NPASS Compound

Natural Product: NPC145722

Natural Product ID	NPC145722
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Wuweizisu B
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL402435
PubChem CID	158103
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 57 60 0 0 0 0 0 0 0 0999 V2000 -2.2248 -3.8812 -0.6177 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7709 -2.4352 -0.3495 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7495 -2.4544 0.7794 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3311 -1.5208 0.3324 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5255 -2.1710 0.2935 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6593 -1.5101 -0.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5892 -0.1911 -0.5942 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4001 0.4949 -0.5711 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3131 -0.1830 -0.1052 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7521 0.8132 -0.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0746 0.7480 -0.5708 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9484 -0.3210 -1.0590 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9217 -1.5297 -0.1256 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0801 -1.0806 1.3133 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8189 1.8808 -0.5196 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2612 3.0624 -0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9351 3.0624 0.4355 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1609 1.9305 0.3974 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1321 1.8432 0.8443 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4452 1.5139 2.2098 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6547 4.3710 0.8798 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6725 5.2151 0.3797 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7602 4.3382 0.1529 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2110 1.7920 -0.9946 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8713 2.1096 -2.3430 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7149 0.4853 -1.0598 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5660 1.2277 -0.1992 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8422 -2.1982 -0.1874 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9579 -3.5232 0.2317 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9703 -3.8258 -1.4383 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3275 -4.4018 -1.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6176 -4.3535 0.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2684 -2.1352 -1.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2928 -3.4655 0.7762 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1698 -2.1920 1.7469 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5464 -3.2022 0.6312 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9931 0.0522 -1.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6490 -0.6478 -2.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8578 -2.0950 -0.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3248 -1.9525 1.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0057 -0.4374 1.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2560 -0.4669 1.6713 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8533 1.9439 -0.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0066 2.4126 2.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5289 1.3091 2.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1810 0.7074 2.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4087 5.6770 -0.5884 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0148 5.9466 1.1403 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7309 2.6571 -2.7919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5862 1.2255 -2.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0529 2.8454 -2.2963 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7727 0.6931 0.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1911 2.2512 -0.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5418 1.3068 -0.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4394 -3.7522 1.1754 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0354 -3.7711 0.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6231 -4.2178 -0.5760 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 11 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 17 21 1 0 21 22 1 0 22 23 1 0 8 24 1 0 24 25 1 0 7 26 1 0 26 27 1 0 6 28 1 0 28 29 1 0 13 2 1 0 23 16 1 0 9 4 1 0 18 10 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 6 3 34 1 0 3 35 1 0 5 36 1 0 12 37 1 0 12 38 1 0 13 39 1 6 14 40 1 0 14 41 1 0 14 42 1 0 15 43 1 0 20 44 1 0 20 45 1 0 20 46 1 0 22 47 1 0 22 48 1 0 25 49 1 0 25 50 1 0 25 51 1 0 27 52 1 0 27 53 1 0 27 54 1 0 29 55 1 0 29 56 1 0 29 57 1 0 M END

Standard InCHIKey	RTZKSTLPRTWFEV-OLZOCXBDSA-N
Standard InCHI	InChI=1S/C23H28O6/c1-12-7-14-9-16(24-3)20(25-4)22(26-5)18(14)19-15(8-13(12)2)10-17-21(23(19)27-6)29-11-28-17/h9-10,12-13H,7-8,11H2,1-6H3/t12-,13+/m1/s1
SMILES	C[C@@H]1Cc2cc(c(c(c2-c2c(C[C@@H]1C)cc1c(c2OC)OCO1)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	400.19	Volume:	409.061 ? Van der Waals volume.
Dense:	0.978	LogP:	3.082 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.145 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.624 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	22.0
TPSA:	55.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.754	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.534	Fsp³:	0.478
MCE-18:	79.059 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.699	Fluc inhibitor:	0.339 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.525 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.149 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.308	Promiscuous compounds:	0.475

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.783	MDCK Permeability:	-4.674
Pgp-inhibitor:	0.69	Pgp-substrate:	0.038
PAMPA:	0.014 ? 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):	0.0
20% Bioavailability (F20%):	0.012	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.174

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.948	MRP1:	0.997
Plasma Protein Binding (PPB):	94.723%	Volume Distribution (VD):	0.237
Fu:	3.872% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.946
OATP1B3 inhibitor:	0.927	BCRP inhibitor:	0.014
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.971
CYP2C9-inhibitor:	0.95	CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.882	CYP2D6-substrate:	0.992
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.993
CYP2B6-substrate:	0.961	CYP2C8-inhibitor:	0.058
HLM stability:	0.835 ? 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):

4.856

Half-life (T1/2):

0.631

ADMET: Toxicity

hERG Blockers:	0.3	hERG Blockers (10um):	0.647
Human Hepatotoxicity (H-HT):	0.473	Drug-induced Liver Injury (DILI):	0.522
AMES Toxicity:	0.506	Rat Oral Acute Toxicity:	0.51
Maximum Recommended Daily Dose:	0.52	Skin Sensitization:	0.51
Carcinogencity:	0.899	Eye Corrosion:	0.004
Eye Irritation:	0.516	Respiratory Toxicity:	0.854
Drug-induced Neurotoxicity:	0.807	Ototoxicity:	0.462
Hematotoxicity:	0.678	Drug-induced Nephrotoxicity:	0.434
Genotoxicity:	0.365	RPMI-8226 Immunitoxicity:	0.197
A549 Cytotoxicity:	0.382	Hek293 Cytotoxicity:	0.647
BCF:	2.638 ? 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:	4.351 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.464 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.993 ? 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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s40502-015-0143-x]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1093/pcp/pcg054]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1134/S1021443709050069]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO210	Uvaria calamistrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075755]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO210	Uvaria calamistrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000019]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO11248	Tachigalia paniculata	n.a.	n.a.	n.a.	leaves	n.a.	n.a.	PMID[12444671]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO10540	Passiflora incarnata	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2026709]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34684838]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39683057]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11642	Dacrydium cupressinum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14255	Streptomyces flocculus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14354	Artemisia cina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11248	Tachigalia paniculata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO210	Uvaria calamistrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13166	Nicotiana undulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13568	Hypoxylon rubiginosum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12684	Trigonella grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5189	Glycine tomentella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10540	Passiflora incarnata	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11488	Alstonia muelleriana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7998	Senecio paludaffinis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10540	Passiflora incarnata	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10540	Passiflora incarnata	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11248	Tachigalia paniculata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5189	Glycine tomentella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12001	Saccharomyces pastori	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21854	Pterocladiella tenuis	Species	Gelidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18805	Tripolium pannonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO210	Uvaria calamistrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14255	Streptomyces flocculus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19635	Coreopsis nodosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7998	Senecio paludaffinis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22666	Haematococcus lacustris	Species	Haematococcaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13166	Nicotiana undulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO731	Panax schinseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11488	Alstonia muelleriana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14354	Artemisia cina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10540	Passiflora incarnata	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11642	Dacrydium cupressinum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12684	Trigonella grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13568	Hypoxylon rubiginosum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Inhibition	3
IC50	17
Activity	16
Survival	1

Activity Type	# Activity
Individual protein	3
Cell line	17
Others	14
Non-molecular	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	12.72	%	PMID[23062825]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-4.27	%	PMID[23062825]
NPT591	Individual protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	=	73.0	nM	PMID[35390715]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	100000.0	nM	PMID[18063366]
NPT1086	Cell line	SK-HEP1	Homo sapiens	IC50	>	100000.0	nM	PMID[18063366]
NPT2548	Cell line	SNU-638	Homo sapiens	IC50	>	100000.0	nM	PMID[18063366]
NPT2548	Cell line	SNU-638	Homo sapiens	IC50	=	23100.0	nM	PMID[18063366]
NPT396	Cell line	T47D	Homo sapiens	IC50	>	100000.0	nM	PMID[18063366]
NPT396	Cell line	T47D	Homo sapiens	IC50	=	19200.0	nM	PMID[18063366]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	88100.0	nM	PMID[18063366]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	14100.0	nM	PMID[18063366]
NPT111	Cell line	K562	Homo sapiens	IC50	=	62600.0	nM	PMID[18063366]
NPT111	Cell line	K562	Homo sapiens	IC50	=	22000.0	nM	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	IC50	=	87800.0	nM	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	IC50	=	21100.0	nM	PMID[18063366]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	52400.0	nM	PMID[16562834]
NPT71	Cell line	HEK293	Homo sapiens	Inhibition	=	-17.8	%	PMID[24018191]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	128.0	%	PMID[25302569]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	102.0	%	PMID[25302569]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	64.8	%	PMID[25302569]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	8.8	%	PMID[25302569]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	26.4	%	PMID[25302569]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[27919656]
NPT2	Others	Unspecified	n.a.	Activity	=	66.0	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	42.0	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	94.0	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	121.0	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	232.0	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	283.0	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	39.0	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	38.0	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	40.4	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	36.9	%	PMID[25302569]
NPT2	Others	Unspecified	n.a.	Activity	=	22.7	%	PMID[25302569]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21742	Cell line	L02	Homo sapiens	Survival	=	42.8	%	PMID[24602900]

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 NPC145722 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	25872
0.1-0.2	21678
0.2-0.3	1879
0.3-0.4	257
0.4-0.5	102
0.5-0.6	40
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC256776
1.0	High Similarity	NPC185680
0.9459	High Similarity	NPC32189
0.7838	Intermediate Similarity	NPC283114
0.7838	Intermediate Similarity	NPC207702
0.7838	Intermediate Similarity	NPC149008
0.75	Intermediate Similarity	NPC220577
0.7347	Intermediate Similarity	NPC230538
0.7347	Intermediate Similarity	NPC229172
0.7347	Intermediate Similarity	NPC103637
0.7347	Intermediate Similarity	NPC36531
0.7083	Intermediate Similarity	NPC53722
0.7083	Intermediate Similarity	NPC201404
0.7083	Intermediate Similarity	NPC290714
0.7059	Intermediate Similarity	NPC76415
0.7059	Intermediate Similarity	NPC218510
0.6939	Remote Similarity	NPC172171
0.6939	Remote Similarity	NPC239254
0.6939	Remote Similarity	NPC133934
0.6744	Remote Similarity	NPC87295
0.6667	Remote Similarity	NPC304821
0.66	Remote Similarity	NPC184684
0.66	Remote Similarity	NPC184641
0.6102	Remote Similarity	NPC473323
0.6071	Remote Similarity	NPC166506
0.6071	Remote Similarity	NPC110763
0.6071	Remote Similarity	NPC85141
0.6	Remote Similarity	NPC473425
0.5957	Remote Similarity	NPC216434
0.5957	Remote Similarity	NPC103448
0.5957	Remote Similarity	NPC606558
0.5833	Remote Similarity	NPC324962
0.58	Remote Similarity	NPC141493
0.5763	Remote Similarity	NPC191352
0.5714	Remote Similarity	NPC206737
0.5714	Remote Similarity	NPC289258
0.5714	Remote Similarity	NPC611061
0.5686	Remote Similarity	NPC865
0.5625	Remote Similarity	NPC63061
0.5625	Remote Similarity	NPC475229
0.56	Remote Similarity	NPC326144
0.5593	Remote Similarity	NPC154971
0.5593	Remote Similarity	NPC121661
0.5577	Remote Similarity	NPC184928
0.5532	Remote Similarity	NPC474295
0.5517	Remote Similarity	NPC73467
0.5484	Remote Similarity	NPC126405
0.5484	Remote Similarity	NPC53669
0.5484	Remote Similarity	NPC77237
0.5484	Remote Similarity	NPC297271
0.5484	Remote Similarity	NPC224472
0.5484	Remote Similarity	NPC16791
0.5484	Remote Similarity	NPC217708
0.5424	Remote Similarity	NPC189239
0.5424	Remote Similarity	NPC252286
0.5417	Remote Similarity	NPC102256
0.5417	Remote Similarity	NPC475868
0.5349	Remote Similarity	NPC471182
0.5312	Remote Similarity	NPC280778
0.5246	Remote Similarity	NPC471154
0.5231	Remote Similarity	NPC83049
0.5231	Remote Similarity	NPC320471
0.5231	Remote Similarity	NPC118162
0.5185	Remote Similarity	NPC327651
0.5161	Remote Similarity	NPC198461
0.5091	Remote Similarity	NPC318286
0.5077	Remote Similarity	NPC475756
0.5075	Remote Similarity	NPC29727

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC145722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5042
0.1-0.2	3972
0.2-0.3	130
0.3-0.4	6
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