Natural Product: NPC471362

Natural Product IDNPC471362
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.
 2-Epicaseabalansin C
IUPAC Name [(1R,3S,5S,6aR,7S,8S,10R,10aR)-1-acetyloxy-3-ethoxy-10-methoxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] acetate
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL2419869
PubChem CID 73347668
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0001757] Colensane and clerodane diterpenoids

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 TWFKTSOJWWQSLG-OCJOVGQOSA-N
Standard InCHI InChI=1S/C27H40O7/c1-9-16(3)11-12-26(7)17(4)13-23(30-8)27-21(14-20(15-22(26)27)32-18(5)28)24(31-10-2)34-25(27)33-19(6)29/h9,14,17,20,22-25H,1,3,10-13,15H2,2,4-8H3/t17-,20+,22+,23+,24-,25-,26-,27-/m0/s1
SMILES CCOC1C2=CC(CC3C2(C(CC(C3(C)CCC(=C)C=C)C)OC)C(O1)OC(=O)C)OC(=O)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
NPO32459 casearia balansae Species Salicaceae Eukaryota leaves and twigs n.a. n.a. PMID[24033131]
NPO32459 casearia balansae Species Salicaceae Eukaryota twigs n.a. n.a. PMID[25286284]
NPO32459 casearia balansae Species Salicaceae Eukaryota Leaves n.a. n.a. PMID[26699618]
NPO32459 casearia balansae Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]

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
NPT1374 Cell line WI-38 Homo sapiens IC50 = 57600.0 nM PMID[12444684]
NPT81 Cell line A549 Homo sapiens IC50 = 45200.0 nM PMID[25237727]
NPT146 Cell line SK-OV-3 Homo sapiens IC50 = 99800.0 nM PMID[11809056]
NPT90 Cell line DU-145 Homo sapiens IC50 = 51700.0 nM PMID[15920768]
NPT306 Cell line PC-3 Homo sapiens IC50 = 46400.0 nM PMID[19514743]

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 NPC471362 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
1.0 High Similarity NPC471372
0.9091 High Similarity NPC472189
0.8929 High Similarity NPC171598
0.8596 High Similarity NPC481018
0.8448 Intermediate Similarity NPC481020
0.8333 Intermediate Similarity NPC488649
0.8305 Intermediate Similarity NPC318917
0.8305 Intermediate Similarity NPC481019
0.8167 Intermediate Similarity NPC472186
0.8167 Intermediate Similarity NPC472188
0.8033 Intermediate Similarity NPC471366
0.8033 Intermediate Similarity NPC476800
0.8033 Intermediate Similarity NPC488237
0.7903 Intermediate Similarity NPC481017
0.7538 Intermediate Similarity NPC472187
0.7302 Intermediate Similarity NPC488236
0.697 Remote Similarity NPC473545
0.6825 Remote Similarity NPC606965
0.6462 Remote Similarity NPC132395
0.6462 Remote Similarity NPC471364
0.6462 Remote Similarity NPC488651
0.6462 Remote Similarity NPC488648
0.6462 Remote Similarity NPC600724
0.625 Remote Similarity NPC603601
0.6176 Remote Similarity NPC473204
0.6087 Remote Similarity NPC471365
0.5915 Remote Similarity NPC48548
0.5833 Remote Similarity NPC471363
0.5735 Remote Similarity NPC479934
0.5652 Remote Similarity NPC479935
0.5652 Remote Similarity NPC479936
0.5652 Remote Similarity NPC488235
0.561 Remote Similarity NPC488962
0.5606 Remote Similarity NPC488650
0.5606 Remote Similarity NPC481022
0.5571 Remote Similarity NPC479943
0.5479 Remote Similarity NPC488963
0.5429 Remote Similarity NPC479939
0.5417 Remote Similarity NPC479940
0.5417 Remote Similarity NPC7644
0.5405 Remote Similarity NPC488219
0.5352 Remote Similarity NPC479937
0.5342 Remote Similarity NPC238397
0.5333 Remote Similarity NPC488221
0.5333 Remote Similarity NPC488220
0.5333 Remote Similarity NPC488216
0.5278 Remote Similarity NPC479938
0.5135 Remote Similarity NPC217921
0.5135 Remote Similarity NPC88013
0.5135 Remote Similarity NPC475889
0.5135 Remote Similarity NPC7613
0.5135 Remote Similarity NPC479942
0.5135 Remote Similarity NPC135015
0.5067 Remote Similarity NPC479941
0.5063 Remote Similarity NPC486752

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471362 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