NPASS Compound

Natural Product: NPC284948

Natural Product ID	NPC284948
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cynarin
IUPAC Name	(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
Synonyms	Cynaricine; NSC-91529
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL487258
PubChem CID	5281769
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic acids and derivatives

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 61 63 0 0 0 0 0 0 0 0999 V2000 -3.1017 -0.8917 2.3667 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2226 -0.4607 1.1978 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2983 -0.7967 0.2505 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1746 -1.6293 0.5134 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0755 -0.8430 0.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2578 -1.5241 0.7925 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4719 -1.1346 0.1383 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8802 0.1937 0.1264 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1435 1.0243 0.7100 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1039 0.6450 -0.5261 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9240 -0.1628 -1.1521 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1506 0.1765 -1.8281 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9303 -0.7868 -2.4250 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0883 -0.4328 -3.0767 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4846 0.8783 -3.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7248 1.8380 -2.5589 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5563 1.4866 -1.9005 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1014 3.1797 -2.6115 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6692 1.2114 -3.8136 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1322 -3.0172 0.5717 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2172 -3.3109 -0.6123 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1888 -2.8621 -0.3453 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8294 -2.6690 -1.5766 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3469 -4.6343 -0.9503 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3380 -1.2436 2.2416 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4105 -0.7180 2.6961 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3620 -1.4973 3.1554 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3825 0.4158 0.8660 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2664 0.7393 1.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4127 1.5907 1.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3177 1.8954 2.5323 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4216 2.6923 2.3428 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6972 3.2400 1.1116 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8200 2.9509 0.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6945 2.1420 0.2718 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0602 3.4831 -1.1696 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7968 4.0508 0.8725 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1796 -1.9641 1.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 -0.6150 -0.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0651 0.1556 0.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3604 1.6884 -0.5020 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6171 -1.2225 -1.1448 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5823 -1.8166 -2.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6893 -1.2070 -3.5384 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0105 2.3126 -1.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9508 3.7618 -1.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5360 1.2411 -3.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7504 -3.5376 1.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1166 -3.4935 0.3236 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5937 -2.7326 -1.5074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6860 -3.6965 0.2262 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1283 -2.3554 -2.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2622 -4.9353 -0.7704 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5507 -2.0467 4.0084 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4978 0.7899 -0.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1360 0.3561 2.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0971 1.4646 3.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1197 2.9263 3.1492 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0323 1.9394 -0.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4006 4.1294 -1.5993 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5331 3.6389 0.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 6 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 15 19 1 0 6 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 6 25 1 0 25 26 2 0 25 27 1 0 2 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 22 4 1 0 35 30 1 0 17 12 1 0 4 38 1 1 5 39 1 0 5 40 1 0 10 41 1 0 11 42 1 0 13 43 1 0 14 44 1 0 17 45 1 0 18 46 1 0 19 47 1 0 20 48 1 0 20 49 1 0 21 50 1 6 22 51 1 1 23 52 1 0 24 53 1 0 27 54 1 0 28 55 1 0 29 56 1 0 31 57 1 0 32 58 1 0 35 59 1 0 36 60 1 0 37 61 1 0 M END

Standard InCHIKey	YDDUMTOHNYZQPO-RVXRWRFUSA-N
Standard InCHI	InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
SMILES	O=C(O[C@@H]1C[C@](OC(=O)/C=C/c2ccc(c(c2)O)O)(C[C@H]([C@@H]1O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.13	Volume:	491.768 ? Van der Waals volume.
Dense:	1.05	LogP:	1.427 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.554 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.717 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	211.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.164	Fsp³:	0.24
MCE-18:	81.29 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.829	Fluc inhibitor:	0.999 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.22 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.637 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.453	Promiscuous compounds:	0.318

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.581	MDCK Permeability:	-5.119
Pgp-inhibitor:	0.0	Pgp-substrate:	0.003
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):	0.325
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.132
Plasma Protein Binding (PPB):	74.75%	Volume Distribution (VD):	0.105
Fu:	21.457% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.859
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

7.312

Half-life (T1/2):

2.452

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.198
Human Hepatotoxicity (H-HT):	0.475	Drug-induced Liver Injury (DILI):	0.694
AMES Toxicity:	0.67	Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.843	Skin Sensitization:	1.0
Carcinogencity:	0.24	Eye Corrosion:	0.001
Eye Irritation:	0.578	Respiratory Toxicity:	0.049
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.901
Hematotoxicity:	0.013	Drug-induced Nephrotoxicity:	0.442
Genotoxicity:	0.963	RPMI-8226 Immunitoxicity:	0.011
A549 Cytotoxicity:	0.845	Hek293 Cytotoxicity:	0.137
BCF:	0.668 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.431 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.782 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.532 ? 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
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 17560738]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11627-001-0052-8]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2015.01.015]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
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]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/JMPR.9000078]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10553679]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720520]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12055308]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[12130858]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15070765]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15730262]
NPO14484	Echinacea purpurea	Species	Asteraceae	Eukaryota	root	n.a.	n.a.	PMID[15921428]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[16462067]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643020]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	roots	Gabon	1987	PMID[18327911]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
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]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19276083]
NPO14484	Echinacea purpurea	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[19374389]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20448045]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20509707]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20550123]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20843794]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO1528	Dalea elegans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21561780]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22194604]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22530813]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964677]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24516143]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25028392]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26099993]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26466957]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26774486]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26938998]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27242221]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27276091]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27807341]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28156114]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29400471]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30726671]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3430163]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37324556]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37770099]
NPO14484	Echinacea purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37959750]
NPO43006	Achillea milefollium	Genus	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38611571]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38754641]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8917504]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[97292]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14484	Echinacea purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4471	Blumea densiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1785	Corallina rubens	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6024	Cratoxylum formosum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1528	Dalea elegans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11062	Euonymus grandiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO480	Hygrophila erecta	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8685	Hymenocallis arenicola	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9525	Relicina samoensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24513	Streptomyces cyaneofuscatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO743	Wardomyces inflatus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18273	Merendera sobolifera	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11062	Euonymus grandiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14484	Echinacea purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	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]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14484	Echinacea purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8685	Hymenocallis arenicola	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11062	Euonymus grandiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28334	Pyrola decorata	Species	Ericaceae	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]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9124	Inula japonica	Species	Asteraceae	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]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11144	Centella asiatica	Species	Apiaceae	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]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28161	Stephania sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28691	Streptomyces odorifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27867	Turbo argyrostoma	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20395	Athanasia crithmifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28053	Quercus serrata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29353	Benzoin praecox	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28374	Pleogyne cunninghami	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28073	Crateva nurvala	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28200	Unonopsis glaucopetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28131	Polygala amara	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27943	Cardamine pinnata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29115	Rhinella arenarum	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5721	Psorothamnus spinosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28633	Bystropogon origanifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4471	Blumea densiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO480	Hygrophila erecta	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6331	Jacobaea subalpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18861	Pyxine coccifera	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28303	Pleogyne cunninghamii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24513	Streptomyces cyaneofuscatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27990	Schizonepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9525	Relicina samoensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO743	Wardomyces inflatus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11062	Euonymus grandiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6024	Cratoxylum formosum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28670	Mortierella elongata	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18273	Merendera sobolifera	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25704	Tetraneuris acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16819	Preussia aemulans	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28269	Rubus rosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8685	Hymenocallis arenicola	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1785	Corallina rubens	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1528	Dalea elegans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14484	Echinacea purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9124	Inula japonica	Species	Asteraceae	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
NPO18296	Diospyros kaki	n.a.	n.a.	13359.86 Â± 1.93	n.a.	n.a.	Î¼g/mL	PMID[37324556]
NPO43006	Achillea milefollium	n.a.	n.a.	0 Â± 0	n.a.	n.a.	Âµg/g	PMID[38611571]
NPO43006	Achillea milefollium	n.a.	n.a.	74.99 Â± 34.59	n.a.	n.a.	Âµg/g	PMID[38611571]
NPO43006	Achillea milefollium	n.a.	n.a.	30.2 Â± 34.59	n.a.	n.a.	Âµg/g	PMID[38611571]
NPO43006	Achillea milefollium	n.a.	n.a.	28.49 Â± 23.71	n.a.	n.a.	Âµg/g	PMID[38611571]
NPO43006	Achillea milefollium	n.a.	n.a.	2.87 Â± 6.75	n.a.	n.a.	Âµg/g	PMID[38611571]

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
IC50	2
Activity	19
Inhibition	9
ED50	1

Activity Type	# Activity
Individual protein	9
Cell line	18
Organism	1
Others	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	1600.0	nM	PMID[9986720]
NPT13	Individual protein	Tyrosine-protein kinase LCK	Homo sapiens	Inhibition	=	12.0	%	PMID[19427202]
NPT2739	Individual protein	Tyrosinase	Mus musculus	Inhibition	>	20.0	%	PMID[30030001]
NPT36	Individual protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	7.0	%	PMID[19427202]
NPT37	Individual protein	Signal transducer and activator of transcription 1-alpha/beta	Homo sapiens	Inhibition	=	4.0	%	PMID[19427202]
NPT39	Individual protein	Signal transducer and activator of transcription 5B	Homo sapiens	Inhibition	=	-1.0	%	PMID[19427202]
NPT5061	Individual protein	Alanine aminotransferase 1	Homo sapiens	Activity	=	103.0	U/L	PMID[3430163]
NPT5061	Individual protein	Alanine aminotransferase 1	Homo sapiens	Activity	=	110.0	U/L	PMID[3430163]
NPT38	Individual protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	=	7.0	%	PMID[19427202]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell line	Jurkat	Homo sapiens	Inhibition	=	-53.0	%	PMID[16539370]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	17.6	%	PMID[3430163]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	17.9	%	PMID[3430163]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	16.5	%	PMID[3430163]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	16.3	%	PMID[3430163]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	16.8	%	PMID[3430163]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	13.9	%	PMID[3430163]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	13.3	%	PMID[3430163]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	95.0	%	PMID[6677713]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	84.0	%	PMID[6677713]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	48.0	%	PMID[6677713]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	20.0	IU/L	PMID[6677713]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	27.0	IU/L	PMID[6677713]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	51.0	IU/L	PMID[6677713]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	13.02	%	PMID[25497988]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	77.2	%	PMID[28248102]
NPT24776	Cell line	B16-F1	Mus musculus	Inhibition	=	61.0	%	PMID[30030001]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	ED50	=	4.0	uM	PMID[9986720]
NPT2	Others	Unspecified	n.a.	Activity	=	126.0	U/L	PMID[3430163]
NPT2	Others	Unspecified	n.a.	Activity	=	123.0	U/L	PMID[3430163]
NPT2	Others	Unspecified	n.a.	IC50	>	2000000.0	nM	PMID[26395057]

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 NPC284948 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	9416
0.1-0.2	37291
0.2-0.3	2706
0.3-0.4	332
0.4-0.5	68
0.5-0.6	22
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC303090
1.0	High Similarity	NPC301382
1.0	High Similarity	NPC37331
0.9333	High Similarity	NPC220664
0.85	High Similarity	NPC283560
0.85	High Similarity	NPC24295
0.7826	Intermediate Similarity	NPC471076
0.7826	Intermediate Similarity	NPC192568
0.7143	Intermediate Similarity	NPC319628
0.6552	Remote Similarity	NPC224208
0.6552	Remote Similarity	NPC41661
0.6515	Remote Similarity	NPC37250
0.6515	Remote Similarity	NPC142703
0.6515	Remote Similarity	NPC152942
0.6515	Remote Similarity	NPC9991
0.6515	Remote Similarity	NPC302857
0.6515	Remote Similarity	NPC600892
0.6324	Remote Similarity	NPC477334
0.6154	Remote Similarity	NPC13818
0.5797	Remote Similarity	NPC471027
0.5672	Remote Similarity	NPC219428
0.5625	Remote Similarity	NPC488563
0.5507	Remote Similarity	NPC295492
0.5507	Remote Similarity	NPC303683
0.5507	Remote Similarity	NPC274891
0.5417	Remote Similarity	NPC278068
0.5357	Remote Similarity	NPC473275
0.5278	Remote Similarity	NPC205751
0.5278	Remote Similarity	NPC206095
0.5278	Remote Similarity	NPC35702
0.5278	Remote Similarity	NPC224389
0.5238	Remote Similarity	NPC474275
0.5224	Remote Similarity	NPC258469
0.5224	Remote Similarity	NPC43158
0.5224	Remote Similarity	NPC610147
0.5195	Remote Similarity	NPC156875
0.5161	Remote Similarity	NPC217052
0.5161	Remote Similarity	NPC329344
0.5161	Remote Similarity	NPC237506
0.5161	Remote Similarity	NPC32626
0.5139	Remote Similarity	NPC477333

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC284948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3018
0.1-0.2	5997
0.2-0.3	131
0.3-0.4	3
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6190	Approved

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