NPASS Compound

Natural Product: NPC4455

Natural Product ID	NPC4455
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sudachitin
IUPAC Name	5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxychromen-4-one
Synonyms	sudachitin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL479233
PubChem CID	12443122
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 42 44 0 0 0 0 0 0 0 0999 V2000 4.1380 -2.6234 0.3560 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8581 -1.5077 0.8579 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2193 -0.2799 0.9581 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9149 -0.0810 0.5950 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2736 1.1653 0.6991 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0084 2.2177 1.1900 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3185 2.0229 1.5559 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9251 0.8011 1.4470 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2574 0.6168 1.8224 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8798 1.2740 0.2856 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2021 2.4534 0.3616 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1307 2.5364 -0.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7803 3.6082 0.0194 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7297 1.4071 -0.5060 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0638 1.3975 -0.9298 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6530 0.2432 -1.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9296 -0.9267 -1.4590 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6087 -0.9288 -1.0423 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0001 0.2381 -0.5631 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2584 0.2075 -0.1731 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9116 -2.1185 -1.1147 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8967 -3.0301 -0.0246 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5778 -2.0520 -1.9406 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9665 0.2481 -1.8135 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0729 -0.0078 -1.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7367 2.5991 -0.8468 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7538 -3.5317 0.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1414 -2.6930 0.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0104 -2.5449 -0.7610 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3342 -0.9198 0.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5335 3.1931 1.2800 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8529 2.8861 1.9370 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4916 -0.2775 2.2606 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6514 3.3461 0.7231 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0057 -3.6536 -0.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9305 -2.5009 0.9454 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7712 -3.7236 -0.0628 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0949 -2.0069 -2.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7870 -0.6367 -0.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9261 -0.4229 -1.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4099 0.9784 -0.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0507 3.0273 0.0132 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 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 18 21 1 0 21 22 1 0 17 23 1 0 16 24 1 0 24 25 1 0 15 26 1 0 8 3 1 0 20 10 1 0 19 14 1 0 1 27 1 0 1 28 1 0 1 29 1 0 4 30 1 0 6 31 1 0 7 32 1 0 9 33 1 0 11 34 1 0 22 35 1 0 22 36 1 0 22 37 1 0 23 38 1 0 25 39 1 0 25 40 1 0 25 41 1 0 26 42 1 0 M END

Standard InCHIKey	XRHHDQSPFPQKMS-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H16O8/c1-23-12-6-8(4-5-9(12)19)11-7-10(20)13-14(21)17(24-2)15(22)18(25-3)16(13)26-11/h4-7,19,21-22H,1-3H3
SMILES	COc1cc(ccc1O)c1cc(=O)c2c(c(c(c(c2o1)OC)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	360.08	Volume:	343.445 ? Van der Waals volume.
Dense:	1.048	LogP:	2.11 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.221 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.245 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	18.0
TPSA:	118.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.65	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.596	Fsp³:	0.167
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:	0.415	Fluc inhibitor:	0.437 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.877 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.64 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.353	Promiscuous compounds:	0.865

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.197	MDCK Permeability:	-4.804
Pgp-inhibitor:	0.49	Pgp-substrate:	0.263
PAMPA:	0.069 ? 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):	0.008
20% Bioavailability (F20%):	0.155	30% Bioavailability (F30%):	0.38
50% Bioavailability (F50%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03	MRP1:	0.951
Plasma Protein Binding (PPB):	95.816%	Volume Distribution (VD):	-0.509
Fu:	4.927% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.979
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.983
BSEP inhibitor:	0.822

ADMET: Metabolism

CYP1A2-inhibitor:	0.753	CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.199	CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.863	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.996	CYP2D6-substrate:	0.632
CYP3A4-inhibitor:	0.024	CYP3A4-substrate:	0.038
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.917
HLM stability:	0.729 ? 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):

3.893

Half-life (T1/2):

1.632

ADMET: Toxicity

hERG Blockers:	0.082	hERG Blockers (10um):	0.513
Human Hepatotoxicity (H-HT):	0.422	Drug-induced Liver Injury (DILI):	0.7
AMES Toxicity:	0.476	Rat Oral Acute Toxicity:	0.399
Maximum Recommended Daily Dose:	0.464	Skin Sensitization:	0.811
Carcinogencity:	0.645	Eye Corrosion:	0.343
Eye Irritation:	0.975	Respiratory Toxicity:	0.717
Drug-induced Neurotoxicity:	0.149	Ototoxicity:	0.18
Hematotoxicity:	0.237	Drug-induced Nephrotoxicity:	0.134
Genotoxicity:	0.406	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.303	Hek293 Cytotoxicity:	0.443
BCF:	0.871 ? 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:	3.524 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.277 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.818 ? 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]
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]
NPO129	Biebersteinia orphanidis	Species	Biebersteiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11198823]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15128261]
NPO20577	Citrus sudachi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933871]
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]
NPO20577	Citrus sudachi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26558	Physocarpus capitatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO129	Biebersteinia orphanidis	Species	Biebersteiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9277	Ammothamnus songoricus	Species	Fabaceae	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]
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]
NPO26779	Helianthus strumosus	Species	Asteraceae	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]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26779	Helianthus strumosus	Species	Asteraceae	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]
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]
NPO26706	Dictyota pardalis	Species	Dictyotaceae	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]
NPO129	Biebersteinia orphanidis	Species	Biebersteiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12676	Berberis mingetsensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20577	Citrus sudachi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26558	Physocarpus capitatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26852	Cryptocarya konishii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26114	Dorstenia convexa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9277	Ammothamnus songoricus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10843	Melanelixia subglabra	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4202	Kopsia terengganensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26779	Helianthus strumosus	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	1
IZ	3

Activity Type	# Activity
Organism	3
Individual protein	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	=	4466.84	nM	PMID[18585047]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	IZ	=	14.0	mm	PMID[16933871]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[16933871]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	25.4	mm	PMID[16933871]

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 NPC4455 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	31095
0.1-0.2	15677
0.2-0.3	2414
0.3-0.4	509
0.4-0.5	110
0.5-0.6	32
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7736	Intermediate Similarity	NPC275836
0.7368	Intermediate Similarity	NPC227325
0.7321	Intermediate Similarity	NPC183597
0.7321	Intermediate Similarity	NPC146165
0.7222	Intermediate Similarity	NPC602963
0.7193	Intermediate Similarity	NPC288669
0.7091	Intermediate Similarity	NPC274327
0.7018	Intermediate Similarity	NPC83508
0.6897	Remote Similarity	NPC128863
0.6842	Remote Similarity	NPC600155
0.6724	Remote Similarity	NPC280339
0.65	Remote Similarity	NPC47781
0.6441	Remote Similarity	NPC167815
0.623	Remote Similarity	NPC183950
0.623	Remote Similarity	NPC137062
0.6	Remote Similarity	NPC312924
0.5932	Remote Similarity	NPC301323
0.5902	Remote Similarity	NPC20830
0.5833	Remote Similarity	NPC188203
0.5806	Remote Similarity	NPC115323
0.5714	Remote Similarity	NPC606105
0.5667	Remote Similarity	NPC191459
0.5667	Remote Similarity	NPC284552
0.5652	Remote Similarity	NPC602497
0.5645	Remote Similarity	NPC253634
0.5574	Remote Similarity	NPC130894
0.5574	Remote Similarity	NPC231018
0.5556	Remote Similarity	NPC610401
0.55	Remote Similarity	NPC131624
0.5484	Remote Similarity	NPC201136
0.541	Remote Similarity	NPC241498
0.541	Remote Similarity	NPC600177
0.5397	Remote Similarity	NPC204854
0.5323	Remote Similarity	NPC100887
0.5312	Remote Similarity	NPC78302
0.5312	Remote Similarity	NPC256612
0.5312	Remote Similarity	NPC196439
0.5312	Remote Similarity	NPC2476
0.5263	Remote Similarity	NPC475942
0.5246	Remote Similarity	NPC7973
0.5246	Remote Similarity	NPC250822
0.5238	Remote Similarity	NPC222830
0.5231	Remote Similarity	NPC19687
0.5161	Remote Similarity	NPC71334
0.5156	Remote Similarity	NPC255350
0.5079	Remote Similarity	NPC176775
0.5079	Remote Similarity	NPC276409
0.5063	Remote Similarity	NPC111249

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC4455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5840
0.1-0.2	3250
0.2-0.3	56
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
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
0.5156	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