NPASS Compound

Structure

CID13818 OpenBabel06191715342D 37 39 0 0 1 0 0 0 0 0999 V2000 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 13 1 0 0 0 0 2 6 2 0 0 0 0 2 14 1 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 25 1 0 0 0 0 12 20 1 0 0 0 0 12 25 1 0 0 0 0 15 17 2 0 0 0 0 15 26 1 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 23 1 0 0 0 0 19 36 1 6 0 0 0 20 23 1 0 0 0 0 20 37 1 1 0 0 0 21 30 2 0 0 0 0 21 36 1 0 0 0 0 22 31 2 0 0 0 0 22 37 1 0 0 0 0 23 32 1 6 0 0 0 24 25 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.13
Volume:	491.768
LogP:	1.896
LogD:	0.443
LogS:	-1.952
# Rotatable Bonds:	9
TPSA:	211.28
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	3.829
Fsp3:	0.24
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.358
MDCK Permeability:	9.563703315507155e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.657
Human Intestinal Absorption (HIA):	0.674
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	98.29451751708984%
Volume Distribution (VD):	0.341
Pgp-substrate:	1.545695185661316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.295
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.552
CYP2C9-substrate:	0.224
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	3.241
Half-life (T1/2):	0.946

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.23
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.702
Skin Sensitization:	0.887
Carcinogencity:	0.239
Eye Corrosion:	0.003
Eye Irritation:	0.118
Respiratory Toxicity:	0.033

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC13818

Natural Product ID:	NPC13818
*Common Name:**	KRZBCHWVBQOTNZ-PSEXTPKNSA-N
IUPAC Name:	n.a.
Synonyms:	3,5-Dicaffeoyl Quinic Acid; 3,5-Dicaffeoylquinic Acid; 3,5-Dicaffeoylquinicacid; Rel-3,5-Dicaffeoylquinic Acid
Standard InCHIKey:	KRZBCHWVBQOTNZ-PSEXTPKNSA-N
Standard InCHI:	InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
SMILES:	O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249447
PubChem CID:	NA
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

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/np980153o]
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]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1248/cpb.47.1521]
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096846]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
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]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	tenerife	n.a.	PMID[10924166]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11000036]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678669]
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]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662092]
NPO30518.1	Solidago virgaaurea var. gigantea	Varieties	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15022716]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15070765]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15679308]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730248]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15730262]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	Leaves	Khon Kaen, Thailand	2002-APR	PMID[15921434]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309323]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[16462067]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[1686898]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO32635	hubertia sp.	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822297]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Shells; Leaves	n.a.	n.a.	PMID[18163585]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	roots	Gabon	1987	PMID[18327911]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO29981	Suaeda glauca	Species	Chenopodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18481014]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	ground entire plants	Hainan Province, China	2004-APR	PMID[19061389]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19276083]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
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]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[21226514]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21338052]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21469692]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21469692]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22194604]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22220686]
NPO23708	Aster koraiensis	Species	Asteraceae	Eukaryota	aerial parts	Euidang-myun, Gongju city, Chungchengnam-do, Republic of Korea	2007-Aug	PMID[22264115]
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]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO32535	dracocephalum ruyschiana	Species	Lamiaceae	Eukaryota	aerial parts	Mongolian	n.a.	PMID[23356964]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964677]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094434]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24279991]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24516143]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25028392]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25420236]
NPO32468	tripolium vulgare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25981689]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[26281591]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26466957]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26606246]
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]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27807341]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Green Leafy Covers	n.a.	n.a.	PMID[28520428]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31017778]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3404159]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[8158164]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158164]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8917504]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8951168]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	Brazilian propolis	n.a.	PMID[9677271]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[97292]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	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]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7541	Ormosia hosiei	Species	Fabaceae	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]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	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]
NPO29846	Lonicera dasystyla	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26785	Taraxacum mongolicum	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]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30003	Lonicera confuse	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26785	Taraxacum mongolicum	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]
NPO11144	Centella asiatica	Species	Apiaceae	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]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	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]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4836	Sideritis arborescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17179	Elizabethkingia meningoseptica	Species	Flavobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18861	Pyxine coccifera	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21493	Bunodosoma caissarum	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28200	Unonopsis glaucopetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6331	Jacobaea subalpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8950	Stilpnopappus pickelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27990	Schizonepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1049	Tethya amamensis	Species	Tethyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17606	Millettia ichthyochtona	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1541	Clusia ellipticifolia	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7793	Matricaria matricarioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3445	Dumoria heckeli	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8433	Bongardia chrysogonum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16819	Preussia aemulans	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5166	Adonis sutchuenensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2323	Plantago lundborgii	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO117	Acacia armata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13682	Lonchocarpus laxiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28131	Polygala amara	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18250	Conus tessulatus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20395	Athanasia crithmifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28269	Rubus rosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28161	Stephania sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17281	Echinaster echinophorus	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28633	Bystropogon origanifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28691	Streptomyces odorifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28303	Pleogyne cunninghamii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10980	Petasites japonicus	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]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8132	Fritillaria meleagris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27867	Turbo argyrostoma	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19991	Mantella aurantiaca	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO643	Astragalus ernestii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	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]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2008	Streptomyces ehimensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27943	Cardamine pinnata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16201	Pteris altissima	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23708	Aster koraiensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29115	Rhinella arenarum	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18716	Parmelia caraccensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25140	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28670	Mortierella elongata	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8306	Berneuxia thibetica	Species	Diapensiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5339	Isophysis tasmanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18273	Merendera sobolifera	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28374	Pleogyne cunninghami	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5721	Psorothamnus spinosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1706	Eragrostis curvula	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19061	Ceratozamia kuesteriana	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25704	Tetraneuris acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1203	Solanum pseudoquina	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28073	Crateva nurvala	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28614	Zieria smithii	Species	Rutaceae	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	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference
NPO25145	NPC13818	Other	n.a.	0.581250008	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO9788	NPC13818	Other (beverage)	n.a.	6.345666915	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO320	NPC13818	Other (beverage)	n.a.	6.345666915	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO9788	NPC13818	Other (beverage)	n.a.	1.549999952	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO320	NPC13818	Other (beverage)	n.a.	1.549999952	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO163	NPC13818	Raw	n.a.	2.096666654	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO9788	NPC13818	Tea Or Coffee	n.a.	2.65199995	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO320	NPC13818	Tea Or Coffee	n.a.	4.420000076	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO25145	NPC13818	n.a.	n.a.	0.439999998	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

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

Biological Activity

Activity Type	# Activity
EC50	2
ED50	3
IC50	24
LD50	1
Others	44

Activity Type	# Activity
Cell Line	7
CELL-LINE	1
Individual Protein	12
NON-MOLECULAR	4
Organism	20
Others	26
Protein Family	2
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT460	Cell Line	MT2	Homo sapiens	LD5	=	290.0	uM	PMID[502445]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	1300.0	nM	PMID[502445]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	640.0	nM	PMID[502449]
NPT460	Cell Line	MT2	Homo sapiens	LD50	=	300.0	uM	PMID[502449]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	0.66	ug.mL-1	PMID[502450]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	5.9	ug.mL-1	PMID[502454]
NPT25	Cell Line	MT4	Homo sapiens	CC100	>	50.0	ug ml-1	PMID[502456]
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	88.0	nM	PMID[502457]
NPT1270	Individual Protein	Aldo-keto reductase family 1 member B10	Homo sapiens	IC50	=	130.0	nM	PMID[502457]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	20.0	%	PMID[502458]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	42.0	%	PMID[502458]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	97.0	%	PMID[502458]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	37900.0	nM	PMID[502470]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	Inhibition	>	20.0	%	PMID[502472]
NPT804	Cell Line	HT-22	Mus musculus	EC50	>	100000.0	nM	PMID[502473]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	ED50	=	2.0	uM	PMID[502445]
NPT2	Others	Unspecified		IC50	=	666000.0	nM	PMID[502448]
NPT2	Others	Unspecified		IC50	=	85900.0	nM	PMID[502448]
NPT2	Others	Unspecified		IC50	=	902000.0	nM	PMID[502448]
NPT2	Others	Unspecified		Activity	=	50.9	%	PMID[502448]
NPT2	Others	Unspecified		Activity	=	121.1	%	PMID[502448]
NPT2	Others	Unspecified		Activity	=	97.5	%	PMID[502448]
NPT2	Others	Unspecified		Activity	=	160.8	%	PMID[502448]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	ED50	=	1.9	uM	PMID[502449]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	ED50	=	1.0	ug ml-1	PMID[502450]
NPT27	Others	Unspecified		TI	=	150.0	n.a.	PMID[502450]
NPT2	Others	Unspecified		FC	=	10.0	n.a.	PMID[502451]
NPT2	Others	Unspecified		IC50	=	23600.0	nM	PMID[502453]
NPT1	Others	Radical scavenging activity		IC50	=	5.6	ug.mL-1	PMID[502454]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.9	ug.mL-1	PMID[502454]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	51.5	%	PMID[502454]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.3	ug.mL-1	PMID[502456]
NPT1	Others	Radical scavenging activity		EC50	=	16.0	ug.mL-1	PMID[502456]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC100	>	12.5	ug ml-1	PMID[502456]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	50.0	%	PMID[502458]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	40.0	%	PMID[502458]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	20.0	%	PMID[502458]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	44.0	%	PMID[502458]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	>	50.0	%	PMID[502458]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	53.0	%	PMID[502458]
NPT32	Organism	Mus musculus	Mus musculus	FC	=	2.0	n.a.	PMID[502458]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	66.0	%	PMID[502458]
NPT35	Others	n.a.		IC50	=	6600.0	nM	PMID[502459]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	300.0	nM	PMID[502459]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	=	16400.0	nM	PMID[502460]
NPT1	Others	Radical scavenging activity		IC50	=	32400.0	nM	PMID[502461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	30.0	%	PMID[502463]
NPT339	Organism	Influenza A virus H3N2	Influenza A virus H3N2	IC50	=	4900.0	nM	PMID[502463]
NPT27	Others	Unspecified		Papp	=	0.26	ucm/s	PMID[502464]
NPT27	Others	Unspecified		Papp	=	0.25	ucm/s	PMID[502464]
NPT27	Others	Unspecified		Papp	=	0.21	ucm/s	PMID[502464]
NPT27	Others	Unspecified		Papp	=	0.13	ucm/s	PMID[502464]
NPT27	Others	Unspecified		Papp	=	0.68	ucm/s	PMID[502464]
NPT27	Others	Unspecified		Papp	=	0.05	ucm/s	PMID[502464]
NPT27	Others	Unspecified		Ratio	=	5.1	n.a.	PMID[502464]
NPT27	Others	Unspecified		Papp	=	0.72	ucm/s	PMID[502464]
NPT27	Others	Unspecified		Papp	=	0.14	ucm/s	PMID[502464]
NPT35	Others	n.a.		LogD	=	-1.04	n.a.	PMID[502464]
NPT2	Others	Unspecified		IC50	=	390000.0	nM	PMID[502466]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	143240.0	nM	PMID[502467]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	>	500000.0	nM	PMID[502467]
NPT2	Others	Unspecified		IC50	=	1900.0	nM	PMID[502468]
NPT862	Individual Protein	Epoxide hydratase	Homo sapiens	IC50	=	2800.0	nM	PMID[502469]
NPT862	Individual Protein	Epoxide hydratase	Homo sapiens	Inhibition	=	81.3	%	PMID[502469]
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	25.5	%	PMID[502471]
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	24.2	%	PMID[502471]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	8.33	mm	PMID[502471]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	=	0.0	mm	PMID[502471]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	0.0	mm	PMID[502471]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	6.67	mm	PMID[502471]
NPT24776	CELL-LINE	B16-F1	Mus musculus	Inhibition	=	26.0	%	PMID[502472]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC13818 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	1273
0.2-0.3	3194
0.3-0.4	7323
0.4-0.5	10285
0.5-0.6	5734
0.6-0.7	8324
0.7-0.8	5817
0.8-0.85	293
0.85-0.9	60
0.9-0.95	25
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477335
1.0	High Similarity	NPC471027
1.0	High Similarity	NPC297517
1.0	High Similarity	NPC224389
1.0	High Similarity	NPC35702
1.0	High Similarity	NPC206095
0.9926	High Similarity	NPC258469
0.9926	High Similarity	NPC284948
0.9926	High Similarity	NPC43158
0.9926	High Similarity	NPC277315
0.9926	High Similarity	NPC37331
0.9926	High Similarity	NPC220664
0.9926	High Similarity	NPC303090
0.9926	High Similarity	NPC319628
0.9926	High Similarity	NPC192831
0.9926	High Similarity	NPC472016
0.9776	High Similarity	NPC302857
0.9776	High Similarity	NPC37250
0.9776	High Similarity	NPC142703
0.9776	High Similarity	NPC278068
0.9776	High Similarity	NPC152942
0.9776	High Similarity	NPC219428
0.9704	High Similarity	NPC26241
0.9704	High Similarity	NPC295492
0.9704	High Similarity	NPC474875
0.9704	High Similarity	NPC476820
0.9704	High Similarity	NPC205751
0.9704	High Similarity	NPC274891
0.9704	High Similarity	NPC303683
0.9704	High Similarity	NPC476819
0.9638	High Similarity	NPC477333
0.963	High Similarity	NPC24295
0.963	High Similarity	NPC283560
0.9571	High Similarity	NPC192568
0.9571	High Similarity	NPC471076
0.9504	High Similarity	NPC42464
0.95	High Similarity	NPC322660
0.9478	High Similarity	NPC68517
0.9437	High Similarity	NPC306343
0.9433	High Similarity	NPC43123
0.9407	High Similarity	NPC233350
0.9407	High Similarity	NPC182217
0.9407	High Similarity	NPC70680
0.9306	High Similarity	NPC163883
0.9306	High Similarity	NPC93498
0.9291	High Similarity	NPC98356
0.9241	High Similarity	NPC19380
0.9241	High Similarity	NPC146277
0.9236	High Similarity	NPC477334
0.9149	High Similarity	NPC50221
0.9149	High Similarity	NPC114242
0.9116	High Similarity	NPC145425
0.9103	High Similarity	NPC252979
0.9054	High Similarity	NPC473275
0.9054	High Similarity	NPC470896
0.9044	High Similarity	NPC25581
0.9044	High Similarity	NPC18074
0.9044	High Similarity	NPC5419
0.9044	High Similarity	NPC61
0.9014	High Similarity	NPC22176
0.9014	High Similarity	NPC121573
0.9014	High Similarity	NPC226738
0.9014	High Similarity	NPC190587
0.9	High Similarity	NPC179505
0.9	High Similarity	NPC156709
0.8978	High Similarity	NPC168799
0.8978	High Similarity	NPC155209
0.8971	High Similarity	NPC198388
0.8958	High Similarity	NPC229264
0.8913	High Similarity	NPC474895
0.8897	High Similarity	NPC142528
0.8857	High Similarity	NPC67349
0.8857	High Similarity	NPC279676
0.8803	High Similarity	NPC38473
0.88	High Similarity	NPC134925
0.8777	High Similarity	NPC106406
0.8767	High Similarity	NPC120621
0.8767	High Similarity	NPC248257
0.8741	High Similarity	NPC477277
0.8741	High Similarity	NPC477278
0.8733	High Similarity	NPC203757
0.8732	High Similarity	NPC12218
0.8732	High Similarity	NPC75763
0.8732	High Similarity	NPC105525
0.8732	High Similarity	NPC225036
0.8725	High Similarity	NPC44730
0.8716	High Similarity	NPC140151
0.8707	High Similarity	NPC92117
0.8707	High Similarity	NPC75945
0.8705	High Similarity	NPC471749
0.8701	High Similarity	NPC227297
0.8696	High Similarity	NPC318799
0.8671	High Similarity	NPC477279
0.8662	High Similarity	NPC239943
0.8639	High Similarity	NPC472969
0.863	High Similarity	NPC473867
0.8623	High Similarity	NPC237506
0.8623	High Similarity	NPC32626
0.8623	High Similarity	NPC217052
0.8623	High Similarity	NPC329344
0.8621	High Similarity	NPC474692
0.8621	High Similarity	NPC160378
0.8603	High Similarity	NPC475695
0.8601	High Similarity	NPC289690
0.8601	High Similarity	NPC288452
0.86	High Similarity	NPC44260
0.86	High Similarity	NPC205037
0.86	High Similarity	NPC16024
0.86	High Similarity	NPC61152
0.86	High Similarity	NPC3746
0.8592	High Similarity	NPC302583
0.8592	High Similarity	NPC84789
0.8592	High Similarity	NPC310252
0.8592	High Similarity	NPC100558
0.859	High Similarity	NPC471823
0.8581	High Similarity	NPC98809
0.8581	High Similarity	NPC476394
0.8571	High Similarity	NPC283081
0.8571	High Similarity	NPC221383
0.8571	High Similarity	NPC143892
0.8571	High Similarity	NPC299090
0.8551	High Similarity	NPC94810
0.8542	High Similarity	NPC9218
0.8535	High Similarity	NPC128403
0.8533	High Similarity	NPC95498
0.8533	High Similarity	NPC106818
0.8533	High Similarity	NPC75695
0.8533	High Similarity	NPC246566
0.8523	High Similarity	NPC259576
0.8523	High Similarity	NPC221091
0.8523	High Similarity	NPC32197
0.8511	High Similarity	NPC886
0.8511	High Similarity	NPC287597
0.8511	High Similarity	NPC34293
0.8511	High Similarity	NPC248150
0.8493	Intermediate Similarity	NPC229036
0.8493	Intermediate Similarity	NPC470130
0.8477	Intermediate Similarity	NPC87403
0.8467	Intermediate Similarity	NPC243891
0.8467	Intermediate Similarity	NPC300329
0.8456	Intermediate Similarity	NPC85565
0.8451	Intermediate Similarity	NPC123988
0.8451	Intermediate Similarity	NPC18646
0.8442	Intermediate Similarity	NPC287872
0.8442	Intermediate Similarity	NPC74319
0.8435	Intermediate Similarity	NPC108455
0.8435	Intermediate Similarity	NPC258671
0.8435	Intermediate Similarity	NPC53884
0.8431	Intermediate Similarity	NPC239019
0.8431	Intermediate Similarity	NPC247629
0.8429	Intermediate Similarity	NPC108553
0.8421	Intermediate Similarity	NPC191046
0.8421	Intermediate Similarity	NPC327032
0.8421	Intermediate Similarity	NPC194095
0.8417	Intermediate Similarity	NPC226855
0.8411	Intermediate Similarity	NPC476434
0.8411	Intermediate Similarity	NPC267091
0.8403	Intermediate Similarity	NPC328273
0.8403	Intermediate Similarity	NPC321638
0.8403	Intermediate Similarity	NPC321184
0.8403	Intermediate Similarity	NPC171134
0.84	Intermediate Similarity	NPC473091
0.8397	Intermediate Similarity	NPC90905
0.8397	Intermediate Similarity	NPC4013
0.8392	Intermediate Similarity	NPC156892
0.8389	Intermediate Similarity	NPC98009
0.8389	Intermediate Similarity	NPC28776
0.8389	Intermediate Similarity	NPC473138
0.8387	Intermediate Similarity	NPC289346
0.8387	Intermediate Similarity	NPC24164
0.838	Intermediate Similarity	NPC135127
0.8378	Intermediate Similarity	NPC474465
0.8377	Intermediate Similarity	NPC114179
0.8377	Intermediate Similarity	NPC160512
0.8377	Intermediate Similarity	NPC172419
0.8377	Intermediate Similarity	NPC289322
0.8377	Intermediate Similarity	NPC156818
0.8377	Intermediate Similarity	NPC472860
0.8377	Intermediate Similarity	NPC226759
0.8377	Intermediate Similarity	NPC38779
0.8377	Intermediate Similarity	NPC238419
0.8377	Intermediate Similarity	NPC133984
0.8377	Intermediate Similarity	NPC68324
0.837	Intermediate Similarity	NPC472271
0.837	Intermediate Similarity	NPC147654
0.8367	Intermediate Similarity	NPC473090
0.8367	Intermediate Similarity	NPC183824
0.8367	Intermediate Similarity	NPC304956
0.8355	Intermediate Similarity	NPC266084
0.8355	Intermediate Similarity	NPC473544
0.8355	Intermediate Similarity	NPC475145
0.8355	Intermediate Similarity	NPC475216
0.8355	Intermediate Similarity	NPC83663
0.8355	Intermediate Similarity	NPC475595
0.8355	Intermediate Similarity	NPC475162
0.8333	Intermediate Similarity	NPC472859
0.8333	Intermediate Similarity	NPC25389
0.8333	Intermediate Similarity	NPC78363
0.8333	Intermediate Similarity	NPC478242
0.8333	Intermediate Similarity	NPC260425

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC13818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	770
0.2-0.3	1688
0.3-0.4	2745
0.4-0.5	2034
0.5-0.6	1072
0.6-0.7	473
0.7-0.8	83
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9926	High Similarity	NPD6190	Approved
0.8312	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD230	Phase 1
0.8276	Intermediate Similarity	NPD7266	Discontinued
0.8037	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6166	Phase 2
0.784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD9269	Phase 2
0.7785	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD7685	Pre-registration
0.7744	Intermediate Similarity	NPD3818	Discontinued
0.7736	Intermediate Similarity	NPD3882	Suspended
0.7722	Intermediate Similarity	NPD2801	Approved
0.7712	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD5402	Approved
0.7671	Intermediate Similarity	NPD6233	Phase 2
0.7658	Intermediate Similarity	NPD1934	Approved
0.764	Intermediate Similarity	NPD6234	Discontinued
0.7632	Intermediate Similarity	NPD8166	Discontinued
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.7628	Intermediate Similarity	NPD1653	Approved
0.7613	Intermediate Similarity	NPD1512	Approved
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6797	Phase 2
0.7603	Intermediate Similarity	NPD3764	Approved
0.759	Intermediate Similarity	NPD5844	Phase 1
0.7578	Intermediate Similarity	NPD7075	Discontinued
0.756	Intermediate Similarity	NPD7251	Discontinued
0.7554	Intermediate Similarity	NPD9545	Approved
0.7547	Intermediate Similarity	NPD37	Approved
0.7534	Intermediate Similarity	NPD3027	Phase 3
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.753	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD4966	Approved
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD9268	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD7054	Approved
0.7484	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8150	Discontinued
0.744	Intermediate Similarity	NPD7074	Phase 3
0.744	Intermediate Similarity	NPD7472	Approved
0.7438	Intermediate Similarity	NPD6801	Discontinued
0.7425	Intermediate Similarity	NPD7228	Approved
0.7412	Intermediate Similarity	NPD7808	Phase 3
0.7397	Intermediate Similarity	NPD9494	Approved
0.7394	Intermediate Similarity	NPD3787	Discontinued
0.7391	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1613	Approved
0.7372	Intermediate Similarity	NPD6799	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6798	Discontinued
0.7365	Intermediate Similarity	NPD7473	Discontinued
0.7362	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3455	Phase 2
0.7349	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5403	Approved
0.7333	Intermediate Similarity	NPD7199	Phase 2
0.7303	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8434	Phase 2
0.7226	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5401	Approved
0.7181	Intermediate Similarity	NPD7095	Approved
0.716	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD6385	Approved
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7086	Intermediate Similarity	NPD4062	Phase 3
0.7078	Intermediate Similarity	NPD1510	Phase 2
0.7078	Intermediate Similarity	NPD7033	Discontinued
0.7076	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7819	Suspended
0.7066	Intermediate Similarity	NPD5494	Approved
0.7055	Intermediate Similarity	NPD7411	Suspended
0.7051	Intermediate Similarity	NPD1549	Phase 2
0.7047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD9570	Approved
0.703	Intermediate Similarity	NPD5353	Approved
0.7007	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6535	Approved
0.7	Intermediate Similarity	NPD6534	Approved
0.6993	Remote Similarity	NPD4340	Discontinued
0.6993	Remote Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD5536	Phase 2
0.6987	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7435	Discontinued
0.697	Remote Similarity	NPD8455	Phase 2
0.6962	Remote Similarity	NPD3750	Approved
0.6954	Remote Similarity	NPD7039	Approved
0.6954	Remote Similarity	NPD6559	Discontinued
0.6954	Remote Similarity	NPD7240	Approved
0.6954	Remote Similarity	NPD7038	Approved
0.6943	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5242	Approved
0.6939	Remote Similarity	NPD1608	Approved
0.6928	Remote Similarity	NPD826	Approved
0.6928	Remote Similarity	NPD825	Approved
0.6928	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD1551	Phase 2
0.6906	Remote Similarity	NPD3022	Approved
0.6906	Remote Similarity	NPD3021	Approved
0.6902	Remote Similarity	NPD6781	Approved
0.6902	Remote Similarity	NPD6778	Approved
0.6902	Remote Similarity	NPD6782	Approved
0.6902	Remote Similarity	NPD6780	Approved
0.6902	Remote Similarity	NPD6777	Approved
0.6902	Remote Similarity	NPD6776	Approved
0.6902	Remote Similarity	NPD6779	Approved
0.6901	Remote Similarity	NPD2629	Approved
0.6894	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7700	Phase 2
0.6885	Remote Similarity	NPD7699	Phase 2
0.6875	Remote Similarity	NPD8313	Approved
0.6875	Remote Similarity	NPD8312	Approved
0.6871	Remote Similarity	NPD1535	Discovery
0.6863	Remote Similarity	NPD6663	Approved
0.6855	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4110	Phase 3
0.6846	Remote Similarity	NPD3225	Approved
0.6845	Remote Similarity	NPD8319	Approved
0.6845	Remote Similarity	NPD3749	Approved
0.6845	Remote Similarity	NPD8320	Phase 1
0.6832	Remote Similarity	NPD4357	Discontinued
0.6829	Remote Similarity	NPD3226	Approved
0.6826	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1481	Phase 2
0.6821	Remote Similarity	NPD5736	Approved
0.6818	Remote Similarity	NPD1240	Approved
0.6815	Remote Similarity	NPD5408	Approved
0.6815	Remote Similarity	NPD5405	Approved
0.6815	Remote Similarity	NPD5404	Approved
0.6815	Remote Similarity	NPD2796	Approved
0.6815	Remote Similarity	NPD5406	Approved
0.6813	Remote Similarity	NPD3887	Approved
0.6813	Remote Similarity	NPD2354	Approved
0.6805	Remote Similarity	NPD919	Approved
0.6802	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7097	Phase 1
0.679	Remote Similarity	NPD3146	Approved
0.679	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2532	Approved
0.679	Remote Similarity	NPD2534	Approved
0.679	Remote Similarity	NPD2533	Approved
0.6786	Remote Similarity	NPD7768	Phase 2
0.6774	Remote Similarity	NPD555	Phase 2
0.6772	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7874	Approved
0.6752	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6273	Approved
0.6744	Remote Similarity	NPD3926	Phase 2
0.6742	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4198	Discontinued
0.6735	Remote Similarity	NPD17	Approved
0.6731	Remote Similarity	NPD6653	Approved
0.6731	Remote Similarity	NPD1607	Approved
0.673	Remote Similarity	NPD5958	Discontinued
0.673	Remote Similarity	NPD4534	Discontinued
0.6727	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7458	Discontinued
0.6725	Remote Similarity	NPD6959	Discontinued
0.6725	Remote Similarity	NPD1247	Approved
0.6712	Remote Similarity	NPD1894	Discontinued
0.6711	Remote Similarity	NPD2861	Phase 2
0.6709	Remote Similarity	NPD2438	Suspended
0.6702	Remote Similarity	NPD7698	Approved
0.6702	Remote Similarity	NPD7697	Approved
0.6702	Remote Similarity	NPD7696	Phase 3
0.669	Remote Similarity	NPD9493	Approved
0.669	Remote Similarity	NPD228	Approved
0.6689	Remote Similarity	NPD1470	Approved
0.6689	Remote Similarity	NPD1203	Approved
0.6689	Remote Similarity	NPD2797	Approved
0.6688	Remote Similarity	NPD3268	Approved
0.6687	Remote Similarity	NPD1652	Phase 2
0.6686	Remote Similarity	NPD7229	Phase 3
0.6685	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD2982	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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