NPASS Compound

Natural Product: NPC28337

Natural Product ID	NPC28337
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Euparin
IUPAC Name	1-(6-hydroxy-2-prop-1-en-2-yl-1-benzofuran-5-yl)ethanone
Synonyms	Euparin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503938
PubChem CID	119039
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

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 29 0 0 0 0 0 0 0 0999 V2000 -3.9053 1.5871 -0.5448 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5632 0.3523 -0.2548 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5732 -0.7046 -0.0634 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1226 0.0469 -0.1241 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0921 0.9492 -0.2801 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0693 0.2423 -0.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4180 0.6240 -0.0984 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4035 -0.3000 0.1503 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7999 0.0786 0.1276 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7034 -0.7934 0.3638 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2651 1.4573 -0.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0216 -1.5937 0.4218 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6960 -1.9860 0.4515 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3154 -1.0500 0.1990 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6217 -1.1314 0.1602 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0456 -2.5182 0.6723 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1682 2.3620 -0.6852 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9421 1.8725 -0.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7843 -0.8632 1.0274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5186 -0.3935 -0.5231 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2408 -1.6801 -0.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1608 2.0126 -0.5200 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6773 1.6519 -0.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3297 2.0799 0.7540 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5938 1.9343 -0.9292 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2473 1.3746 -0.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4345 -2.9954 0.6649 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3034 -2.6159 1.6624 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 8 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 12 16 1 0 15 4 1 0 14 6 1 0 1 17 1 0 1 18 1 0 3 19 1 0 3 20 1 0 3 21 1 0 5 22 1 0 7 23 1 0 11 24 1 0 11 25 1 0 11 26 1 0 13 27 1 0 16 28 1 0 M END

Standard InCHIKey	OPUFDNZTKHPZHM-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C13H12O3/c1-7(2)12-5-9-4-10(8(3)14)11(15)6-13(9)16-12/h4-6,15H,1H2,2-3H3
SMILES	C=C(C)c1cc2cc(C(=O)C)c(cc2o1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	216.08	Volume:	226.843 ? Van der Waals volume.
Dense:	0.953	LogP:	3.084 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.02 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.818 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	12.0
TPSA:	50.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.783	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.641	Fsp³:	0.154
MCE-18:	13.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.298	Fluc inhibitor:	0.332 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.979 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.359 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.73	Promiscuous compounds:	0.081

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.918	MDCK Permeability:	-4.627
Pgp-inhibitor:	0.517	Pgp-substrate:	0.015
PAMPA:	0.089 ? 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):	0.003
20% Bioavailability (F20%):	0.191	30% Bioavailability (F30%):	0.42
50% Bioavailability (F50%):	0.821

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.755	MRP1:	0.92
Plasma Protein Binding (PPB):	97.752%	Volume Distribution (VD):	-0.265
Fu:	2.145% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.973
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.426
BSEP inhibitor:	0.939

ADMET: Metabolism

CYP1A2-inhibitor:	0.108	CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.052	CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.024	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.686	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.043	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.02	CYP2C8-inhibitor:	0.962
HLM stability:	0.573 ? 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):

4.39

Half-life (T1/2):

1.486

ADMET: Toxicity

hERG Blockers:	0.105	hERG Blockers (10um):	0.483
Human Hepatotoxicity (H-HT):	0.523	Drug-induced Liver Injury (DILI):	0.659
AMES Toxicity:	0.714	Rat Oral Acute Toxicity:	0.377
Maximum Recommended Daily Dose:	0.362	Skin Sensitization:	0.557
Carcinogencity:	0.748	Eye Corrosion:	0.357
Eye Irritation:	0.993	Respiratory Toxicity:	0.803
Drug-induced Neurotoxicity:	0.233	Ototoxicity:	0.235
Hematotoxicity:	0.418	Drug-induced Nephrotoxicity:	0.181
Genotoxicity:	0.671	RPMI-8226 Immunitoxicity:	0.107
A549 Cytotoxicity:	0.223	Hek293 Cytotoxicity:	0.306
BCF:	1.154 ? 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:	3.611 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.043 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.224 ? 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
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	Whole plant	Songyang County, Zhejiang Province, China	n.a.	PMID[15387644]
NPO451	Dracaena deisteliana	Species	Teiidae	Eukaryota	stems	Yaound, village of Bangoua, near Bangangt	2007-APR	PMID[20553003]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21391659]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30653318]
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882437]
NPO6035	Streptomyces flavofungini	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9205	Hartwrightia floridana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6897	Petersianthus macrocarpus	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1282	Haminoea fusari	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22160	Polygonatum cyrtonema	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7123	Aria intermedia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26664	Senecio nudicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6401	Ligularia stenocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22160	Polygonatum cyrtonema	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26664	Senecio nudicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6401	Ligularia stenocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26664	Senecio nudicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22160	Polygonatum cyrtonema	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6401	Ligularia stenocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22160	Polygonatum cyrtonema	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22160	Polygonatum cyrtonema	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6206	Ursinia nudicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6897	Petersianthus macrocarpus	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25771	Magnolia stellata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6401	Ligularia stenocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7123	Aria intermedia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7124	Ophiorrhiza acuminata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9831	Acacia catechuoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9205	Hartwrightia floridana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1282	Haminoea fusari	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13143	Musineon divaricatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO451	Dracaena deisteliana	Species	Teiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26664	Senecio nudicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25827	Echinops giganteus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26546	Gnaphalium obtusifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10328	Sida hermaphrodita	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6035	Streptomyces flavofungini	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26225	Solanum hindsianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22160	Polygonatum cyrtonema	Species	Asparagaceae	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

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
Potency	9
Inhibition	4
ED50	4
IC50	2
MIC	1
Activity	2
FR50	1
pED50	1

Activity Type	# Activity
Individual protein	7
Cell line	3
Organism	8
Others	4
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	446.7	nM	PubChem BioAssay data set
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	98.85	%	PMID[23571415]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	94.93	%	PMID[23571415]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	6.0	ug ml-1	PMID[8882437]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	6.0	ug ml-1	PMID[8882437]
NPT81	Cell line	A549	Homo sapiens	ED50	=	22.0	ug ml-1	PMID[8882437]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	FR50	=	0.42	n.a.	DOI[10.1016/S0305-1978(96)00100-7]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	29.0	ug.mL-1	PMID[8882437]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	83.0	%	PMID[9784153]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	10.5	day	PMID[9784153]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	13.7	%	PMID[21391659]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	12.6	%	PMID[21391659]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	pED50	=	5.92	n.a.	PMID[27385567]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	=	1.2	10'-9mol/cm2	PMID[27385567]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	252.0	ug.mL-1	PMID[8882437]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	111.0	ug.mL-1	PMID[8882437]
NPT2	Others	Unspecified	n.a.	Potency	=	6309.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	4466.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3162.3	nM	PubChem BioAssay data set

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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
-	Artemia	LC50	=	44.0	ug.mL-1	PMID[8882437]
-	Artemia salina	LC50	=	58.9	ppm	DOI[10.1016/S0305-1978(96)00100-7]

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 NPC28337 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	23605
0.1-0.2	24429
0.2-0.3	1799
0.3-0.4	23
0.4-0.5	0
0.5-0.6	1
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	Natural Product ID
0.54	Remote Similarity	NPC29638

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC28337 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3312
0.1-0.2	5726
0.2-0.3	112
0.3-0.4	0
0.4-0.5	0
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