Natural Product: NPC133909

Natural Product IDNPC133909
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Davidigenin
IUPAC Name 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
Synonyms Davidigenin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL192877
PubChem CID 442342
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

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 UDGKKUWYNITJRX-UHFFFAOYSA-N
Standard InCHI InChI=1S/C15H14O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-2,4-7,9,16-17,19H,3,8H2
SMILES Oc1ccc(cc1)CCC(=O)c1ccc(cc1O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   258.09 Volume:   267.589
?
Van der Waals volume.
Dense:   0.965 LogP:   2.42
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.566
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.841
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   13.0
TPSA:   77.76
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   3.0 Rings:   2.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.737 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.935 Fsp3:   0.133
MCE-18:   12.0
?
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:   0 PAINS Alert:   0
Colloidal aggregators:   0.44 Fluc inhibitor:   0.713
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.179
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.165
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.88 Promiscuous compounds:   0.194

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.649 MDCK Permeability:   -4.84
Pgp-inhibitor:   0.751 Pgp-substrate:   0.042
PAMPA:   0.249
?
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):   0.002
20% Bioavailability (F20%):   0.057 30% Bioavailability (F30%):   0.734
50% Bioavailability (F50%):   0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.001 MRP1:   0.291
Plasma Protein Binding (PPB):   94.348% Volume Distribution (VD):   0.02
Fu: 6.718%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.985
OATP1B3 inhibitor:   0.999 BCRP inhibitor:   0.361
BSEP inhibitor:   0.987

ADMET: Metabolism

CYP1A2-inhibitor:   0.822 CYP1A2-substrate:   0.795
CYP2C19-inhibitor:   0.404 CYP2C19-substrate:   0.542
CYP2C9-inhibitor:   0.92 CYP2C9-substrate:   0.964
CYP2D6-inhibitor:   0.999 CYP2D6-substrate:   0.997
CYP3A4-inhibitor:   0.002 CYP3A4-substrate:   0.116
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.912
?
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):  4.003 Half-life (T1/2):  1.654

ADMET: Toxicity

hERG Blockers:  0.112 hERG Blockers (10um):  0.655
Human Hepatotoxicity (H-HT):  0.378 Drug-induced Liver Injury (DILI):  0.009
AMES Toxicity:  0.267 Rat Oral Acute Toxicity:  0.281
Maximum Recommended Daily Dose:  0.571 Skin Sensitization:  0.671
Carcinogencity:  0.275 Eye Corrosion:  0.208
Eye Irritation:  0.994 Respiratory Toxicity:  0.822
Drug-induced Neurotoxicity:  0.436 Ototoxicity:  0.14
Hematotoxicity:  0.078 Drug-induced Nephrotoxicity:  0.107
Genotoxicity:  0.882 RPMI-8226 Immunitoxicity:  0.03
A549 Cytotoxicity:  0.279 Hek293 Cytotoxicity:  0.79
BCF:   1.338
?
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:   3.899
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.428
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.133
?
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
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11164-015-2099-x]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s40502-015-0143-x]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1093/pcp/pcg054]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1134/S1021443709050069]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1134/S1021443711030101]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO15395 Euphorbia portlandica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[16792416]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26690274]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[39683057]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO8391 Cortinarius sinapicolor Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15395 Euphorbia portlandica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12031 Schinopsis lorentzii Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15395 Euphorbia portlandica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8485 Magnolia odora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15395 Euphorbia portlandica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12031 Schinopsis lorentzii Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8485 Magnolia odora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15395 Euphorbia portlandica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10862 Mammillaria runyonii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8391 Cortinarius sinapicolor Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae 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
NPT108 Individual protein Estrogen receptor alpha Homo sapiens IC50 n.a. 1000000.0 nM PMID[15887952]
NPT248 Individual protein Estrogen receptor beta Homo sapiens IC50 n.a. 1000000.0 nM PMID[15887952]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[26690274]
NPT82 Cell line MDA-MB-231 Homo sapiens IC50 > 10000.0 nM PMID[26690274]
NPT886 Cell line NIH3T3 Mus musculus Activity = 24.04 % PMID[28571822]
NPT886 Cell line NIH3T3 Mus musculus Activity = 15.74 % PMID[28571822]
NPT886 Cell line NIH3T3 Mus musculus Activity = 12.69 % PMID[28571822]
NPT886 Cell line NIH3T3 Mus musculus Activity = 3.1 % PMID[28571822]
NPT22 Organism Bacillus subtilis subsp. spizizenii Bacillus subtilis subsp. spizizenii MIC = 120.0 ug.mL-1 PMID[20058934]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 120.0 ug.mL-1 PMID[20058934]
NPT22 Organism Bacillus subtilis subsp. spizizenii Bacillus subtilis subsp. spizizenii MBC = 0.5 mg/ml PMID[20058934]
NPT28438 Unchecked Unchecked n.a. IC50 > 10000.0 nM PMID[36940414]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Activity = 0.0 % PMID[521818]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Activity = 50.0 % PMID[521818]
NPT20 Organism Candida albicans Candida albicans MIC = 1000.0 ug.mL-1 PMID[20058934]
NPT20 Organism Candida albicans Candida albicans MBC = 2.0 mg/ml PMID[20058934]
NPT20904 Cell line Hep 3B2 Homo sapiens Activity = 103.82 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Activity = 105.82 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Activity = 115.77 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Activity = 140.41 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Activity = 22.37 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Activity = 18.61 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Activity = 11.83 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Activity = 4.16 % PMID[28571822]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 120.0 ug.mL-1 PMID[20058934]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 250.0 ug.mL-1 PMID[20058934]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 0.5 mg/ml PMID[20058934]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MBC = 0.5 mg/ml PMID[20058934]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 2000.0 ug.mL-1 PMID[20058934]
NPT19 Organism Escherichia coli Escherichia coli MIC = 4000.0 ug.mL-1 PMID[20058934]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MBC = 4.0 mg/ml PMID[20058934]
NPT1 Others Radical scavenging activity n.a. EC50 > 1000.0 ug.mL-1 PMID[20058934]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT886 Cell line NIH3T3 Mus musculus Survival = 60.63 % PMID[28571822]
NPT886 Cell line NIH3T3 Mus musculus Survival = 84.04 % PMID[28571822]
NPT886 Cell line NIH3T3 Mus musculus Survival = 113.1 % PMID[28571822]
NPT886 Cell line NIH3T3 Mus musculus Survival = 122.68 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Survival = 59.32 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Survival = 83.44 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Survival = 94.94 % PMID[28571822]
NPT20904 Cell line Hep 3B2 Homo sapiens Survival = 103.7 % PMID[28571822]





 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 NPC133909 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
0.8378 Intermediate Similarity NPC156139
0.7368 Intermediate Similarity NPC242895
0.7021 Intermediate Similarity NPC474110
0.6744 Remote Similarity NPC286336
0.6341 Remote Similarity NPC120488
0.6341 Remote Similarity NPC102829
0.625 Remote Similarity NPC608363
0.6098 Remote Similarity NPC159525
0.5909 Remote Similarity NPC82225
0.5814 Remote Similarity NPC233056
0.5714 Remote Similarity NPC607946
0.5556 Remote Similarity NPC175552
0.5556 Remote Similarity NPC161617
0.5556 Remote Similarity NPC600232
0.55 Remote Similarity NPC119860
0.5417 Remote Similarity NPC18877
0.5254 Remote Similarity NPC609169
0.5217 Remote Similarity NPC604715
0.52 Remote Similarity NPC282957
0.5185 Remote Similarity NPC608786
0.5128 Remote Similarity NPC260000
0.5106 Remote Similarity NPC485643
0.5098 Remote Similarity NPC601405

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC133909 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