Structure

Physi-Chem Properties

Molecular Weight:  208.07
Volume:  212.234
LogP:  2.383
LogD:  2.489
LogS:  -1.661
# Rotatable Bonds:  4
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.45
Synthetic Accessibility Score:  2.021
Fsp3:  0.182
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.62
MDCK Permeability:  2.2613819965044968e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.019
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.35
30% Bioavailability (F30%):  0.842

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.197
Plasma Protein Binding (PPB):  92.2585678100586%
Volume Distribution (VD):  0.357
Pgp-substrate:  6.236161231994629%

ADMET: Metabolism

CYP1A2-inhibitor:  0.964
CYP1A2-substrate:  0.186
CYP2C19-inhibitor:  0.513
CYP2C19-substrate:  0.081
CYP2C9-inhibitor:  0.612
CYP2C9-substrate:  0.868
CYP2D6-inhibitor:  0.424
CYP2D6-substrate:  0.671
CYP3A4-inhibitor:  0.457
CYP3A4-substrate:  0.246

ADMET: Excretion

Clearance (CL):  15.766
Half-life (T1/2):  0.922

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.1
Drug-inuced Liver Injury (DILI):  0.046
AMES Toxicity:  0.285
Rat Oral Acute Toxicity:  0.741
Maximum Recommended Daily Dose:  0.12
Skin Sensitization:  0.947
Carcinogencity:  0.54
Eye Corrosion:  0.075
Eye Irritation:  0.909
Respiratory Toxicity:  0.161

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC294555

Natural Product ID:  NPC294555
Common Name*:   WDKYDMULARNCIS-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  WDKYDMULARNCIS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3
SMILES:  CCOC(=O)C=Cc1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   66883
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric 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
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)88710-5]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np50070a031]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[11374950]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[11473439]
NPO1033 Plectranthus nummularius Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[11558608]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[12141863]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. Indonesia n.a. PMID[12467611]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota aerial parts Bangdung, Indonesia 2000-Aug PMID[12608860]
NPO24753 Ballota limbata Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[15056960]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. Taiwan n.a. PMID[15104497]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[15165144]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[15844878]
NPO25104 Grindelia scorzonerifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15844947]
NPO20454 Bidens pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[16041399]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[16209522]
NPO11507 Entada africana Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16989528]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[17279797]
NPO28581 Aspergillus fumisynnematus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17523650]
NPO21944 Laurencia mariannensis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[18076141]
NPO9392 Elaeodendron alluaudianum Species Celastraceae Eukaryota n.a. stem n.a. PMID[19058971]
NPO9392 Elaeodendron alluaudianum Species Celastraceae Eukaryota n.a. Madagascar Rainforest n.a. PMID[19058971]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota rhizomes n.a. n.a. PMID[19739599]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. PMID[20488581]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[20583752]
NPO5877 Morus yunnanensis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[22165973]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23022271]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23186307]
NPO24718 Streptomyces parvulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23423168]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[23876370]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[26473275]
NPO23000 Zephyranthes carinata Species Amaryllidaceae Eukaryota Whole Plants n.a. n.a. PMID[28898076]
NPO3549 Euonymus maackii Species Celastraceae Eukaryota Seeds n.a. n.a. PMID[31713425]
NPO20454 Bidens pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[469551]
NPO23108 Pinus flexilis Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[9834165]
NPO23226 Satureja montana Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23141 Angelica ursina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23286 Galium mollugo Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22685 Astragalus bisulcatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24771 Boenninghausenia albiflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO24753 Ballota limbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23286 Galium mollugo Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1033 Plectranthus nummularius Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22685 Astragalus bisulcatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22071 Gentiana olivieri Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21881 Stephania succifera Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO60 Neoshirakia japonica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22462 Chlorophytum malayense Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7043 Fuligo candida Species Physaraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3549 Euonymus maackii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23141 Angelica ursina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25266 Baccharoides lasiopus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24771 Boenninghausenia albiflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23853 Senegalia mellifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21807 Lindera umbellata Species Lauraceae 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]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24771 Boenninghausenia albiflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24321 Vicia amoena Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22685 Astragalus bisulcatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23108 Pinus flexilis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4048 Inga longispica Species Oecophoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24491 Flindersia xanthoxyla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28581 Aspergillus fumisynnematus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24558 Calea lantanoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9358 Pseuduvaria indochinensis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23144 Brachyglottis bidwillii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9392 Elaeodendron alluaudianum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24112 Pisaster giganteus Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21384 Tetraria capillaris Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8401 Pteris setuloso-costulata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6370 Roemeria carica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24522 Sepia officinalis Species Sepiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22518 Gnetum cleistostachyum Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19819 Trichoderma viride Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22462 Chlorophytum malayense Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25065 Gardenia imperialis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11153 Entada polystachya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25190 Lonchocarpus atropurpureus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25150 Haliclona cribricutis Species Chalinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22952 Senecio grandiflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20100 Ephedra lomatolepis Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22015 Clausena indica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24657 Bothriocline ripensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22685 Astragalus bisulcatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22197 Eriogaster lanestris Species Lasiocampidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25104 Grindelia scorzonerifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22717 Pinus thunbergii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22773 Teucrium alyssifolium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO60 Neoshirakia japonica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21881 Stephania succifera Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22395 Ardisia macrocarpa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15449 Echium rubrum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO249 Dysosma pleianthum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24687 Sabadilla officinalis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23183 Pinus halepensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24968 Delphinus globiceps Species Delphinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11507 Entada africana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24020 Raputia praetermissa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23365 Drummondita hassellii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24771 Boenninghausenia albiflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21545 Maytenus guianensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9786 Monomeria barbata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23000 Zephyranthes carinata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20964 Picradeniopsis oppositifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24753 Ballota limbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25225 Radianthus kuekenthali n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24718 Streptomyces parvulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23749 Achillea nana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7043 Fuligo candida Species Physaraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7066 Gomesa radicans Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24935 Coronilla cretica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14865 Vitex limonifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20454 Bidens pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22911 Enterococcus faecalis Species Enterococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5877 Morus yunnanensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13694 Rhodococcus erythropolis Species 0cardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24899 Chroogomphus helveticus Species Gomphidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3549 Euonymus maackii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23853 Senegalia mellifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21796 Lepidium graminifolium Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24405 Farlowia mollis Species Dumontiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19691 Mycena fagetorum Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21140 Igernella notabilis Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23286 Galium mollugo Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23141 Angelica ursina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23062 Melibe leonina Species Dendronotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11684 Iberis sempervirens Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22071 Gentiana olivieri Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16275 Pterocaulon rugosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21944 Laurencia mariannensis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1033 Plectranthus nummularius Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20726 Ophioplocus japonicus Species Ophiolepididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22025 Drosera indica Species Droseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14049 Fumaria indica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7320 Nicotiana gossei Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4360 Hendersonula toruloidea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13383 Schumanniophyton magnificum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25129 Tricholoma acerbum Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23101 Ircinia aruensis Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12994 Choriaster granulatus Species Oreasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10353 Rauvolfia tetraphylla Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17874 Mus striatus Species Muridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21758 Thiocystis gelatinosa Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14664 Stevia salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24321 Vicia amoena Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22137 Vernonia serratuloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21745 Phleum africanum Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14529 Asterias rubens Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21680 Saussurea triangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25266 Baccharoides lasiopus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24588 Phellinus igniarius Species Hymenochaetaceae 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

☑ 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

☑ 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 NPC294555 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID

  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 NPC294555 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage

  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