NPASS Compound

Natural Product: NPC138360

Natural Product ID	NPC138360
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3',4'-Didemethylnobiletin
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
Synonyms	3',4'-Didemethylnobiletin; Sideritiflavone 5-Methyl Ether
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL438292
PubChem CID	5318041
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002593] 8-O-methylated flavonoids

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 47 0 0 0 0 0 0 0 0999 V2000 -4.2856 -2.3971 0.6454 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5402 -1.8185 -0.3527 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6263 -0.8371 -0.3527 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2914 -1.1184 -0.1757 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9237 -2.4165 -0.0008 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5758 -3.3250 -1.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3005 -0.1354 -0.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9555 -0.4241 0.0010 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8814 0.5395 0.0031 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5340 1.8534 -0.1715 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2054 2.1885 -0.3527 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1616 3.3851 -0.5180 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7207 1.1779 -0.3497 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0537 1.4783 -0.5281 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0349 0.4729 -0.5332 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3495 0.8153 -0.7144 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2700 1.1350 0.2812 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3920 2.8034 -0.7010 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7299 3.6852 0.3530 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2808 0.1756 0.1953 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2860 1.0899 0.2113 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6284 0.7187 0.3980 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9651 -0.6012 0.5721 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9512 -1.5339 0.5571 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6329 -1.1517 0.3720 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2896 -2.8733 0.7335 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2988 -0.9603 0.7566 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1095 -1.8273 1.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0833 -3.4455 0.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3721 -2.3078 0.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3851 -4.0895 -1.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5987 -2.7899 -1.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3958 -3.8185 -0.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2425 2.6754 -0.1788 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1248 0.4071 0.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8318 1.1414 1.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6812 2.1466 0.0606 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8327 3.6446 0.4648 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2379 3.4354 1.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4908 4.7384 0.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0945 2.1503 0.0801 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4285 1.4439 0.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8421 -1.8960 0.3620 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0953 -3.2726 0.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9958 -0.2625 0.8523 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 4 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 14 18 1 0 18 19 1 0 9 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 15 3 1 0 25 20 1 0 13 7 2 0 1 28 1 0 1 29 1 0 1 30 1 0 6 31 1 0 6 32 1 0 6 33 1 0 10 34 1 0 17 35 1 0 17 36 1 0 17 37 1 0 19 38 1 0 19 39 1 0 19 40 1 0 21 41 1 0 22 42 1 0 25 43 1 0 26 44 1 0 27 45 1 0 M END

Standard InCHIKey	ZDLYNMZEAFURQY-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C19H18O8/c1-23-15-14-12(22)8-13(9-5-6-10(20)11(21)7-9)27-16(14)18(25-3)19(26-4)17(15)24-2/h5-8,20-21H,1-4H3
SMILES	COc1c(OC)c2oc(cc(=O)c2c(c1OC)OC)c1ccc(c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	374.1	Volume:	360.741 ? Van der Waals volume.
Dense:	1.037	LogP:	1.687 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.851 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	18.0
TPSA:	107.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.657	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.602	Fsp³:	0.211
MCE-18:	20.0 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.135	Fluc inhibitor:	0.344 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.934 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.663 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.321	Promiscuous compounds:	0.523

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.16	MDCK Permeability:	-4.757
Pgp-inhibitor:	0.06	Pgp-substrate:	0.023
PAMPA:	0.181 ? 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):	0.018
20% Bioavailability (F20%):	0.839	30% Bioavailability (F30%):	0.845
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148	MRP1:	0.987
Plasma Protein Binding (PPB):	94.625%	Volume Distribution (VD):	-0.412
Fu:	4.95% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.91
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.889
BSEP inhibitor:	0.705

ADMET: Metabolism

CYP1A2-inhibitor:	0.121	CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.039	CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.012	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.354	CYP2D6-substrate:	0.751
CYP3A4-inhibitor:	0.181	CYP3A4-substrate:	0.585
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.943
HLM stability:	0.641 ? 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):

11.495

Half-life (T1/2):

1.584

ADMET: Toxicity

hERG Blockers:	0.12	hERG Blockers (10um):	0.668
Human Hepatotoxicity (H-HT):	0.374	Drug-induced Liver Injury (DILI):	0.785
AMES Toxicity:	0.358	Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.513	Skin Sensitization:	0.94
Carcinogencity:	0.707	Eye Corrosion:	0.36
Eye Irritation:	0.947	Respiratory Toxicity:	0.617
Drug-induced Neurotoxicity:	0.153	Ototoxicity:	0.332
Hematotoxicity:	0.195	Drug-induced Nephrotoxicity:	0.061
Genotoxicity:	0.389	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.559	Hek293 Cytotoxicity:	0.456
BCF:	1.462 ? 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:	3.653 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.919 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.139 ? 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
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plantsci.2006.08.002]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)88710-5]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(01)00432-0]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096857]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO40877	Malagasy connaraceous	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[14510616]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15128261]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18357995]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23186307]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507152]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25919052]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31836445]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33321838]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34771092]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432812]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36987013]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37176852]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37751472]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836118]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836125]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38786901]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26042	Agnorhiza bolanderi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7552	Alligator mississippiensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18352	Anaxagorea clavata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25090	Araujia sericifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24929	Aria pallescens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25144	Artemisia monogyna	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24556	Bassia butyracea	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20833	Beyeria brevifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25529	Bursaria spinosa	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25471	Chromolaena pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25187	Cladonia evansii	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23567	Coccus fagi	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25326	Dendrosenecio kilimanjari	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24511	Dipterocarpus alatus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24640	Echinops amplexicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25234	Epaltes gariepina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24383	Ficus formosana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24218	Fusarium gibbosum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25671	Gardenia fosbergii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1794	Ilex affinis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25291	Lactarius scrobiculatus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23963	Odixia angusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23453	Pheidole pallidula	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24830	Prosopis glandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24068	Prunus laurocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7445	Pteris prolifera	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25390	Pterocarpus grandiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23691	Pyrosoma giganteum	Species	Pyrosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24675	Quercus aegilops	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24291	Rhizobium phaseoli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28665	Sesbania punicea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24987	Simira eliezeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20823	Stenostomum lucidum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24599	Streptomyces althioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25699	Vitex madiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31311	Citrus reticulate	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31311	Citrus reticulate	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20823	Stenostomum lucidum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24383	Ficus formosana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23567	Coccus fagi	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7552	Alligator mississippiensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23691	Pyrosoma giganteum	Species	Pyrosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7445	Pteris prolifera	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24929	Aria pallescens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24218	Fusarium gibbosum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24987	Simira eliezeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24511	Dipterocarpus alatus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25529	Bursaria spinosa	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25291	Lactarius scrobiculatus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24068	Prunus laurocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25471	Chromolaena pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1794	Ilex affinis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24599	Streptomyces althioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24291	Rhizobium phaseoli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23453	Pheidole pallidula	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25144	Artemisia monogyna	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24556	Bassia butyracea	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25326	Dendrosenecio kilimanjari	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25187	Cladonia evansii	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25234	Epaltes gariepina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18352	Anaxagorea clavata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25671	Gardenia fosbergii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25699	Vitex madiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26042	Agnorhiza bolanderi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25390	Pterocarpus grandiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25090	Araujia sericifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24640	Echinops amplexicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20833	Beyeria brevifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24830	Prosopis glandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28665	Sesbania punicea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24675	Quercus aegilops	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23963	Odixia angusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25045	Senecio squalidus	Species	Asteraceae	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
IC50	7
AC50	1
GI	1

Activity Type	# Activity
Cell line	3
Individual protein	1
Others	4
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	IC50	=	32.36	nM	PMID[18585047]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	71180.0	nM	PMID[17391969]
NPT116	Cell line	HL-60	Homo sapiens	AC50	>	100000.0	nM	PMID[17391969]
NPT521	Cell line	RBL-2H3	Rattus norvegicus	IC50	=	203000.0	nM	PMID[14510616]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI	=	26.5	%	PMID[23199882]
NPT2	Others	Unspecified	n.a.	IC50	=	12300.0	nM	PMID[22047798]
NPT2	Others	Unspecified	n.a.	IC50	=	10800.0	nM	PMID[22047798]

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 NPC138360 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	30227
0.1-0.2	16430
0.2-0.3	2532
0.3-0.4	490
0.4-0.5	146
0.5-0.6	19
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8163	Intermediate Similarity	NPC226973
0.7692	Intermediate Similarity	NPC50715
0.7547	Intermediate Similarity	NPC167815
0.7037	Intermediate Similarity	NPC201136
0.7037	Intermediate Similarity	NPC604569
0.6863	Remote Similarity	NPC40818
0.6667	Remote Similarity	NPC283002
0.6481	Remote Similarity	NPC85233
0.625	Remote Similarity	NPC188203
0.614	Remote Similarity	NPC605047
0.5965	Remote Similarity	NPC100887
0.5818	Remote Similarity	NPC607658
0.569	Remote Similarity	NPC231018
0.5614	Remote Similarity	NPC165512
0.5593	Remote Similarity	NPC108406
0.5593	Remote Similarity	NPC25270
0.5593	Remote Similarity	NPC162313
0.5517	Remote Similarity	NPC488084
0.5484	Remote Similarity	NPC258331
0.541	Remote Similarity	NPC196439
0.541	Remote Similarity	NPC608258
0.5333	Remote Similarity	NPC22472
0.5323	Remote Similarity	NPC227325
0.5323	Remote Similarity	NPC606105
0.5254	Remote Similarity	NPC71334
0.5172	Remote Similarity	NPC129680
0.5167	Remote Similarity	NPC176775
0.5085	Remote Similarity	NPC250822
0.5082	Remote Similarity	NPC134677

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC138360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5682
0.1-0.2	3400
0.2-0.3	64
0.3-0.4	2
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