NPASS Compound

Natural Product: NPC252558

Natural Product ID	NPC252558
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OVSQVDMCBVZWGM-WVTKYERHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44259091
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 53 56 0 0 0 0 0 0 0 0999 V2000 0.4702 2.1747 -1.8289 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2733 3.5110 -2.1641 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1492 4.4757 -1.7527 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2237 4.0720 -1.0003 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4133 2.7509 -0.6714 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5378 1.7502 -1.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7325 0.3680 -0.6722 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8058 -0.6178 -0.7031 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2009 -1.8864 -0.2743 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4285 -2.8588 -0.2663 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5005 -2.1103 0.1681 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9350 -3.3332 0.5990 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2213 -3.5594 1.0396 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1155 -2.5118 1.0495 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6763 -1.2824 0.6156 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3820 -1.0472 0.1703 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9797 0.1062 -0.2342 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4366 -2.6854 1.4876 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0394 -4.3983 0.5930 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4769 -0.4706 -1.1058 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5693 -0.2126 -0.2566 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5147 0.7641 -0.8555 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8475 0.6723 -0.0928 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4998 0.2267 1.3112 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9199 -1.1429 1.2547 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8781 -2.2458 1.6241 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8629 -2.4871 0.7051 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2549 -1.4075 0.0594 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5934 0.3386 2.1575 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6040 -0.2940 -0.7616 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7952 0.5000 -2.1991 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1281 5.0207 -0.5690 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9508 5.8141 -2.0890 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2583 1.4982 -2.2323 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5856 3.8111 -2.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2620 2.4392 -0.0768 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5369 -4.5332 1.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3856 -0.4663 0.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1340 -2.1383 1.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9165 -4.9038 1.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1707 0.1369 0.7114 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1793 1.8215 -0.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3181 1.6572 -0.1233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7521 0.9866 1.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1070 -1.1820 2.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3994 -2.0072 2.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3266 -3.1878 1.8126 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7315 -2.7660 1.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3509 -0.2111 1.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5859 -0.1786 -0.5978 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4139 -0.3619 -2.4985 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5249 5.0774 0.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6356 6.5145 -1.8966 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 4 32 1 0 3 33 1 0 6 1 1 0 17 7 1 0 28 21 1 0 16 11 1 0 1 34 1 0 2 35 1 0 5 36 1 0 13 37 1 0 15 38 1 0 18 39 1 0 19 40 1 0 21 41 1 1 22 42 1 0 23 43 1 0 24 44 1 1 25 45 1 1 26 46 1 0 26 47 1 0 27 48 1 0 29 49 1 0 30 50 1 0 31 51 1 0 32 52 1 0 33 53 1 0 M END

Standard InCHIKey	OVSQVDMCBVZWGM-WVTKYERHSA-N
Standard InCHI	InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17?,18?,21+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1C(C([C@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	464.1	Volume:	421.937 ? Van der Waals volume.
Dense:	1.1	LogP:	0.815 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.094 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.795 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	210.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.229	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.008	Fsp³:	0.286
MCE-18:	91.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.68	Fluc inhibitor:	0.255 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.925 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.776 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.257	Promiscuous compounds:	0.84

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.331	MDCK Permeability:	-4.999
Pgp-inhibitor:	0.0	Pgp-substrate:	0.259
PAMPA:	0.99 ? 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):	0.862
20% Bioavailability (F20%):	0.986	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.75
Plasma Protein Binding (PPB):	85.161%	Volume Distribution (VD):	-0.044
Fu:	14.267% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.513
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.498
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.012	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.634	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.137
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.774 ? 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):

3.932

Half-life (T1/2):

2.43

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.269
Human Hepatotoxicity (H-HT):	0.605	Drug-induced Liver Injury (DILI):	0.92
AMES Toxicity:	0.919	Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.483	Skin Sensitization:	0.999
Carcinogencity:	0.332	Eye Corrosion:	0.0
Eye Irritation:	0.685	Respiratory Toxicity:	0.096
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.883
Hematotoxicity:	0.051	Drug-induced Nephrotoxicity:	0.037
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.919	Hek293 Cytotoxicity:	0.847
BCF:	0.528 ? 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:	3.147 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.609 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.851 ? 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
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-015-0798-z]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.fitote.2006.01.011]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plaphy.2005.07.013]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1078/0176-1617-00195]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1155/2014/609649]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.5897/AJB11.1524]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757735]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14735439]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	flower	n.a.	PMID[15481244]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	callus	n.a.	PMID[15715262]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17156960]
NPO2798	Geranium thunbergii	Species	Geraniaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17225459]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24066589]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25620156]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422318]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28218000]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28445039]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30024167]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30676026]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO8500	Acanthopanax gracilistylus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32319765]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32456033]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32560389]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235013]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36336219]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38217369]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409699]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8699184]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18313	Erodium stephanianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15687	Geranium wilfordii	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28231	Abelmoschus manihot	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16698	Geranium carolinianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2798	Geranium thunbergii	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1596	Taraxacum borealisinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23327	Taraxacum coreanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13668	Taraxacum platycarpum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28231	Abelmoschus manihot	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15687	Geranium wilfordii	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18313	Erodium stephanianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28231	Abelmoschus manihot	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15687	Geranium wilfordii	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8500	Acanthopanax gracilistylus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18313	Erodium stephanianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16698	Geranium carolinianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18313	Erodium stephanianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16145	Apocynum venetum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1596	Taraxacum borealisinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8500	Acanthopanax gracilistylus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15687	Geranium wilfordii	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13668	Taraxacum platycarpum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23327	Taraxacum coreanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28231	Abelmoschus manihot	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO753	Acanthopanax sessiliflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2798	Geranium thunbergii	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18313	Erodium stephanianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16698	Geranium carolinianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13668	Taraxacum platycarpum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16698	Geranium carolinianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28231	Abelmoschus manihot	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23327	Taraxacum coreanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2798	Geranium thunbergii	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18313	Erodium stephanianum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8500	Acanthopanax gracilistylus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26785	Taraxacum mongolicum	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

Molecular-level activity

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

In vitro activity

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

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 NPC252558 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	23307
0.1-0.2	22724
0.2-0.3	2475
0.3-0.4	781
0.4-0.5	240
0.5-0.6	40
0.6-0.7	80
0.7-0.8	1
0.8-0.85	17
0.85-0.9	10
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC145038
1.0	High Similarity	NPC56077
1.0	High Similarity	NPC281131
1.0	High Similarity	NPC253662
1.0	High Similarity	NPC179950
1.0	High Similarity	NPC88789
1.0	High Similarity	NPC491374
0.8971	High Similarity	NPC77672
0.8971	High Similarity	NPC133671
0.8971	High Similarity	NPC135391
0.8971	High Similarity	NPC78263
0.8971	High Similarity	NPC250069
0.8955	High Similarity	NPC67037
0.8955	High Similarity	NPC255615
0.8696	High Similarity	NPC19388
0.8696	High Similarity	NPC240431
0.8696	High Similarity	NPC55786
0.8429	Intermediate Similarity	NPC127546
0.8429	Intermediate Similarity	NPC57625
0.8429	Intermediate Similarity	NPC173637
0.8429	Intermediate Similarity	NPC317489
0.8429	Intermediate Similarity	NPC223424
0.8429	Intermediate Similarity	NPC600591
0.8312	Intermediate Similarity	NPC156869
0.831	Intermediate Similarity	NPC64305
0.8289	Intermediate Similarity	NPC29958
0.8219	Intermediate Similarity	NPC60735
0.8219	Intermediate Similarity	NPC26230
0.8182	Intermediate Similarity	NPC471748
0.8133	Intermediate Similarity	NPC203050
0.8133	Intermediate Similarity	NPC225434
0.8108	Intermediate Similarity	NPC120099
0.8082	Intermediate Similarity	NPC472459
0.8	Intermediate Similarity	NPC288084
0.7973	Intermediate Similarity	NPC175107
0.7838	Intermediate Similarity	NPC42773
0.7838	Intermediate Similarity	NPC45522
0.7838	Intermediate Similarity	NPC325555
0.7838	Intermediate Similarity	NPC226304
0.7808	Intermediate Similarity	NPC136042
0.7792	Intermediate Similarity	NPC254855
0.7792	Intermediate Similarity	NPC94610
0.7746	Intermediate Similarity	NPC34531
0.7632	Intermediate Similarity	NPC609478
0.76	Intermediate Similarity	NPC599850
0.7564	Intermediate Similarity	NPC116864
0.7564	Intermediate Similarity	NPC244776
0.7534	Intermediate Similarity	NPC111929
0.7534	Intermediate Similarity	NPC320283
0.7534	Intermediate Similarity	NPC41121
0.75	Intermediate Similarity	NPC276222
0.75	Intermediate Similarity	NPC274618
0.75	Intermediate Similarity	NPC118284
0.75	Intermediate Similarity	NPC608147
0.7407	Intermediate Similarity	NPC605592
0.7375	Intermediate Similarity	NPC139320
0.7308	Intermediate Similarity	NPC605784
0.7297	Intermediate Similarity	NPC135599
0.7297	Intermediate Similarity	NPC73855
0.7297	Intermediate Similarity	NPC113968
0.7297	Intermediate Similarity	NPC328940
0.7297	Intermediate Similarity	NPC277174
0.7297	Intermediate Similarity	NPC606877
0.7284	Intermediate Similarity	NPC67326
0.7273	Intermediate Similarity	NPC488071
0.7237	Intermediate Similarity	NPC84362
0.7195	Intermediate Similarity	NPC203259
0.7195	Intermediate Similarity	NPC33054
0.7195	Intermediate Similarity	NPC155877
0.7195	Intermediate Similarity	NPC176740
0.7195	Intermediate Similarity	NPC471725
0.7195	Intermediate Similarity	NPC134532
0.7195	Intermediate Similarity	NPC602582
0.7191	Intermediate Similarity	NPC292019
0.7191	Intermediate Similarity	NPC202908
0.7105	Intermediate Similarity	NPC297987
0.7013	Intermediate Similarity	NPC488080
0.7013	Intermediate Similarity	NPC169977
0.7	Intermediate Similarity	NPC170052
0.7	Intermediate Similarity	NPC135846
0.6905	Remote Similarity	NPC255157
0.6905	Remote Similarity	NPC259896
0.6883	Remote Similarity	NPC8573
0.6875	Remote Similarity	NPC223747
0.686	Remote Similarity	NPC37668
0.6835	Remote Similarity	NPC235260
0.6835	Remote Similarity	NPC155763
0.6835	Remote Similarity	NPC219904
0.6795	Remote Similarity	NPC52550
0.6707	Remote Similarity	NPC95866
0.6667	Remote Similarity	NPC54802
0.6667	Remote Similarity	NPC470405
0.6667	Remote Similarity	NPC197304
0.6667	Remote Similarity	NPC116458
0.6667	Remote Similarity	NPC246943
0.6667	Remote Similarity	NPC265530
0.6628	Remote Similarity	NPC488073
0.6582	Remote Similarity	NPC305811
0.6582	Remote Similarity	NPC24043
0.6556	Remote Similarity	NPC223426
0.6548	Remote Similarity	NPC480466
0.6548	Remote Similarity	NPC471079
0.6543	Remote Similarity	NPC101026
0.6543	Remote Similarity	NPC488077
0.6543	Remote Similarity	NPC197285
0.6543	Remote Similarity	NPC601710
0.6538	Remote Similarity	NPC289667
0.6538	Remote Similarity	NPC143851
0.6522	Remote Similarity	NPC189564
0.6517	Remote Similarity	NPC471669
0.6517	Remote Similarity	NPC76831
0.65	Remote Similarity	NPC21100
0.6484	Remote Similarity	NPC81042
0.6471	Remote Similarity	NPC173582
0.6471	Remote Similarity	NPC265885
0.6471	Remote Similarity	NPC181465
0.6471	Remote Similarity	NPC215710
0.6471	Remote Similarity	NPC163242
0.6471	Remote Similarity	NPC272068
0.6471	Remote Similarity	NPC473438
0.6471	Remote Similarity	NPC253788
0.6456	Remote Similarity	NPC282987
0.6452	Remote Similarity	NPC219043
0.6437	Remote Similarity	NPC253521
0.6437	Remote Similarity	NPC154741
0.6437	Remote Similarity	NPC113836
0.642	Remote Similarity	NPC159579
0.642	Remote Similarity	NPC191306
0.641	Remote Similarity	NPC476771
0.6375	Remote Similarity	NPC271692
0.6341	Remote Similarity	NPC224530
0.6324	Remote Similarity	NPC286342
0.6322	Remote Similarity	NPC129264
0.6292	Remote Similarity	NPC270448
0.6279	Remote Similarity	NPC39834
0.6267	Remote Similarity	NPC78697
0.6265	Remote Similarity	NPC206123
0.625	Remote Similarity	NPC470125
0.625	Remote Similarity	NPC277205
0.625	Remote Similarity	NPC37919
0.625	Remote Similarity	NPC153755
0.625	Remote Similarity	NPC470718
0.625	Remote Similarity	NPC609879
0.6237	Remote Similarity	NPC203145
0.622	Remote Similarity	NPC182121
0.6211	Remote Similarity	NPC470712
0.6207	Remote Similarity	NPC304741
0.6173	Remote Similarity	NPC27640
0.6154	Remote Similarity	NPC135831
0.6111	Remote Similarity	NPC122467
0.6105	Remote Similarity	NPC48984
0.6087	Remote Similarity	NPC292929
0.6071	Remote Similarity	NPC88023
0.6071	Remote Similarity	NPC309025
0.6049	Remote Similarity	NPC189142
0.6049	Remote Similarity	NPC77660
0.6047	Remote Similarity	NPC251417
0.6022	Remote Similarity	NPC602448
0.6	Remote Similarity	NPC488072
0.6	Remote Similarity	NPC476215
0.5978	Remote Similarity	NPC476472
0.5978	Remote Similarity	NPC294815
0.5978	Remote Similarity	NPC85751
0.5978	Remote Similarity	NPC16194
0.5978	Remote Similarity	NPC19240
0.5978	Remote Similarity	NPC89127
0.5978	Remote Similarity	NPC220173
0.5977	Remote Similarity	NPC476773
0.5977	Remote Similarity	NPC609888
0.5976	Remote Similarity	NPC245014
0.5957	Remote Similarity	NPC214621
0.5957	Remote Similarity	NPC34267
0.5957	Remote Similarity	NPC14187
0.5934	Remote Similarity	NPC473327
0.5926	Remote Similarity	NPC249281
0.5926	Remote Similarity	NPC476772
0.5918	Remote Similarity	NPC279473
0.5904	Remote Similarity	NPC59534
0.5904	Remote Similarity	NPC138927
0.5904	Remote Similarity	NPC117260
0.59	Remote Similarity	NPC470713
0.5889	Remote Similarity	NPC61904
0.5889	Remote Similarity	NPC296018
0.5889	Remote Similarity	NPC64425
0.5889	Remote Similarity	NPC488074
0.5833	Remote Similarity	NPC129217
0.5825	Remote Similarity	NPC192539
0.5824	Remote Similarity	NPC245452
0.5783	Remote Similarity	NPC58716
0.5783	Remote Similarity	NPC46420
0.5783	Remote Similarity	NPC45638
0.5778	Remote Similarity	NPC35167
0.5765	Remote Similarity	NPC85707
0.5765	Remote Similarity	NPC21666
0.5732	Remote Similarity	NPC112755
0.5732	Remote Similarity	NPC170675
0.5732	Remote Similarity	NPC254306
0.5714	Remote Similarity	NPC216496
0.5714	Remote Similarity	NPC480441
0.5714	Remote Similarity	NPC126784

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC252558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5831
0.1-0.2	3239
0.2-0.3	66
0.3-0.4	6
0.4-0.5	6
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7195	Intermediate Similarity	NPD6797	Phase 2
0.5474	Remote Similarity	NPD7251	Phase 2

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