Structure

Physi-Chem Properties

Molecular Weight:  344.13
Volume:  345.797
LogP:  2.387
LogD:  1.914
LogS:  -3.379
# Rotatable Bonds:  3
TPSA:  85.97
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.512
Synthetic Accessibility Score:  3.738
Fsp3:  0.368
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.796
MDCK Permeability:  2.1824866053066216e-05
Pgp-inhibitor:  0.509
Pgp-substrate:  0.017
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  84.93338775634766%
Volume Distribution (VD):  1.434
Pgp-substrate:  10.110835075378418%

ADMET: Metabolism

CYP1A2-inhibitor:  0.701
CYP1A2-substrate:  0.936
CYP2C19-inhibitor:  0.87
CYP2C19-substrate:  0.25
CYP2C9-inhibitor:  0.807
CYP2C9-substrate:  0.824
CYP2D6-inhibitor:  0.736
CYP2D6-substrate:  0.307
CYP3A4-inhibitor:  0.563
CYP3A4-substrate:  0.407

ADMET: Excretion

Clearance (CL):  7.215
Half-life (T1/2):  0.575

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.971
Drug-inuced Liver Injury (DILI):  0.907
AMES Toxicity:  0.089
Rat Oral Acute Toxicity:  0.064
Maximum Recommended Daily Dose:  0.309
Skin Sensitization:  0.107
Carcinogencity:  0.708
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.034

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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  Natural Product: NPC218943

Natural Product ID:  NPC218943
Common Name*:   DBIKJXXBCAHHMC-VQTJNVASSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  DBIKJXXBCAHHMC-VQTJNVASSA-N
Standard InCHI:  InChI=1S/C20H26O7/c1-25-17-11-14(6-7-15(17)23)20(24)19(12-22)27-16-8-5-13(4-3-9-21)10-18(16)26-2/h5-8,10-11,19-24H,3-4,9,12H2,1-2H3/t19-,20+/m0/s1
SMILES:  COc1cc(ccc1O)[C@H]([C@H](CO)Oc1ccc(CCCO)cc1OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   13893597
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2005.10.025]
NPO19975 Pycnandra acuminata Species Sapotaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2007.07.001]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds Mengha, Yunnan Province, China 1991-Aug PMID[11277741]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[11325233]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota Seeds n.a. n.a. PMID[11430002]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[11520245]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[12045343]
NPO25119 Euonymus laxiflorus Species Celastraceae Eukaryota n.a. leaf n.a. PMID[12713415]
NPO25119 Euonymus laxiflorus Species Celastraceae Eukaryota n.a. stem n.a. PMID[12713415]
NPO25119 Euonymus laxiflorus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12713415]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota seeds n.a. n.a. PMID[12762787]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[12762809]
NPO19263 Bulbinella floribunda Species Asphodelaceae Eukaryota roots n.a. n.a. PMID[12828488]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[1324982]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. heartwood n.a. PMID[13465274]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[14695801]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[1536925]
NPO6412 Echinacea pallida Species Asteraceae Eukaryota root n.a. n.a. PMID[15921428]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16180822]
NPO25344 Caryocar villosum Species Caryocaraceae Eukaryota Fruits n.a. n.a. PMID[16792411]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[17512094]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[1791484]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. spore n.a. PMID[18827358]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19376614]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies Nagano, Japan 2008-MAY PMID[20039640]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[20384295]
NPO23525 Physalis sordida Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[20575572]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies n.a. n.a. PMID[20702092]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies n.a. n.a. PMID[21924611]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[22014750]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[22044278]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting body n.a. n.a. PMID[22047696]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[23944995]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. seed n.a. PMID[24225786]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[26222905]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26231157]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[26477735]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29192771]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[30169038]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. The ‘Dolina Mogilnicy’ Organic Farming Products Cooperative (Wolkowo, Poland) 2016-Oct PMID[31416184]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[3509958]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[6114991]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[9635497]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25428 Ceriops decandra Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14387 Dalbergia ecastaphyllum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15954 Pyrenula japonica Species Pyrenulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25608 Zanthoxylum acutifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2749 Baccharis dracunculifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6856.1 Artemisia ludoviciana subsp. mexicana Subspecies Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16326 Scopolia parviflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23583 Taonia australasica Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12118 Cleistopholis staudtii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17444 Gleichenia japonica Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21570 Blumea eriantha Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18071 Euryops pedunculatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25119 Euonymus laxiflorus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23725 Dytiscus marginalis Species Dytiscidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24442 Calycotome villosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10751 Bothriocline laxa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26095 Hypericum revolutum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25244 Scopolia atropoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1695 Monascus pilosus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO940 Vernonia anisochaetoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17104 Pithecellobium racemosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5584 Aldisa sanguinea Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25687 Archidendron ellipticum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23219 Lactarius sanguifluus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14507.1 Quercus ithaburensis subsp. macrolepis Subspecies Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25063 Ongokea gore Species Aptandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11280 Aphanoascus terreus Species Onygenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25608 Zanthoxylum acutifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15594 Aplidiopsis confluata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO22012 Cipadessa fruticosa Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12828 Dysidea tupha Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5534 Alternaria kikuchiana Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO619 Ankistrodesmus braunii Species Selenastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11339 Litsea salicifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23336 Cladonia impexa Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17917 Thamnophis sirtalis Species Colubridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16049 Cryptocarya pleurosperma Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4759 Helleborus multifidus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18993 Araiostegiella perdurans Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22863 Littorina littorea Species Littorinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10010 Evernia vulpina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4322 Scabiosa succisa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8058 Pluchea odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6861 Galium dasypodum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24251 Taxus drupacea Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25344 Caryocar villosum Species Caryocaraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22056 Streptomyces roseoverticillatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25428 Ceriops decandra Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25401 Glochidion philippicum Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2993 0totodarus sloanii Species Ommastrephidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4274 Alcyonium utinomii Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15954 Pyrenula japonica Species Pyrenulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6231 Cortinarius odoratus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25486 Zaluzania grayana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24534 Senecio heliopsis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2749 Baccharis dracunculifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO849 Euonymus tingens Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24666 Codium dwarkense Species Codiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23456 Palaquium canaliculatum Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24710 Achillea biebersteinii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17141 Lonchocarpus longistylus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12602 Leuzea centauroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12630 Senecio oxyodontus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20636 Myoporum platycarpum Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25656 Rhizoctonia repens Species Ceratobasidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16326 Scopolia parviflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO218 Acer carpinifolium Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22536 Cladosporium cucumerinum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6856.1 Artemisia ludoviciana subsp. mexicana Subspecies Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15487 Gymnopus confluens Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24149 Paracoccus denitrificans Species Rhodobacteraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19263 Bulbinella floribunda Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5016 Glossogyne tenuifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3408 Viguiera decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25067 Sanicula epipactis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11747 Ocimum tenuiflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10970 Osmorhiza aristata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23525 Physalis sordida Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4949 Salvia yosgadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25578 Chiton tuberculatus Species Chitonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25632 Sarcophyton buitendijki Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25157 Cymbastela coralliophila Species Axinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3956 Maesa ramentacea Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24860 Euphorbia formosana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24325 Ilex brevicuspis Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11134 Himalaiella deltoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1242 Balanops australiana Species Balanopaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7606 Salacia lehmbachii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1489 Pseudoplexaura flagellosa Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1390 Melolontha melolontha Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11506 Stipa vaseyi Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8129 Inocybe geophylla Species Inocybaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19975 Pycnandra acuminata Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7007 Eucalyptus jenseni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11755 Banisteriopsis caapi Species Malpighiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16210 Androcymbium palaestinum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14387 Dalbergia ecastaphyllum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7760 Macrolepiota neomastoidea Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25517 Colladonia triquetra n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3743 Sideritis brevibracteata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24903 Diplazium esculentum Species Athyriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5261 Sideroxylon cubense Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24483 Acrisione denticulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17757 Plectranthus saccatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25760 Aspergillus striatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14001 Ceroplastes pseudoceriferus Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8609 Hopea utilis Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15740 Garcinia purpurea Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25064 Streptomyces purpurogeneiscleroticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6412 Echinacea pallida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7874 Helichrysum lepidissimum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17600 Gnathotrichus sulcatus Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7449 Eleutherobia albiflora Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25453 Solidago petiolaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

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

  NP Quantity Composition/Concentration

Organism ID 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 NPC218943 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 NPC218943 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