Similarity	NPC231018
0.9456	High Similarity	NPC86485
0.9456	High Similarity	NPC280937
0.9456	High Similarity	NPC128961
0.9456	High Similarity	NPC47781
0.9456	High Similarity	NPC22519
0.9456	High Similarity	NPC176775
0.9456	High Similarity	NPC274327
0.9456	High Similarity	NPC160951
0.9448	High Similarity	NPC328119
0.9396	High Similarity	NPC476981
0.9396	High Similarity	NPC19097
0.9392	High Similarity	NPC213622
0.9392	High Similarity	NPC241774
0.9392	High Similarity	NPC183597
0.9392	High Similarity	NPC32557
0.9392	High Similarity	NPC167815
0.9392	High Similarity	NPC92659
0.9392	High Similarity	NPC276059
0.9392	High Similarity	NPC227325
0.9392	High Similarity	NPC138360
0.9392	High Similarity	NPC208197
0.9392	High Similarity	NPC163780
0.9392	High Similarity	NPC2476
0.9392	High Similarity	NPC196439
0.9392	High Similarity	NPC128863
0.9392	High Similarity	NPC4455
0.9392	High Similarity	NPC50715
0.9392	High Similarity	NPC280339
0.9392	High Similarity	NPC201136
0.9392	High Similarity	NPC122623
0.9392	High Similarity	NPC146165
0.9392	High Similarity	NPC34725
0.9392	High Similarity	NPC189960
0.9388	High Similarity	NPC39732
0.9388	High Similarity	NPC212678
0.9388	High Similarity	NPC188203
0.9388	High Similarity	NPC162313
0.9388	High Similarity	NPC120163
0.9388	High Similarity	NPC293183
0.9388	High Similarity	NPC275836
0.9388	High Similarity	NPC275722
0.9388	High Similarity	NPC198826
0.9388	High Similarity	NPC187498
0.9388	High Similarity	NPC57030
0.9388	High Similarity	NPC60972
0.9388	High Similarity	NPC83508
0.9388	High Similarity	NPC301323
0.9388	High Similarity	NPC239128
0.9388	High Similarity	NPC25270
0.9388	High Similarity	NPC71334
0.9388	High Similarity	NPC301123
0.9388	High Similarity	NPC241498
0.9388	High Similarity	NPC100887
0.9388	High Similarity	NPC256283
0.9388	High Similarity	NPC292460
0.9388	High Similarity	NPC222830
0.9388	High Similarity	NPC131624
0.9388	High Similarity	NPC156222
0.9379	High Similarity	NPC195202
0.9379	High Similarity	NPC261548
0.9366	High Similarity	NPC185607
0.9357	High Similarity	NPC44573
0.9329	High Similarity	NPC257277
0.9329	High Similarity	NPC472916
0.9329	High Similarity	NPC180340
0.9329	High Similarity	NPC49824
0.9329	High Similarity	NPC178854
0.9324	High Similarity	NPC476289
0.9324	High Similarity	NPC75279
0.9324	High Similarity	NPC250822
0.9324	High Similarity	NPC276409
0.932	High Similarity	NPC149614
0.932	High Similarity	NPC474663
0.932	High Similarity	NPC198615
0.932	High Similarity	NPC262623
0.932	High Similarity	NPC117579
0.931	High Similarity	NPC117463
0.931	High Similarity	NPC93034
0.931	High Similarity	NPC119660
0.931	High Similarity	NPC12200
0.931	High Similarity	NPC33265
0.931	High Similarity	NPC62536
0.931	High Similarity	NPC470511
0.9272	High Similarity	NPC476980
0.9267	High Similarity	NPC224137
0.9267	High Similarity	NPC93376
0.9267	High Similarity	NPC75215
0.9267	High Similarity	NPC227192
0.9267	High Similarity	NPC203891
0.9267	High Similarity	NPC110070
0.9267	High Similarity	NPC101830
0.9267	High Similarity	NPC189179
0.9267	High Similarity	NPC181960
0.9267	High Similarity	NPC470402
0.9262	High Similarity	NPC2928
0.9262	High Similarity	NPC201451
0.9262	High Similarity	NPC37392
0.9262	High Similarity	NPC44079
0.9262	High Similarity	NPC26227
0.9262	High Similarity	NPC472909
0.9257	High Similarity	NPC40033
0.9257	High Similarity	NPC142540
0.9252	High Similarity	NPC5840
0.9252	High Similarity	NPC239363
0.9252	High Similarity	NPC50728
0.9252	High Similarity	NPC156953
0.9252	High Similarity	NPC189270
0.9252	High Similarity	NPC45873
0.9252	High Similarity	NPC184136
0.9252	High Similarity	NPC29056
0.9252	High Similarity	NPC179183
0.9252	High Similarity	NPC166753
0.9247	High Similarity	NPC476342
0.9214	High Similarity	NPC77955
0.9211	High Similarity	NPC258331
0.9211	High Similarity	NPC165549
0.9205	High Similarity	NPC238405
0.9205	High Similarity	NPC22472
0.9205	High Similarity	NPC288669
0.9205	High Similarity	NPC204854
0.9205	High Similarity	NPC190487
0.9205	High Similarity	NPC191459
0.9205	High Similarity	NPC193842
0.9205	High Similarity	NPC130894
0.9205	High Similarity	NPC18772
0.9205	High Similarity	NPC7846
0.9205	High Similarity	NPC253634
0.9205	High Similarity	NPC300943
0.9205	High Similarity	NPC154304
0.9205	High Similarity	NPC105242
0.9205	High Similarity	NPC9609
0.9205	High Similarity	NPC115798
0.9205	High Similarity	NPC25495
0.9205	High Similarity	NPC143828
0.9205	High Similarity	NPC19687
0.9205	High Similarity	NPC152166
0.9205	High Similarity	NPC104459
0.9205	High Similarity	NPC176300
0.9205	High Similarity	NPC18607
0.9205	High Similarity	NPC257914
0.9205	High Similarity	NPC261004
0.9205	High Similarity	NPC4481
0.92	High Similarity	NPC247017
0.92	High Similarity	NPC292107
0.92	High Similarity	NPC474520
0.92	High Similarity	NPC245546
0.92	High Similarity	NPC265511
0.92	High Similarity	NPC98661
0.92	High Similarity	NPC43243
0.92	High Similarity	NPC303255

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 NPC205522 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	457
0.1-0.2	1034
0.2-0.3	1809
0.3-0.4	2747
0.4-0.5	1699
0.5-0.6	916
0.6-0.7	343
0.7-0.8	102
0.8-0.85	25
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9456	High Similarity	NPD2801	Approved
0.9145	High Similarity	NPD5494	Approved
0.9007	High Similarity	NPD3817	Phase 2
0.8881	High Similarity	NPD2796	Approved
0.8874	High Similarity	NPD1934	Approved
0.8844	High Similarity	NPD1511	Approved
0.8824	High Similarity	NPD3882	Suspended
0.8725	High Similarity	NPD1512	Approved
0.8718	High Similarity	NPD1247	Approved
0.8693	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD3818	Discontinued
0.8533	High Similarity	NPD4378	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD3926	Phase 2
0.8467	Intermediate Similarity	NPD6799	Approved
0.8438	Intermediate Similarity	NPD6166	Phase 2
0.8438	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD5402	Approved
0.8395	Intermediate Similarity	NPD7054	Approved
0.8354	Intermediate Similarity	NPD919	Approved
0.8344	Intermediate Similarity	NPD7472	Approved
0.8301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1510	Phase 2
0.8258	Intermediate Similarity	NPD4380	Phase 2
0.8255	Intermediate Similarity	NPD1549	Phase 2
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD7819	Suspended
0.8199	Intermediate Similarity	NPD6232	Discontinued
0.8193	Intermediate Similarity	NPD7808	Phase 3
0.8188	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.817	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7473	Discontinued
0.8153	Intermediate Similarity	NPD6801	Discontinued
0.8151	Intermediate Similarity	NPD1240	Approved
0.8141	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8095	Intermediate Similarity	NPD1933	Approved
0.8065	Intermediate Similarity	NPD920	Approved
0.8063	Intermediate Similarity	NPD7075	Discontinued
0.8054	Intermediate Similarity	NPD3748	Approved
0.8041	Intermediate Similarity	NPD1607	Approved
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7973	Intermediate Similarity	NPD447	Suspended
0.7961	Intermediate Similarity	NPD1243	Approved
0.7949	Intermediate Similarity	NPD5403	Approved
0.7935	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5401	Approved
0.7905	Intermediate Similarity	NPD943	Approved
0.7895	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2935	Discontinued
0.7875	Intermediate Similarity	NPD1465	Phase 2
0.7826	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3750	Approved
0.777	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.7751	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5242	Approved
0.7697	Intermediate Similarity	NPD6959	Discontinued
0.766	Intermediate Similarity	NPD5536	Phase 2
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7647	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD6385	Approved
0.764	Intermediate Similarity	NPD6386	Approved
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3749	Approved
0.7616	Intermediate Similarity	NPD230	Phase 1
0.7613	Intermediate Similarity	NPD2800	Approved
0.7613	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5353	Approved
0.7602	Intermediate Similarity	NPD6559	Discontinued
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.7564	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.756	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD6844	Discontinued
0.7484	Intermediate Similarity	NPD2344	Approved
0.7484	Intermediate Similarity	NPD2532	Approved
0.7484	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD2534	Approved
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2403	Approved
0.7453	Intermediate Similarity	NPD1653	Approved
0.7452	Intermediate Similarity	NPD4628	Phase 3
0.745	Intermediate Similarity	NPD3018	Phase 2
0.745	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7434	Intermediate Similarity	NPD1613	Approved
0.7434	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3027	Phase 3
0.7347	Intermediate Similarity	NPD3972	Approved
0.7347	Intermediate Similarity	NPD2981	Phase 2
0.7341	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD9494	Approved
0.7329	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7286	Phase 2
0.732	Intermediate Similarity	NPD4307	Phase 2
0.7315	Intermediate Similarity	NPD3266	Approved
0.7315	Intermediate Similarity	NPD1203	Approved
0.7315	Intermediate Similarity	NPD3267	Approved
0.7308	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD6099	Approved
0.7297	Intermediate Similarity	NPD2983	Phase 2
0.7297	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2982	Phase 2
0.7296	Intermediate Similarity	NPD2309	Approved
0.7296	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.726	Intermediate Similarity	NPD17	Approved
0.7257	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1241	Discontinued
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD4965	Approved
0.7246	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9717	Approved
0.7226	Intermediate Similarity	NPD6651	Approved
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4357	Discontinued
0.719	Intermediate Similarity	NPD1296	Phase 2
0.719	Intermediate Similarity	NPD3268	Approved
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.7114	Intermediate Similarity	NPD1608	Approved
0.7102	Intermediate Similarity	NPD7685	Pre-registration
0.7099	Intermediate Similarity	NPD7390	Discontinued
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7086	Intermediate Similarity	NPD2797	Approved
0.7083	Intermediate Similarity	NPD4288	Approved
0.7083	Intermediate Similarity	NPD5978	Approved
0.7083	Intermediate Similarity	NPD5977	Approved
0.7081	Intermediate Similarity	NPD3887	Approved
0.7078	Intermediate Similarity	NPD411	Approved
0.7075	Intermediate Similarity	NPD9268	Approved
0.7066	Intermediate Similarity	NPD6279	Approved
0.7066	Intermediate Similarity	NPD6280	Approved
0.7062	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD4908	Phase 1
0.7055	Intermediate Similarity	NPD3146	Approved
0.7055	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD422	Phase 1
0.7044	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2353	Approved
0.7035	Intermediate Similarity	NPD7229	Phase 3
0.702	Intermediate Similarity	NPD3225	Approved
0.702	Intermediate Similarity	NPD1876	Approved
0.7006	Intermediate Similarity	NPD5890	Approved
0.7006	Intermediate Similarity	NPD5889	Approved
0.7	Intermediate Similarity	NPD9269	Phase 2
0.7	Intermediate Similarity	NPD6971	Discontinued
0.6987	Remote Similarity	NPD3140	Approved
0.6987	Remote Similarity	NPD3142	Approved
0.6981	Remote Similarity	NPD3539	Phase 1
0.6973	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2163	Approved
0.6971	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5005	Approved
0.6968	Remote Similarity	NPD5006	Approved
0.6968	Remote Similarity	NPD6798	Discontinued
0.6957	Remote Similarity	NPD1652	Phase 2
0.6957	Remote Similarity	NPD4360	Phase 2
0.6957	Remote Similarity	NPD4363	Phase 3
0.6952	Remote Similarity	NPD6782	Approved
0.6952	Remote Similarity	NPD6780	Approved
0.6952	Remote Similarity	NPD6777	Approved
0.6952	Remote Similarity	NPD6781	Approved
0.6952	Remote Similarity	NPD6778	Approved
0.6952	Remote Similarity	NPD6776	Approved
0.6952	Remote Similarity	NPD6779	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data