Natural Product: NPC92125

Natural Product IDNPC92125
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 PKNGEQDEJRDPJZ-KJYWYCLQSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 23656471
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003509] 3-prenylated chalcones

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 PKNGEQDEJRDPJZ-KJYWYCLQSA-N
Standard InCHI InChI=1S/C26H30O4/c1-18(2)9-8-10-19(3)13-15-21-23(28)17-24(30-4)25(26(21)29)22(27)16-14-20-11-6-5-7-12-20/h5-7,9,11-14,16-17,28-29H,8,10,15H2,1-4H3/b16-14+,19-13+
SMILES CC(=CCC/C(=C/Cc1c(cc(c(C(=O)/C=C/c2ccccc2)c1O)OC)O)/C)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   406.21 Volume:   449.935
?
Van der Waals volume.
Dense:   0.903 LogP:   6.121
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   4.251
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.994
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   9.0 Rigid Bonds:   16.0
TPSA:   66.76
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   2.0 Rings:   2.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.294 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.737 Fsp3:   0.269
MCE-18:   15.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   1.0 Fluc inhibitor:   0.996
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.622
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.928
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.557 Promiscuous compounds:   0.104

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.133 MDCK Permeability:   -4.691
Pgp-inhibitor:   1.0 Pgp-substrate:   0.0
PAMPA:   0.003
?
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):   0.001
20% Bioavailability (F20%):   0.187 30% Bioavailability (F30%):   0.615
50% Bioavailability (F50%):   0.942

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.001 MRP1:   0.04
Plasma Protein Binding (PPB):   97.968% Volume Distribution (VD):   0.219
Fu: 1.916%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.137
BSEP inhibitor:   1.0

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   1.0
CYP2C19-inhibitor:   0.07 CYP2C19-substrate:   1.0
CYP2C9-inhibitor:   1.0 CYP2C9-substrate:   0.519
CYP2D6-inhibitor:   0.999 CYP2D6-substrate:   0.92
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.848
?
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):  7.108 Half-life (T1/2):  0.698

ADMET: Toxicity

hERG Blockers:  0.234 hERG Blockers (10um):  0.623
Human Hepatotoxicity (H-HT):  0.811 Drug-induced Liver Injury (DILI):  0.774
AMES Toxicity:  0.18 Rat Oral Acute Toxicity:  0.267
Maximum Recommended Daily Dose:  0.499 Skin Sensitization:  0.973
Carcinogencity:  0.139 Eye Corrosion:  0.001
Eye Irritation:  0.855 Respiratory Toxicity:  0.915
Drug-induced Neurotoxicity:  0.642 Ototoxicity:  0.382
Hematotoxicity:  0.321 Drug-induced Nephrotoxicity:  0.555
Genotoxicity:  0.576 RPMI-8226 Immunitoxicity:  0.154
A549 Cytotoxicity:  0.402 Hek293 Cytotoxicity:  0.557
BCF:   2.092
?
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:   5.25
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   7.009
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   6.619
?
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
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[10514313]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. root n.a. PMID[10514313]
NPO27986 Lonchocarpus chiricanus Species Fabaceae Eukaryota Root barks n.a. n.a. PMID[11421729]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[11575962]
NPO27695 Centaurea sonchifolia Species n.a. n.a. n.a. n.a. n.a. PMID[1624943]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota rhizomes Pindaya Township, Shan State, Myanmar 2004-NOV PMID[17896818]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[27508308]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[28099006]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. n.a. PMID[3349210]
NPO4164 Salvia virgata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38611827]
NPO28385 Iris kashmiriana Species Tarachodidae Eukaryota n.a. n.a. n.a. PMID[39433747]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[8176404]
NPO28412 Amorphophallus konjac Species Araceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27986 Lonchocarpus chiricanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28206 Aniba santalodora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28003 Astragalus circassicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28063 Beilschmiedia madang Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8961 Bethencourtia palmensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27882 Boswellia ovalifoliolata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25499 Campanula choziatowskyi Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17337 Centaurea scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27695 Centaurea sonchifolia Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO1184 Colchicum filifolium Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11849 Cynoglossum macrostylum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26342 Dialium excelsum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27397 Drymaria cordata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27455 Dysidea fragilis Species Dysideidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28044 Erythrina hypaphorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28426 Etmopterus spinax Species Etmopteridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27145 Euphorbia hylonoma Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27916 Hardenbergia violacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27637 Heliotropium scabrum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27613 Helleborus macranthus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28385 Iris kashmiriana Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19383 Lactarius mitissimus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26553 Lemonia spectabilis Species Lemoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9354 Lepechinia urbanii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23156 Maclura cochinchinensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27702 Matricaria sabulosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27057 Matsucoccus josephi Species Margarodidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28313 Mentzelia decapetala Species Loasaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2030 Mimosa pigra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16156 Mucuna holtonii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28289 Nepytia freemani Species Geometridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27506 Orgyia pseudotsugata Species Lymantriidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25835 Parmotrema nilgherrense Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5970.1 Petunia axillaris subsp. parodii Subspecies Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27642 Podocarpus dacrydioides Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26476 Preussia terricola Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27816 Pterocaulon serrulatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16298 Quercus marilandica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27614 Salix rosmarinifolia Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28083 Salvia lavanduloides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26321 Salvia patens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4164 Salvia virgata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27338 Senecio platyphylloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27854 Sphaeria rousseliana n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO27234 Thalassiosira weissflogii Species Thalassiosiraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. Database[FooDB]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. Database[FooDB]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27882 Boswellia ovalifoliolata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23156 Maclura cochinchinensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27397 Drymaria cordata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26342 Dialium excelsum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16298 Quercus marilandica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25835 Parmotrema nilgherrense Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27854 Sphaeria rousseliana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27916 Hardenbergia violacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26476 Preussia terricola Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27882 Boswellia ovalifoliolata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27338 Senecio platyphylloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27816 Pterocaulon serrulatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17337 Centaurea scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28313 Mentzelia decapetala Species Loasaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28206 Aniba santalodora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28083 Salvia lavanduloides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23156 Maclura cochinchinensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1184 Colchicum filifolium Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27642 Podocarpus dacrydioides Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27057 Matsucoccus josephi Species Margarodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27145 Euphorbia hylonoma Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28289 Nepytia freemani Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27986 Lonchocarpus chiricanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28063 Beilschmiedia madang Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27613 Helleborus macranthus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27637 Heliotropium scabrum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8961 Bethencourtia palmensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27397 Drymaria cordata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27702 Matricaria sabulosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9354 Lepechinia urbanii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27695 Centaurea sonchifolia Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4164 Salvia virgata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28385 Iris kashmiriana Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27455 Dysidea fragilis Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27234 Thalassiosira weissflogii Species Thalassiosiraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26553 Lemonia spectabilis Species Lemoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26321 Salvia patens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28003 Astragalus circassicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19383 Lactarius mitissimus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28426 Etmopterus spinax Species Etmopteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28412 Amorphophallus konjac Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2030 Mimosa pigra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25499 Campanula choziatowskyi Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28044 Erythrina hypaphorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16156 Mucuna holtonii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5970.1 Petunia axillaris subsp. parodii Subspecies Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11849 Cynoglossum macrostylum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27506 Orgyia pseudotsugata Species Lymantriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27614 Salix rosmarinifolia Species Salicaceae 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

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 NPC92125 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
0.8525 High Similarity NPC477242
0.7049 Intermediate Similarity NPC25287
0.6935 Remote Similarity NPC249606
0.6571 Remote Similarity NPC483812
0.6066 Remote Similarity NPC150399
0.589 Remote Similarity NPC64915
0.5882 Remote Similarity NPC23126
0.5811 Remote Similarity NPC488436
0.5753 Remote Similarity NPC228504
0.5735 Remote Similarity NPC266689
0.5735 Remote Similarity NPC21350
0.5714 Remote Similarity NPC195796
0.5676 Remote Similarity NPC213896
0.5658 Remote Similarity NPC226025
0.5658 Remote Similarity NPC278778
0.5634 Remote Similarity NPC274109
0.56 Remote Similarity NPC470328
0.56 Remote Similarity NPC262039
0.56 Remote Similarity NPC209614
0.56 Remote Similarity NPC164272
0.56 Remote Similarity NPC470327
0.5571 Remote Similarity NPC264112
0.557 Remote Similarity NPC287328
0.5526 Remote Similarity NPC22192
0.5526 Remote Similarity NPC185276
0.5513 Remote Similarity NPC282009
0.5455 Remote Similarity NPC470326
0.5429 Remote Similarity NPC321980
0.5397 Remote Similarity NPC87231
0.5352 Remote Similarity NPC316769
0.5333 Remote Similarity NPC290133
0.5323 Remote Similarity NPC91105
0.5316 Remote Similarity NPC45849
0.5316 Remote Similarity NPC472626
0.5312 Remote Similarity NPC33728
0.5312 Remote Similarity NPC488443
0.527 Remote Similarity NPC153979
0.5238 Remote Similarity NPC188646
0.5231 Remote Similarity NPC62952
0.5231 Remote Similarity NPC65761
0.5152 Remote Similarity NPC488444
0.5152 Remote Similarity NPC472029
0.5125 Remote Similarity NPC210459
0.5072 Remote Similarity NPC105157
0.5072 Remote Similarity NPC11561
0.5063 Remote Similarity NPC298692

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC92125 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