Natural Product: NPC266931

Natural Product IDNPC266931
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.
 N-Feruloyl Serotonin
IUPAC Name (E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Synonyms N-Feruloyl Serotonin; N-Feruloylserotonin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL564482
PubChem CID 5969616
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000183] Tryptamines and derivatives
          • [CHEMONTID:0001637] Serotonins
            • [CHEMONTID:0004271] N-acylserotonins

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 WGHKJYWENWLOMY-XVNBXDOJSA-N
Standard InCHI InChI=1S/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)/b7-3+
SMILES COc1cc(/C=C/C(=NCCc2c[nH]c3c2cc(O)cc3)O)ccc1O

  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
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[ 17560738]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11816-015-0350-y]
NPO11352 Centaurea cyanus Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(91)83628-X]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. aerial part n.a. PMID[17520525]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[22966846]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11352 Centaurea cyanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11352 Centaurea cyanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO11352 Centaurea cyanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11352 Centaurea cyanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11352 Centaurea cyanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11144 Centella asiatica Species Apiaceae 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
NPT2739 Individual protein Tyrosinase Mus musculus Activity = 29.0 % PMID[19524439]
NPT2739 Individual protein Tyrosinase Mus musculus IC50 = 216000.0 nM PMID[19524439]
NPT30 Individual protein Cyclooxygenase-1 Homo sapiens Inhibition = 2.7 % PMID[22386242]
NPT31 Individual protein Cyclooxygenase-2 Homo sapiens Inhibition = 18.8 % PMID[22386242]
NPT741 Individual protein Tyrosinase Homo sapiens Activity = 48.0 % PMID[19524439]
NPT526 Individual protein Alpha-glucosidase MAL62 Saccharomyces cerevisiae Ki = 129800.0 nM DOI[10.1007/s00044-011-9699-9]
NPT526 Individual protein Alpha-glucosidase MAL62 Saccharomyces cerevisiae IC50 = 99800.0 nM DOI[10.1007/s00044-011-9699-9]
NPT43 Individual protein Tyrosinase Agaricus bisporus IC50 = 8000.0 nM PMID[21377874]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT319 Cell line B16 Mus musculus Activity = 100.0 % PMID[19524439]
NPT319 Cell line B16 Mus musculus IC50 = 23000.0 nM PMID[19524439]
NPT113 Cell line RAW264.7 Mus musculus IC50 = 123140.0 nM PMID[29102229]
NPT113 Cell line RAW264.7 Mus musculus IC50 = 14740.0 nM PMID[29102229]
NPT113 Cell line RAW264.7 Mus musculus Inhibition = 52.17 % PMID[29102229]
NPT113 Cell line RAW264.7 Mus musculus Inhibition = 25.1 % PMID[29102229]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 81000.0 nM PMID[25456382]
NPT1 Others Radical scavenging activity n.a. EC50 = 22800.0 nM PMID[21377874]

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 NPC266931 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
0.7794 Intermediate Similarity NPC99666
0.6056 Remote Similarity NPC195749
0.6056 Remote Similarity NPC35961
0.6 Remote Similarity NPC214869
0.5833 Remote Similarity NPC178571
0.5833 Remote Similarity NPC155838
0.5352 Remote Similarity NPC186898
0.5316 Remote Similarity NPC156704
0.5263 Remote Similarity NPC299583
0.5065 Remote Similarity NPC153644
0.5065 Remote Similarity NPC204848
0.5065 Remote Similarity NPC160607
0.5065 Remote Similarity NPC41473
0.5065 Remote Similarity NPC312770

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC266931 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