NPASS Compound

Natural Product: NPC2476

Natural Product ID	NPC2476
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-Demethylnobiletin
IUPAC Name	2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxychromen-4-one
Synonyms	5-demethyl nobiletin; 5-demethylnobiletin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL75978
PubChem CID	358832
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 48 50 0 0 0 0 0 0 0 0999 V2000 6.3419 -2.5547 -1.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1286 -1.2746 -0.5790 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8685 -0.7936 -0.2690 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7895 -1.6232 -0.4762 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4909 -1.1930 -0.1815 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2688 0.0800 0.3255 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3569 0.8788 0.5199 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6554 0.4694 0.2332 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7610 1.2821 0.4310 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5388 2.5801 0.9467 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8904 0.4665 0.6179 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5469 1.7049 1.1080 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7340 2.1044 1.3942 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0149 3.2566 1.8458 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7476 1.1725 1.1648 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0375 1.5115 1.4305 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0291 0.5906 1.2034 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6837 -0.6475 0.7132 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3746 -0.9802 0.4476 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3556 -0.0508 0.6750 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1101 -0.3719 0.4211 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0816 -2.2447 -0.0466 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0569 -2.4762 -1.4261 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6846 -1.5793 0.4832 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3328 -1.6586 -0.7550 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3382 0.9631 1.4833 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1765 1.5696 0.5286 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3062 2.7875 1.9259 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1304 -3.2838 -0.2760 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4240 -2.6067 -1.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7271 -2.7471 -1.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9305 -2.6335 -0.8749 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6621 -1.8503 -0.3482 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2308 1.8587 0.9050 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4855 3.0640 1.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8800 2.5945 1.8382 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0206 3.1860 0.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3331 2.4204 1.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1048 -2.9811 -1.7040 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0702 -1.5140 -1.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9438 -3.1004 -1.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4497 -2.7241 -1.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3570 -1.2281 -0.7282 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7159 -1.1320 -1.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5180 2.5790 0.8153 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0562 0.9083 0.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6598 1.6900 -0.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5229 3.5309 1.2695 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 6 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 19 22 1 0 22 23 1 0 18 24 1 0 24 25 1 0 17 26 1 0 26 27 1 0 16 28 1 0 8 3 1 0 21 11 1 0 20 15 1 0 1 29 1 0 1 30 1 0 1 31 1 0 4 32 1 0 5 33 1 0 7 34 1 0 10 35 1 0 10 36 1 0 10 37 1 0 12 38 1 0 23 39 1 0 23 40 1 0 23 41 1 0 25 42 1 0 25 43 1 0 25 44 1 0 27 45 1 0 27 46 1 0 27 47 1 0 28 48 1 0 M END

Standard InCHIKey	DOFJNFPSMUCECH-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C20H20O8/c1-23-12-7-6-10(8-14(12)24-2)13-9-11(21)15-16(22)18(25-3)20(27-5)19(26-4)17(15)28-13/h6-9,22H,1-5H3
SMILES	COc1ccc(cc1OC)c1cc(=O)c2c(c(c(c(c2o1)OC)OC)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	388.12	Volume:	378.037 ? Van der Waals volume.
Dense:	1.027	LogP:	2.252 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.453 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.77 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	18.0
TPSA:	96.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.688	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.46	Fsp³:	0.25
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:	0
Colloidal aggregators:	0.105	Fluc inhibitor:	0.437 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.769 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.653 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.32	Promiscuous compounds:	0.52

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.984	MDCK Permeability:	-4.687
Pgp-inhibitor:	0.885	Pgp-substrate:	0.246
PAMPA:	0.03 ? 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):	0.021
20% Bioavailability (F20%):	0.068	30% Bioavailability (F30%):	0.078
50% Bioavailability (F50%):	0.881

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103	MRP1:	0.981
Plasma Protein Binding (PPB):	97.196%	Volume Distribution (VD):	-0.284
Fu:	2.308% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.846
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.976
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.892	CYP1A2-substrate:	0.366
CYP2C19-inhibitor:	0.169	CYP2C19-substrate:	0.612
CYP2C9-inhibitor:	0.103	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.958	CYP2D6-substrate:	0.691
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	0.423
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.92
HLM stability:	0.605 ? 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):

5.163

Half-life (T1/2):

1.761

ADMET: Toxicity

hERG Blockers:	0.108	hERG Blockers (10um):	0.523
Human Hepatotoxicity (H-HT):	0.408	Drug-induced Liver Injury (DILI):	0.706
AMES Toxicity:	0.379	Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.399	Skin Sensitization:	0.607
Carcinogencity:	0.756	Eye Corrosion:	0.44
Eye Irritation:	0.932	Respiratory Toxicity:	0.817
Drug-induced Neurotoxicity:	0.397	Ototoxicity:	0.175
Hematotoxicity:	0.431	Drug-induced Nephrotoxicity:	0.22
Genotoxicity:	0.192	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.207	Hek293 Cytotoxicity:	0.458
BCF:	1.472 ? 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:	3.572 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.768 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.94 ? 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
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)88710-5]
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075761]
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]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15128261]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
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]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23186307]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
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]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25919052]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29303577]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30892891]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
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]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34964904]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35268681]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432812]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36529712]
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]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38308284]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38786901]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39410132]
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]
NPO7317	Citrus aurantium	Species	Rutaceae	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]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28829	Pelvetia wrightii	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25969	Aspergillus nomius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28017	Aster altaicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4776	Cassia roxburghii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29402	Launaea arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29013	Annulohypoxylon cohaerens	Species	Xylariaceae	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]
NPO23256	Mentha arvensis	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]
NPO23256	Mentha arvensis	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]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	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]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17476	Austrotaxus spicata	Species	Taxaceae	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]
NPO10082	Citrus unshiu	Species	Rutaceae	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]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	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]
NPO7317	Citrus aurantium	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]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12182	Murraya exotica	Species	Rutaceae	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]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	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]
NPO28017	Aster altaicus	Species	Asteraceae	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]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	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]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1150	Juncus effusus	Species	Juncaceae	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]
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]
NPO17476	Austrotaxus spicata	Species	Taxaceae	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]
NPO26540	Echinopsis spachiana	Species	Cactaceae	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]
NPO29402	Launaea arborescens	Species	Asteraceae	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]
NPO29194	Harziella entomophila	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28665	Sesbania punicea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29013	Annulohypoxylon cohaerens	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4776	Cassia roxburghii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	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]
NPO25969	Aspergillus nomius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28870	Clausena lenis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11524	Macrotomia ugamensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28808	Piptanthus mongolicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29157	Reichardia gaditana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28829	Pelvetia wrightii	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2387	Antennaria geyeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28974	Smilax ornata	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28017	Aster altaicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12182	Murraya exotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9312	Placopecten magellanicus	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2715	Murraya paniculata	Species	Rutaceae	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	8
Inhibition	1
Potency	7
GI50	56
AC50	1
Ratio IC50	1
GI	1

Activity Type	# Activity
Individual protein	7
Cell line	61
Protein complex	2
Others	4
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT518	Protein complex	Tubulin	Homo sapiens	IC50	>	40000.0	nM	PMID[9632366]
NPT518	Protein complex	Tubulin	Homo sapiens	Inhibition	=	5.0	%	PMID[9632366]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	3981.1	nM	PubChem BioAssay data set
NPT45	Individual protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	10000.0	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	17000.0	nM	PMID[9632366]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	2070.0	nM	PMID[17391969]
NPT116	Cell line	HL-60	Homo sapiens	AC50	=	5870.0	nM	PMID[17391969]
NPT519	Cell line	SH-SY5Y	Homo sapiens	IC50	=	32500.0	nM	PMID[18282757]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	12000.0	nM	PMID[19054677]
NPT520	Cell line	3T3-L1	Mus musculus	IC50	=	57000.0	nM	PMID[19054677]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	3732.5	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	86496.79	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	27415.74	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	19543.39	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	14454.4	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	39719.15	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	10000.0	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	67142.89	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	8974.29	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	50933.09	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	47752.93	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	91201.08	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	10115.79	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	20417.38	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	4275.63	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	12560.3	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	53088.44	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	58748.94	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI	=	17.2	%	PMID[23199882]
NPT2	Others	Unspecified	n.a.	IC50	=	5000.0	nM	PMID[10096854]
NPT2	Others	Unspecified	n.a.	IC50	=	3000.0	nM	PMID[22047798]
NPT2	Others	Unspecified	n.a.	IC50	=	42400.0	nM	PMID[22047798]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	6.0	n.a.	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 NPC2476 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	29221
0.1-0.2	17613
0.2-0.3	2368
0.3-0.4	444
0.4-0.5	136
0.5-0.6	50
0.6-0.7	9
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
0.8235	Intermediate Similarity	NPC250822
0.7925	Intermediate Similarity	NPC176775
0.75	Intermediate Similarity	NPC196439
0.7368	Intermediate Similarity	NPC227325
0.7321	Intermediate Similarity	NPC183597
0.7273	Intermediate Similarity	NPC231018
0.7193	Intermediate Similarity	NPC224137
0.7193	Intermediate Similarity	NPC7846
0.7143	Intermediate Similarity	NPC163780
0.7143	Intermediate Similarity	NPC201136
0.7018	Intermediate Similarity	NPC69394
0.7018	Intermediate Similarity	NPC608498
0.6607	Remote Similarity	NPC85233
0.6491	Remote Similarity	NPC205522
0.6441	Remote Similarity	NPC183878
0.6441	Remote Similarity	NPC255350
0.6333	Remote Similarity	NPC92659
0.6333	Remote Similarity	NPC12200
0.6066	Remote Similarity	NPC256612
0.6066	Remote Similarity	NPC283600
0.6066	Remote Similarity	NPC195202
0.5932	Remote Similarity	NPC110639
0.5833	Remote Similarity	NPC143828
0.5806	Remote Similarity	NPC189179
0.5806	Remote Similarity	NPC235215
0.5806	Remote Similarity	NPC474520
0.5763	Remote Similarity	NPC75279
0.5738	Remote Similarity	NPC134677
0.5667	Remote Similarity	NPC274327
0.5574	Remote Similarity	NPC145379
0.5574	Remote Similarity	NPC608038
0.5556	Remote Similarity	NPC128863
0.5556	Remote Similarity	NPC4481
0.5556	Remote Similarity	NPC604422
0.541	Remote Similarity	NPC71334
0.541	Remote Similarity	NPC113089
0.541	Remote Similarity	NPC306821
0.541	Remote Similarity	NPC215932
0.541	Remote Similarity	NPC292107
0.5397	Remote Similarity	NPC176300
0.5397	Remote Similarity	NPC178854
0.5397	Remote Similarity	NPC146165
0.5362	Remote Similarity	NPC213622
0.5345	Remote Similarity	NPC283002
0.5333	Remote Similarity	NPC333230
0.5323	Remote Similarity	NPC62536
0.5323	Remote Similarity	NPC105242
0.5312	Remote Similarity	NPC4455
0.5312	Remote Similarity	NPC160951
0.5246	Remote Similarity	NPC23955
0.5246	Remote Similarity	NPC602963
0.5238	Remote Similarity	NPC22472
0.5238	Remote Similarity	NPC50715
0.5231	Remote Similarity	NPC19687
0.5231	Remote Similarity	NPC47781
0.5167	Remote Similarity	NPC136278
0.5161	Remote Similarity	NPC77955
0.5161	Remote Similarity	NPC275836
0.5161	Remote Similarity	NPC239128
0.5161	Remote Similarity	NPC600177
0.5156	Remote Similarity	NPC280339
0.5156	Remote Similarity	NPC167815
0.5156	Remote Similarity	NPC60972
0.5143	Remote Similarity	NPC183
0.5082	Remote Similarity	NPC201547
0.5079	Remote Similarity	NPC33265
0.5079	Remote Similarity	NPC70853
0.5079	Remote Similarity	NPC120163
0.5079	Remote Similarity	NPC276409
0.5075	Remote Similarity	NPC485299
0.5075	Remote Similarity	NPC605634

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC2476 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5275
0.1-0.2	3800
0.2-0.3	67
0.3-0.4	6
0.4-0.5	1
0.5-0.6	0
0.6-0.7	1
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
0.6441	Remote Similarity	NPD2801	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