NPASS Compound

Natural Product: NPC115216

Natural Product ID	NPC115216
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ABVCUBUIXWJYSE-GQUPQBGVSA-O
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	443648
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0001361] Anthocyanins [CHEMONTID:0002996] Anthocyanidin-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 52 55 0 0 0 0 0 0 0 0999 V2000 -1.0751 2.5075 0.8768 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2282 3.8913 0.9557 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4248 4.4786 0.6073 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4395 3.6549 0.1871 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 2.2963 0.1149 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0656 1.6779 0.4619 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9885 0.2332 0.2663 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8313 -0.4860 0.0801 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9747 -1.9015 -0.0937 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1793 -2.4980 -0.0788 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2946 -3.8714 -0.2506 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5332 -4.4775 -0.2356 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6466 -3.6883 -0.0466 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5125 -2.3391 0.1204 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2827 -1.7074 0.1092 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1368 -0.4460 0.2640 O 0 0 0 0 0 3 0 0 0 0 0 0 -5.8703 -4.3308 -0.0378 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1358 -4.6082 -0.4361 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3730 -0.0253 0.0372 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5880 0.4395 -0.0061 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4449 0.1628 1.2524 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5669 -0.7675 0.8787 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5028 0.0685 -0.0116 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5669 0.7429 -1.0038 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2439 0.9377 -2.3406 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5274 -0.2918 -2.8857 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3747 0.0338 -1.1200 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1015 1.0006 0.8392 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0181 -1.7797 0.0654 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0296 1.3398 1.7148 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6014 5.8749 0.6789 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1307 2.1333 1.2116 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4226 4.5110 1.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3712 4.1442 -0.0806 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0960 1.6841 -0.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0921 -2.5162 -0.2425 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5947 -5.5422 -0.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4229 -1.7480 0.2682 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3239 -4.6357 0.8240 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7284 -4.7301 -1.3436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6225 1.5742 -0.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7472 -0.2669 2.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0735 -1.1790 1.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2480 -0.5715 -0.5027 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3122 1.7423 -0.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1559 1.5486 -2.2136 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6036 1.5061 -3.0409 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3555 -0.2566 -3.8562 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3550 0.5301 1.6596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7396 -2.3505 -0.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4503 2.1333 1.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3267 6.1683 1.3510 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 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 13 17 1 0 11 18 1 0 8 19 1 0 19 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 24 27 1 0 23 28 1 0 22 29 1 0 21 30 1 0 3 31 1 0 6 1 1 0 16 7 2 0 27 20 1 0 15 10 1 0 1 32 1 0 2 33 1 0 4 34 1 0 5 35 1 0 9 36 1 0 12 37 1 0 14 38 1 0 17 39 1 0 18 40 1 0 20 41 1 6 21 42 1 1 22 43 1 1 23 44 1 6 24 45 1 1 25 46 1 0 25 47 1 0 26 48 1 0 28 49 1 0 29 50 1 0 30 51 1 0 31 52 1 0 M CHG 1 16 1 M END

Standard InCHIKey	ABVCUBUIXWJYSE-GQUPQBGVSA-O
Standard InCHI	InChI=1S/C21H20O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25)/p+1/t16-,17-,18+,19-,21-/m1/s1
SMILES	c1cc(ccc1c1c(cc2c(cc(cc2[o+]1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	433.11	Volume:	405.675 ? Van der Waals volume.
Dense:	1.068	LogP:	0.455 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.256 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.09 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	23.0
TPSA:	171.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.29	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.139	Fsp³:	0.286
MCE-18:	84.259 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.701	Fluc inhibitor:	0.354 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.958 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.846 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.537	Promiscuous compounds:	0.648

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.52	MDCK Permeability:	-4.942
Pgp-inhibitor:	0.0	Pgp-substrate:	0.642
PAMPA:	0.973 ? 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):	0.152
20% Bioavailability (F20%):	0.712	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.042
Plasma Protein Binding (PPB):	84.399%	Volume Distribution (VD):	0.006
Fu:	16.382% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.731
BSEP inhibitor:	0.018

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.838	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.938	CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.042
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.407 ? 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):

2.635

Half-life (T1/2):

3.214

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.034
Human Hepatotoxicity (H-HT):	0.992	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.794	Skin Sensitization:	1.0
Carcinogencity:	1.0	Eye Corrosion:	0.0
Eye Irritation:	0.999	Respiratory Toxicity:	0.834
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.009
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.001
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.014
A549 Cytotoxicity:	0.041	Hek293 Cytotoxicity:	0.886
BCF:	0.855 ? 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:	3.171 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.258 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.862 ? 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
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[ 10835233]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11627-001-0052-8]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	WrocÃ…â€šaw, Poland	2004Ã¢â‚¬â€œ2005	DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003Ã¢â‚¬â€œ2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0021-9258(18)90865-3]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(02)00136-X]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(02)00136-X]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1023/A:1024390522259]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Leaves (mother plant)	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Roots (runner plant)	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruits	Suwon, Korea	2012-Nov	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Leaves	Suwon, Korea		DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Runners	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Leaves (runner plant)	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Roots (mother plant)	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[10395493]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775096]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11534769]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1453178]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568772]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[1622242]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	fruit	n.a.	PMID[16417304]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16659156]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16668466]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO41945	A new engineered strain of Forsythia koreana [PLR; CYP81Q1]	Strain	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19887541]
NPO14284	Delphinium shawurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20351801]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20963508]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21381697]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21608987]
NPO25279	Carya cathayensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22330636]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	Tekirdag, Turkey		PMID[24499198]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25053043]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070365]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[25369450]
NPO41417	Four strain Escherichia coli polyculture	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28588129]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[36557810]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36560643]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36838852]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[37570937]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39138188]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39527985]
NPO23715	Dictyota dichotoma	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39728138]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[8988596]
NPO3949	Ceramium rubrum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25279	Carya cathayensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23715	Dictyota dichotoma	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12982	Dysidea amblia	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6347	Iryanthera paraensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11912	Peltogyne porphyrocardia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10887	Pseudeurotium zonatum	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25553	Eugenia umbelliflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28601	Aspergillus falconensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15160	Gutierrezia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24151	Fitchia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14043	Caulerpa serrulata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7713	Euplotes raikovi	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Bulb	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Hypocotyl	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25404	Embelia kilimandscharica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25404	Embelia kilimandscharica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21314	Trametes sanguinea	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3244	Ascidia ahodori	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4512	Fagraea gracilipes	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15160	Gutierrezia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13160	Garcinia xipshuanbannaensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6347	Iryanthera paraensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15253	Helichrysum graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11912	Peltogyne porphyrocardia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11128	Ratibida mexicana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13311	Agelas linnaei	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10191	Ormosia balansae	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15626	Alternaria japonica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7713	Euplotes raikovi	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO965	Bleekeria vitiensis	Species	Plesiopidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14043	Caulerpa serrulata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10887	Pseudeurotium zonatum	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12756	Roboastra tigris	Species	Polyceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6221	Nostoc carneum	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14284	Delphinium shawurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9860.1	Pinus brutia var. eldarica	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28601	Aspergillus falconensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12982	Dysidea amblia	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3949	Ceramium rubrum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4968	Lepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24346	Cryptocarya foveolata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21314	Trametes sanguinea	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25553	Eugenia umbelliflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25635	Ricinodendron africanum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25279	Carya cathayensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23898	Caesalpinia magnifoliolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24151	Fitchia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25404	Embelia kilimandscharica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6992	Ahnfeltia paradoxa	Species	Ahnfeltiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23715	Dictyota dichotoma	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18751	Amphilophium crucigerum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23844	Phlegmacium vitellinum	n.a.	n.a.	n.a.	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
NPO10339	Fragaria x ananassa	n.a.	Fruits	0.996	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO10339	Fragaria x ananassa	n.a.	Fruits	47.14171	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO19774	Rubus idaeus	n.a.	Fruits	1.65032	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO21349	Punica granatum	n.a.	n.a.	0.335	n.a.	n.a.	mg/100mL	Database [Phenol-Explorer]
NPO21349	Punica granatum	n.a.	n.a.	0.46	n.a.	n.a.	mg/100mL	Database [Phenol-Explorer]
NPO23715	Dictyota dichotoma	n.a.	n.a.	0.11	n.a.	n.a.	Âµg/mg	PMID[39728138]

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 NPC115216 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	20846
0.1-0.2	25866
0.2-0.3	2283
0.3-0.4	720
0.4-0.5	131
0.5-0.6	1
0.6-0.7	4
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC168579
0.8235	Intermediate Similarity	NPC76176
0.8116	Intermediate Similarity	NPC125755
0.803	Intermediate Similarity	NPC37793
0.7794	Intermediate Similarity	NPC277867
0.7681	Intermediate Similarity	NPC603591
0.7361	Intermediate Similarity	NPC161700
0.6447	Remote Similarity	NPC473480
0.6438	Remote Similarity	NPC280945
0.6164	Remote Similarity	NPC138227
0.6071	Remote Similarity	NPC473621
0.5882	Remote Similarity	NPC15538

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC115216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6619
0.1-0.2	2477
0.2-0.3	43
0.3-0.4	10
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data