NPASS Compound

Natural Product: NPC93730

Natural Product ID	NPC93730
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Flavonol
IUPAC Name	3-hydroxy-2-phenylchromen-4-one
Synonyms	NCI-57653; NSC-57653
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL294009
PubChem CID	11349
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 28 30 0 0 0 0 0 0 0 0999 V2000 2.0973 -2.3927 -1.4445 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5751 -1.4069 -0.8794 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1775 -1.3164 -0.8415 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5092 -2.3270 -1.4335 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3835 -0.2400 -0.2243 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4226 0.6783 0.3156 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7194 0.6309 0.3016 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3681 -0.4377 -0.3101 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7454 -0.4750 -0.3174 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5082 0.5206 0.2668 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8651 1.5760 0.8709 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4732 1.6276 0.8863 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8255 -0.0636 -0.1372 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7599 -0.9074 -0.6354 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1331 -0.6531 -0.5025 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5703 0.4747 0.1458 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6052 1.3286 0.6501 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2677 1.0971 0.5301 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5718 -3.2750 -1.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2386 -1.3045 -0.7924 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5861 0.5102 0.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3984 2.3940 1.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9371 2.4434 1.3529 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4783 -1.7939 -1.1456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8407 -1.3628 -0.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6339 0.6567 0.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9622 2.2218 1.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5709 1.7962 0.9420 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 3 5 2 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 5 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 8 2 1 0 18 13 1 0 12 7 1 0 4 19 1 0 9 20 1 0 10 21 1 0 11 22 1 0 12 23 1 0 14 24 1 0 15 25 1 0 16 26 1 0 17 27 1 0 18 28 1 0 M END

Standard InCHIKey	HVQAJTFOCKOKIN-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H
SMILES	O=c1c(O)c(oc2c1cccc2)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	238.06	Volume:	247.606 ? Van der Waals volume.
Dense:	0.961	LogP:	2.687 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.325 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.058 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	18.0
TPSA:	50.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.708	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.806	Fsp³:	0.0
MCE-18:	15.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.462	Fluc inhibitor:	0.762 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.662 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.29 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.883	Promiscuous compounds:	0.603

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.719	MDCK Permeability:	-4.7
Pgp-inhibitor:	0.989	Pgp-substrate:	0.018
PAMPA:	0.362 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.024	30% Bioavailability (F30%):	0.557
50% Bioavailability (F50%):	0.806

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337	MRP1:	0.771
Plasma Protein Binding (PPB):	98.303%	Volume Distribution (VD):	-0.522
Fu:	0.824% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.975
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.894
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.284	CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.975
CYP2C9-inhibitor:	0.96	CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.654	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.104	CYP3A4-substrate:	0.372
CYP2B6-substrate:	0.034	CYP2C8-inhibitor:	0.975
HLM stability:	0.907 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.599

Half-life (T1/2):

1.033

ADMET: Toxicity

hERG Blockers:	0.117	hERG Blockers (10um):	0.497
Human Hepatotoxicity (H-HT):	0.483	Drug-induced Liver Injury (DILI):	0.866
AMES Toxicity:	0.536	Rat Oral Acute Toxicity:	0.451
Maximum Recommended Daily Dose:	0.464	Skin Sensitization:	0.555
Carcinogencity:	0.729	Eye Corrosion:	0.69
Eye Irritation:	0.988	Respiratory Toxicity:	0.608
Drug-induced Neurotoxicity:	0.247	Ototoxicity:	0.114
Hematotoxicity:	0.22	Drug-induced Nephrotoxicity:	0.113
Genotoxicity:	0.598	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.132	Hek293 Cytotoxicity:	0.215
BCF:	1.178 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.298 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.048 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.783 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11627-001-0052-8]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22305790]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35268681]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235241]
NPO53835	Cnicus benedictus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37997548]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38308284]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38986200]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39410132]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[8158164]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158164]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53835	Cnicus benedictus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27261	Carica papaya	Species	Caricaceae	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	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference
NPO27261	Carica papaya	Raw	Leaf	100	0	200	mg/100g	Database [DUKE]
NPO53835	Cnicus benedictus	Hydro-methanolic extract	Roots	0.85Â±0.15	n.a.	n.a.	%	PMID[37997548]
NPO53835	Cnicus benedictus	Hydro-methanolic extract	Roots	0.94Â±0.14	n.a.	n.a.	%	PMID[37997548]

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
Inhibition	6
IC50	21
Potency	26
Ratio IC50	2
Kd	1
Activity	44
Ki	10
MIC	16
EC50	5
ED50	1
pID50	1
Emax	2
Rmax	2
ID50	2
Protection	1

Activity Type	# Activity
Individual protein	60
Cell line	13
Organism	39
Others	11
Tissue	12
Protein complex	1
Protein-protein interaction	2
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1119	Individual protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	>	100000.0	nM	PMID[17869117]
NPT1139	Individual protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	IC50	>	100000.0	nM	PMID[17869117]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	IC50	=	23500.0	nM	PMID[19592245]
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT1621	Individual protein	Calmodulin	Homo sapiens	IC50	=	55200.0	nM	PMID[21129983]
NPT1621	Individual protein	Calmodulin	Homo sapiens	Ratio IC50	=	0.36	n.a.	PMID[21129983]
NPT1139	Individual protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	=	9300.0	nM	PMID[22487176]
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	=	9200.0	nM	PMID[22487176]
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	32642.7	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	730.8	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	7943.3	nM	PubChem BioAssay data set
NPT1604	Individual protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	90.0	nM	PMID[28458135]
NPT1356	Individual protein	Protein disulfide-isomerase	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35471830]
NPT1356	Individual protein	Protein disulfide-isomerase	Homo sapiens	Ki	n.a.	n.a.	n.a.	PMID[35471830]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	7079.5	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	3981.1	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	89125.1	nM	PubChem BioAssay data set
NPT702	Individual protein	UDP-glucuronosyltransferase 1-6	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[10836148]
NPT695	Individual protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Activity	=	531.0	pm/min/mg	PMID[10836148]
NPT703	Individual protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	Activity	=	600.0	pm/min/mg	PMID[10836148]
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	102.57	%	PMID[23571415]
NPT4064	Individual protein	Hormone-sensitive lipase	Rattus norvegicus	Inhibition	=	23.0	%	PMID[18808096]
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT444	Individual protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	133.45	%	PMID[23571415]
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	73000.0	nM	PMID[17869117]
NPT967	Individual protein	Xanthine dehydrogenase	Homo sapiens	IC50	>	100000.0	nM	PMID[9461655]
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT901	Individual protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Activity	=	370.0	pm/min/mg	PMID[10836148]
NPT696	Individual protein	UDP-glucuronosyltransferase 2A1	Homo sapiens	Activity	=	320.0	pm/min/mg	PMID[10836148]
NPT901	Individual protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Activity	=	114.0	pm/min/mg	PMID[10836148]
NPT901	Individual protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Activity	=	50.0	pm/min/mg	PMID[10836148]
NPT902	Individual protein	UDP-glucuronosyltransferase 1A4	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[10836148]
NPT696	Individual protein	UDP-glucuronosyltransferase 2A1	Homo sapiens	Activity	=	163.0	pm/min/mg	PMID[10836148]
NPT948	Individual protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	5540.0	nM	PMID[22487176]
NPT948	Individual protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	5630.0	nM	PMID[22487176]
NPT949	Individual protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	6590.0	nM	PMID[22487176]
NPT949	Individual protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	6650.0	nM	PMID[22487176]
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	15848.9	nM	PubChem BioAssay data set
NPT711	Individual protein	Aldose reductase	Bos taurus	Inhibition	=	0.0	%	PMID[10354396]
NPT1567	Protein complex	DNA gyrase	Escherichia coli K-12	IC50	>	500.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80881-7]
NPT865	Individual protein	Fatty acid synthase	Homo sapiens	IC50	>	100000.0	nM	PMID[16870425]
NPT865	Individual protein	Fatty acid synthase	Homo sapiens	Inhibition	=	6.5	%	PMID[16870425]
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Kd	=	10000.0	nM	PMID[21723648]
NPT699	Individual protein	UDP-glucuronosyltransferase 1-10	Homo sapiens	Activity	=	30.0	pm/min/mg	PMID[10836148]
NPT699	Individual protein	UDP-glucuronosyltransferase 1-10	Homo sapiens	Activity	=	35.0	pm/min/mg	PMID[10836148]
NPT694	Individual protein	UDP-glucuronosyltransferase 1-3	Homo sapiens	Activity	=	604.0	pm/min/mg	PMID[10836148]
NPT903	Individual protein	UDP-glucuronosyltransferase 1-7	Homo sapiens	Activity	=	57.0	pm/min/mg	PMID[10836148]
NPT704	Individual protein	UDP-glucuronosyltransferase 2B15	Homo sapiens	Activity	=	64.0	pm/min/mg	PMID[10836148]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	=	5210.0	nM	PMID[22487176]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	=	5100.0	nM	PMID[22487176]
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3.2	nM	PubChem BioAssay data set
NPT52	Individual protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	Ki	=	3530.0	nM	PMID[34726055]
NPT52	Individual protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	IC50	=	1750.0	nM	PMID[34726055]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.2	ug ml-1	PMID[469554]
NPT759	Cell line	H9	Homo sapiens	IC50	=	17000.0	nM	PMID[8158164]
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	-17.6	%	PMID[21493073]
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	-10.0	%	PMID[21493073]
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	-12.6	%	PMID[21493073]
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	-31.6	%	PMID[21493073]
NPT1629	Cell line	CWR22R	Homo sapiens	Activity	=	80.0	%	PMID[22789812]
NPT1629	Cell line	CWR22R	Homo sapiens	Activity	=	124.0	%	PMID[22789812]
NPT1629	Cell line	CWR22R	Homo sapiens	Activity	=	92.0	%	PMID[22789812]
NPT1629	Cell line	CWR22R	Homo sapiens	Activity	=	100.0	%	PMID[22789812]
NPT1629	Cell line	CWR22R	Homo sapiens	IC50	=	14900.0	nM	PMID[22789812]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	64.6	%	PMID[23771043]
NPT492	Cell line	Caco-2	Homo sapiens	IC50	=	42100.0	nM	PMID[28793973]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	125.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80881-7]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	24000.0	nM	PMID[16722653]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	pID50	=	6.538	n.a.	PMID[20696502]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	>	83.0	ug.mL-1	PMID[31427220]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	EC50	=	2200.0	nM	PMID[30234295]
NPT177	Tissue	Aorta	Rattus norvegicus	EC50	=	7585.78	nM	PMID[18307286]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	91.0	%	PMID[18307286]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	70.0	%	PMID[18307286]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	83.0	%	PMID[18307286]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[9461655]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	1.06	MU	PMID[19944611]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	203600.0	nM	PMID[21129983]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	248300.0	nM	PMID[21129983]
NPT177	Tissue	Aorta	Rattus norvegicus	Emax	=	67.77	%	PMID[21129983]
NPT177	Tissue	Aorta	Rattus norvegicus	Emax	=	29.8	%	PMID[21129983]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	83.0	ug.mL-1	PMID[31427220]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	EC50	=	33000.0	nM	PMID[30234295]
NPT633	Organism	Leishmania donovani	Leishmania donovani	EC50	=	3000.0	nM	PMID[30234295]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	125.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80881-7]
NPT1521	Organism	Stenotrophomonas maltophilia	Stenotrophomonas maltophilia	MIC	>	125.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80881-7]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	125.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80881-7]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	125.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80881-7]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	13000.0	nM	PMID[8158164]
NPT1	Others	Radical scavenging activity	n.a.	Inhibition	=	66.0	%	DOI[10.1007/s00044-007-9060-5]
NPT2847	Tissue	Thoracic aorta	Rattus norvegicus	IC50	=	4265.8	nM	DOI[10.1039/C0MD00240B]
NPT2847	Tissue	Thoracic aorta	Rattus norvegicus	Rmax	=	19.0	%	DOI[10.1039/C0MD00240B]
NPT2847	Tissue	Thoracic aorta	Rattus norvegicus	Rmax	=	20.0	%	DOI[10.1039/C0MD00240B]
NPT2	Others	Unspecified	n.a.	Ratio IC50	<	0.73	n.a.	PMID[17869117]
NPT35	Others	n.a.	n.a.	Activity	=	0.707	MU	PMID[19944611]
NPT35	Others	n.a.	n.a.	Activity	=	34.7	mg/L	PMID[19944611]
NPT2	Others	Unspecified	n.a.	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	>	83.0	ug.mL-1	PMID[31427220]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	9100.0	nM	PMID[27411733]
NPT2	Others	Unspecified	n.a.	ID50	>	419.7	uM	PMID[1378087]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Protection	=	47.0	%	PMID[8523407]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	9.2	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	60.1	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	35.7	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	7.7	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	2.09	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-16.04	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-15.66	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-5.92	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1.93	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-10.05	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-2.36	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-20.2	%	PMID[20346546]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-6.04	%	PMID[20346546]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC93730 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	35419
0.1-0.2	12382
0.2-0.3	1793
0.3-0.4	204
0.4-0.5	47
0.5-0.6	10
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7347	Intermediate Similarity	NPC605146
0.7174	Intermediate Similarity	NPC299379
0.6809	Remote Similarity	NPC128216
0.58	Remote Similarity	NPC187432
0.5745	Remote Similarity	NPC32298
0.549	Remote Similarity	NPC51443
0.5385	Remote Similarity	NPC74881
0.537	Remote Similarity	NPC26227
0.5273	Remote Similarity	NPC152042
0.5192	Remote Similarity	NPC22783
0.5179	Remote Similarity	NPC281207
0.5094	Remote Similarity	NPC193805
0.5088	Remote Similarity	NPC269652

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC93730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6040
0.1-0.2	2972
0.2-0.3	125
0.3-0.4	11
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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