Natural Product: NPC189474

Natural Product IDNPC189474
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.
 (+)-Epiaschantin
IUPAC Name 5-[(3S,3aR,6R,6aR)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole
Synonyms (+)-Epiaschantin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL480876
PubChem CID 10408679
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans

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 ONDWGDNAFRAXCN-YJPXFSGGSA-N
Standard InCHI InChI=1S/C22H24O7/c1-23-18-7-13(8-19(24-2)22(18)25-3)21-15-10-26-20(14(15)9-27-21)12-4-5-16-17(6-12)29-11-28-16/h4-8,14-15,20-21H,9-11H2,1-3H3/t14-,15-,20+,21-/m0/s1
SMILES COc1cc(cc(c1OC)OC)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1)OCO2

  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
NPO3793 Artemisia rutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(86)80021-8]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. stem n.a. DOI[10.1021/np960034d]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. DOI[10.3987/R-1980-04-0397]
NPO1270 Potamogeton malaianus Species Potamogetonaceae Eukaryota n.a. n.a. n.a. PMID[11277765]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. PMID[14987061]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10250 Alectoria rigida Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3793 Artemisia rutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9851 Ethulia conyzoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1270 Potamogeton malaianus Species Potamogetonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10250 Alectoria rigida Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9851 Ethulia conyzoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1270 Potamogeton malaianus Species Potamogetonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3793 Artemisia rutifolia Species Asteraceae 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
NPT168 Cell line P388 Mus musculus ED50 = 1.5 ug ml-1 PMID[14987061]
NPT1081 Cell line BXPC-3 Homo sapiens ED50 > 10.0 ug ml-1 PMID[14987061]
NPT83 Cell line MCF7 Homo sapiens ED50 > 10.0 ug ml-1 PMID[14987061]
NPT395 Cell line SF-268 Homo sapiens ED50 > 10.0 ug ml-1 PMID[14987061]
NPT397 Cell line NCI-H460 Homo sapiens ED50 > 10.0 ug ml-1 PMID[14987061]
NPT575 Cell line KM-20L2 Homo sapiens ED50 > 10.0 ug ml-1 PMID[14987061]
NPT90 Cell line DU-145 Homo sapiens ED50 > 10.0 ug ml-1 PMID[14987061]

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 NPC189474 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
0.8605 High Similarity NPC227160
0.8605 High Similarity NPC82111
0.8537 High Similarity NPC171928
0.8537 High Similarity NPC158526
0.8537 High Similarity NPC129687
0.8537 High Similarity NPC33611
0.8537 High Similarity NPC16830
0.8537 High Similarity NPC100223
0.7907 Intermediate Similarity NPC148893
0.7907 Intermediate Similarity NPC222127
0.7907 Intermediate Similarity NPC25333
0.7907 Intermediate Similarity NPC49235
0.7907 Intermediate Similarity NPC82862
0.7755 Intermediate Similarity NPC298317
0.7755 Intermediate Similarity NPC255566
0.7115 Intermediate Similarity NPC88640
0.7115 Intermediate Similarity NPC101153
0.7115 Intermediate Similarity NPC193666
0.7115 Intermediate Similarity NPC123526
0.7115 Intermediate Similarity NPC608725
0.7073 Intermediate Similarity NPC281864
0.7073 Intermediate Similarity NPC328682
0.7073 Intermediate Similarity NPC54321
0.6977 Remote Similarity NPC121783
0.6977 Remote Similarity NPC34902
0.6977 Remote Similarity NPC18449
0.6604 Remote Similarity NPC474139
0.6604 Remote Similarity NPC483653
0.6471 Remote Similarity NPC185071
0.6471 Remote Similarity NPC14022
0.6471 Remote Similarity NPC601703
0.6304 Remote Similarity NPC473092
0.6304 Remote Similarity NPC473093
0.6304 Remote Similarity NPC8050
0.625 Remote Similarity NPC606146
0.6226 Remote Similarity NPC469981
0.6122 Remote Similarity NPC312199
0.5918 Remote Similarity NPC165155
0.5918 Remote Similarity NPC57119
0.5918 Remote Similarity NPC158471
0.5918 Remote Similarity NPC24490
0.5918 Remote Similarity NPC226862
0.5893 Remote Similarity NPC12728
0.5882 Remote Similarity NPC136750
0.5882 Remote Similarity NPC266848
0.5745 Remote Similarity NPC271208
0.5745 Remote Similarity NPC233224
0.5745 Remote Similarity NPC610263
0.5686 Remote Similarity NPC483654
0.5571 Remote Similarity NPC486098
0.5556 Remote Similarity NPC27843
0.5556 Remote Similarity NPC7171
0.55 Remote Similarity NPC311057
0.55 Remote Similarity NPC600032
0.549 Remote Similarity NPC209229
0.5472 Remote Similarity NPC192255
0.5455 Remote Similarity NPC165128
0.54 Remote Similarity NPC480478
0.5345 Remote Similarity NPC47181
0.5323 Remote Similarity NPC265154
0.5306 Remote Similarity NPC50683
0.5306 Remote Similarity NPC72046
0.5306 Remote Similarity NPC261812
0.5306 Remote Similarity NPC112571
0.5306 Remote Similarity NPC65183
0.5306 Remote Similarity NPC285725
0.5283 Remote Similarity NPC488505
0.5273 Remote Similarity NPC143895
0.5263 Remote Similarity NPC101807
0.5254 Remote Similarity NPC287124
0.5254 Remote Similarity NPC477702
0.5231 Remote Similarity NPC486102
0.5102 Remote Similarity NPC31530
0.5088 Remote Similarity NPC135777
0.5088 Remote Similarity NPC7744
0.5085 Remote Similarity NPC166884
0.5085 Remote Similarity NPC141569
0.5085 Remote Similarity NPC477701

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC189474 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