NPASS Compound

Natural Product: NPC162689

Natural Product ID	NPC162689
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-Phenylquinoline
IUPAC Name	2-phenylquinoline
Synonyms	2-Phenylquinoline
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL89786
PubChem CID	71545
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines

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 27 29 0 0 0 0 0 0 0 0999 V2000 4.5497 0.7466 0.9105 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5358 1.6915 0.9616 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2201 1.3373 0.7524 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8492 0.0160 0.4805 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8656 -0.8930 0.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1911 -0.5484 0.6446 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4526 -0.3211 0.2652 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0296 -1.5993 -0.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3146 -1.8706 -0.2029 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2175 -0.8318 -0.1230 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7825 0.4430 0.1479 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4788 0.6584 0.3316 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7276 1.4604 0.2194 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0775 1.2547 0.0322 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4969 -0.0306 -0.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5653 -1.0534 -0.3127 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5764 1.0583 1.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7960 2.7136 1.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4093 2.0632 0.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6665 -1.9367 0.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9522 -1.3008 0.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7607 -2.4017 -0.0629 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6235 -2.8822 -0.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3856 2.4786 0.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7929 2.0877 0.0973 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5378 -0.2590 -0.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8545 -2.0807 -0.5241 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 4 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 6 1 1 0 12 7 1 0 16 10 1 0 1 17 1 0 2 18 1 0 3 19 1 0 5 20 1 0 6 21 1 0 8 22 1 0 9 23 1 0 13 24 1 0 14 25 1 0 15 26 1 0 16 27 1 0 M END

Standard InCHIKey	FSEXLNMNADBYJU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C15H11N/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-11H
SMILES	c1ccc(cc1)c1ccc2c(n1)cccc2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	205.09	Volume:	232.232 ? Van der Waals volume.
Dense:	0.883	LogP:	4.045 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.886 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.091 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	17.0
TPSA:	12.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.587	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.399	Fsp³:	0.0
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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.582	Fluc inhibitor:	0.999 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.791 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.333 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.703	Promiscuous compounds:	0.34

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.373	MDCK Permeability:	-4.642
Pgp-inhibitor:	0.707	Pgp-substrate:	0.036
PAMPA:	0.199 ? 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):	0.0
20% Bioavailability (F20%):	0.065	30% Bioavailability (F30%):	0.237
50% Bioavailability (F50%):	0.452

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972	MRP1:	0.661
Plasma Protein Binding (PPB):	98.044%	Volume Distribution (VD):	0.11
Fu:	1.152% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.888
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.429
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.939	CYP1A2-substrate:	0.546
CYP2C19-inhibitor:	0.813	CYP2C19-substrate:	0.599
CYP2C9-inhibitor:	0.995	CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.997	CYP2D6-substrate:	0.486
CYP3A4-inhibitor:	0.069	CYP3A4-substrate:	0.894
CYP2B6-substrate:	0.488	CYP2C8-inhibitor:	1.0
HLM stability:	0.904 ? 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):

7.618

Half-life (T1/2):

1.212

ADMET: Toxicity

hERG Blockers:	0.359	hERG Blockers (10um):	0.671
Human Hepatotoxicity (H-HT):	0.678	Drug-induced Liver Injury (DILI):	0.682
AMES Toxicity:	0.773	Rat Oral Acute Toxicity:	0.448
Maximum Recommended Daily Dose:	0.521	Skin Sensitization:	0.424
Carcinogencity:	0.671	Eye Corrosion:	0.048
Eye Irritation:	0.977	Respiratory Toxicity:	0.788
Drug-induced Neurotoxicity:	0.906	Ototoxicity:	0.296
Hematotoxicity:	0.433	Drug-induced Nephrotoxicity:	0.762
Genotoxicity:	0.57	RPMI-8226 Immunitoxicity:	0.059
A549 Cytotoxicity:	0.202	Hek293 Cytotoxicity:	0.471
BCF:	1.606 ? 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:	4.403 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.003 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.05 ? 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
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374942]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499324]
NPO16032	Xanthoparmelia quintaria	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19489	Tylosema esculentum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18402	Tecoma peroba	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO83	Saccharina angustata	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16708	Pinus abies	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16452	Iochroma coccineum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19680	Haminoea orteai	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17868	Eucryphia glutinosa	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18897	Cephalosporium gregatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14518	Ateleia herbert-smithii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18972	Astropecten indicus	Species	Astropectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19065	Galipea longiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19065	Galipea longiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16452	Iochroma coccineum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19065	Galipea longiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16708	Pinus abies	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14518	Ateleia herbert-smithii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18897	Cephalosporium gregatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO83	Saccharina angustata	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17868	Eucryphia glutinosa	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18402	Tecoma peroba	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18972	Astropecten indicus	Species	Astropectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16032	Xanthoparmelia quintaria	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19680	Haminoea orteai	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19489	Tylosema esculentum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	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
Ki	1
Potency	7
Inhibition	61
MIC	9
IC90	2
Kd	1
Activity	2

Activity Type	# Activity
Individual protein	6
Organism	74
Protein complex	1
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	20596.2	nM	PubChem BioAssay data set
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT157	Individual protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT535	Individual protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT1496	Protein complex	Glutamate NMDA receptor	Rattus norvegicus	Ki	>	35000.0	nM	PMID[12182873]
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	250.0	ug.mL-1	PMID[18752959]
NPT3954	Organism	Human T-lymphotropic virus 1	Human T-lymphotropic virus 1	Inhibition	=	0.0	%	PMID[12617915]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	250.0	ug.mL-1	PMID[18752959]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	125.0	ug.mL-1	PMID[18752959]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	=	16.0	ug.mL-1	PMID[18752959]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	25.0	ug.mL-1	PMID[18752959]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	25.0	ug.mL-1	PMID[18752959]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	0.0	%	PMID[18752959]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC90	=	100.0	ug.mL-1	DOI[10.1021/np50099a013]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC90	=	100.0	ug.mL-1	DOI[10.1021/np50099a013]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	250.0	ug.mL-1	PMID[18752959]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	>	250.0	ug.mL-1	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	31.2	ug.mL-1	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	100.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	0.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	32.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	77.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	50.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	29.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	13.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	4.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	99.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	87.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	35.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	84.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	33.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	7.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	12.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	47.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	34.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	14.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	83.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	54.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	22.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	74.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	15.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	5.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	67.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	46.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	17.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	45.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	10.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	88.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	76.0	%	PMID[18752959]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	21.0	%	PMID[18752959]
NPT3641	Organism	Mucor circinelloides	Mucor circinelloides	Activity	=	98.1	%	PMID[35245665]
NPT3641	Organism	Mucor circinelloides	Mucor circinelloides	Activity	=	98.2	%	PMID[35245665]
NPT2	Others	Unspecified	n.a.	Kd	>	1000000.0	nM	PMID[21183345]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3548.1	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

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 NPC162689 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	43877
0.1-0.2	5382
0.2-0.3	513
0.3-0.4	73
0.4-0.5	10
0.5-0.6	3
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
0.5714	Remote Similarity	NPC608537
0.5581	Remote Similarity	NPC32298
0.5106	Remote Similarity	NPC26850

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC162689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7528
0.1-0.2	1509
0.2-0.3	102
0.3-0.4	10
0.4-0.5	1
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