NPASS Compound

Natural Product: NPC33144

Natural Product ID	NPC33144
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Zearalenone
IUPAC Name	(2E,11S)-15,17-dihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,15,17-tetraene-7,13-dione
Synonyms	Zearalenone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL454173
PubChem CID	5281576
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues [CHEMONTID:0001788] Zearalenones

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 45 46 0 0 0 0 0 0 0 0999 V2000 -1.8970 3.1155 -1.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3903 1.9959 -0.4726 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1760 0.7042 -0.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5019 0.6793 0.1485 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8731 -0.8408 0.0639 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7585 -1.5524 0.8238 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2173 -0.9560 1.7153 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4083 -2.9022 0.4333 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2552 -3.1631 -0.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1002 -2.9876 0.0482 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7330 -1.7134 0.3576 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8596 -1.3348 -0.2709 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6408 -0.1534 -0.1217 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2433 1.1331 0.1087 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8496 1.5698 0.2262 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5211 1.9561 1.3714 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0732 1.5802 -0.7781 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1492 2.1964 0.2624 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6055 3.4761 0.5015 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4938 1.9791 0.1830 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9163 0.6947 -0.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0419 -0.3443 -0.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2943 0.3957 -0.1437 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6347 3.7059 -0.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0445 3.8301 -1.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2829 2.8688 -2.2654 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3890 2.3268 0.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5240 -0.1077 -0.1827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3263 0.4547 -1.6380 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2985 1.2357 -0.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4267 0.9329 1.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8088 -1.0383 0.5645 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7740 -1.1211 -0.9788 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2568 -3.5759 1.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3135 -3.4078 -0.0397 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4078 -2.6899 -1.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3443 -4.2782 -0.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8236 -3.6269 -0.5946 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1664 -3.6041 1.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3773 -1.0043 1.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2249 -2.0592 -1.0193 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0320 4.1264 1.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1949 2.7811 0.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4018 -1.3729 -0.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7132 0.0957 0.7234 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 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 14 18 1 0 18 19 1 0 18 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 17 2 1 0 22 13 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 1 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 8 34 1 0 8 35 1 0 9 36 1 0 9 37 1 0 10 38 1 0 10 39 1 0 11 40 1 0 12 41 1 0 19 42 1 0 20 43 1 0 22 44 1 0 23 45 1 0 M END

Standard InCHIKey	MBMQEIFVQACCCH-QBODLPLBSA-N
Standard InCHI	InChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+/t12-/m0/s1
SMILES	C[C@H]1CCCC(=O)CCC/C=C/c2c(C(=O)O1)c(O)cc(c2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	318.15	Volume:	330.904 ? Van der Waals volume.
Dense:	0.961	LogP:	2.339 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.552 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.4 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	21.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.714	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.705	Fsp³:	0.444
MCE-18:	46.0 ? 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:	0.097	Fluc inhibitor:	0.525 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.299 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.393 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.428	Promiscuous compounds:	0.269

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.958	MDCK Permeability:	-4.749
Pgp-inhibitor:	0.859	Pgp-substrate:	0.003
PAMPA:	0.003 ? 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%):	0.007	30% Bioavailability (F30%):	0.659
50% Bioavailability (F50%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	0.889
Plasma Protein Binding (PPB):	88.884%	Volume Distribution (VD):	0.219
Fu:	11.69% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.825
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.452	CYP1A2-substrate:	0.204
CYP2C19-inhibitor:	0.087	CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.876	CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.823	CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.829
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.994 ? 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):

4.518

Half-life (T1/2):

0.916

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.163
Human Hepatotoxicity (H-HT):	0.745	Drug-induced Liver Injury (DILI):	0.7
AMES Toxicity:	0.489	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.914	Skin Sensitization:	0.996
Carcinogencity:	0.164	Eye Corrosion:	0.305
Eye Irritation:	0.995	Respiratory Toxicity:	0.509
Drug-induced Neurotoxicity:	0.379	Ototoxicity:	0.138
Hematotoxicity:	0.035	Drug-induced Nephrotoxicity:	0.546
Genotoxicity:	0.498	RPMI-8226 Immunitoxicity:	0.163
A549 Cytotoxicity:	0.715	Hek293 Cytotoxicity:	0.74
BCF:	0.48 ? 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:	3.071 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.299 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.652 ? 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
NPO27821.1	Pochonia chlamydosporia	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12828470]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499313]
NPO40515	Chaetomium chiversii	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499313]
NPO41348	Alternaria tenuissima + Fusarium culmorum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22776416]
NPO41349	Alternaria tenuissima + Fusarium graminearum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22776416]
NPO41426	Fusarium tricinctum + Streptomyces lividans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[35518011]
NPO41426	Fusarium tricinctum + Streptomyces lividans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	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	179
Tm	22
Activity	1
EC50	1
IC50	10
Inhibition	4

Activity Type	# Activity
Individual protein	103
Cell line	29
Single protein	3
Organism	2
Protein family	2
Others	77
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	20157.9	nM	PMID[10395498]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	25154	nM	PMID[11374948]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	3341.5	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	52473.3	nM	PMID[17417631]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	12606.9	nM	PMID[17993275]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	13180.7	nM	PMID[16378371]
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	37491.9	nM	PMID[19685913]
NPT162	Individual protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	10566.6	nM	PMID[20092288]
NPT162	Individual protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	14270.7	nM	PMID[19845338]
NPT163	Individual protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	52958.7	nM	DrugMatrix in vitro pharmacology data
NPT1265	Individual protein	Serine/threonine-protein kinase PIM1	Homo sapiens	Tm	=	3.0	degrees C	PMID[19097799]
NPT1700	Individual protein	Serine/threonine-protein kinase PIM2	Homo sapiens	Tm	=	2.6	degrees C	PMID[19097799]
NPT1701	Individual protein	Serine/threonine-protein kinase PIM3	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT3221	Individual protein	Serine/threonine-protein kinase GAK	Homo sapiens	Tm	=	2.4	degrees C	PMID[19097799]
NPT1692	Individual protein	Mitogen-activated protein kinase 6	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1616	Individual protein	MAP kinase p38 beta	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1437	Individual protein	Tyrosine-protein kinase FES	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1431	Individual protein	Mitogen-activated protein kinase kinase kinase 5	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT3331	Individual protein	Serine/threonine-protein kinase MST2	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1706	Individual protein	Serine/threonine-protein kinase 2	Homo sapiens	Tm	=	4.4	degrees C	PMID[19097799]
NPT1707	Individual protein	Serine/threonine-protein kinase 10	Homo sapiens	Tm	=	4.6	degrees C	PMID[19097799]
NPT1691	Individual protein	Dual specificity mitogen-activated protein kinase kinase 6	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1684	Individual protein	Casein kinase I gamma 1	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1702	Individual protein	Serine/threonine-protein kinase PLK4	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1697	Individual protein	Serine/threonine-protein kinase PAK6	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1581	Individual protein	Carbonyl reductase [NADPH] 1	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1581	Individual protein	Carbonyl reductase [NADPH] 1	Homo sapiens	Tm	=	3.6	degrees C	PMID[19097799]
NPT1581	Individual protein	Carbonyl reductase [NADPH] 1	Homo sapiens	Activity	=	5.7	%	PMID[24960143]
NPT248	Individual protein	Estrogen receptor beta	Homo sapiens	EC50	=	110.0	nM	PMID[24592914]
NPT210	Individual protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	25118.9	nM	PMID[23398362]
NPT3263	Individual protein	Protein tyrosine kinase 2 beta	Homo sapiens	IC50	=	6922.0	nM	PMID[19738023]
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	25118.9	nM	PMID[19226154]
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PMID[11520225]
NPT150	Individual protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	15848.9	nM	PMID[23501116]
NPT151	Individual protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	11220.2	nM	PMID[17629329]
NPT151	Individual protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	14125.4	nM	PMID[26000707]
NPT151	Individual protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	4466.8	nM	PMID[19581457]
NPT149	Individual protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	39810.7	nM	PMID[18955522]
NPT149	Individual protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	DrugMatrix in vitro pharmacology data
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	398.1	nM	PMID[12444692]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	316.2	nM	PMID[25798528]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	10.0	nM	PMID[19114678]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	25.1	nM	PMID[10869203]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	141.3	nM	PMID[9548847]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	50118.7	nM	DrugMatrix in vivo data: Hematology
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	12.6	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[19615900]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	5011.9	nM	PMID[14643343]
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[15730248]
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[24479418]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	39810.7	nM	DrugMatrix in vitro pharmacology data
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[12608854]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[20624681]
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[20061160]
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[25304895]
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[19919060]
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[17239591]
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	2818.4	nM	PMID[25437914]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	48557.7	nM	PMID[11831887]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	53080.4	nM	PMID[12873498]
NPT102	Individual protein	Interleukin-8	Homo sapiens	Potency	n.a.	74978.0	nM	PMID[26443078]
NPT102	Individual protein	Interleukin-8	Homo sapiens	Potency	n.a.	59557.2	nM	PMID[16134928]
NPT103	Individual protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	42163.2	nM	PMID[17848089]
NPT103	Individual protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	74978.0	nM	PMID[18348533]
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	2818.4	nM	PMID[17261619]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	105909.3	nM	PMID[21984958]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	17782.8	nM	PMID[15974616]
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	31622.8	nM	PMID[23675610]
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[26331986]
NPT540	Individual protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[12713401]
NPT540	Individual protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[19841147]
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	91.51	%	PMID[22694318]
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	14125.4	nM	PMID[8864235]
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	11220.2	nM	PMID[10346970]
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	14988.9	nM	PMID[19805556]
NPT54	Individual protein	Nonstructural protein 1	Influenza A virus	Potency	=	10000.0	nM	PMID[25218912]
NPT791	Individual protein	Cruzipain	Trypanosoma cruzi	Potency	=	39810.7	nM	PMID[20627740]
NPT98	Individual protein	HERG	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[16933872]
NPT98	Individual protein	HERG	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[8289059]
NPT99	Individual protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[23855338]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	-1.04	%	PMID[19105653]
NPT89	Individual protein	Seed lipoxygenase-1	Glycine max	IC50	=	51000.0	nM	DrugMatrix in vitro pharmacology data
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	55.9	%	PMID[24911880]
NPT22938	Single protein	Carbonyl reductase [NADPH] 3	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT93	Individual protein	Survival motor neuron protein	Homo sapiens	Potency	=	28183.8	nM	PMID[21314138]
NPT93	Individual protein	Survival motor neuron protein	Homo sapiens	Potency	=	4466.8	nM	PMID[7760068]
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	31622.8	nM	PMID[12182864]
NPT60	Individual protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	50118.7	nM	PMID[23792351]
NPT46	Individual protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[18077363]
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[23558238]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	1.81	%	PMID[10075777]
NPT74	Individual protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	47199.5	nM	PMID[25798528]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	Tm	=	2.3	degrees C	PMID[19097799]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	IC50	=	2402.0	nM	PMID[26077494]
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[22871217]
NPT546	Individual protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[18293903]
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[10924160]

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	=	39810.7	nM	PMID[25646964]
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	50118.7	nM	PMID[13678412]
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	25118.9	nM	PMID[18676881]
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	1000.0	nM	PMID[19904995]
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	100000.0	nM	PMID[18227183]
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	79432.8	nM	PubChem BioAssay data set
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	63095.7	nM	PMID[19451283]
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	25000.0	nM	PMID[15844934]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	>	25000.0	nM	DrugMatrix in vitro pharmacology data
NPT395	Cell line	SF-268	Homo sapiens	IC50	>	50000.0	nM	PMID[20541427]
NPT91	Cell line	KB	Homo sapiens	IC50	=	46300.0	nM	PMID[23089527]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	104720.0	nM	PMID[20405847]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	40580.0	nM	PMID[25646964]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	13115.4	nM	PMID[8864241]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	15848.9	nM	PMID[21889336]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	138210.0	nM	PMID[27311894]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	71.5	nM	PMID[23035772]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	8025	nM	PMID[23006147]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	52958.7	nM	PMID[18163588]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	37148.3	nM	PMID[15387649]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	47199.5	nM	PMID[17190444]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	13.3	nM	PMID[18053715]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10566.6	nM	PMID[9548875]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	22418.5	nM	PMID[22691179]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	9331.2	nM	PMID[1602301]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23439	nM	PMID[19008110]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	83.9	nM	PMID[20805391]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2343.9	nM	PMID[20350811]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	19980.5	nM	PMID[23910596]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	52958.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	4473.1	nM	PMID[20110137]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	17965.7	nM	PMID[8350094]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23439	nM	PMID[18378710]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	22617.5	nM	PMID[11929285]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	15871.1	nM	PMID[11858752]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	46766.9	nM	PMID[26341134]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	52958.7	nM	Open TG-GATES in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23439	nM	PMID[23398362]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	22418.5	nM	PMID[14640534]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	52473.3	nM	Open TG-GATES in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	Potency	n.a.	52473.3	nM	Open TG-GATES in vivo data: Organ Weight
NPT2	Others	Unspecified	n.a.	Potency	n.a.	20890	nM	DrugMatrix in vivo data: Hematology
NPT2	Others	Unspecified	n.a.	Potency	n.a.	42066.6	nM	PMID[19651906]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12606.9	nM	PMID[9873376]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	52958.7	nM	PMID[18172002]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	142.7	nM	PMID[19231864]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	16593.5	nM	PMID[25127165]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	6667.1	nM	PMID[23398362]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	22418.5	nM	PMID[11960501]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	47199.5	nM	PMID[19487444]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	47199.5	nM	PMID[19716307]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	47199.5	nM	PMID[19854650]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12718.8	nM	PMID[23131412]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	33414.7	nM	PMID[12161151]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	18618.2	nM	PMID[26225905]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	19980.5	nM	PMID[18426954]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	16593.5	nM	DOI[10.6019/CHEMBL3301361]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	25377.2	nM	PMID[25397992]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	46766.9	nM	PMID[10560729]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	19980.5	nM	PMID[22931472]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12606.9	nM	PMID[20619938]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	4	nM	PMID[23977995]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	16593.5	nM	PMID[24448419]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	42066.6	nM	PMID[18177007]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	8393.4	nM	PMID[20614907]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	14270.7	nM	PMID[19528279]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	25154	nM	PMID[18336006]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23439	nM	PMID[17512094]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	17807.7	nM	PMID[18316521]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	7152.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	9417.5	nM	PMID[17896816]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	20890	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11747.3	nM	PMID[17958396]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	19980.5	nM	PMID[19674905]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	52958.7	nM	Open TG-GATES in vivo data: Hematology
NPT2	Others	Unspecified	n.a.	Potency	n.a.	47199.5	nM	PMID[12502328]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	47199.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	46766.9	nM	PMID[18183025]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	52958.7	nM	PMID[22998443]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	25154	nM	PMID[18053715]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	29780.9	nM	PMID[16274989]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23655.8	nM	PMID[18396905]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26299	nM	PMID[26327273]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23439	nM	PMID[18484774]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	58876	nM	PMID[12444673]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	20890	nM	PMID[17665953]
NPT2	Others	Unspecified	n.a.	Potency	=	29092.9	nM	PMID[25238284]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	5804.8	nM	PMID[18180352]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	33491.5	nM	PMID[9051914]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	37578.0	nM	PMID[22545792]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	nM	PMID[9214736]

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 recovery	=	89.0	%	PMID[11879067]
Triticum aestivum	n.a.	Drug recovery	=	32.0	%	PMID[11879067]
Triticum aestivum	n.a.	Drug uptake	=	11.0	ug/kg	PMID[11879067]

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference
-	Rattus norvegicus	LEL	=	0.18	mg/day	ToxVal
-	Rattus norvegicus	LEL	=	20.0	mg/kg-day	ToxVal
-	Rattus norvegicus	LEL	=	2.0	mg/kg-day	ToxVal
-	Rattus norvegicus	LEL	=	1.0	mg/kg-day	ToxVal
-	Rattus norvegicus	LEL	=	1.0	mg/day	ToxVal
-	Rattus norvegicus	LEL	=	0.03	mg/day	ToxVal
-	Rattus norvegicus	LEL	=	1.0	mg	ToxVal
-	Rattus norvegicus	NOAEL	=	1.25	mg/kg-day	ToxVal
-	Rattus norvegicus	LOAEL	=	2.5	mg/kg-day	ToxVal
-	Rattus norvegicus	LEL	=	1.25	mg/kg-day	ToxVal
-	Rattus norvegicus	LD50	>	16000.0	mg/kg	ToxVal
-	Rattus norvegicus	NOEL	<	2.88	mg/kg-day	ToxVal
-	Mus musculus	LEL	=	10.0	mg/kg-day	ToxVal
-	Mus musculus	LEL	=	0.025	mg/kg-day	ToxVal
-	Mus musculus	LEL	=	5.0	mg/kg-day	ToxVal
-	Mus musculus	LEL	=	2.0	mg/kg-day	ToxVal
-	Mus musculus	LEL	=	1.0	mg/kg-day	ToxVal
-	Mus musculus	NEL	=	7.5	mg/kg-day	ToxVal
-	Mus musculus	LEL	=	15.0	mg/kg-day	ToxVal
-	Mus musculus	LEL	=	7.5	mg/kg-day	ToxVal
-	Mus musculus	NOEL	=	20.0	mg/kg-day	ToxVal
-	Oryctolagus cuniculus	LEL	=	1.0	mg/kg-day	ToxVal
-	Sus scrofa domesticus	PMTDI	=	0.0005	mg/kg-day	ToxVal
-	Sus scrofa domesticus	LOEL	=	0.2	mg/kg-day	ToxVal
-	Sus scrofa domesticus	NOEL	=	0.04	mg/kg-day	ToxVal
-	Sus scrofa domesticus	NOEL	=	0.01	mg/kg-day	ToxVal

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 NPC33144 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	11816
0.1-0.2	36106
0.2-0.3	1791
0.3-0.4	107
0.4-0.5	26
0.5-0.6	5
0.6-0.7	3
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
0.6066	Remote Similarity	NPC191835
0.6066	Remote Similarity	NPC610163
0.6032	Remote Similarity	NPC158472
0.5556	Remote Similarity	NPC609527
0.5556	Remote Similarity	NPC611086
0.5385	Remote Similarity	NPC472035
0.5211	Remote Similarity	NPC599920
0.5072	Remote Similarity	NPC474385

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC33144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4364
0.1-0.2	4749
0.2-0.3	36
0.3-0.4	1
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