NPASS Compound

Natural Product: NPC169398

Natural Product ID	NPC169398
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ligstroside
IUPAC Name	methyl (4S,5E,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms	Ligstroside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1086877
PubChem CID	14136859
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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 69 71 0 0 0 0 0 0 0 0999 V2000 -0.2889 2.6354 0.6916 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0831 1.6698 -0.0422 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8399 0.3582 -0.2121 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3450 -0.2103 0.3916 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6252 0.0725 -0.3302 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8358 -0.5025 0.2827 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2052 -1.6964 0.2179 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7255 0.2979 1.0367 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8798 -0.2060 1.6340 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8855 -0.8116 0.6947 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3778 0.1594 -0.3090 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7251 0.2602 -1.5143 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1459 1.1648 -2.4916 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2306 1.9822 -2.2708 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8922 1.8857 -1.0602 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4677 0.9942 -0.1126 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6894 2.8907 -3.1958 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1543 -1.6052 0.7890 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6227 -2.3578 0.0283 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2235 -1.7852 -1.1132 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7733 -0.4717 -1.0260 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0006 -0.6304 -0.3980 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9921 -0.1582 -1.2482 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9396 -1.2544 -1.6734 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8918 -1.6060 -0.5687 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3201 -0.4141 0.2333 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9485 0.8494 -0.5258 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4778 2.0379 0.2855 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8552 2.0060 0.4153 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5891 0.9079 -0.6382 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6978 -0.3697 0.4336 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2339 -2.5116 0.2920 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6619 -0.8042 -2.7676 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7705 -2.1556 1.9594 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5724 -3.3834 2.2695 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5963 -1.4608 2.8317 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1721 -2.0686 3.9738 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3015 2.2610 1.5473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2914 3.3425 0.0608 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0337 3.3335 1.2017 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0072 2.0223 -0.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4759 0.3164 1.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 1.2016 -0.3128 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6287 -0.1802 -1.3955 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3816 0.6359 2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5879 -1.0049 2.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5637 -1.7519 0.2424 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7802 -1.0677 1.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8669 -0.3432 -1.7734 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6296 1.2386 -3.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7410 2.5269 -0.8944 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0025 0.9382 0.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6602 3.1888 -3.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7889 -3.3751 0.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9002 -0.0361 -2.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4817 0.2192 -2.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3904 -2.1819 -1.9527 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7787 -2.1580 -0.9718 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8211 -0.3715 1.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4853 0.9244 -1.4958 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1839 2.9942 -0.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0490 2.0059 1.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2931 2.6138 -0.2509 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0928 -1.2856 0.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6111 -1.9416 0.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5603 -1.2088 -2.7118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6552 -1.2600 4.5632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3647 -2.4907 4.6185 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9331 -2.8145 3.6757 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 14 17 1 0 4 18 1 0 18 19 2 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 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 24 33 1 0 18 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 21 3 1 0 30 23 1 0 16 11 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 4 42 1 1 5 43 1 0 5 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 12 49 1 0 13 50 1 0 15 51 1 0 16 52 1 0 17 53 1 0 19 54 1 0 21 55 1 6 23 56 1 6 24 57 1 6 25 58 1 6 26 59 1 1 27 60 1 6 28 61 1 0 28 62 1 0 29 63 1 0 31 64 1 0 32 65 1 0 33 66 1 0 37 67 1 0 37 68 1 0 37 69 1 0 M END

Standard InCHIKey	GMQXOLRKJQWPNB-MVVLSVRYSA-N
Standard InCHI	InChI=1S/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3+/t16-,18+,20+,21-,22+,24-,25-/m0/s1
SMILES	C/C=C/1[C@H](CC(=O)OCCc2ccc(cc2)O)C(=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	524.19	Volume:	502.314 ? Van der Waals volume.
Dense:	1.044	LogP:	1.045 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.312 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.188 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	21.0
TPSA:	181.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.21	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.574	Fsp³:	0.52
MCE-18:	74.105 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.48	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.079 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.395 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.15

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.871	MDCK Permeability:	-5.144
Pgp-inhibitor:	0.003	Pgp-substrate:	0.483
PAMPA:	0.959 ? 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):	0.084
20% Bioavailability (F20%):	0.182	30% Bioavailability (F30%):	0.941
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.705
Plasma Protein Binding (PPB):	74.145%	Volume Distribution (VD):	-0.274
Fu:	24.722% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.081
BSEP inhibitor:	0.347

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.236
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.013	CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.01
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.83 ? 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):

2.576

Half-life (T1/2):

1.937

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.187
Human Hepatotoxicity (H-HT):	0.804	Drug-induced Liver Injury (DILI):	0.924
AMES Toxicity:	0.796	Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.239	Skin Sensitization:	1.0
Carcinogencity:	0.283	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.304	Ototoxicity:	0.95
Hematotoxicity:	0.375	Drug-induced Nephrotoxicity:	0.839
Genotoxicity:	0.995	RPMI-8226 Immunitoxicity:	0.07
A549 Cytotoxicity:	0.229	Hek293 Cytotoxicity:	0.495
BCF:	0.481 ? 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:	3.17 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.918 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.942 ? 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
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/(SICI)1097-0010(199909)79:12<1620::AID-JSFA410>3.0.CO;2-G]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80Ã‚Â°N and longitude 4Ã‚Â°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1007/s00217-002-0656-1]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1007/s00217-015-2561-4]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-015-0761-z]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s12010-013-0354-4]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.foodchem.2007.07.014]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.foodchem.2010.05.061]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.foodchem.2010.05.061]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.indcrop.2013.08.051]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.ssnmr.2006.05.001]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.yclnex.2017.01.002; 10.31989/ffhd.v6i3.245]DOI[10.1016/j.yclnex.2017.01.002; 10.31989/ffhd.v6i3.245]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/S-2006-958077]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1080/09064710.2011.598543]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1111/j.1365-2621.1989.tb04709.x]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1111/j.1745-4530.2009.00507.x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1186/s40064-015-0831-z]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1501/Tarimbil_0000001065]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.15835/NBHA4017181]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.17221/540/2012-CJFS]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.2137/145960607781635822]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.2478/aoas-2014-0072]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.3136/NSKKK.48.606]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.3390/agriculture2030244]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11411539]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12802735]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[15563205]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18384095]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros AgrÃƒÂ³nomos de Albacete	2007	PMID[19256538]
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000781]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014168]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540838]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295708]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[25026919]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25102361]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25306330]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[25977015]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[26351516]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[27556441]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Aug	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Cracow, Poland	2008-Sep	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Sep	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Oct	PMID[31206724]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[31619015]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35986990]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36770740]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985747]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37087263]
NPO53555	Vitis riparia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446586]
NPO42254	Vitis californica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446586]
NPO3690	Vitis amurensis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446586]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446586]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37924762]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38306771]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38474614]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893452]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Flowers	n.a.		PMID[9301422]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[9301422]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16845	Euodia bodinieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4877	Euodia officinalis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8314	Euodia ruticarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3690	Vitis amurensis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53555	Vitis riparia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3690	Vitis amurensis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18105	Fructus ligustri lucidi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO3690	Vitis amurensis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4877	Euodia officinalis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8314	Euodia ruticarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16845	Euodia bodinieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18340	Ligustrum lucidum	Species	Oleaceae	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
NPO17024	Vitis vinifera	n.a.	n.a.	0.0032 Â± 0.0004	n.a.	n.a.	mg/100g	PMID[37446586]
NPO28608	Olea europaea	n.a.	Fruits	1025	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	Oil	n.a.	0.32 Â± 0.44	n.a.	n.a.	mg/g	PMID[38306771]
NPO28608	Olea europaea	Oil	n.a.	0.07 Â± 0.24	n.a.	n.a.	mg/g	PMID[38306771]
NPO28608	Olea europaea	Oil	n.a.	0.06 Â± 0.20	n.a.	n.a.	mg/g	PMID[38306771]
NPO28608	Olea europaea	n.a.	Fruits	302	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	622	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1428	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1261	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1555	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1512	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1861	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1398	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1147	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	2061	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	2106	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1474	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1801	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	695	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	832	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1203	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1348	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1777	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	1410	n.a.	n.a.	mg/kg	PMID[36985747]
NPO28608	Olea europaea	n.a.	Fruits	2925	n.a.	n.a.	mg/kg	PMID[36985747]
NPO3690	Vitis amurensis	n.a.	n.a.	0.0074 Â± 0.0009	n.a.	n.a.	mg/100g	PMID[37446586]
NPO42254	Vitis californica	n.a.	n.a.	0.0066 Â± 0.0012	n.a.	n.a.	mg/100g	PMID[37446586]
NPO53555	Vitis riparia	n.a.	n.a.	0.0078 Â± 0.0014	n.a.	n.a.	mg/100g	PMID[37446586]
NPO7269	Aronia melanocarpa	Ultrasonic extraction	Fruits	2.19 Â± 0.14	n.a.	n.a.	%	PMID[38893452]

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
Inhibition	3
EC50	2
IC50	1

Activity Type	# Activity
Cell line	4
Others	1
Non-molecular	1

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
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	-9.3	%	PMID[20000781]
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	-76.4	%	PMID[20000781]
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	-9.8	%	PMID[20000781]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[28551177]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	100000.0	nM	PMID[21955940]
NPT1	Others	Radical scavenging activity	n.a.	EC50	>	100000.0	nM	PMID[21955940]

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 NPC169398 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	7244
0.1-0.2	36377
0.2-0.3	5486
0.3-0.4	632
0.4-0.5	88
0.5-0.6	12
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8961	High Similarity	NPC469364
0.8961	High Similarity	NPC609284
0.8784	High Similarity	NPC296643
0.8784	High Similarity	NPC299576
0.8608	High Similarity	NPC65262
0.8608	High Similarity	NPC84429
0.8608	High Similarity	NPC101686
0.8025	Intermediate Similarity	NPC23677
0.7722	Intermediate Similarity	NPC600692
0.764	Intermediate Similarity	NPC488387
0.7619	Intermediate Similarity	NPC198577
0.7556	Intermediate Similarity	NPC488386
0.7349	Intermediate Similarity	NPC488383
0.7	Intermediate Similarity	NPC303451
0.7	Intermediate Similarity	NPC72358
0.6744	Remote Similarity	NPC488388
0.6702	Remote Similarity	NPC488389
0.641	Remote Similarity	NPC469543
0.625	Remote Similarity	NPC488384
0.5638	Remote Similarity	NPC469367
0.5612	Remote Similarity	NPC488385
0.5567	Remote Similarity	NPC246893
0.5429	Remote Similarity	NPC488390
0.5417	Remote Similarity	NPC157338
0.5122	Remote Similarity	NPC6414
0.5122	Remote Similarity	NPC610085
0.5106	Remote Similarity	NPC202391
0.5106	Remote Similarity	NPC296659
0.5104	Remote Similarity	NPC240592
0.5104	Remote Similarity	NPC117346
0.5052	Remote Similarity	NPC212808

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC169398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3495
0.1-0.2	5498
0.2-0.3	155
0.3-0.4	2
0.4-0.5	0
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