Natural Product: NPC147821

Natural Product IDNPC147821
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 7R,8S-Guaiacylglycerol-8-O-4'-(Coniferyl Alcohol)Ether
IUPAC Name (1R,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]propane-1,3-diol
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1761713
PubChem CID 14274760
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey FYEZJIXULOZDRT-YIYNPQHWSA-N
Standard InCHI InChI=1S/C20H24O7/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/h3-8,10-11,19-24H,9,12H2,1-2H3/b4-3+/t19-,20+/m0/s1
SMILES COc1cc(ccc1O)[C@H]([C@H](CO)Oc1ccc(/C=C/CO)cc1OC)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   376.15 Volume:   380.44
?
Van der Waals volume.
Dense:   0.989 LogP:   1.16
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.469
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.071
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   9.0 Rigid Bonds:   13.0
TPSA:   108.61
?
Topological Polar Surface Area.
 H-Bond Acceptor:   7.0
H-Bond Donor:   4.0 Rings:   2.0
Heavy Atoms:   7.0

MedChem Properties

QED Drug-Likeness Score:   0.529 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.235 Fsp3:   0.3
MCE-18:   28.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   0
Colloidal aggregators:   0.472 Fluc inhibitor:   0.802
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.035
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.308
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.339 Promiscuous compounds:   0.482

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.179 MDCK Permeability:   -4.882
Pgp-inhibitor:   0.062 Pgp-substrate:   0.023
PAMPA:   0.383
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.052
20% Bioavailability (F20%):   0.84 30% Bioavailability (F30%):   0.97
50% Bioavailability (F50%):   0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.011
Plasma Protein Binding (PPB):   71.425% Volume Distribution (VD):   0.079
Fu: 29.876%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.998
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.779
BSEP inhibitor:   0.892

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.677 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.001 CYP2C9-substrate:   0.013
CYP2D6-inhibitor:   1.0 CYP2D6-substrate:   0.001
CYP3A4-inhibitor:   0.001 CYP3A4-substrate:   0.001
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.754
HLM stability:   0.067
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  8.826 Half-life (T1/2):  1.797

ADMET: Toxicity

hERG Blockers:  0.132 hERG Blockers (10um):  0.239
Human Hepatotoxicity (H-HT):  0.878 Drug-induced Liver Injury (DILI):  0.377
AMES Toxicity:  0.534 Rat Oral Acute Toxicity:  0.016
Maximum Recommended Daily Dose:  0.288 Skin Sensitization:  0.937
Carcinogencity:  0.265 Eye Corrosion:  0.0
Eye Irritation:  0.448 Respiratory Toxicity:  0.113
Drug-induced Neurotoxicity:  0.454 Ototoxicity:  0.879
Hematotoxicity:  0.105 Drug-induced Nephrotoxicity:  0.61
Genotoxicity:  0.43 RPMI-8226 Immunitoxicity:  0.083
A549 Cytotoxicity:  0.301 Hek293 Cytotoxicity:  0.474
BCF:   0.392
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   2.849
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.412
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.467
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2005.10.025]
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. n.a. 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. leaf n.a. PMID[12713415]
NPO19263 Bulbinella floribunda Species Asphodelaceae Eukaryota roots n.a. n.a. PMID[12828488]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[14695801]
NPO25344 Caryocar villosum Species Caryocaraceae Eukaryota Fruits n.a. n.a. PMID[16792411]
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]
NPO24614 Streptomyces lucensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19115838]
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]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota leaves and twigs n.a. n.a. PMID[21435874]
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]
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]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37939623]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38641286]
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]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[9635497]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25608 Zanthoxylum acutifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2749 Baccharis dracunculifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25428 Ceriops decandra Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25119 Euonymus laxiflorus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25219 Aconitum kirinense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19263 Bulbinella floribunda Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21570 Blumea eriantha Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25344 Caryocar villosum Species Caryocaraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14387 Dalbergia ecastaphyllum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24483 Acrisione denticulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23219 Lactarius sanguifluus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25401 Glochidion philippicum Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24710 Achillea biebersteinii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22012 Cipadessa fruticosa Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24666 Codium dwarkense Species Codiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25632 Sarcophyton buitendijki Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23583 Taonia australasica Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23358 Ehretia ovalifolia Species Ehretiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19562 Lomatium nuttallii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25155 Pseudomonas mendocina Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO6387 Pyrenophora lolii Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24835 Rhapis excelsa Species Arecaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24614 Streptomyces lucensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25219 Aconitum kirinense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2749 Baccharis dracunculifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25428 Ceriops decandra Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14387 Dalbergia ecastaphyllum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25608 Zanthoxylum acutifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6387 Pyrenophora lolii Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29118 Euonymus alatus Species Celastraceae 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]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21570 Blumea eriantha Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20636 Myoporum platycarpum Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25453 Solidago petiolaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22056 Streptomyces roseoverticillatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24710 Achillea biebersteinii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11134 Himalaiella deltoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23725 Dytiscus marginalis Species Dytiscidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22012 Cipadessa fruticosa Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2749 Baccharis dracunculifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22863 Littorina littorea Species Littorinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25401 Glochidion philippicum Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25219 Aconitum kirinense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19263 Bulbinella floribunda Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25632 Sarcophyton buitendijki 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]
NPO24442 Calycotome villosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25063 Ongokea gore Species Aptandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24251 Taxus drupacea Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24666 Codium dwarkense Species Codiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22536 Cladosporium cucumerinum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23219 Lactarius sanguifluus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25608 Zanthoxylum acutifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25486 Zaluzania grayana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25656 Rhizoctonia repens Species Ceratobasidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17104 Pithecellobium racemosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24835 Rhapis excelsa Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25344 Caryocar villosum Species Caryocaraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23456 Palaquium canaliculatum Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23525 Physalis sordida Species Solanaceae 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]
NPO25119 Euonymus laxiflorus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25244 Scopolia atropoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24534 Senecio heliopsis 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]
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]
NPO14387 Dalbergia ecastaphyllum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24614 Streptomyces lucensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25687 Archidendron ellipticum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23336 Cladonia impexa Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23358 Ehretia ovalifolia Species Ehretiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25157 Cymbastela coralliophila Species Axinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24903 Diplazium esculentum Species Athyriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6387 Pyrenophora lolii Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24483 Acrisione denticulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25064 Streptomyces purpurogeneiscleroticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23583 Taonia australasica Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25428 Ceriops decandra Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24149 Paracoccus denitrificans Species Rhodobacteraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25578 Chiton tuberculatus Species Chitonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25155 Pseudomonas mendocina Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19562 Lomatium nuttallii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

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



  NP Quantity Composition/Concentration

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

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



 Biological Activity

Molecular-level activity

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

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell line RAW264.7 Mus musculus IC50 = 63600.0 nM PMID[21435874]

In vivo activity

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





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC147821 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC319625
1.0 High Similarity NPC183181
1.0 High Similarity NPC41706
0.8393 Intermediate Similarity NPC476387
0.8393 Intermediate Similarity NPC237594
0.8393 Intermediate Similarity NPC119060
0.8 Intermediate Similarity NPC114901
0.8 Intermediate Similarity NPC48990
0.7857 Intermediate Similarity NPC7903
0.7857 Intermediate Similarity NPC160991
0.7069 Intermediate Similarity NPC58607
0.7069 Intermediate Similarity NPC191037
0.7069 Intermediate Similarity NPC178284
0.7018 Intermediate Similarity NPC9370
0.7018 Intermediate Similarity NPC287495
0.678 Remote Similarity NPC601893
0.6721 Remote Similarity NPC267291
0.6557 Remote Similarity NPC111247
0.6557 Remote Similarity NPC292056
0.6528 Remote Similarity NPC470413
0.6102 Remote Similarity NPC184447
0.5946 Remote Similarity NPC260397
0.5932 Remote Similarity NPC310854
0.5849 Remote Similarity NPC78918
0.5849 Remote Similarity NPC139617
0.5775 Remote Similarity NPC114119
0.5775 Remote Similarity NPC471415
0.5758 Remote Similarity NPC472969
0.5692 Remote Similarity NPC481839
0.5606 Remote Similarity NPC249791
0.5577 Remote Similarity NPC227894
0.5556 Remote Similarity NPC470827
0.5522 Remote Similarity NPC118787
0.5469 Remote Similarity NPC16208
0.5467 Remote Similarity NPC107145
0.5395 Remote Similarity NPC473909
0.5303 Remote Similarity NPC163332
0.5303 Remote Similarity NPC75695
0.519 Remote Similarity NPC470769
0.5156 Remote Similarity NPC72529
0.5082 Remote Similarity NPC94276
0.5082 Remote Similarity NPC109822
0.5082 Remote Similarity NPC605984
0.5077 Remote Similarity NPC293701
0.5062 Remote Similarity NPC470828

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC147821 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data