Natural Product: NPC5796

Natural Product IDNPC5796
Common Name
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The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Aucuparin
IUPAC Name 2,6-dimethoxy-4-phenylphenol
Synonyms Aucuparin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1079777
PubChem CID 442508
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000041] Biphenyls and derivatives

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 KCKBEANTNJGRCV-UHFFFAOYSA-N
Standard InCHI InChI=1S/C14H14O3/c1-16-12-8-11(9-13(17-2)14(12)15)10-6-4-3-5-7-10/h3-9,15H,1-2H3
SMILES COc1cc(cc(c1O)OC)c1ccccc1

  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
NPO13029 Sorbus aucuparia Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[18635332]
NPO4001 Berberis koreana Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[19813743]
NPO10507 Sorbus decora Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[20738101]
NPO4001 Berberis koreana Species Berberidaceae Eukaryota trunk Jeju island, Korea 2005-Dec PMID[21420296]
NPO4001 Berberis koreana Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[21420296]
NPO3204 Centaurea malacitana Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[9358646]
NPO13029 Sorbus aucuparia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3204 Centaurea malacitana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3628 Solanum aethiopicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13029 Sorbus aucuparia Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13029 Sorbus aucuparia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13029 Sorbus aucuparia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10507 Sorbus decora Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13029 Sorbus aucuparia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14617 Aloe hijazensis Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10507 Sorbus decora Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13029 Sorbus aucuparia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6180 Ocotea puberula Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4001 Berberis koreana Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3204 Centaurea malacitana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3628 Solanum aethiopicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13408 Cordeauxia edulis 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

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell line A549 Homo sapiens IC50 > 10000.0 nM PMID[19813743]
NPT146 Cell line SK-OV-3 Homo sapiens IC50 > 10000.0 nM PMID[19813743]
NPT147 Cell line SK-MEL-2 Homo sapiens IC50 > 10000.0 nM PMID[19813743]
NPT148 Cell line HCT-15 Homo sapiens IC50 > 10000.0 nM PMID[19813743]
NPT76 Cell line C6 Rattus norvegicus Activity = 116.96 % PMID[26706168]
NPT76 Cell line C6 Rattus norvegicus Activity = 125.76 % PMID[26706168]
NPT34 Cell line BV-2 Mus musculus IC50 = 50150.0 nM PMID[26706168]

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 NPC5796 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
0.6471 Remote Similarity NPC266555
0.6471 Remote Similarity NPC206487
0.6286 Remote Similarity NPC154866
0.5806 Remote Similarity NPC303521
0.5806 Remote Similarity NPC15805
0.5556 Remote Similarity NPC167934
0.5102 Remote Similarity NPC22517

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC5796 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