NPASS Compound

Natural Product: NPC158537

Natural Product ID	NPC158537
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KMOUJOKENFFTPU-NFRVFMFJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44257792
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 51 54 0 0 0 0 0 0 0 0999 V2000 -5.6564 0.6442 -0.6762 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9056 1.1190 -1.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0439 0.4350 -0.6411 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8758 -0.7321 0.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6049 -1.2130 0.4090 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4674 -0.5313 0.0408 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1268 -0.9982 0.3740 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8606 -2.1464 1.0776 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5701 -2.5521 1.3719 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3183 -3.5992 2.0139 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5439 -1.7484 0.9257 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2262 -2.0719 1.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7910 -1.2380 0.7066 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5336 -0.0899 0.0034 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8198 0.1983 -0.2223 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8437 -0.6052 0.2238 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1021 -0.2877 -0.0160 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5126 0.7502 -0.4666 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8856 0.6539 -0.3560 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5929 0.6441 -1.6969 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6430 1.6951 -1.8294 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6036 1.6464 -0.6593 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7678 1.5897 0.6101 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2161 0.3928 1.3819 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6267 0.4942 1.4784 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4243 1.7096 0.4007 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3865 0.5092 -0.8208 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1478 2.9811 -1.9081 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1896 -0.6021 -1.8676 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0350 -3.2243 1.8773 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3085 0.9188 -0.9816 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7536 1.1848 -0.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0367 2.0387 -1.5710 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7757 -1.2807 0.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 -2.1307 0.9664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6691 -2.7687 1.4225 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8051 -1.5263 0.9194 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0656 1.0814 -0.7651 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1500 -0.2611 0.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7983 0.7861 -2.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2332 1.4975 -2.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2063 2.5754 -0.7103 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0663 2.4945 1.2249 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7761 0.2886 2.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0727 -0.5213 0.7333 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0614 -0.3793 1.3866 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3319 0.7811 -1.0317 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9015 3.5987 -1.7684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2805 -0.8394 -2.8375 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4698 -3.2502 2.7873 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4132 1.8889 -1.2448 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 14 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 24 25 1 0 23 26 1 0 22 27 1 0 21 28 1 0 20 29 1 0 12 30 1 0 3 31 1 0 6 1 1 0 17 7 1 0 26 19 1 0 16 11 1 0 1 32 1 0 2 33 1 0 4 34 1 0 5 35 1 0 8 36 1 0 13 37 1 0 15 38 1 0 19 39 1 1 20 40 1 0 21 41 1 6 22 42 1 1 23 43 1 0 24 44 1 0 24 45 1 0 25 46 1 0 27 47 1 0 28 48 1 0 29 49 1 0 30 50 1 0 31 51 1 0 M END

Standard InCHIKey	KMOUJOKENFFTPU-NFRVFMFJSA-N
Standard InCHI	InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16?,18-,19+,20?,21-/m1/s1
SMILES	c1cc(ccc1c1cc(=O)c2c(cc(cc2o1)O[C@H]1C([C@H]([C@@H](C(CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	432.11	Volume:	404.357 ? Van der Waals volume.
Dense:	1.069	LogP:	1.078 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.327 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.495 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	170.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.331	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.804	Fsp³:	0.286
MCE-18:	84.259 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.655	Fluc inhibitor:	0.272 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.984 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.892 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.261	Promiscuous compounds:	0.417

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.333	MDCK Permeability:	-5.018
Pgp-inhibitor:	0.0	Pgp-substrate:	0.818
PAMPA:	0.999 ? 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):	0.733
20% Bioavailability (F20%):	0.87	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.627
Plasma Protein Binding (PPB):	82.628%	Volume Distribution (VD):	0.03
Fu:	16.926% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.921
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.451
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:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.399
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.943
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):

3.309

Half-life (T1/2):

3.082

ADMET: Toxicity

hERG Blockers:	0.062	hERG Blockers (10um):	0.29
Human Hepatotoxicity (H-HT):	0.523	Drug-induced Liver Injury (DILI):	0.91
AMES Toxicity:	0.714	Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.269	Skin Sensitization:	0.792
Carcinogencity:	0.434	Eye Corrosion:	0.0
Eye Irritation:	0.45	Respiratory Toxicity:	0.065
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.757
Hematotoxicity:	0.064	Drug-induced Nephrotoxicity:	0.148
Genotoxicity:	0.893	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.21	Hek293 Cytotoxicity:	0.646
BCF:	0.421 ? 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:	2.84 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.265 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.512 ? 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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11627-001-0052-8]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12088434]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29726697]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34332066]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34443694]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34453492]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34770961]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35631245]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37020229]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37226152]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257205]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38370080]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38381096]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38695450]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39407547]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25547	Spirodela polyrhiza	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25902	Glechoma grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25547	Spirodela polyrhiza	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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
NPO20440	Chrysanthemum x morifolium	n.a.	Flowers	0.0101	n.a.	n.a.	mg/g of FW	DOI[10.3136/fstr.15.499]
NPO22782	Lens culinaris	n.a.	Seeds	0.18	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

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 NPC158537 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	24673
0.1-0.2	21156
0.2-0.3	2580
0.3-0.4	871
0.4-0.5	346
0.5-0.6	97
0.6-0.7	74
0.7-0.8	0
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC39360
1.0	High Similarity	NPC29763
1.0	High Similarity	NPC210003
0.8696	High Similarity	NPC189142
0.8696	High Similarity	NPC77660
0.8429	Intermediate Similarity	NPC95090
0.8429	Intermediate Similarity	NPC27408
0.8406	Intermediate Similarity	NPC331652
0.8286	Intermediate Similarity	NPC261866
0.8219	Intermediate Similarity	NPC601144
0.8108	Intermediate Similarity	NPC311830
0.7945	Intermediate Similarity	NPC27942
0.7733	Intermediate Similarity	NPC22832
0.7733	Intermediate Similarity	NPC243930
0.7671	Intermediate Similarity	NPC93337
0.7671	Intermediate Similarity	NPC297987
0.7671	Intermediate Similarity	NPC146792
0.7671	Intermediate Similarity	NPC323593
0.7671	Intermediate Similarity	NPC203500
0.7568	Intermediate Similarity	NPC105025
0.7403	Intermediate Similarity	NPC607707
0.7333	Intermediate Similarity	NPC610763
0.7297	Intermediate Similarity	NPC19709
0.7284	Intermediate Similarity	NPC65003
0.7179	Intermediate Similarity	NPC116458
0.7179	Intermediate Similarity	NPC246943
0.716	Intermediate Similarity	NPC44931
0.7067	Intermediate Similarity	NPC83283
0.7067	Intermediate Similarity	NPC143851
0.6974	Remote Similarity	NPC277205
0.6974	Remote Similarity	NPC37919
0.6974	Remote Similarity	NPC136042
0.6914	Remote Similarity	NPC8856
0.6905	Remote Similarity	NPC64051
0.6883	Remote Similarity	NPC84362
0.6883	Remote Similarity	NPC181712
0.6842	Remote Similarity	NPC58053
0.6753	Remote Similarity	NPC259152
0.6711	Remote Similarity	NPC473043
0.6709	Remote Similarity	NPC282169
0.6709	Remote Similarity	NPC307938
0.6667	Remote Similarity	NPC186807
0.6667	Remote Similarity	NPC58716
0.6667	Remote Similarity	NPC270675
0.6667	Remote Similarity	NPC190003
0.6667	Remote Similarity	NPC45638
0.6667	Remote Similarity	NPC195685
0.6625	Remote Similarity	NPC601710
0.6623	Remote Similarity	NPC289667
0.6623	Remote Similarity	NPC45618
0.6588	Remote Similarity	NPC122809
0.6582	Remote Similarity	NPC201292
0.6575	Remote Similarity	NPC191154
0.6543	Remote Similarity	NPC605784
0.6538	Remote Similarity	NPC197896
0.6538	Remote Similarity	NPC168822
0.6538	Remote Similarity	NPC313163
0.6517	Remote Similarity	NPC101636
0.6517	Remote Similarity	NPC298171
0.6512	Remote Similarity	NPC64425
0.6444	Remote Similarity	NPC472994
0.6418	Remote Similarity	NPC234133
0.641	Remote Similarity	NPC249281
0.641	Remote Similarity	NPC108831
0.641	Remote Similarity	NPC182634
0.6395	Remote Similarity	NPC115674
0.6364	Remote Similarity	NPC210961
0.6341	Remote Similarity	NPC602805
0.631	Remote Similarity	NPC472607
0.6296	Remote Similarity	NPC191306
0.6296	Remote Similarity	NPC285197
0.6279	Remote Similarity	NPC210073
0.6267	Remote Similarity	NPC134819
0.6265	Remote Similarity	NPC601586
0.625	Remote Similarity	NPC65711
0.6222	Remote Similarity	NPC475382
0.622	Remote Similarity	NPC80188
0.618	Remote Similarity	NPC229409
0.618	Remote Similarity	NPC35119
0.617	Remote Similarity	NPC472993
0.6145	Remote Similarity	NPC88023
0.6145	Remote Similarity	NPC220169
0.6145	Remote Similarity	NPC309025
0.6122	Remote Similarity	NPC298666
0.6118	Remote Similarity	NPC606546
0.6098	Remote Similarity	NPC80140
0.6098	Remote Similarity	NPC609451
0.6092	Remote Similarity	NPC22062
0.6092	Remote Similarity	NPC473634
0.6092	Remote Similarity	NPC138811
0.6049	Remote Similarity	NPC46420
0.6049	Remote Similarity	NPC84265
0.6049	Remote Similarity	NPC24043
0.6044	Remote Similarity	NPC195257
0.6024	Remote Similarity	NPC486578
0.6024	Remote Similarity	NPC605067
0.6	Remote Similarity	NPC77672
0.6	Remote Similarity	NPC133671
0.6	Remote Similarity	NPC135391
0.6	Remote Similarity	NPC32641
0.6	Remote Similarity	NPC256188
0.6	Remote Similarity	NPC78263
0.6	Remote Similarity	NPC250069
0.5955	Remote Similarity	NPC46202
0.5938	Remote Similarity	NPC164704
0.593	Remote Similarity	NPC251417
0.5914	Remote Similarity	NPC179862
0.5909	Remote Similarity	NPC607513
0.5904	Remote Similarity	NPC20505
0.5882	Remote Similarity	NPC276377
0.5833	Remote Similarity	NPC284960
0.5824	Remote Similarity	NPC473623
0.5814	Remote Similarity	NPC172807
0.5802	Remote Similarity	NPC238376
0.5773	Remote Similarity	NPC25523
0.5761	Remote Similarity	NPC488089
0.5745	Remote Similarity	NPC253685
0.5732	Remote Similarity	NPC8573
0.5732	Remote Similarity	NPC234739
0.573	Remote Similarity	NPC150164
0.5682	Remote Similarity	NPC603300
0.5663	Remote Similarity	NPC488080
0.5663	Remote Similarity	NPC169977
0.5652	Remote Similarity	NPC209296
0.5652	Remote Similarity	NPC150767
0.5647	Remote Similarity	NPC608742
0.5612	Remote Similarity	NPC470715
0.561	Remote Similarity	NPC110349
0.5595	Remote Similarity	NPC222936
0.5595	Remote Similarity	NPC198324
0.5595	Remote Similarity	NPC182045
0.5595	Remote Similarity	NPC60966
0.5579	Remote Similarity	NPC484301
0.5556	Remote Similarity	NPC479405
0.5556	Remote Similarity	NPC311850
0.5556	Remote Similarity	NPC3583
0.5542	Remote Similarity	NPC145038
0.5542	Remote Similarity	NPC56077
0.5542	Remote Similarity	NPC281131
0.5542	Remote Similarity	NPC253662
0.5542	Remote Similarity	NPC161749
0.5542	Remote Similarity	NPC179950
0.5542	Remote Similarity	NPC88789
0.5542	Remote Similarity	NPC491374
0.5529	Remote Similarity	NPC168584
0.5521	Remote Similarity	NPC14187
0.55	Remote Similarity	NPC470716
0.55	Remote Similarity	NPC488083
0.5495	Remote Similarity	NPC479404
0.5495	Remote Similarity	NPC186816
0.5484	Remote Similarity	NPC124155
0.5476	Remote Similarity	NPC22195
0.5476	Remote Similarity	NPC245014
0.5476	Remote Similarity	NPC10807
0.5476	Remote Similarity	NPC271692
0.5476	Remote Similarity	NPC21190
0.5476	Remote Similarity	NPC161881
0.5476	Remote Similarity	NPC73511
0.5444	Remote Similarity	NPC275454
0.5437	Remote Similarity	NPC470717
0.5435	Remote Similarity	NPC240306
0.5432	Remote Similarity	NPC603508
0.5422	Remote Similarity	NPC348541
0.5417	Remote Similarity	NPC108406
0.5412	Remote Similarity	NPC117260
0.5392	Remote Similarity	NPC68592
0.5385	Remote Similarity	NPC473512
0.5385	Remote Similarity	NPC129827
0.5385	Remote Similarity	NPC183672
0.5385	Remote Similarity	NPC470720
0.5368	Remote Similarity	NPC80068
0.5366	Remote Similarity	NPC600396
0.5357	Remote Similarity	NPC64305
0.5357	Remote Similarity	NPC609879
0.5352	Remote Similarity	NPC127447
0.5352	Remote Similarity	NPC29353
0.5349	Remote Similarity	NPC488071
0.5319	Remote Similarity	NPC72016
0.5301	Remote Similarity	NPC159707
0.5301	Remote Similarity	NPC194593
0.53	Remote Similarity	NPC480441
0.5287	Remote Similarity	NPC197285
0.5281	Remote Similarity	NPC4390
0.5244	Remote Similarity	NPC288084
0.5233	Remote Similarity	NPC472459
0.5233	Remote Similarity	NPC100720
0.5233	Remote Similarity	NPC599850
0.5213	Remote Similarity	NPC479403
0.52	Remote Similarity	NPC137062
0.52	Remote Similarity	NPC473278
0.5192	Remote Similarity	NPC198199
0.5185	Remote Similarity	NPC199172
0.5176	Remote Similarity	NPC282987
0.5176	Remote Similarity	NPC105511
0.5172	Remote Similarity	NPC611303
0.5169	Remote Similarity	NPC203050
0.5169	Remote Similarity	NPC469931
0.5169	Remote Similarity	NPC488072
0.5169	Remote Similarity	NPC225434
0.5146	Remote Similarity	NPC132111

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5750
0.1-0.2	3304
0.2-0.3	80
0.3-0.4	6
0.4-0.5	8
0.5-0.6	2
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
0.5652	Remote Similarity	NPD7054	Phase 4
0.5542	Remote Similarity	NPD4381	Clinical (unspecified phase)

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