Natural Product: NPC2771

Natural Product IDNPC2771
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 4'-Methoxyflavone
IUPAC Name 2-(4-methoxyphenyl)chromen-4-one
Synonyms 4'-Methoxyflavone; 4-Methoxy Flavone
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL16312
PubChem CID 77793
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002596] 4'-O-methylated flavonoids

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 OMICQBVLCVRFGN-UHFFFAOYSA-N
Standard InCHI InChI=1S/C16H12O3/c1-18-12-8-6-11(7-9-12)16-10-14(17)13-4-2-3-5-15(13)19-16/h2-10H,1H3
SMILES COc1ccc(cc1)c1cc(=O)c2c(o1)cccc2

  Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. fruit n.a. PMID[20663508]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24507928]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9544566]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28809 Cullen corylifolium 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
NPT261 Individual protein Monoamine oxidase A Homo sapiens Inhibition = 40.0 % PMID[20045650]
NPT149 Individual protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 1000.0 nM PubChem BioAssay data set
NPT151 Individual protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 14125.4 nM PubChem BioAssay data set
NPT109 Individual protein Cytochrome P450 3A4 Homo sapiens Potency = 1995.3 nM PubChem BioAssay data set
NPT154 Individual protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 11220.2 nM PubChem BioAssay data set
NPT157 Individual protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 19952.6 nM PubChem BioAssay data set
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 8912.5 nM PubChem BioAssay data set
NPT1602 Individual protein Neuraminidase Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 = 8740.0 nM PMID[31744778]
NPT582 Individual protein Monoamine oxidase B Homo sapiens IC50 = 27870.0 nM PMID[20045650]
NPT483 Individual protein Prelamin-A/C Homo sapiens Potency = 11220.2 nM PubChem BioAssay data set
NPT537 Individual protein Ras-related protein Rab-9A Homo sapiens Potency = 1995.3 nM PubChem BioAssay data set
NPT501 Individual protein Alpha-galactosidase A Homo sapiens Potency = 44668.4 nM PubChem BioAssay data set
NPT585 Individual protein Nuclear receptor subfamily 0 group B member 1 Homo sapiens IC50 > 67535.0 nM PubChem BioAssay data set
NPT501 Individual protein Alpha-galactosidase A Homo sapiens Potency n.a. 12589.3 nM PubChem BioAssay data set
NPT72 Individual protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 105.58 % PMID[23571415]
NPT48 Individual protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 31622.8 nM PubChem BioAssay data set
NPT48 Individual protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 3981.1 nM PubChem BioAssay data set
NPT94 Individual protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 31622.8 nM PubChem BioAssay data set
NPT54 Individual protein Nonstructural protein 1 Influenza A virus Potency = 12589.3 nM PubChem BioAssay data set
NPT538 Individual protein Niemann-Pick C1 protein Homo sapiens Potency = 2511.9 nM PubChem BioAssay data set
NPT61 Individual protein Beta-glucocerebrosidase Homo sapiens Potency n.a. 22387.2 nM PubChem BioAssay data set
NPT61 Individual protein Beta-glucocerebrosidase Homo sapiens Potency n.a. 5623.4 nM PubChem BioAssay data set
NPT584 Individual protein NACHT, LRR and PYD domains-containing protein 3 Homo sapiens IC50 = 31000.0 nM PubChem BioAssay data set
NPT584 Individual protein NACHT, LRR and PYD domains-containing protein 3 Homo sapiens IC50 = 5400.0 nM PubChem BioAssay data set
NPT7 Individual protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 12589.3 nM PubChem BioAssay data set
NPT484 Individual protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 6012.0 nM PubChem BioAssay data set
NPT7 Individual protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 28183.8 nM PubChem BioAssay data set
NPT444 Individual protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 79432.8 nM PubChem BioAssay data set
NPT588 Individual protein Tankyrase-1 Homo sapiens IC50 = 70.79 nM PMID[24116873]
NPT588 Individual protein Tankyrase-1 Homo sapiens IC50 = 71.0 nM PMID[24116873]
NPT73 Individual protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 201.12 % PMID[23571415]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 98.35 % DOI[10.6019/CHEMBL4495564]
NPT93 Individual protein Survival motor neuron protein Homo sapiens Potency = 10000.0 nM PubChem BioAssay data set
NPT51 Individual protein Microtubule-associated protein tau Homo sapiens Potency = 12589.3 nM PubChem BioAssay data set
NPT46 Individual protein Thyroid hormone receptor beta-1 Homo sapiens Potency = 158489.3 nM PubChem BioAssay data set
NPT51 Individual protein Microtubule-associated protein tau Homo sapiens Potency = 2818.4 nM PubChem BioAssay data set
NPT583 Individual protein Inositol monophosphatase 1 Rattus norvegicus Potency = 28183.8 nM PubChem BioAssay data set
NPT535 Individual protein Parathyroid hormone receptor Homo sapiens Potency n.a. 39810.7 nM PubChem BioAssay data set
NPT581 Individual protein Cyclooxygenase-2 Mus musculus Inhibition = 38.9 % PMID[14980657]
NPT536 Nucleic acid microRNA 21 Homo sapiens Potency = 5847.9 nM PubChem BioAssay data set
NPT539 Individual protein Cellular tumor antigen p53 Homo sapiens Potency = 10000.0 nM PubChem BioAssay data set
NPT539 Individual protein Cellular tumor antigen p53 Homo sapiens Potency = 25118.9 nM PubChem BioAssay data set
NPT443 Individual protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 12589.3 nM PubChem BioAssay data set
NPT443 Individual protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 8912.5 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 20587.8 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 11577.4 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT384 Cell line TK-10 Homo sapiens Activity = 82.0 % PMID[17383189]
NPT83 Cell line MCF7 Homo sapiens Activity = 100.0 % PMID[17383189]
NPT139 Cell line HT-29 Homo sapiens Activity = 100.0 % PMID[17383189]
NPT65 Cell line HepG2 Homo sapiens Potency n.a. 2818.4 nM PubChem BioAssay data set
NPT71 Cell line HEK293 Homo sapiens IC50 > 67535.0 nM PubChem BioAssay data set
NPT65 Cell line HepG2 Homo sapiens GI < 50.0 % DOI[10.1007/s00044-012-0423-1]
NPT112 Cell line MOLT-4 Homo sapiens GI50 = 99200.0 nM DOI[10.1007/s00044-012-0423-1]
NPT83 Cell line MCF7 Homo sapiens GI50 = 61800.0 nM DOI[10.1007/s00044-012-0423-1]
NPT113 Cell line RAW264.7 Mus musculus Activity = 111.45 % PMID[28408221]
NPT113 Cell line RAW264.7 Mus musculus Inhibition = 8.76 % PMID[28408221]
NPT616 Cell line MDCK Canis lupus familiaris CC50 = 191800.0 nM PMID[31744778]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 14715.7 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2332.3 nM PubChem BioAssay data set
NPT587 Tissue Liver microsome Rattus norvegicus IC50 = 60.0 ug.mL-1 DOI[10.1007/s00044-012-0423-1]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.08 % DOI[10.6019/CHEMBL4495565]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM DOI[10.6019/CHEMBL4651402]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM DOI[10.6019/CHEMBL4651402]
NPT28438 Unchecked Unchecked n.a. log(ratio) = 0.13 n.a. PMID[35576701]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. deltaA = 0.24 n.a. PMID[20565070]
NPT586 Organism Giardia Giardia Potency n.a. 23053.0 nM PubChem BioAssay data set
NPT29337 Protein family Cytochrome P450 Homo sapiens Inhibition = 27.0 % PMID[35576701]
NPT29337 Protein family Cytochrome P450 Homo sapiens Inhibition = 20.0 % PMID[35576701]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 6.3 ug.mL-1 PMID[11170636]
NPT2 Others Unspecified n.a. Activity = 0.0 n.a. PMID[8882428]
NPT2 Others Unspecified n.a. Ratio IC50 > 3.6 n.a. PMID[20045650]
NPT2 Others Unspecified n.a. Potency = 12589.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency = 11.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 1258.9 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 12589.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 22387.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 17782.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 1778.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 3162.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 7079.5 nM PubChem BioAssay data set
NPT742 Organism Influenza A virus Influenza A virus EC50 = 9.36 nM PMID[31744778]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT29 Organism Rattus norvegicus Rattus norvegicus Protection = 21.0 % PMID[8523407]





 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 NPC2771 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
0.7755 Intermediate Similarity NPC77955
0.7755 Intermediate Similarity NPC608264
0.75 Intermediate Similarity NPC483772
0.7292 Intermediate Similarity NPC604293
0.7143 Intermediate Similarity NPC603094
0.7111 Intermediate Similarity NPC32298
0.6863 Remote Similarity NPC608669
0.6731 Remote Similarity NPC125887
0.6731 Remote Similarity NPC483774
0.6604 Remote Similarity NPC266597
0.6604 Remote Similarity NPC604085
0.66 Remote Similarity NPC607644
0.6481 Remote Similarity NPC480173
0.6471 Remote Similarity NPC284424
0.64 Remote Similarity NPC22783
0.64 Remote Similarity NPC196034
0.6296 Remote Similarity NPC605146
0.5965 Remote Similarity NPC605336
0.5926 Remote Similarity NPC599976
0.5849 Remote Similarity NPC101294
0.5818 Remote Similarity NPC113089
0.5769 Remote Similarity NPC41721
0.5741 Remote Similarity NPC14958
0.5714 Remote Similarity NPC250266
0.569 Remote Similarity NPC606525
0.5536 Remote Similarity NPC156222
0.5536 Remote Similarity NPC29353
0.5439 Remote Similarity NPC184136
0.5439 Remote Similarity NPC231772
0.5439 Remote Similarity NPC57030
0.5439 Remote Similarity NPC22519
0.5439 Remote Similarity NPC145379
0.537 Remote Similarity NPC40818
0.537 Remote Similarity NPC193805
0.5345 Remote Similarity NPC603662
0.5273 Remote Similarity NPC602026
0.5179 Remote Similarity NPC333230
0.5179 Remote Similarity NPC129680
0.5167 Remote Similarity NPC604422
0.5167 Remote Similarity NPC607642
0.5094 Remote Similarity NPC602460

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC2771 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