NPASS Compound

Natural Product: NPC109816

Natural Product ID	NPC109816
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NIABBGMPPWXWOJ-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003540] Flavonoid-8-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 70 74 0 0 0 0 0 0 0 0999 V2000 -3.8135 4.6885 -0.4328 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0718 5.1284 -0.8796 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9740 4.2312 -1.4072 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6181 2.9080 -1.4859 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 2.5009 -1.0409 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4600 3.3746 -0.5108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1761 2.8880 -0.0637 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2293 3.7376 0.4607 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0072 3.2451 0.8808 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8207 4.0597 1.3509 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2790 1.9053 0.7814 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4922 1.3780 1.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7106 0.0223 1.0611 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6987 -0.7751 0.5189 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5097 -0.2590 0.1092 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7294 1.1040 0.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8759 1.5894 -0.1505 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4718 -1.0999 -0.4191 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4461 -1.7534 0.3689 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7958 -1.4196 -0.1448 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7095 -2.6014 -0.3139 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9915 -3.8324 -0.8074 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4929 -3.6376 -0.8415 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1234 -3.1042 0.3691 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2402 -4.9028 0.0508 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6923 -2.2888 -1.2543 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3932 -0.5304 0.7495 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8858 -2.1525 0.3721 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8870 -0.5842 1.4431 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0064 -0.7654 0.6057 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4155 -2.2196 0.5150 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8081 -2.3479 -0.0507 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2938 -1.0582 -0.6834 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1522 0.0410 0.3165 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2053 1.4198 -0.3152 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2953 1.5185 -1.1656 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0715 -0.0818 1.1693 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6011 -0.8159 -1.8762 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8468 -3.3213 -1.0498 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4338 -2.7843 1.7896 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4455 2.2110 1.7156 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2267 4.6828 -1.8498 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1803 5.4600 -0.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3708 6.1634 -0.8266 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3367 2.1938 -1.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1339 1.4634 -1.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4381 4.8136 0.5489 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2671 -1.4157 1.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7382 -0.8931 -1.1243 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2229 -2.8079 0.6472 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3230 -4.1490 -1.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0378 -4.6423 -0.9397 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1642 -3.0463 -1.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8597 -5.7030 -0.3636 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3056 -2.5173 -2.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3298 -0.8604 1.6854 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0719 -2.6527 1.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8395 -0.3605 -0.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7090 -2.7822 -0.1276 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5547 -2.6078 0.7452 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3513 -1.2311 -0.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0670 -0.0110 0.9779 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3939 2.1277 0.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2501 1.6860 -0.7971 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1113 1.9211 -2.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8655 -1.5512 -2.4955 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0059 -3.2782 -1.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2381 -3.7596 1.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0555 2.7281 1.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7292 5.4141 -1.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 21 26 1 0 20 27 1 0 14 28 1 0 13 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 12 41 1 0 3 42 1 0 6 1 1 0 17 7 1 0 24 19 1 0 37 30 1 0 16 11 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 8 47 1 0 19 48 1 0 20 49 1 0 21 50 1 0 22 51 1 0 23 52 1 0 23 53 1 0 25 54 1 0 26 55 1 0 27 56 1 0 28 57 1 0 30 58 1 0 31 59 1 0 32 60 1 0 33 61 1 0 34 62 1 0 35 63 1 0 35 64 1 0 36 65 1 0 38 66 1 0 39 67 1 0 40 68 1 0 41 69 1 0 42 70 1 0 M END

Standard InCHIKey	NIABBGMPPWXWOJ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C26H28O16/c27-6-13-16(32)18(34)20(36)26(40-13)41-23-17(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-22(14)24(21(23)37)42-25-19(35)15(31)11(30)7-38-25/h1-5,11,13,15-16,18-20,25-28,30-37H,6-7H2
SMILES	c1cc(ccc1c1cc(=O)c2c(c(c(c(c2o1)OC1C(C(C(CO1)O)O)O)O)OC1C(C(C(C(CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.14	Volume:	535.022 ? Van der Waals volume.
Dense:	1.114	LogP:	-1.336 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.043 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.111 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.142	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.776	Fsp³:	0.423
MCE-18:	120.378 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.172	Fluc inhibitor:	0.051 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.798 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.827 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.158	Promiscuous compounds:	0.427

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.37	MDCK Permeability:	-4.908
Pgp-inhibitor:	0.0	Pgp-substrate:	0.905
PAMPA:	1.0 ? 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):	0.93
20% Bioavailability (F20%):	0.957	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.793
Plasma Protein Binding (PPB):	79.188%	Volume Distribution (VD):	-0.034
Fu:	20.368% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.542	BCRP inhibitor:	0.053
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.84	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.961
HLM stability:	0.001 ? 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):

1.974

Half-life (T1/2):

3.724

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.365
Human Hepatotoxicity (H-HT):	0.47	Drug-induced Liver Injury (DILI):	0.585
AMES Toxicity:	0.462	Rat Oral Acute Toxicity:	0.186
Maximum Recommended Daily Dose:	0.318	Skin Sensitization:	0.113
Carcinogencity:	0.076	Eye Corrosion:	0.0
Eye Irritation:	0.01	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.063	Ototoxicity:	0.989
Hematotoxicity:	0.018	Drug-induced Nephrotoxicity:	0.048
Genotoxicity:	0.542	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.081	Hek293 Cytotoxicity:	0.776
BCF:	0.271 ? 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:	2.594 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.51 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.422 ? 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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11164-015-2099-x]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s40502-015-0143-x]
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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1134/S1021443711030101]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
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]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39683057]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24613	Arisaema consanguineum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24715	Arisaema heterophyllum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24613	Arisaema consanguineum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24715	Arisaema heterophyllum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15711	Radix glycyrrhizae preparata	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24613	Arisaema consanguineum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8180	Radix glycyrrhizae praeparata	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15161.1	Isodon lophanthoides var. gerardiana	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24613	Arisaema consanguineum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	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]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24715	Arisaema heterophyllum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Molecular-level activity

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

In vitro activity

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

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC109816 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	22686
0.1-0.2	23512
0.2-0.3	2584
0.3-0.4	771
0.4-0.5	248
0.5-0.6	45
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9028	High Similarity	NPC259152
0.6667	Remote Similarity	NPC472607
0.631	Remote Similarity	NPC93337
0.6235	Remote Similarity	NPC105025
0.619	Remote Similarity	NPC39360
0.619	Remote Similarity	NPC29763
0.619	Remote Similarity	NPC210003
0.6118	Remote Similarity	NPC146792
0.6	Remote Similarity	NPC83283
0.5977	Remote Similarity	NPC198324
0.5862	Remote Similarity	NPC610763
0.5747	Remote Similarity	NPC8573
0.5556	Remote Similarity	NPC168584
0.5506	Remote Similarity	NPC45638
0.5455	Remote Similarity	NPC58053
0.5455	Remote Similarity	NPC143851
0.5444	Remote Similarity	NPC201292
0.5417	Remote Similarity	NPC473512
0.5417	Remote Similarity	NPC129827
0.5395	Remote Similarity	NPC275836
0.5393	Remote Similarity	NPC189142
0.5393	Remote Similarity	NPC77660
0.5333	Remote Similarity	NPC186807
0.5333	Remote Similarity	NPC58716
0.5333	Remote Similarity	NPC488080
0.5333	Remote Similarity	NPC169977
0.5326	Remote Similarity	NPC601710
0.5281	Remote Similarity	NPC45618
0.5269	Remote Similarity	NPC602805
0.5222	Remote Similarity	NPC282987
0.5222	Remote Similarity	NPC95090
0.5222	Remote Similarity	NPC27408
0.5169	Remote Similarity	NPC331652
0.5165	Remote Similarity	NPC24043
0.5165	Remote Similarity	NPC472385
0.5161	Remote Similarity	NPC601144
0.5158	Remote Similarity	NPC172807
0.5155	Remote Similarity	NPC47923
0.5111	Remote Similarity	NPC261866
0.5111	Remote Similarity	NPC77672
0.5111	Remote Similarity	NPC133671
0.5111	Remote Similarity	NPC135391
0.5111	Remote Similarity	NPC78263
0.5111	Remote Similarity	NPC250069
0.5109	Remote Similarity	NPC27942
0.5106	Remote Similarity	NPC311830
0.5055	Remote Similarity	NPC297987
0.5055	Remote Similarity	NPC168822
0.5055	Remote Similarity	NPC323593
0.5055	Remote Similarity	NPC203500
0.5054	Remote Similarity	NPC191306
0.5054	Remote Similarity	NPC210094
0.5054	Remote Similarity	NPC609451
0.5052	Remote Similarity	NPC603300

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC109816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5602
0.1-0.2	3465
0.2-0.3	68
0.3-0.4	14
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