Natural Product: NPC157081

Natural Product IDNPC157081
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 HEIKOEZNFLUAEJ-OAPWRRNMSA-N
IUPAC Name n.a.
Synonyms (-)-Ampelopsin H
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1939278
PubChem CID 21606291
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran 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 HEIKOEZNFLUAEJ-OAPWRRNMSA-N
Standard InCHI InChI=1S/C56H42O12/c57-31-9-1-25(2-10-31)43-47-39(65)23-41-49(45(29-17-35(61)21-36(62)18-29)55(67-41)27-5-13-33(59)14-6-27)53(47)52-44(26-3-11-32(58)12-4-26)48-40(66)24-42-50(54(48)51(43)52)46(30-19-37(63)22-38(64)20-30)56(68-42)28-7-15-34(60)16-8-28/h1-24,43-46,51-52,55-66H/t43-,44-,45-,46-,51+,52+,55+,56+/m1/s1
SMILES Oc1ccc(cc1)[C@@H]1c2c(O)cc3c(c2[C@@H]2[C@H]1c1c([C@H]2c2ccc(cc2)O)c(O)cc2c1[C@@H](c1cc(O)cc(c1)O)[C@@H](O2)c1ccc(cc1)O)[C@@H](c1cc(O)cc(c1)O)[C@@H](O3)c1ccc(cc1)O

  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
NPO14547 Ilex pubescens Species Aquifoliaceae Eukaryota n.a. n.a. n.a. PMID[15787443]
NPO26194 Shorea roxburghii Species Dipterocarpaceae Eukaryota Barks n.a. n.a. PMID[22209731]
NPO12673 Phyllanthus acidus Species Phyllanthaceae Eukaryota Roots n.a. n.a. PMID[30207470]
NPO9711 Leccinum aurantiacum Species Boletaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15134 Alnus glutinosa Species Betulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16347 Viguiera greggii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14547 Ilex pubescens Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11728 Shorea hemsleyana Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26194 Shorea roxburghii Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO913 Pelophylax plancyi Species Ranidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14028 Guizotia abyssinica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14547 Ilex pubescens Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15134 Alnus glutinosa Species Betulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14547 Ilex pubescens Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO913 Pelophylax plancyi Species Ranidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15134 Alnus glutinosa Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14547 Ilex pubescens Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15134 Alnus glutinosa Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12673 Phyllanthus acidus Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26194 Shorea roxburghii Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11728 Shorea hemsleyana Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9711 Leccinum aurantiacum Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13369 Morinda longiflora Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16347 Viguiera greggii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO913 Pelophylax plancyi Species Ranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14028 Guizotia abyssinica 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
NPT462 Individual protein Sucrase-isomaltase Rattus norvegicus IC50 = 97100.0 nM PMID[22209731]
NPT68 Individual protein Aldose reductase Rattus norvegicus IC50 = 50200.0 nM PMID[22209731]
NPT671 Individual protein Acidic alpha-glucosidase Rattus norvegicus IC50 = 178000.0 nM PMID[22209731]

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 NPC157081 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 NPC218801
0.7937 Intermediate Similarity NPC122980
0.7937 Intermediate Similarity NPC148516
0.7937 Intermediate Similarity NPC107862
0.7937 Intermediate Similarity NPC177172
0.7879 Intermediate Similarity NPC233886
0.7778 Intermediate Similarity NPC180605
0.7761 Intermediate Similarity NPC105073
0.7761 Intermediate Similarity NPC224528
0.6212 Remote Similarity NPC242774
0.6212 Remote Similarity NPC231712
0.6212 Remote Similarity NPC224921
0.6212 Remote Similarity NPC237546
0.6119 Remote Similarity NPC120633
0.5797 Remote Similarity NPC473018
0.5692 Remote Similarity NPC76424
0.5692 Remote Similarity NPC15109
0.5692 Remote Similarity NPC291103
0.5692 Remote Similarity NPC11727
0.5469 Remote Similarity NPC175765
0.5441 Remote Similarity NPC478982
0.5362 Remote Similarity NPC149633
0.5211 Remote Similarity NPC488747
0.5172 Remote Similarity NPC176804
0.5172 Remote Similarity NPC71686
0.5143 Remote Similarity NPC173203
0.5143 Remote Similarity NPC163508
0.5075 Remote Similarity NPC141717

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC157081 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