NPASS Compound

Natural Product: NPC87395

Natural Product ID	NPC87395
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MVOUGOXRXQDXDC-RSPRXDBDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	442665
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-glycosides [CHEMONTID:0003535] Flavonoid 8-C-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 71 75 0 0 0 0 0 0 0 0999 V2000 -3.9203 2.3302 0.8826 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1472 1.7415 -0.2905 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4929 2.8924 -1.0204 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7046 2.3576 -2.1800 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0008 1.0938 -1.7554 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9652 1.0102 -0.2584 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0698 -0.1077 0.1689 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2862 0.1668 0.4073 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1701 -0.8086 0.8045 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6412 -2.0662 0.9531 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3238 -2.3712 0.7295 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1863 -3.6417 0.8844 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5718 -4.5743 1.2458 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5258 -3.9094 0.6475 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3428 -2.8909 0.2552 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7693 -3.0786 -0.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3675 -4.3006 0.1198 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7157 -4.4080 -0.1566 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4974 -3.3475 -0.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9008 -2.1263 -0.7043 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5494 -1.9954 -0.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8393 -3.5293 -0.8246 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8287 -1.6797 0.1138 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5631 -1.3854 0.3291 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 -3.0762 1.3503 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5712 -0.4320 1.0202 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5223 -0.6434 -0.0659 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8328 0.4974 -0.9715 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2263 1.7112 -0.1841 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7827 1.5282 1.2237 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8257 2.8925 1.8907 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6513 2.8053 3.2666 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5991 0.8813 1.4206 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6411 1.7612 -0.1652 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8091 0.7656 -1.8859 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7511 -1.0153 0.5398 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6931 1.4861 0.2209 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2503 0.8197 0.2030 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2673 0.9983 -2.3252 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8001 3.3019 -2.6900 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5001 3.7471 -1.4709 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3644 2.1459 1.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1268 3.3943 0.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 1.7909 1.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9147 1.3177 -0.9673 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8672 3.4931 -0.3068 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4249 2.1323 -3.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5752 0.2106 -2.1169 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6246 1.9771 0.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9261 -4.9112 0.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8456 -5.1850 0.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1869 -5.3726 -0.0471 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5081 -1.2911 -1.0252 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1145 -1.0192 -0.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5365 -3.4084 -0.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9206 -3.6206 0.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9006 -1.0373 1.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3101 -1.5851 -0.6756 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7152 0.2665 -1.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8558 2.6560 -0.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5825 0.9396 1.7566 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0840 3.5404 1.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8439 3.3028 1.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9271 3.3743 3.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9209 0.9902 0.3876 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0891 1.5120 -2.4535 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6136 -1.7498 1.1935 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6230 2.1636 0.9628 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6651 1.9063 -2.3339 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5393 3.9684 -2.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3177 4.6977 -1.2797 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 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 19 22 1 0 15 23 1 0 23 24 1 0 10 25 1 0 9 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 29 34 1 0 28 35 1 0 27 36 1 0 8 37 1 0 6 38 1 0 5 39 1 0 4 40 1 0 3 41 1 0 38 2 1 0 24 7 1 0 33 26 1 0 24 11 2 0 21 16 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 6 3 46 1 1 4 47 1 6 5 48 1 6 6 49 1 1 14 50 1 0 17 51 1 0 18 52 1 0 20 53 1 0 21 54 1 0 22 55 1 0 25 56 1 0 26 57 1 1 27 58 1 6 28 59 1 6 29 60 1 6 30 61 1 1 31 62 1 0 31 63 1 0 32 64 1 0 34 65 1 0 35 66 1 0 36 67 1 0 37 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 M END

Standard InCHIKey	MVOUGOXRXQDXDC-RSPRXDBDSA-N
Standard InCHI	InChI=1S/C27H30O14/c1-8-17(31)21(35)23(37)27(39-8)16-20(34)15(26-24(38)22(36)18(32)13(7-28)41-26)19(33)14-11(30)6-12(40-25(14)16)9-2-4-10(29)5-3-9/h2-6,8,13,17-18,21-24,26-29,31-38H,7H2,1H3/t8-,13+,17-,18+,21+,22-,23+,24+,26-,27-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](c2c(c(c(c3c(=O)cc(c4ccc(cc4)O)oc23)O)[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.16	Volume:	534.737 ? Van der Waals volume.
Dense:	1.081	LogP:	0.35 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.942 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.132 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	30.0
TPSA:	250.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.172	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.823	Fsp³:	0.444
MCE-18:	122.949 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.618	Fluc inhibitor:	0.099 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.677 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.575 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.188	Promiscuous compounds:	0.331

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.385	MDCK Permeability:	-5.029
Pgp-inhibitor:	0.0	Pgp-substrate:	0.88
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):	0.814
20% Bioavailability (F20%):	0.608	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.611
Plasma Protein Binding (PPB):	84.147%	Volume Distribution (VD):	0.03
Fu:	13.106% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.325
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.001
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.011
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.09 ? 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):

2.272

Half-life (T1/2):

7.966

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.065
Human Hepatotoxicity (H-HT):	0.664	Drug-induced Liver Injury (DILI):	0.976
AMES Toxicity:	0.901	Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.133	Skin Sensitization:	0.997
Carcinogencity:	0.056	Eye Corrosion:	0.0
Eye Irritation:	0.21	Respiratory Toxicity:	0.012
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.92
Hematotoxicity:	0.275	Drug-induced Nephrotoxicity:	0.708
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.236
A549 Cytotoxicity:	0.581	Hek293 Cytotoxicity:	0.633
BCF:	0.346 ? 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:	2.825 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.407 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.532 ? 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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s40502-015-0143-x]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90113-8]
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]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987049]
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]
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.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	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]
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]
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]
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]
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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO782	Viola tricolor	Species	Violaceae	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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO782	Viola tricolor	Species	Violaceae	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 NPC87395 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	19889
0.1-0.2	27648
0.2-0.3	1929
0.3-0.4	323
0.4-0.5	45
0.5-0.6	17
0.6-0.7	4
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC112701
0.8158	Intermediate Similarity	NPC326592
0.8158	Intermediate Similarity	NPC109594
0.72	Intermediate Similarity	NPC209846
0.6923	Remote Similarity	NPC482721
0.6883	Remote Similarity	NPC328740
0.6883	Remote Similarity	NPC289774
0.625	Remote Similarity	NPC117418
0.5976	Remote Similarity	NPC53545
0.5952	Remote Similarity	NPC10807
0.5952	Remote Similarity	NPC161881
0.5732	Remote Similarity	NPC268193
0.573	Remote Similarity	NPC190393
0.5543	Remote Similarity	NPC47923
0.5506	Remote Similarity	NPC111249
0.5495	Remote Similarity	NPC44947
0.5495	Remote Similarity	NPC472607
0.5422	Remote Similarity	NPC56232
0.5422	Remote Similarity	NPC150123
0.5422	Remote Similarity	NPC608009
0.5181	Remote Similarity	NPC477897
0.5176	Remote Similarity	NPC289771
0.5176	Remote Similarity	NPC611357
0.5106	Remote Similarity	NPC603300
0.5056	Remote Similarity	NPC602537

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5627
0.1-0.2	3471
0.2-0.3	46
0.3-0.4	5
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