Natural Product: NPC73505

Natural Product IDNPC73505
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.
 Prenylterphenyllin B
IUPAC Name 5-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-2-(4-hydroxyphenyl)-3,6-dimethoxyphenol
Synonyms Prenylterphenyllin B
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1795459
PubChem CID 53356515
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0002042] Terphenyls
          • [CHEMONTID:0002126] P-terphenyls

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 IWVBXHCTGZHCPU-UHFFFAOYSA-N
Standard InCHI InChI=1S/C25H26O5/c1-15(2)5-6-18-13-17(9-12-21(18)27)20-14-22(29-3)23(24(28)25(20)30-4)16-7-10-19(26)11-8-16/h5,7-14,26-28H,6H2,1-4H3
SMILES CC(=CCc1cc(ccc1O)c1cc(c(c2ccc(cc2)O)c(c1OC)O)OC)C

  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
NPO9892 Aspergillus taichungensis Species Aspergillaceae Eukaryota isolated from the root soil of the mangrove plant Acrostichum aureum n.a. n.a. PMID[21486068]
NPO9892 Aspergillus taichungensis Species Aspergillaceae Eukaryota a root soil fungus isolated from the mangrove plant Acrostichum aureum n.a. n.a. PMID[21486068]
NPO9892 Aspergillus taichungensis Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21486068]
NPO13765 Acrostichum aureum Species Pteridaceae Eukaryota n.a. aerial part n.a. PMID[21899268]
NPO13765 Acrostichum aureum Species Pteridaceae Eukaryota n.a. aerial part n.a. PMID[22906240]
NPO13272 Ulva lactuca Species Ulvaceae Eukaryota n.a. n.a. n.a. PMID[39769283]
NPO9892 Aspergillus taichungensis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12872 Taraxacum disseminatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11049 Solanum capsicastrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12686 Sideritis hirsuta Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14461 Vibrio fluvialis Species Vibrionaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO13272 Ulva lactuca Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13272 Ulva lactuca Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11049 Solanum capsicastrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13272 Ulva lactuca Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11049 Solanum capsicastrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13272 Ulva lactuca Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11049 Solanum capsicastrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12872 Taraxacum disseminatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11828 Mucor hiemalis Species Mucoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22797 Fleroya stipulosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13272 Ulva lactuca Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7010 Anthocleista procera Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14461 Vibrio fluvialis Species Vibrionaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13868 Gnaphalium oligandrum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11049 Solanum capsicastrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9892 Aspergillus taichungensis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10556 Eria jarensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12686 Sideritis hirsuta Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13765 Acrostichum aureum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26896 Wulfenia orientalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14357 Ixeris denticulata 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
NPT116 Cell line HL-60 Homo sapiens IC50 = 38600.0 nM PMID[21486068]
NPT168 Cell line P388 Mus musculus IC50 = 12570.0 nM PMID[21486068]
NPT81 Cell line A549 Homo sapiens IC50 > 100000.0 nM PMID[21486068]

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 NPC73505 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
0.92 High Similarity NPC295719
0.8491 Intermediate Similarity NPC34431
0.8036 Intermediate Similarity NPC485412
0.75 Intermediate Similarity NPC165026
0.6333 Remote Similarity NPC485411
0.6327 Remote Similarity NPC90615
0.5849 Remote Similarity NPC25111
0.5556 Remote Similarity NPC272157
0.5185 Remote Similarity NPC201145

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC73505 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