NPASS Compound

Natural Product: NPC233570

Natural Product ID	NPC233570
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Atrazine
IUPAC Name	6-chloro-4-N-ethyl-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine
Synonyms	Atrazine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL15063
PubChem CID	2256
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000098] Triazines [CHEMONTID:0004105] 1,3,5-triazines [CHEMONTID:0004639] Halo-S-triazines [CHEMONTID:0004721] Chloro-s-triazines

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 28 0 0 0 0 0 0 0 0999 V2000 4.3989 0.5595 -0.8186 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1559 -0.5593 0.1541 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8387 -1.1008 0.0029 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7562 -0.4331 0.2238 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8668 0.8474 0.6197 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7219 1.5515 0.8527 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8853 3.2110 1.3656 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.4795 0.9558 0.6832 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6027 -0.3242 0.2876 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7072 -0.9351 0.1121 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0109 -0.3755 0.3023 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0257 -1.4682 0.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2730 0.7384 -0.6777 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5478 -1.0015 0.0628 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4016 0.4685 -1.2593 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3628 1.5586 -0.3089 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6637 0.5459 -1.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3524 -0.1907 1.1851 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8788 -1.3734 -0.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3475 1.5054 0.8647 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1433 0.0404 1.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0800 -1.5674 -1.0832 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0043 -1.2470 0.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6456 -2.4613 0.3853 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1381 0.5160 -1.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5057 1.6975 -0.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3662 0.8492 -1.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4987 -2.0073 -0.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 3 4 5 1 0 5 6 2 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 11 12 1 0 11 13 1 0 9 14 1 0 14 4 1 0 1 15 1 0 1 16 1 0 1 17 1 0 2 18 1 0 2 19 1 0 8 20 1 0 11 21 1 0 12 22 1 0 12 23 1 0 12 24 1 0 13 25 1 0 13 26 1 0 13 27 1 0 14 28 1 0 M END

Standard InCHIKey	MXWJVTOOROXGIU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C8H14ClN5/c1-4-10-7-12-6(9)13-8(14-7)11-5(2)3/h5H,4H2,1-3H3,(H2,10,11,12,13,14)
SMILES	CCN=c1nc(Cl)[nH]c(=NC(C)C)[nH]1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	215.09	Volume:	200.653 ? Van der Waals volume.
Dense:	1.072	LogP:	1.56 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.624 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.973 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	8.0
TPSA:	69.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.746	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.156	Fsp³:	0.625
MCE-18:	7.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.171	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.215 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.056	Promiscuous compounds:	0.096

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.922	MDCK Permeability:	-4.786
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.737 ? 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%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.74
Plasma Protein Binding (PPB):	96.099%	Volume Distribution (VD):	0.257
Fu:	4.119% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.902
OATP1B3 inhibitor:	0.985	BCRP inhibitor:	0.0
BSEP inhibitor:	0.911

ADMET: Metabolism

CYP1A2-inhibitor:	0.987	CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.627	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.94	CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.184	CYP3A4-substrate:	0.064
CYP2B6-substrate:	0.02	CYP2C8-inhibitor:	0.022
HLM stability:	0.824 ? 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):

10.337

Half-life (T1/2):

1.398

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.38
Human Hepatotoxicity (H-HT):	0.966	Drug-induced Liver Injury (DILI):	0.933
AMES Toxicity:	0.915	Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.724	Skin Sensitization:	0.975
Carcinogencity:	0.969	Eye Corrosion:	0.006
Eye Irritation:	0.913	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.788	Ototoxicity:	0.719
Hematotoxicity:	0.594	Drug-induced Nephrotoxicity:	0.873
Genotoxicity:	0.97	RPMI-8226 Immunitoxicity:	0.051
A549 Cytotoxicity:	0.018	Hek293 Cytotoxicity:	0.323
BCF:	0.795 ? 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:	3.297 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.561 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.087 ? 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
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
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]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	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	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	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
EC50	2
Potency	17
Inhibition	10
Activity	93
IC50	11
Selectivity ratio	1
Ratio	1
GI	10
IC50 relative	1

Activity Type	# Activity
Individual protein	23
Cell line	2
Organism	111
Single protein	1
Others	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	177.8	nM	PubChem BioAssay data set
NPT100	Individual protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	4466.8	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT158	Individual protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	89125.1	nM	PubChem BioAssay data set
NPT103	Individual protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	2660.3	nM	PubChem BioAssay data set
NPT3010	Individual protein	Triosephosphate isomerase, chloroplastic	Secale cereale	Inhibition	=	26.5	%	PMID[19658403]
NPT3010	Individual protein	Triosephosphate isomerase, chloroplastic	Secale cereale	Activity	=	7.2	nmol/sec	PMID[19658403]
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT5365	Individual protein	Photosystem Q(B) protein	Poa annua	Ratio	>	625.0	n.a.	DOI[10.1584/jpestics.26.236]
NPT5365	Individual protein	Photosystem Q(B) protein	Poa annua	IC50	=	160.0	nM	DOI[10.1584/jpestics.26.236]
NPT5365	Individual protein	Photosystem Q(B) protein	Poa annua	IC50	>	100000.0	nM	DOI[10.1584/jpestics.26.236]
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	96.21	%	PMID[23571415]
NPT484	Individual protein	Luciferin 4-monooxygenase	Photinus pyralis	EC50	>	112219.0	nM	PubChem BioAssay data set
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	133.79	%	PMID[23571415]
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	26.02	%	DOI[10.6019/CHEMBL4495564]
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PubChem BioAssay data set
NPT5357	Individual protein	Cytochrome b6-f complex subunit 4	Spinacia oleracea	IC50	=	186.21	nM	DOI[10.1584/jpestics.30.39]
NPT5357	Individual protein	Cytochrome b6-f complex subunit 4	Spinacia oleracea	IC50	=	281.84	nM	DOI[10.1584/jpestics.26.257]
NPT5363	Individual protein	Chloroplast thylakoid membrane protein (psbA)	Chenopodium album	Selectivity ratio	=	324.0	n.a.	DOI[10.1584/jpestics.30.39]
NPT5363	Individual protein	Chloroplast thylakoid membrane protein (psbA)	Chenopodium album	IC50	=	61659.5	nM	DOI[10.1584/jpestics.30.39]
NPT5363	Individual protein	Chloroplast thylakoid membrane protein (psbA)	Chenopodium album	IC50	=	190.55	nM	DOI[10.1584/jpestics.30.39]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT71	Cell line	HEK293	Homo sapiens	Potency	n.a.	5623.4	nM	PubChem BioAssay data set
NPT130	Organism	Digitaria sanguinalis	Digitaria sanguinalis	GI	=	0.0	%	PMID[21970768]
NPT130	Organism	Digitaria sanguinalis	Digitaria sanguinalis	GI	=	70.0	%	PMID[21970768]
NPT5355	Organism	Echinochloa crus-galli var. formosensis	Echinochloa crus-galli var. formosensis	IC50	=	181.97	nM	PMID[12400699]
NPT5355	Organism	Echinochloa crus-galli var. formosensis	Echinochloa crus-galli var. formosensis	IC50	=	141253.75	nM	PMID[12400699]
NPT5362	Organism	Persicaria longiseta	Persicaria longiseta	Activity	=	91.0	%	DOI[10.1584/jpestics.26.257]
NPT125	Organism	Chenopodium album	Chenopodium album	Activity	=	91.0	%	DOI[10.1584/jpestics.26.257]
NPT125	Organism	Chenopodium album	Chenopodium album	Activity	=	100.0	%	DOI[10.1584/jpestics.23.268]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.23	%	DOI[10.6019/CHEMBL4495565]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50 relative	n.a.	n.a.	n.a.	ECBD screening data for assay EOS300033
NPT1641	Organism	Lolium perenne	Lolium perenne	GI	=	80.0	%	PMID[21970768]
NPT1641	Organism	Lolium perenne	Lolium perenne	GI	=	100.0	%	PMID[21970768]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	26.0	%	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	37.0	%	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	36.0	%	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	21.0	%	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	15.0	%	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	20.0	%	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	28.0	%	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	40.0	%	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.057	uM/L	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.53	uM/L	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.55	uM/L	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	2.5	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	1.7	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	1.0	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	1.1	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	1.5	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	5.7	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	5.3	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	5.5	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.12	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.11	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.1	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	18.0	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	23.5	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	22.0	nmol/sec	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.9	micromol/m2/s	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.43	micromol/m2/s	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	-0.51	micromol/m2/s	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.0	micromol/m2/s	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	0.22	micromol/m2/s	PMID[21999101]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	=	-0.52	micromol/m2/s	PMID[21999101]
NPT120	Organism	Zea mays	Zea mays	Activity	=	3.35	m	DOI[10.1016/j.cropro.2007.11.020]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	1.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	4.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	81.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	2.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	8.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	87.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	5.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	7.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	14.0	%	PMID[21308951]
NPT5356	Organism	Amaranthus tuberculatus	Amaranthus tuberculatus	Activity	=	83.0	%	PMID[21308951]
NPT5325	Organism	Schoenoplectiella juncoides	Schoenoplectiella juncoides	Activity	=	76.0	%	DOI[10.1584/jpestics.26.257]
NPT5273	Organism	Stellaria media	Stellaria media	GI	=	90.0	%	PMID[21970768]
NPT132	Organism	Amaranthus retroflexus	Amaranthus retroflexus	GI	=	100.0	%	PMID[21970768]
NPT5273	Organism	Stellaria media	Stellaria media	GI	=	100.0	%	PMID[21970768]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	100.0	%	PMID[21970768]
NPT193	Organism	Brassica napus	Brassica napus	Inhibition	=	100.0	%	PMID[21970768]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	10.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	31.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	25.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	24.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	103.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	35.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	27.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	15.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	26.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	20.0	%	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	0.74	uM/L	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	0.85	uM/L	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	0.46	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	0.71	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	1.2	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	1.0	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	1.4	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	3.6	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	3.5	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	4.5	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	0.13	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	0.1	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	12.2	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	14.2	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	15.0	nmol/sec	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	-1.67	micromol/m2/s	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	-1.56	micromol/m2/s	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	-1.32	micromol/m2/s	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	-1.35	micromol/m2/s	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	-1.04	micromol/m2/s	PMID[21999101]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Activity	=	-0.61	micromol/m2/s	PMID[21999101]
NPT5326	Organism	Echinochloa oryzicola	Echinochloa oryzicola	Activity	=	30.0	g	PMID[12400699]
NPT5324	Organism	Monochoria vaginalis	Monochoria vaginalis	Activity	=	100.0	%	DOI[10.1584/jpestics.26.257]
NPT5326	Organism	Echinochloa oryzicola	Echinochloa oryzicola	Activity	=	91.0	%	DOI[10.1584/jpestics.26.257]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Activity	=	26.0	%	DOI[10.1584/jpestics.23.268]
NPT5273	Organism	Stellaria media	Stellaria media	Activity	=	100.0	%	DOI[10.1584/jpestics.23.268]
NPT5358	Organism	Digitaria ciliaris	Digitaria ciliaris	Activity	=	0.0	%	DOI[10.1584/jpestics.23.268]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	68519.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	19269.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	76880.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	67.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	930.0	nM	PMID[9677276]
NPT2	Others	Unspecified	n.a.	EC50	>	112219.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	446.7	nM	PubChem BioAssay data set
NPT124	Organism	Poa annua	Poa annua	GI	=	0.0	%	PMID[21970768]
NPT1339	Organism	Arabidopsis thaliana	Arabidopsis thaliana	GI	=	99.0	%	PMID[21970768]

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
Triticum aestivum	n.a.	Drug uptake	=	2.26	ppm	PMID[21999101]
Lolium multiflorum	n.a.	Drug uptake	=	4.75	ppm	PMID[21999101]
Homo sapiens	Zone of skin	log Kp	=	-5.56	n.a.	PMID[17300161]
Lolium multiflorum	Shoot	Drug uptake	=	6.0	ppm	PMID[21999101]
Lolium multiflorum	Shoot	Drug uptake	=	5.9	ppm	PMID[21999101]
Lolium multiflorum	Shoot	Drug uptake	=	4.52	ppm	PMID[21999101]
Lolium multiflorum	Shoot	Drug uptake	=	4.22	ppm	PMID[21999101]
Lolium multiflorum	Shoot	Drug uptake	=	3.11	ppm	PMID[21999101]
Triticum aestivum	Shoot	Drug uptake	=	1.38	ppm	PMID[21999101]
Triticum aestivum	Shoot	Drug uptake	=	5.67	ppm	PMID[21999101]
Triticum aestivum	Shoot	Drug uptake	=	1.94	ppm	PMID[21999101]
Triticum aestivum	Shoot	Drug uptake	=	0.35	ppm	PMID[21999101]

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 NPC233570 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	45724
0.1-0.2	4130
0.2-0.3	4
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC233570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7034
0.1-0.2	2112
0.2-0.3	4
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