Structure

Physi-Chem Properties

Molecular Weight:  346.14
Volume:  348.433
LogP:  0.419
LogD:  1.124
LogS:  -2.432
# Rotatable Bonds:  4
TPSA:  93.06
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.451
Synthetic Accessibility Score:  5.02
Fsp3:  0.474
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.185
MDCK Permeability:  0.00015472964150831103
Pgp-inhibitor:  0.011
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.078
20% Bioavailability (F20%):  0.666
30% Bioavailability (F30%):  0.645

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.062
Plasma Protein Binding (PPB):  67.15390014648438%
Volume Distribution (VD):  0.848
Pgp-substrate:  50.1939697265625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.062
CYP1A2-substrate:  0.049
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.099
CYP2C9-inhibitor:  0.086
CYP2C9-substrate:  0.034
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.082
CYP3A4-inhibitor:  0.122
CYP3A4-substrate:  0.175

ADMET: Excretion

Clearance (CL):  7.043
Half-life (T1/2):  0.71

ADMET: Toxicity

hERG Blockers:  0.105
Human Hepatotoxicity (H-HT):  0.947
Drug-inuced Liver Injury (DILI):  0.914
AMES Toxicity:  0.058
Rat Oral Acute Toxicity:  0.87
Maximum Recommended Daily Dose:  0.976
Skin Sensitization:  0.414
Carcinogencity:  0.249
Eye Corrosion:  0.095
Eye Irritation:  0.128
Respiratory Toxicity:  0.973

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC38392

Natural Product ID:  NPC38392
Common Name*:   Cynaropicrin
IUPAC Name:   [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
Synonyms:   Cynaropicrin
Standard InCHIKey:  KHSCYOFDKADJDJ-NQLMQOPMSA-N
Standard InCHI:  InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1
SMILES:  C=C1C[C@@H]([C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@H](C[C@@H]12)O)OC(=O)C(=C)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL374146
PubChem CID:   119093
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001770] Guaianolides 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
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2005.10.025]
NPO24419 Anvillea garcinii Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[11087618]
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. leaf n.a. PMID[12713415]
NPO25119 Euonymus laxiflorus Species Celastraceae Eukaryota n.a. stem 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]
NPO2291 Saussurea pulchella Species Asteraceae Eukaryota aerial parts n.a. n.a. PMID[18314958]
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]
NPO10471 Scorzonera radiata Species Asteraceae Eukaryota n.a. Mongolian n.a. PMID[19271716]
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]
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[6114991]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO24419 Anvillea garcinii Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8699183]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[9635497]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23343 Cynara cardunculus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2291 Saussurea pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23343 Cynara cardunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30574 Cynara scolymus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1663 Amberboa muricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO9427 Lemna minor Species Araceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9427 Lemna minor Species Araceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23343 Cynara cardunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21021 Hemisteptia lyrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25608 Zanthoxylum acutifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25428 Ceriops decandra Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14834 Trachelospermum asiaticum Species Apocynaceae 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]
NPO1663 Amberboa muricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2749 Baccharis dracunculifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2291 Saussurea pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30115 Aucklandia lappa n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30574 Cynara scolymus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2291 Saussurea pulchella Species Asteraceae 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]
NPO23343 Cynara cardunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1663 Amberboa muricata Species Asteraceae 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]
NPO14834 Trachelospermum asiaticum Species Apocynaceae 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]
NPO25656 Rhizoctonia repens Species Ceratobasidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25401 Glochidion philippicum Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20636 Myoporum platycarpum Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24419 Anvillea garcinii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19263 Bulbinella floribunda Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25453 Solidago petiolaris 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]
NPO25632 Sarcophyton buitendijki Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25727 Tabernaemontana divaricata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9427 Lemna minor Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22056 Streptomyces roseoverticillatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16242 Phlojodicarpus sibiricus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24483 Acrisione denticulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25344 Caryocar villosum Species Caryocaraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25064 Streptomyces purpurogeneiscleroticus Species Streptomycetaceae Bacteria 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]
NPO25687 Archidendron ellipticum Species Fabaceae Eukaryota 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]
NPO25206 Cucurbita moschata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23583 Taonia australasica Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18861 Pyxine coccifera Species Caliciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11433 Candelaria concolor Species Candelariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2291 Saussurea pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23456 Palaquium canaliculatum Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25063 Ongokea gore Species Aptandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO750 Emericellopsis salmosynnemata Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23725 Dytiscus marginalis Species Dytiscidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23525 Physalis sordida Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6394 Shorea robusta Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23336 Cladonia impexa Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22012 Cipadessa fruticosa Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24534 Senecio heliopsis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4480 Phlojodicarpus villosus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5721 Psorothamnus spinosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16819 Preussia aemulans Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24251 Taxus drupacea Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2749 Baccharis dracunculifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21021 Hemisteptia lyrata Species Asteraceae 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]
NPO24574 Berberis orthobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10193 Agave tequilana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24666 Codium dwarkense Species Codiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10471 Scorzonera radiata 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]
NPO1663 Amberboa muricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18273 Merendera sobolifera Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25428 Ceriops decandra Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22536 Cladosporium cucumerinum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25157 Cymbastela coralliophila Species Axinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12790 Lachnosiphonium niloticum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO11001 Ceanothus papillosus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24860 Euphorbia formosana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25119 Euonymus laxiflorus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11464 Centaurea kotschyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24903 Diplazium esculentum Species Athyriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5142 Garcinia pedunculata Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24325 Ilex brevicuspis Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25244 Scopolia atropoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24149 Paracoccus denitrificans Species Rhodobacteraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21570 Blumea eriantha Species Asteraceae 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]
NPO22863 Littorina littorea Species Littorinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14387 Dalbergia ecastaphyllum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25578 Chiton tuberculatus Species Chitonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25377 Ocimum gratissimum Species Lamiaceae 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
NPT2716 Individual Protein UDP-N-acetylglucosamine 1-carboxyvinyltransferase Escherichia coli K-12 IC50 = 19500.0 nM PMID[507033]
NPT2717 Individual Protein UDP-N-acetylglucosamine 1-carboxyvinyltransferase Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) IC50 = 12100.0 nM PMID[507033]
NPT81 Cell Line A549 Homo sapiens ED50 = 24.51 uM PMID[507034]
NPT146 Cell Line SK-OV-3 Homo sapiens ED50 = 7.42 uM PMID[507034]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 4.07 uM PMID[507034]
NPT148 Cell Line HCT-15 Homo sapiens ED50 = 12.13 uM PMID[507034]
NPT91 Cell Line KB Homo sapiens IC50 = 15900.0 nM PMID[507035]
NPT81 Cell Line A549 Homo sapiens IC50 = 16500.0 nM PMID[507035]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 3200.0 nM PMID[507035]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 5800.0 nM PMID[507035]
NPT839 Cell Line L6 Rattus norvegicus IC50 = 2190.0 nM PMID[507039]
NPT2718 Organism Trogoderma granarium Trogoderma granarium Activity = 49.5 n.a. PMID[507036]
NPT777 Organism Tribolium confusum Tribolium confusum Activity = 98.8 n.a. PMID[507036]
NPT733 Organism Sitophilus granarius Sitophilus granarius Activity = 51.6 n.a. PMID[507036]
NPT32 Organism Mus musculus Mus musculus FC = 4.3 n.a. PMID[507037]
NPT32 Organism Mus musculus Mus musculus FC = 1.7 n.a. PMID[507037]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense Activity = 37.1 uM PMID[507038]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense Activity = 33.3 uM PMID[507038]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense Activity = 35.8 uM PMID[507038]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense Activity = 39.6 uM PMID[507038]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense Activity = 49.0 uM PMID[507038]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense Activity = 42.0 uM PMID[507038]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense Activity = 23.0 uM PMID[507038]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense Activity = 34.9 uM PMID[507038]
NPT2 Others Unspecified Inhibition = 51.0 % PMID[507038]
NPT2 Others Unspecified INH = 50.0 uM PMID[507038]
NPT2 Others Unspecified Ratio IC50 = 7.8 n.a. PMID[507039]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 280.0 nM PMID[507039]
NPT2 Others Unspecified Activity = 72.85 RLU PMID[507041]
NPT2 Others Unspecified Activity = 5.67 RLU PMID[507041]
NPT2 Others Unspecified Activity = 134.36 RLU PMID[507041]

☑ 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 NPC38392 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
0.9881 High Similarity NPC19087
0.9765 High Similarity NPC184063
0.9643 High Similarity NPC217983
0.9643 High Similarity NPC207114
0.9639 High Similarity NPC187661
0.9398 High Similarity NPC194859
0.9398 High Similarity NPC224386
0.9222 High Similarity NPC474313
0.9195 High Similarity NPC297474
0.9195 High Similarity NPC54065
0.9176 High Similarity NPC304558
0.9111 High Similarity NPC142529
0.9111 High Similarity NPC91771
0.9091 High Similarity NPC29821
0.9091 High Similarity NPC171360
0.9091 High Similarity NPC133888
0.9091 High Similarity NPC57304
0.9091 High Similarity NPC475925
0.9091 High Similarity NPC293001
0.9091 High Similarity NPC35959
0.9091 High Similarity NPC63193
0.908 High Similarity NPC155935
0.908 High Similarity NPC215556
0.9048 High Similarity NPC128246
0.8977 High Similarity NPC35809
0.8977 High Similarity NPC216284
0.8966 High Similarity NPC79549
0.8929 High Similarity NPC246076
0.8889 High Similarity NPC473331
0.881 High Similarity NPC126248
0.8804 High Similarity NPC311904
0.8791 High Similarity NPC476053
0.8791 High Similarity NPC472873
0.8778 High Similarity NPC475788
0.8778 High Similarity NPC200237
0.8778 High Similarity NPC473273
0.8778 High Similarity NPC473234
0.8778 High Similarity NPC473263
0.8778 High Similarity NPC308656
0.8778 High Similarity NPC60386
0.8778 High Similarity NPC258216
0.8736 High Similarity NPC56593
0.8723 High Similarity NPC171759
0.8696 High Similarity NPC18019
0.8696 High Similarity NPC24956
0.8681 High Similarity NPC198853
0.8667 High Similarity NPC155215
0.8667 High Similarity NPC286341
0.8667 High Similarity NPC191339
0.8652 High Similarity NPC168679
0.8652 High Similarity NPC12872
0.8636 High Similarity NPC118601
0.8636 High Similarity NPC24728
0.8621 High Similarity NPC284534
0.8621 High Similarity NPC300082
0.8621 High Similarity NPC204105
0.8605 High Similarity NPC111409
0.8602 High Similarity NPC471150
0.8587 High Similarity NPC170120
0.8587 High Similarity NPC213698
0.8587 High Similarity NPC163228
0.8571 High Similarity NPC153590
0.8539 High Similarity NPC178875
0.8539 High Similarity NPC471149
0.8523 High Similarity NPC309757
0.8523 High Similarity NPC64153
0.8523 High Similarity NPC236692
0.8511 High Similarity NPC49833
0.8511 High Similarity NPC249171
0.8478 Intermediate Similarity NPC470010
0.8478 Intermediate Similarity NPC470013
0.8478 Intermediate Similarity NPC262133
0.8478 Intermediate Similarity NPC127019
0.8478 Intermediate Similarity NPC323008
0.8462 Intermediate Similarity NPC133698
0.8462 Intermediate Similarity NPC131209
0.8444 Intermediate Similarity NPC283409
0.8444 Intermediate Similarity NPC472872
0.8438 Intermediate Similarity NPC80144
0.8427 Intermediate Similarity NPC201658
0.8404 Intermediate Similarity NPC213947
0.8404 Intermediate Similarity NPC108475
0.8404 Intermediate Similarity NPC161493
0.8404 Intermediate Similarity NPC170143
0.8391 Intermediate Similarity NPC245665
0.8387 Intermediate Similarity NPC52044
0.8387 Intermediate Similarity NPC304886
0.8387 Intermediate Similarity NPC67584
0.8367 Intermediate Similarity NPC44004
0.8333 Intermediate Similarity NPC150923
0.8315 Intermediate Similarity NPC238593
0.8315 Intermediate Similarity NPC470242
0.8298 Intermediate Similarity NPC213078
0.8298 Intermediate Similarity NPC476009
0.8298 Intermediate Similarity NPC126156
0.828 Intermediate Similarity NPC477131
0.8229 Intermediate Similarity NPC186861
0.8229 Intermediate Similarity NPC471381
0.8211 Intermediate Similarity NPC181151
0.8211 Intermediate Similarity NPC304445
0.8211 Intermediate Similarity NPC236580
0.8193 Intermediate Similarity NPC320537
0.8193 Intermediate Similarity NPC143979
0.8191 Intermediate Similarity NPC475900
0.8163 Intermediate Similarity NPC473148
0.8144 Intermediate Similarity NPC67296
0.814 Intermediate Similarity NPC19841
0.8132 Intermediate Similarity NPC91248
0.8125 Intermediate Similarity NPC45125
0.8125 Intermediate Similarity NPC221615
0.8111 Intermediate Similarity NPC162071
0.8111 Intermediate Similarity NPC67493
0.8105 Intermediate Similarity NPC474297
0.8061 Intermediate Similarity NPC86077
0.8046 Intermediate Similarity NPC51507
0.8046 Intermediate Similarity NPC258965
0.8046 Intermediate Similarity NPC6823
0.8046 Intermediate Similarity NPC156658
0.8022 Intermediate Similarity NPC190753
0.8022 Intermediate Similarity NPC186148
0.8022 Intermediate Similarity NPC270270
0.8021 Intermediate Similarity NPC169205
0.8 Intermediate Similarity NPC235792
0.8 Intermediate Similarity NPC54737
0.8 Intermediate Similarity NPC167893
0.7979 Intermediate Similarity NPC472874
0.7979 Intermediate Similarity NPC135776
0.7978 Intermediate Similarity NPC54468
0.7957 Intermediate Similarity NPC301969
0.7957 Intermediate Similarity NPC474323
0.7957 Intermediate Similarity NPC37607
0.7957 Intermediate Similarity NPC206614
0.7938 Intermediate Similarity NPC141191
0.7935 Intermediate Similarity NPC224652
0.7935 Intermediate Similarity NPC58219
0.7935 Intermediate Similarity NPC177629
0.7921 Intermediate Similarity NPC26617
0.7917 Intermediate Similarity NPC185553
0.7917 Intermediate Similarity NPC230800
0.7907 Intermediate Similarity NPC208223
0.79 Intermediate Similarity NPC100487
0.79 Intermediate Similarity NPC203659
0.7889 Intermediate Similarity NPC156485
0.7879 Intermediate Similarity NPC474747
0.7879 Intermediate Similarity NPC225353
0.7857 Intermediate Similarity NPC70865
0.7849 Intermediate Similarity NPC295312
0.7849 Intermediate Similarity NPC4986
0.7849 Intermediate Similarity NPC92974
0.7843 Intermediate Similarity NPC68248
0.7835 Intermediate Similarity NPC477949
0.7822 Intermediate Similarity NPC243998
0.7822 Intermediate Similarity NPC166115
0.7812 Intermediate Similarity NPC193645
0.7812 Intermediate Similarity NPC469873
0.7812 Intermediate Similarity NPC48803
0.7812 Intermediate Similarity NPC275960
0.7812 Intermediate Similarity NPC90121
0.7802 Intermediate Similarity NPC255307
0.7802 Intermediate Similarity NPC165162
0.78 Intermediate Similarity NPC475871
0.78 Intermediate Similarity NPC110989
0.78 Intermediate Similarity NPC475945
0.7789 Intermediate Similarity NPC125674
0.7789 Intermediate Similarity NPC475912
0.7789 Intermediate Similarity NPC228451
0.7789 Intermediate Similarity NPC475838
0.7778 Intermediate Similarity NPC308824
0.7778 Intermediate Similarity NPC242666
0.7767 Intermediate Similarity NPC59489
0.7767 Intermediate Similarity NPC139838
0.7766 Intermediate Similarity NPC71533
0.7766 Intermediate Similarity NPC129419
0.7766 Intermediate Similarity NPC475855
0.7766 Intermediate Similarity NPC246173
0.7766 Intermediate Similarity NPC106510
0.7765 Intermediate Similarity NPC48641
0.7753 Intermediate Similarity NPC47635
0.7742 Intermediate Similarity NPC476803
0.7742 Intermediate Similarity NPC202672
0.7742 Intermediate Similarity NPC476805
0.7732 Intermediate Similarity NPC39859
0.7732 Intermediate Similarity NPC158416
0.7732 Intermediate Similarity NPC284518
0.7732 Intermediate Similarity NPC470883
0.7732 Intermediate Similarity NPC76862
0.7717 Intermediate Similarity NPC475461
0.7717 Intermediate Similarity NPC474949
0.7717 Intermediate Similarity NPC475019
0.7717 Intermediate Similarity NPC305475
0.7708 Intermediate Similarity NPC474338
0.7708 Intermediate Similarity NPC474247
0.7708 Intermediate Similarity NPC167219
0.77 Intermediate Similarity NPC164551
0.7692 Intermediate Similarity NPC158756
0.7692 Intermediate Similarity NPC474780
0.7692 Intermediate Similarity NPC212363
0.7692 Intermediate Similarity NPC114979
0.7692 Intermediate Similarity NPC476804
0.7692 Intermediate Similarity NPC191476

  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 NPC38392 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
0.7921 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD1695 Approved
0.7812 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7524 Intermediate Similarity NPD6371 Approved
0.7396 Intermediate Similarity NPD5785 Approved
0.734 Intermediate Similarity NPD4249 Approved
0.7263 Intermediate Similarity NPD4251 Approved
0.7263 Intermediate Similarity NPD4250 Approved
0.7234 Intermediate Similarity NPD5363 Approved
0.7097 Intermediate Similarity NPD4269 Approved
0.7097 Intermediate Similarity NPD4270 Approved
0.7021 Intermediate Similarity NPD5362 Discontinued
0.6989 Remote Similarity NPD5369 Approved
0.6979 Remote Similarity NPD5786 Approved
0.6909 Remote Similarity NPD6053 Discontinued
0.6882 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6882 Remote Similarity NPD4252 Approved
0.6875 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6698 Approved
0.6869 Remote Similarity NPD46 Approved
0.6842 Remote Similarity NPD7154 Phase 3
0.6832 Remote Similarity NPD5282 Discontinued
0.68 Remote Similarity NPD7983 Approved
0.6737 Remote Similarity NPD6435 Approved
0.6733 Remote Similarity NPD5778 Approved
0.6733 Remote Similarity NPD5779 Approved
0.6731 Remote Similarity NPD4225 Approved
0.6702 Remote Similarity NPD4820 Approved
0.6702 Remote Similarity NPD4821 Approved
0.6702 Remote Similarity NPD4822 Approved
0.6702 Remote Similarity NPD4819 Approved
0.6701 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7639 Approved
0.6667 Remote Similarity NPD4271 Approved
0.6667 Remote Similarity NPD4268 Approved
0.6667 Remote Similarity NPD7640 Approved
0.6632 Remote Similarity NPD4790 Discontinued
0.6571 Remote Similarity NPD7638 Approved
0.6535 Remote Similarity NPD7838 Discovery
0.6526 Remote Similarity NPD5368 Approved
0.6495 Remote Similarity NPD5331 Approved
0.6495 Remote Similarity NPD5332 Approved
0.6471 Remote Similarity NPD7637 Suspended
0.6396 Remote Similarity NPD6686 Approved
0.6379 Remote Similarity NPD7115 Discovery
0.6372 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4238 Approved
0.6316 Remote Similarity NPD4802 Phase 2
0.6316 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6275 Remote Similarity NPD6101 Approved
0.6275 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6262 Remote Similarity NPD8029 Clinical (unspecified phase)
0.625 Remote Similarity NPD6399 Phase 3
0.6239 Remote Similarity NPD7632 Discontinued
0.6226 Remote Similarity NPD7839 Suspended
0.6216 Remote Similarity NPD6008 Approved
0.6167 Remote Similarity NPD8513 Phase 3
0.6167 Remote Similarity NPD8516 Approved
0.6167 Remote Similarity NPD8517 Approved
0.6167 Remote Similarity NPD8515 Approved
0.6154 Remote Similarity NPD8034 Phase 2
0.6154 Remote Similarity NPD6411 Approved
0.6154 Remote Similarity NPD8035 Phase 2
0.6148 Remote Similarity NPD7492 Approved
0.6147 Remote Similarity NPD5344 Discontinued
0.6121 Remote Similarity NPD8133 Approved
0.6106 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6098 Remote Similarity NPD6616 Approved
0.6083 Remote Similarity NPD6319 Approved
0.6083 Remote Similarity NPD6054 Approved
0.608 Remote Similarity NPD7319 Approved
0.6061 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6048 Remote Similarity NPD7078 Approved
0.6047 Remote Similarity NPD3198 Approved
0.604 Remote Similarity NPD1694 Approved
0.6033 Remote Similarity NPD6016 Approved
0.6033 Remote Similarity NPD8268 Approved
0.6033 Remote Similarity NPD8269 Approved
0.6033 Remote Similarity NPD6015 Approved
0.6033 Remote Similarity NPD8266 Approved
0.6033 Remote Similarity NPD8267 Approved
0.6019 Remote Similarity NPD6084 Phase 2
0.6019 Remote Similarity NPD6083 Phase 2
0.6018 Remote Similarity NPD5697 Approved
0.6018 Remote Similarity NPD6412 Phase 2
0.6 Remote Similarity NPD7736 Approved
0.5984 Remote Similarity NPD5988 Approved
0.5984 Remote Similarity NPD6370 Approved
0.5981 Remote Similarity NPD5695 Phase 3
0.5968 Remote Similarity NPD7507 Approved
0.5965 Remote Similarity NPD6899 Approved
0.5965 Remote Similarity NPD7320 Approved
0.5965 Remote Similarity NPD6881 Approved
0.5963 Remote Similarity NPD5696 Approved
0.5962 Remote Similarity NPD5370 Suspended
0.595 Remote Similarity NPD6059 Approved
0.5948 Remote Similarity NPD6649 Approved
0.5948 Remote Similarity NPD6650 Approved
0.5941 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5929 Remote Similarity NPD6675 Approved
0.5929 Remote Similarity NPD5739 Approved
0.5929 Remote Similarity NPD7128 Approved
0.5929 Remote Similarity NPD6402 Approved
0.592 Remote Similarity NPD8293 Discontinued
0.592 Remote Similarity NPD8074 Phase 3
0.5913 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5913 Remote Similarity NPD6014 Approved
0.5913 Remote Similarity NPD6373 Approved
0.5913 Remote Similarity NPD6372 Approved
0.5913 Remote Similarity NPD6013 Approved
0.5913 Remote Similarity NPD6012 Approved
0.5909 Remote Similarity NPD6648 Approved
0.5906 Remote Similarity NPD6007 Clinical (unspecified phase)
0.59 Remote Similarity NPD5209 Approved
0.5889 Remote Similarity NPD9496 Clinical (unspecified phase)
0.5882 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5877 Remote Similarity NPD5701 Approved
0.5865 Remote Similarity NPD6903 Approved
0.5862 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5862 Remote Similarity NPD6883 Approved
0.5862 Remote Similarity NPD7290 Approved
0.5862 Remote Similarity NPD7102 Approved
0.5849 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5847 Remote Similarity NPD4632 Approved
0.5842 Remote Similarity NPD4788 Approved
0.5842 Remote Similarity NPD6695 Phase 3
0.5841 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5841 Remote Similarity NPD4057 Clinical (unspecified phase)
0.584 Remote Similarity NPD8273 Phase 1
0.5826 Remote Similarity NPD6011 Approved
0.5825 Remote Similarity NPD7146 Approved
0.5825 Remote Similarity NPD6409 Approved
0.5825 Remote Similarity NPD7521 Approved
0.5825 Remote Similarity NPD6684 Approved
0.5825 Remote Similarity NPD5330 Approved
0.5825 Remote Similarity NPD7334 Approved
0.5812 Remote Similarity NPD6847 Approved
0.5812 Remote Similarity NPD8130 Phase 1
0.5812 Remote Similarity NPD6869 Approved
0.5812 Remote Similarity NPD6617 Approved
0.5804 Remote Similarity NPD5211 Phase 2
0.5784 Remote Similarity NPD3665 Phase 1
0.5784 Remote Similarity NPD3133 Approved
0.5784 Remote Similarity NPD3666 Approved
0.5763 Remote Similarity NPD8297 Approved
0.5763 Remote Similarity NPD6882 Approved
0.5743 Remote Similarity NPD3667 Approved
0.5739 Remote Similarity NPD6685 Approved
0.5726 Remote Similarity NPD4634 Approved
0.5714 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5714 Remote Similarity NPD1700 Approved
0.5702 Remote Similarity NPD6009 Approved
0.5702 Remote Similarity NPD5141 Approved
0.5701 Remote Similarity NPD5281 Approved
0.5701 Remote Similarity NPD5284 Approved
0.5701 Remote Similarity NPD5693 Phase 1
0.5699 Remote Similarity NPD229 Approved
0.5692 Remote Similarity NPD6845 Suspended
0.5688 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5688 Remote Similarity NPD4629 Approved
0.5688 Remote Similarity NPD5210 Approved
0.5673 Remote Similarity NPD3618 Phase 1
0.566 Remote Similarity NPD4753 Phase 2
0.5659 Remote Similarity NPD5956 Approved
0.5656 Remote Similarity NPD7328 Approved
0.5656 Remote Similarity NPD7327 Approved
0.5645 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5645 Remote Similarity NPD5983 Phase 2
0.5645 Remote Similarity NPD8033 Approved
0.5639 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5631 Remote Similarity NPD4786 Approved
0.5631 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4696 Approved
0.5625 Remote Similarity NPD5285 Approved
0.5625 Remote Similarity NPD5286 Approved
0.562 Remote Similarity NPD6274 Approved
0.5619 Remote Similarity NPD7524 Approved
0.5619 Remote Similarity NPD7750 Discontinued
0.5615 Remote Similarity NPD7260 Phase 2
0.5614 Remote Similarity NPD5765 Approved
0.561 Remote Similarity NPD7516 Approved
0.5607 Remote Similarity NPD5207 Approved
0.5603 Remote Similarity NPD5954 Clinical (unspecified phase)
0.56 Remote Similarity NPD6929 Approved

  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