NPASS Compound

Natural Product: NPC158371

Natural Product ID	NPC158371
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Euscaphic Acid
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8aR,10S,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	Euscaphic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL239075
PubChem CID	471426
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 83 87 0 0 0 0 0 0 0 0999 V2000 -4.5789 -2.1124 1.5196 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9752 -0.6926 1.1570 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6743 -0.7181 -0.1611 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6257 -0.8451 -1.2298 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7834 0.3766 -1.1937 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6443 0.2963 -2.2356 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6996 -0.7938 -1.8792 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9246 -0.5264 -0.6113 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9283 -1.8587 0.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 0.4174 0.1992 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0298 1.0955 1.1617 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4035 0.9421 1.4414 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1522 0.1236 0.4669 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6021 0.5233 0.4096 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8916 1.9254 0.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1408 0.2485 1.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5977 0.5027 1.9240 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3718 0.4366 0.6670 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7977 -0.4282 -0.4064 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4090 -1.8301 -0.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3900 0.0509 -1.7392 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3163 -0.5154 -0.4292 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7118 -0.6876 -1.7956 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2855 -1.1890 -1.5439 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4945 -0.0662 -0.8712 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4399 1.1468 -1.7279 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6566 -0.0672 0.9936 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1281 -0.4037 2.8710 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1506 0.7255 0.0976 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8877 0.2895 1.3235 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4396 1.4765 2.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9339 -0.2973 2.1918 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6094 1.5081 -1.7312 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7395 1.2974 -2.1942 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1043 2.7869 -1.7078 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2936 -2.5828 2.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5699 -2.1493 1.9801 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5893 -2.8022 0.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8064 -0.4573 1.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2840 0.1991 -0.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3532 -1.6092 -0.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0960 -0.8942 -2.2412 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0798 -1.7899 -1.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2485 1.3061 -2.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0706 0.0609 -3.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0305 -0.9262 -2.7619 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2631 -1.7491 -1.8479 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4433 -2.6682 -0.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6433 -1.7456 1.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0217 -2.1496 0.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5672 1.8210 1.8007 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8185 1.9726 1.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4703 0.4861 2.4764 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1976 -0.9307 0.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4465 2.1231 -0.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9961 2.6155 0.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5331 2.4352 0.8944 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5966 0.9159 2.5433 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8613 -0.8182 2.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7742 1.5172 2.3878 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6052 1.4485 0.2197 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0885 -2.4720 -1.0622 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0977 -2.2324 0.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5211 -1.7253 -0.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3368 0.6228 -1.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7288 0.7111 -2.2900 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6657 -0.7889 -2.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0481 -1.4847 0.1048 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2345 -1.5410 -2.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7767 0.1555 -2.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8668 -1.5549 -2.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4256 -1.9807 -0.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0410 0.8039 -2.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4190 1.5873 -1.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1791 1.9030 -1.2466 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5396 -0.8284 1.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9660 -0.0725 3.7854 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1658 1.8631 0.1291 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4584 2.3407 1.3991 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7846 1.7767 2.9389 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4465 1.2616 2.5250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3602 -0.4169 3.0972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6698 3.6224 -1.8015 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 1 0 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 27 1 0 17 28 1 0 10 29 1 0 29 30 1 0 30 31 1 0 30 32 1 1 5 33 1 6 33 34 2 0 33 35 1 0 30 2 1 0 29 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 1 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 9 48 1 0 9 49 1 0 9 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 1 15 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 18 61 1 6 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 21 67 1 0 22 68 1 1 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 27 76 1 0 28 77 1 0 29 78 1 1 31 79 1 0 31 80 1 0 31 81 1 0 32 82 1 0 35 83 1 0 M END

Standard InCHIKey	OXVUXGFZHDKYLS-QUFHAEKXSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	3.051 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.841 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.679 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.382	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.044	Fsp³:	0.9
MCE-18:	110.772 ? 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:	0.644	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.043 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.308	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.54	MDCK Permeability:	-5.114
Pgp-inhibitor:	0.001	Pgp-substrate:	0.037
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):	0.001
20% Bioavailability (F20%):	0.108	30% Bioavailability (F30%):	0.03
50% Bioavailability (F50%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.996
Plasma Protein Binding (PPB):	86.229%	Volume Distribution (VD):	-0.242
Fu:	12.47% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.881	BCRP inhibitor:	0.0
BSEP inhibitor:	0.975

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.159	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.145
HLM stability:	0.004 ? 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):

3.143

Half-life (T1/2):

1.5

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.067
Human Hepatotoxicity (H-HT):	0.493	Drug-induced Liver Injury (DILI):	0.183
AMES Toxicity:	0.152	Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.425	Skin Sensitization:	0.798
Carcinogencity:	0.753	Eye Corrosion:	0.008
Eye Irritation:	0.414	Respiratory Toxicity:	0.811
Drug-induced Neurotoxicity:	0.036	Ototoxicity:	0.846
Hematotoxicity:	0.317	Drug-induced Nephrotoxicity:	0.95
Genotoxicity:	0.553	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.052	Hek293 Cytotoxicity:	0.095
BCF:	0.804 ? 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:	3.505 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.092 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.311 ? 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]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2015.01.015]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	DOI[10.1016/j.tetlet.2016.12.029]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np1003593]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/np50028a032]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np50070a005]
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]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395523]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10553679]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10993241]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473413]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
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]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1279126]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[12951487]
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]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[16462067]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16870425]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
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]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19276083]
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19795885]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	leaves	Botanical Garden of Innsbruck, Austria	n.a.	PMID[20100662]
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]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20515057]
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]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	Twigs	Yangming mountain, Taiwan	2008-APR	PMID[20873721]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21384845]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	Leaves	Huangshan, Anhui Province, China	2008-NOV	PMID[21384845]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21923134]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22194604]
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]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23006989]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23022271]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23632365]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964677]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24013342]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24516143]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25028392]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25245917]
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]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27242221]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27807341]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37770099]
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[38455614]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38732062]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[4421158]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8759159]
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]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834152]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23019	Glycyrrhiza kansuensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24094	Pelargonium reniforme	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17494	Prunella vulgaris	Species	Lamiaceae	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]
NPO23325	Doris verrucosa	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4855	Colchicum speciosum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26876	Rubus parviforlius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24448	Haplopappus ciliatus	Species	Asteraceae	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]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28618	Ursinia alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11737	Henricia aspera	Species	Echinasteridae	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]
NPO6321	Agathosma thymifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12800	Glycine falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22758	Picradeniopsis pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24192	Piptoporus australiensis	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23019	Glycyrrhiza kansuensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18564	Ligularia dentata	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]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO41024	Eriobotrya japonica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24094	Pelargonium reniforme	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23019	Glycyrrhiza kansuensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26876	Rubus parviforlius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO60	Neoshirakia japonica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	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]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	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]
NPO23019	Glycyrrhiza kansuensis	Species	Fabaceae	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]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	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]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25618	Eriobotrya japonica	Species	Rosaceae	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]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	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]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9388	Heliomeris multiflora	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]
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]
NPO22467	Kippistia suaedifolia	Species	Asteraceae	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]
NPO4855	Colchicum speciosum	Species	Colchicaceae	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]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	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]
NPO23325	Doris verrucosa	Species	Dorididae	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]
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]
NPO19177	Euphorbia franckiana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1507	Cissus quinquefolia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25670	Aspergillus foveolatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7372	Rosa laevigata	Species	Rosaceae	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]
NPO23369	Hertia intermedia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	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]
NPO6321	Agathosma thymifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27990	Schizonepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12800	Glycine falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3868	Senecio sinuatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20023	Uncaria gambier	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11165	Spirographis spallanzani	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28670	Mortierella elongata	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25704	Tetraneuris acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11737	Henricia aspera	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28269	Rubus rosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4048	Inga longispica	Species	Oecophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4025	Morina longifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24094	Pelargonium reniforme	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO796	Diphasiastrum alpinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28618	Ursinia alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO60	Neoshirakia japonica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24192	Piptoporus australiensis	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22758	Picradeniopsis pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24448	Haplopappus ciliatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20727	Myliobatis aquila	Species	Myliobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Inhibition	5
FC	1
IC50	10
Activity	20
GI50	3
TC50	1

Activity Type	# Activity
Individual protein	5
Cell line	22
Organism	5
Single protein	1
Non-molecular	2
Others	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual protein	Protease	Human immunodeficiency virus 1	Inhibition	=	0.0	%	PMID[8759159]
NPT3143	Individual protein	Solute carrier family 2, facilitated glucose transporter member 4	Rattus norvegicus	FC	=	0.7	n.a.	PMID[24894556]
NPT50	Individual protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	IC50	>	100000.0	nM	PMID[32345458]
NPT50	Individual protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Inhibition	=	20.0	%	PMID[32345458]
NPT5212	Individual protein	Sentrin-specific protease 1	Homo sapiens	Inhibition	=	66.6	%	PMID[35500202]
NPT21657	Single protein	DNA topoisomerase I	Bos taurus	Inhibition	>	90.0	%	PMID[32345458]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1171	Cell line	HEp-2	Homo sapiens	IC50	=	105700.0	nM	PMID[17889544]
NPT492	Cell line	Caco-2	Homo sapiens	IC50	=	104100.0	nM	PMID[17889544]
NPT81	Cell line	A549	Homo sapiens	IC50	=	95580.0	nM	PMID[17889544]
NPT111	Cell line	K562	Homo sapiens	IC50	=	76710.0	nM	PMID[17889544]
NPT111	Cell line	K562	Homo sapiens	Activity	=	13.58	%	PMID[17889544]
NPT111	Cell line	K562	Homo sapiens	Activity	=	27.75	%	PMID[17889544]
NPT111	Cell line	K562	Homo sapiens	Activity	=	62.93	%	PMID[17889544]
NPT111	Cell line	K562	Homo sapiens	Activity	=	8.04	%	PMID[17889544]
NPT111	Cell line	K562	Homo sapiens	Activity	=	13.87	%	PMID[17889544]
NPT111	Cell line	K562	Homo sapiens	Activity	=	18.69	%	PMID[17889544]
NPT111	Cell line	K562	Homo sapiens	Activity	=	36.33	%	PMID[17889544]
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	85.0	%	PMID[20873721]
NPT397	Cell line	NCI-H460	Homo sapiens	Activity	=	104.0	%	PMID[20873721]
NPT139	Cell line	HT-29	Homo sapiens	Activity	=	85.0	%	PMID[20873721]
NPT404	Cell line	CCRF-CEM	Homo sapiens	Activity	=	89.0	%	PMID[20873721]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	<	50.0	%	PMID[25245917]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	22000.0	nM	PMID[32345458]
NPT81	Cell line	A549	Homo sapiens	GI50	=	43000.0	nM	PMID[32345458]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	41000.0	nM	PMID[32345458]
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	0.1	%	PMID[29353722]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	48.8	%	PMID[29353722]
NPT1452	Cell line	C8166	Homo sapiens	TC50	=	20.0	ug ml-1	PMID[1279126]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	83790.0	nM	PMID[17889544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	28800.0	nM	PMID[11473413]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	0.0	%	PMID[1279126]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	1.0	%	PMID[1279126]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	Activity	=	100.0	%	PMID[1279126]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	37.5	ug.mL-1	PMID[9748372]
NPT2	Others	Unspecified	n.a.	Activity	=	63.57	%	PMID[17889544]
NPT2	Others	Unspecified	n.a.	Activity	=	10.48	%	PMID[17889544]
NPT2	Others	Unspecified	n.a.	Activity	=	30.87	%	PMID[17889544]
NPT338	Organism	Sindbis virus	Sindbis virus	Activity	=	100.0	%	PMID[1279126]
NPT2	Others	Unspecified	n.a.	IC50	=	650000.0	nM	PMID[19795885]
NPT2	Others	Unspecified	n.a.	IC50	=	174590.0	nM	PMID[23632365]

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 NPC158371 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	24624
0.1-0.2	21730
0.2-0.3	2832
0.3-0.4	418
0.4-0.5	138
0.5-0.6	54
0.6-0.7	25
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259733
1.0	High Similarity	NPC207922
0.8571	High Similarity	NPC247139
0.7846	Intermediate Similarity	NPC202728
0.7846	Intermediate Similarity	NPC158059
0.7826	Intermediate Similarity	NPC96693
0.7576	Intermediate Similarity	NPC256247
0.75	Intermediate Similarity	NPC157113
0.7463	Intermediate Similarity	NPC35239
0.7424	Intermediate Similarity	NPC71074
0.7424	Intermediate Similarity	NPC37221
0.7424	Intermediate Similarity	NPC605937
0.7353	Intermediate Similarity	NPC62516
0.7313	Intermediate Similarity	NPC136697
0.7273	Intermediate Similarity	NPC84319
0.7273	Intermediate Similarity	NPC52021
0.7273	Intermediate Similarity	NPC599947
0.7206	Intermediate Similarity	NPC191412
0.7206	Intermediate Similarity	NPC114159
0.7206	Intermediate Similarity	NPC132824
0.7206	Intermediate Similarity	NPC6818
0.7164	Intermediate Similarity	NPC472149
0.7083	Intermediate Similarity	NPC54909
0.7	Intermediate Similarity	NPC187933
0.7	Intermediate Similarity	NPC284865
0.6857	Remote Similarity	NPC118964
0.6857	Remote Similarity	NPC25299
0.6857	Remote Similarity	NPC481322
0.6857	Remote Similarity	NPC148964
0.6849	Remote Similarity	NPC233012
0.6714	Remote Similarity	NPC118519
0.6667	Remote Similarity	NPC235053
0.6575	Remote Similarity	NPC603658
0.6479	Remote Similarity	NPC9613
0.6429	Remote Similarity	NPC88116
0.6389	Remote Similarity	NPC137072
0.6338	Remote Similarity	NPC32407
0.6338	Remote Similarity	NPC263548
0.6338	Remote Similarity	NPC606320
0.6301	Remote Similarity	NPC147232
0.6207	Remote Similarity	NPC482049
0.6207	Remote Similarity	NPC482050
0.6197	Remote Similarity	NPC231063
0.6197	Remote Similarity	NPC282395
0.6197	Remote Similarity	NPC173744
0.6197	Remote Similarity	NPC204961
0.6197	Remote Similarity	NPC73004
0.6197	Remote Similarity	NPC110308
0.6197	Remote Similarity	NPC609452
0.6056	Remote Similarity	NPC306541
0.5974	Remote Similarity	NPC327179
0.5915	Remote Similarity	NPC96916
0.5867	Remote Similarity	NPC20235
0.5867	Remote Similarity	NPC299996
0.5775	Remote Similarity	NPC43686
0.5753	Remote Similarity	NPC300351
0.575	Remote Similarity	NPC600756
0.5658	Remote Similarity	NPC116457
0.5658	Remote Similarity	NPC174663
0.5616	Remote Similarity	NPC51700
0.5616	Remote Similarity	NPC259788
0.5616	Remote Similarity	NPC88716
0.5616	Remote Similarity	NPC255589
0.5616	Remote Similarity	NPC68160
0.5584	Remote Similarity	NPC479743
0.557	Remote Similarity	NPC188833
0.5556	Remote Similarity	NPC25491
0.5556	Remote Similarity	NPC609710
0.5541	Remote Similarity	NPC481360
0.5526	Remote Similarity	NPC203343
0.5526	Remote Similarity	NPC312075
0.5479	Remote Similarity	NPC480946
0.5479	Remote Similarity	NPC187722
0.5479	Remote Similarity	NPC130577
0.5479	Remote Similarity	NPC142415
0.5479	Remote Similarity	NPC102683
0.5467	Remote Similarity	NPC305464
0.5467	Remote Similarity	NPC87095
0.5467	Remote Similarity	NPC19376
0.5467	Remote Similarity	NPC293564
0.5467	Remote Similarity	NPC25848
0.5444	Remote Similarity	NPC488214
0.5435	Remote Similarity	NPC482051
0.5405	Remote Similarity	NPC182797
0.5405	Remote Similarity	NPC52169
0.5405	Remote Similarity	NPC488562
0.5395	Remote Similarity	NPC201657
0.5333	Remote Similarity	NPC106112
0.5333	Remote Similarity	NPC261935
0.5333	Remote Similarity	NPC111214
0.5275	Remote Similarity	NPC482052
0.5263	Remote Similarity	NPC145667
0.5205	Remote Similarity	NPC488506
0.5205	Remote Similarity	NPC220498
0.52	Remote Similarity	NPC307282
0.5195	Remote Similarity	NPC88847
0.5155	Remote Similarity	NPC481234
0.5155	Remote Similarity	NPC479431
0.5132	Remote Similarity	NPC61543
0.5132	Remote Similarity	NPC293048
0.5132	Remote Similarity	NPC225585
0.5067	Remote Similarity	NPC136313
0.5065	Remote Similarity	NPC477288
0.5062	Remote Similarity	NPC230151

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6725
0.1-0.2	2365
0.2-0.3	56
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data