NPASS Compound

Natural Product: NPC328740

Natural Product ID	NPC328740
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-Dihydroxy-2-(4-Hydroxyphenyl)-6-[3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Chromen-4-One
IUPAC Name	5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1601394
PubChem CID	4475102
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-glycosides

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 51 54 0 0 0 0 0 0 0 0999 V2000 -4.9702 -2.4382 -0.2587 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1120 -1.8418 0.9848 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4431 -0.4862 1.0613 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0985 -0.5379 0.8235 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7069 -0.2269 -0.4509 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1571 1.1094 -0.9423 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3698 1.6436 -0.2267 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2074 0.4579 0.1932 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3214 0.9187 0.9145 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1440 2.4421 -1.0657 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1535 2.0834 -0.8508 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2096 -0.2558 -0.4798 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5434 -0.6910 -1.6131 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2551 -1.1119 -2.7521 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8308 -0.7260 -1.6620 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5723 -0.3236 -0.5708 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8961 0.1159 0.5733 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4841 0.1499 0.6196 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1247 0.5988 1.7899 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 0.5167 1.6600 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0339 0.9097 2.6833 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0163 0.4688 1.5771 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6368 0.0344 0.4446 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8789 -0.3343 -0.5574 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0916 -0.0347 0.3079 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6241 -0.4909 -0.8853 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9854 -0.5730 -1.0598 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8837 -0.2131 -0.0767 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3321 0.2382 1.1030 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9491 0.3269 1.2944 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2552 -0.3066 -0.2809 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1054 -2.9203 -0.2623 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6304 -2.5369 1.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1736 -1.7823 1.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5810 -0.1411 2.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0474 -0.9860 -1.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4303 1.0774 -2.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0596 2.2127 0.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6203 -0.0092 -0.7280 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7364 0.2285 1.4603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9772 3.3795 -0.8140 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 2.9475 -0.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5777 -2.0875 -2.8283 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3085 -1.0706 -2.5607 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2364 0.0129 2.6002 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5760 0.7884 2.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9428 -0.7796 -1.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3842 -0.9378 -2.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9879 0.5313 1.9014 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5736 0.6930 2.2536 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6219 -0.0423 -1.1844 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 1 0 7 8 1 0 8 9 1 0 7 10 1 0 6 11 1 0 5 12 1 0 12 13 2 0 13 14 1 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 17 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 28 31 1 0 8 3 1 0 18 12 1 0 30 25 1 0 24 16 1 0 1 32 1 0 2 33 1 0 2 34 1 0 3 35 1 0 5 36 1 0 6 37 1 0 7 38 1 0 8 39 1 0 9 40 1 0 10 41 1 0 11 42 1 0 14 43 1 0 15 44 1 0 19 45 1 0 22 46 1 0 26 47 1 0 27 48 1 0 29 49 1 0 30 50 1 0 31 51 1 0 M END

Standard InCHIKey	MYXNWGACZJSMBT-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2
SMILES	OCC1OC(C(C(C1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	432.11	Volume:	404.357 ? Van der Waals volume.
Dense:	1.069	LogP:	0.256 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.967 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.482 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	181.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.3	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.943	Fsp³:	0.286
MCE-18:	87.63 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.474	Fluc inhibitor:	0.021 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.969 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.832 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.295	Promiscuous compounds:	0.611

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.261	MDCK Permeability:	-5.044
Pgp-inhibitor:	0.0	Pgp-substrate:	0.684
PAMPA:	0.999 ? 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):	0.329
20% Bioavailability (F20%):	0.869	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.824
Plasma Protein Binding (PPB):	83.81%	Volume Distribution (VD):	0.011
Fu:	13.539% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.009
OATP1B3 inhibitor:	0.904	BCRP inhibitor:	0.192
BSEP inhibitor:	0.097

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.974	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.989	CYP2D6-substrate:	0.957
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.051 ? 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):

4.139

Half-life (T1/2):

2.274

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.322
Human Hepatotoxicity (H-HT):	0.536	Drug-induced Liver Injury (DILI):	0.781
AMES Toxicity:	0.622	Rat Oral Acute Toxicity:	0.485
Maximum Recommended Daily Dose:	0.736	Skin Sensitization:	0.444
Carcinogencity:	0.403	Eye Corrosion:	0.0
Eye Irritation:	0.77	Respiratory Toxicity:	0.297
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.678
Hematotoxicity:	0.037	Drug-induced Nephrotoxicity:	0.031
Genotoxicity:	0.96	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.265	Hek293 Cytotoxicity:	0.811
BCF:	0.354 ? 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:	2.647 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.328 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.468 ? 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
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.2478/s11535-012-0017-4]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	seed	n.a.	PMID[10898633]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37120447]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference
NPO26343	Fagopyrum esculentum	Dried Or Powder	n.a.	0.904799998	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO26343	Fagopyrum esculentum	Other	n.a.	0.258825	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

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	34
EC50	1
IC50	7

Activity Type	# Activity
Individual protein	31
Protein-protein interaction	2
Organism	2
Others	7

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3	Individual protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	70794.6	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29092.9	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT156	Individual protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT100	Individual protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT161	Individual protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT105	Individual protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	100000.0	nM	PubChem BioAssay data set
NPT533	Protein-protein interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT803	Individual protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	23934.1	nM	PubChem BioAssay data set
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT3735	Individual protein	Neurotensin receptor 1	Homo sapiens	EC50	=	2710.0	nM	PubChem BioAssay data set
NPT589	Individual protein	Serum albumin	Bos taurus	IC50	>	94115.0	nM	PubChem BioAssay data set
NPT60	Individual protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT59	Individual protein	DNA polymerase beta	Homo sapiens	Potency	=	8912.5	nM	PubChem BioAssay data set
NPT63	Individual protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	89125.1	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT534	Individual protein	Phosphoglycerate kinase, glycosomal	Trypanosoma brucei brucei	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT821	Individual protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT755	Individual protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	63095.7	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	33587.5	nM	PubChem BioAssay data set
NPT47	Individual protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT864	Individual protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT4	Individual protein	Large T antigen	Simian virus 40	IC50	n.a.	21430.0	nM	PubChem BioAssay data set
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	18348.9	nM	PubChem BioAssay data set
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	23099.9	nM	PubChem BioAssay data set
NPT47	Individual protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	7079.5	nM	PubChem BioAssay data set

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.	2936.2	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	7375.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	18570.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	>	94115.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	2619.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	5957.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	n.a.	7050.0	nM	PubChem BioAssay data set

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC328740 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	23759
0.1-0.2	23356
0.2-0.3	2013
0.3-0.4	576
0.4-0.5	114
0.5-0.6	14
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289774
0.8657	High Similarity	NPC53545
0.7838	Intermediate Similarity	NPC111249
0.7826	Intermediate Similarity	NPC268193
0.7792	Intermediate Similarity	NPC47923
0.7361	Intermediate Similarity	NPC112701
0.7215	Intermediate Similarity	NPC603300
0.7083	Intermediate Similarity	NPC289771
0.7067	Intermediate Similarity	NPC10807
0.7067	Intermediate Similarity	NPC161881
0.6849	Remote Similarity	NPC209846
0.6829	Remote Similarity	NPC218488
0.6765	Remote Similarity	NPC10097
0.6709	Remote Similarity	NPC326592
0.6622	Remote Similarity	NPC611357
0.6506	Remote Similarity	NPC604854
0.65	Remote Similarity	NPC109594
0.625	Remote Similarity	NPC139966
0.6071	Remote Similarity	NPC472607
0.6	Remote Similarity	NPC602537
0.593	Remote Similarity	NPC78734
0.5897	Remote Similarity	NPC117418
0.5765	Remote Similarity	NPC190393
0.561	Remote Similarity	NPC304745
0.5584	Remote Similarity	NPC228383
0.5584	Remote Similarity	NPC239644
0.5541	Remote Similarity	NPC486096
0.5506	Remote Similarity	NPC607513
0.5402	Remote Similarity	NPC294629
0.5402	Remote Similarity	NPC131407
0.5395	Remote Similarity	NPC189706
0.5275	Remote Similarity	NPC606373
0.527	Remote Similarity	NPC284220
0.5065	Remote Similarity	NPC603717

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC328740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5790
0.1-0.2	3293
0.2-0.3	57
0.3-0.4	8
0.4-0.5	2
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