NPASS Compound

Natural Product: NPC320287

Natural Product ID	NPC320287
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Permethrin
IUPAC Name	(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Synonyms	Elimite; Lyclear; Lythrin; NIX; Permethrin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1525
PubChem CID	40326
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters [CHEMONTID:0001461] Pyrethroids

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 46 48 0 0 0 0 0 0 0 0999 V2000 4.2609 -2.1789 1.3245 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5927 -0.8475 0.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4986 0.2252 1.9334 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2823 -0.5928 1.5865 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1625 0.0608 0.8547 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0210 -0.2092 1.1813 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3430 0.9501 -0.1661 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3768 1.6166 -0.9159 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5516 0.7494 -1.6693 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7814 0.3531 -1.1938 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6148 -0.4739 -1.9360 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1989 -0.9028 -3.1710 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9724 -0.5086 -3.6482 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1592 0.3072 -2.9066 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8534 -0.8924 -1.4930 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4128 -0.5520 -0.2831 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2075 0.5646 -0.1090 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7689 0.9073 1.1024 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5063 0.0726 2.1816 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7135 -1.0448 2.0167 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1544 -1.3819 0.7998 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5792 1.6614 1.6333 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4842 2.3252 0.9742 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9154 1.6458 0.2431 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.2717 4.0800 0.7849 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.7541 -0.5508 -0.5149 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7748 -2.9557 0.6995 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3276 -2.1541 1.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0312 -2.3875 2.3940 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0261 -0.0216 2.9091 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9693 -1.2871 2.3907 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9442 2.2325 -1.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2007 2.3466 -0.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1424 0.6796 -0.2299 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8221 -1.5573 -3.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6493 -0.8589 -4.6406 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8128 0.6091 -3.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4132 1.2235 -0.9667 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3846 1.7761 1.2284 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9473 0.3450 3.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5140 -1.6953 2.8763 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5449 -2.2647 0.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7269 2.2590 2.0399 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1052 -1.3111 -1.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5130 0.4525 -0.8491 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7820 -0.8140 -0.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 11 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 3 22 1 0 22 23 2 3 23 24 1 0 23 25 1 0 2 26 1 0 4 2 1 0 14 9 1 0 21 16 1 0 1 27 1 0 1 28 1 0 1 29 1 0 3 30 1 0 4 31 1 0 8 32 1 0 8 33 1 0 10 34 1 0 12 35 1 0 13 36 1 0 14 37 1 0 17 38 1 0 18 39 1 0 19 40 1 0 20 41 1 0 21 42 1 0 22 43 1 0 26 44 1 0 26 45 1 0 26 46 1 0 M END

Standard InCHIKey	RLLPVAHGXHCWKJ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3
SMILES	CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	390.08	Volume:	381.804 ? Van der Waals volume.
Dense:	1.022	LogP:	5.947 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.23 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.347 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	17.0
TPSA:	35.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.557	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.041	Fsp³:	0.286
MCE-18:	61.222 ? 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:	0.989	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.789 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.252	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.914	MDCK Permeability:	-4.715
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.972 ? 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%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.98
Plasma Protein Binding (PPB):	99.084%	Volume Distribution (VD):	-0.484
Fu:	0.391% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.18
OATP1B3 inhibitor:	0.936	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.207	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.998
CYP2C9-inhibitor:	0.94	CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.449	CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.998	CYP2C8-inhibitor:	0.988
HLM stability:	0.998 ? 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):

5.686

Half-life (T1/2):

0.563

ADMET: Toxicity

hERG Blockers:	0.226	hERG Blockers (10um):	0.721
Human Hepatotoxicity (H-HT):	0.81	Drug-induced Liver Injury (DILI):	0.156
AMES Toxicity:	0.928	Rat Oral Acute Toxicity:	0.533
Maximum Recommended Daily Dose:	0.835	Skin Sensitization:	0.179
Carcinogencity:	0.851	Eye Corrosion:	0.044
Eye Irritation:	0.844	Respiratory Toxicity:	0.999
Drug-induced Neurotoxicity:	0.696	Ototoxicity:	0.745
Hematotoxicity:	0.343	Drug-induced Nephrotoxicity:	0.173
Genotoxicity:	0.484	RPMI-8226 Immunitoxicity:	0.086
A549 Cytotoxicity:	0.189	Hek293 Cytotoxicity:	0.161
BCF:	3.083 ? 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:	4.939 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.146 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.342 ? 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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32515616]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33444950]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	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	45
AC50	67
Activity	2
Composite Activity - Active	1
Composite Activity - Marginal	1
Alkaline Phosphatase Increase - Index Value	1
Alkaline Phosphatase Increase - Number of Reports	1
SGOT Increase - Index Value	1
SGOT Increase - Number of Reports	1
SGPT Increase - Index Value	1
SGPT Increase - Number of Reports	1
LDH Increase - Number of Reports	1
GGT Increase - Index Value	1
GGT Increase - Number of Reports	1
HepSE_bilirubinemia	1
HepSE_cholecystitis	1
HepSE_cholelithiasis	1
HepSE_cirrhosis	1
HepSE_hepatic failure	1
HepSE_hepatic necrosis	1
HepSE_hepatomegaly	1
HepSE_jaundice	2
HepSE_liver fatty	1
HepSE_liver function tests abnormal	1
HepSE_Combined Scores	1
Ratio EC50	1
EC50	2
LD80	3
Ratio	2
LDH Increase - Index Value	1
HepSE_liver disease	1
Survival	2
HepSE_elevated liver function tests	1
HepSE_hepatitis	1
mortality	21

Activity Type	# Activity
Individual protein	89
Single protein	3
Organism	30
Others	21
Non-molecular	2
Phenotype	27

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	4466.8	nM	PubChem BioAssay data set
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	1.4	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	5.2	nM	PubChem BioAssay data set
NPT155	Individual protein	Aryl hydrocarbon receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	46109.1	nM	PubChem BioAssay data set
NPT158	Individual protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT158	Individual protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT158	Individual protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT1163	Individual protein	Glutamate (NMDA) receptor subunit zeta 1	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT295	Individual protein	Serotonin transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT1464	Individual protein	Phosphodiesterase 4D	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT244	Individual protein	Dopamine D3 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1410	Individual protein	GABA receptor alpha-1 subunit	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT262	Individual protein	Muscarinic acetylcholine receptor M1	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT2879	Individual protein	Equilibrative nucleoside transporter 1	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT292	Individual protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT303	Individual protein	Vasopressin V1a receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT246	Individual protein	Dopamine transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT259	Individual protein	Melanocortin receptor 4	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT264	Individual protein	Muscarinic acetylcholine receptor M3	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT251	Individual protein	Histamine H1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT216	Individual protein	Adenosine A1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT218	Individual protein	Adenosine A3 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT271	Individual protein	Delta opioid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT225	Individual protein	Beta-1 adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT239	Individual protein	Cholecystokinin A receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT263	Individual protein	Muscarinic acetylcholine receptor M2	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT290	Individual protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT252	Individual protein	Histamine H2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT217	Individual protein	Adenosine A2a receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT228	Individual protein	Norepinephrine transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	AC50	=	18161.0	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	=	9700.0	nM	PMID[37468498]
NPT230	Individual protein	Bradykinin B2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT2769	Individual protein	Thromboxane A2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT267	Individual protein	Neuropeptide Y receptor type 1	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT2719	Individual protein	Voltage-gated L-type calcium channel alpha-1C subunit	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT299	Individual protein	Androgen Receptor	Rattus norvegicus	AC50	>	30000.0	nM	PMID[37468498]
NPT1647	Individual protein	Vasopressin V2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT226	Individual protein	Beta-2 adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT272	Individual protein	Kappa opioid receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	22387.2	nM	PubChem BioAssay data set
NPT50	Individual protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	5623.4	nM	PubChem BioAssay data set
NPT540	Individual protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT5301	Individual protein	Motilin receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT987	Individual protein	Histamine H3 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT524	Individual protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT98	Individual protein	HERG	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT4358	Individual protein	Type-1 angiotensin II receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT29430	Single protein	Neuronal acetylcholine receptor protein alpha-4 subunit	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT542	Individual protein	Progesterone receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT63	Individual protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT46	Individual protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	7.1	nM	PubChem BioAssay data set
NPT46	Individual protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	3.2	nM	PubChem BioAssay data set
NPT535	Individual protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT5975	Individual protein	Cyclooxygenase-1	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT28814	Single protein	Ghrelin receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT92	Individual protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT5104	Individual protein	Phosphodiesterase 3A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT864	Individual protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT546	Individual protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT425	Individual protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT543	Individual protein	Pregnane X receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT30151	Single protein	Melanocortin receptor 3	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9528.3	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	16944.1	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	-100.0	%	PMID[18232639]
NPT5733	Organism	Cheumatopsyche	Cheumatopsyche	EC50	=	0.000205	ug.mL-1	DOI[10.1584/jpestics.G08-26]
NPT4388	Organism	Tuta absoluta	Tuta absoluta	LD80	=	2.57	ug/mg	PMID[21953851]
NPT5734	Organism	Daphnia magna	Daphnia magna	EC50	=	0.0006	ug.mL-1	DOI[10.1584/jpestics.G08-26]
NPT4386	Organism	Tetragonisca angustula	Tetragonisca angustula	LD80	=	0.002	ug/mg	PMID[21953851]
NPT4387	Organism	Solenopsis saevissima	Solenopsis saevissima	LD80	=	1.458	ug/mg	PMID[21953851]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	76411.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	15246.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	34376.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	6682.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	21872.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	33780.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54095.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	9200.0	nM	PubChem BioAssay data set
NPT20596	Phenotype	Hepatotoxicity	n.a.	Composite Activity - Active	=	0.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	Composite Activity - Marginal	=	0.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	Alkaline Phosphatase Increase - Index Value	=	0.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	Alkaline Phosphatase Increase - Number of Reports	<	4.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	SGOT Increase - Index Value	=	0.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	SGOT Increase - Number of Reports	<	4.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	SGPT Increase - Index Value	=	0.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	SGPT Increase - Number of Reports	<	4.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	LDH Increase - Number of Reports	<	4.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	GGT Increase - Index Value	=	0.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	GGT Increase - Number of Reports	<	4.0	n.a.	PMID[16472241]
NPT2	Others	Unspecified	n.a.	AC50	>	420000.0	nM	PubChem BioAssay data set
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_bilirubinemia	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_cholecystitis	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_cholelithiasis	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_cirrhosis	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_hepatic failure	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_hepatic necrosis	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_hepatomegaly	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_jaundice	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_liver fatty	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_liver function tests abnormal	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_Combined Scores	=	0.0	n.a.	PMID[22194678]
NPT2	Others	Unspecified	n.a.	Ratio EC50	=	0.47	n.a.	DOI[10.1584/jpestics.G08-26]
NPT2	Others	Unspecified	n.a.	Ratio	=	0.065	n.a.	PMID[21953851]
NPT2	Others	Unspecified	n.a.	Ratio	=	0.00042	n.a.	PMID[21953851]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT20596	Phenotype	Hepatotoxicity	n.a.	LDH Increase - Index Value	=	0.0	n.a.	PMID[16472241]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_liver disease	=	0.0	n.a.	PMID[22194678]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25999	Organism	Ascia monuste	Ascia monuste	mortality	=	100.0	%	PMID[23183889]
NPT780	Organism	Sitophilus zeamais	Sitophilus zeamais	mortality	=	90.0	%	PMID[23183889]
NPT780	Organism	Sitophilus zeamais	Sitophilus zeamais	mortality	=	85.5	%	PMID[23183889]
NPT780	Organism	Sitophilus zeamais	Sitophilus zeamais	mortality	=	17.5	%	PMID[19418526]
NPT21294	Organism	Tineola bisselliella	Tineola bisselliella	Survival	=	0.0	%	PMID[18232639]
NPT26275	Organism	Drosophila suzukii	Drosophila suzukii	mortality	=	100.0	%	PMID[21800409]
NPT734	Organism	Musca domestica	Musca domestica	mortality	=	72.5	%	PMID[19418526]
NPT4388	Organism	Tuta absoluta	Tuta absoluta	mortality	=	97.5	%	PMID[19418526]
NPT4388	Organism	Tuta absoluta	Tuta absoluta	mortality	=	93.2	%	PMID[19418526]
NPT4386	Organism	Tetragonisca angustula	Tetragonisca angustula	mortality	=	100.0	%	PMID[21953851]
NPT4387	Organism	Solenopsis saevissima	Solenopsis saevissima	mortality	=	100.0	%	PMID[21953851]
NPT2	Others	Unspecified	n.a.	Survival	=	96.0	%	PMID[18232639]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_elevated liver function tests	=	0.0	n.a.	PMID[22194678]
NPT20596	Phenotype	Hepatotoxicity	n.a.	HepSE_hepatitis	=	0.0	n.a.	PMID[22194678]
NPT26271	Organism	Periplaneta americana	Periplaneta americana	mortality	=	97.5	%	PMID[19418526]
NPT26272	Organism	Acanthoscelides obtectus	Acanthoscelides obtectus	mortality	=	100.0	%	PMID[23183889]
NPT26271	Organism	Periplaneta americana	Periplaneta americana	mortality	=	87.5	%	PMID[23183889]

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
-	Culex quinquefasciatus	LC50	=	0.16	ppm	PMID[18570364]
-	Culex quinquefasciatus	LC50	=	0.005	ppm	PMID[18570364]
-	Tetragonisca angustula	LD50	=	0.0003	ug/mg	PMID[21953851]
-	Solenopsis saevissima	LD50	=	0.046	ug/mg	PMID[21953851]
-	Tuta absoluta	LD50	=	0.71	ug/mg	PMID[21953851]

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 NPC320287 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	18447
0.1-0.2	31072
0.2-0.3	325
0.3-0.4	11
0.4-0.5	1
0.5-0.6	0
0.6-0.7	1
0.7-0.8	1
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
0.7755	Intermediate Similarity	NPC234956
0.6491	Remote Similarity	NPC251849

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC320287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3102
0.1-0.2	5886
0.2-0.3	154
0.3-0.4	5
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4359	Phase 4
0.7755	Intermediate Similarity	NPD5585	Phase 4
0.6491	Remote Similarity	NPD4870	Pre-clinical

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