Natural Product: NPC77237

Natural Product IDNPC77237
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Arisanschinin N
IUPAC Name n.a.
Synonyms Arisanschinin N
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL2313594
PubChem CID 5321171
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins
        • [CHEMONTID:0001710] Hydrolyzable tannins

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 BKGUPIVDQHHVMV-ZQJDBEKWSA-N
Standard InCHI InChI=1S/C28H34O9/c1-9-14(2)27(29)37-26-17-12-18(31-5)22(32-6)25(34-8)21(17)20-16(10-15(3)28(26,4)30)11-19-23(24(20)33-7)36-13-35-19/h9,11-12,15,26,30H,10,13H2,1-8H3/b14-9-/t15-,26-,28+/m0/s1
SMILES C/C=C(/C)C(=O)O[C@H]1c2cc(c(c(c2-c2c(C[C@H](C)[C@@]1(C)O)cc1c(c2OC)OCO1)OC)OC)OC

  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
NPO14250 Schisandra henryi Species Schisandraceae Eukaryota n.a. stem n.a. PMID[14661856]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[16562834]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[19673515]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[20536188]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[23265871]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[23265871]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[24155209]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[24959987]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[25302569]
NPO14250 Schisandra henryi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25239 Kadsura peltigera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25239 Kadsura peltigera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25239 Kadsura peltigera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14250 Schisandra henryi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25239 Kadsura peltigera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14250 Schisandra henryi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25239 Kadsura peltigera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14250 Schisandra henryi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8584 Schisandra arisanensis Species Schisandraceae 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
NPT744 Cell line IMR-32 Homo sapiens IC50 = 66800.0 nM PMID[28818768]
NPT90 Cell line DU-145 Homo sapiens IC50 = 64700.0 nM PMID[28818768]
NPT2245 Cell line SiHa Homo sapiens IC50 = 51200.0 nM PMID[28818768]
NPT461 Cell line PANC-1 Homo sapiens IC50 = 53600.0 nM PMID[28818768]
NPT82 Cell line MDA-MB-231 Homo sapiens IC50 = 60500.0 nM PMID[28818768]
NPT81 Cell line A549 Homo sapiens IC50 = 55100.0 nM PMID[28818768]
NPT71 Cell line HEK293 Homo sapiens IC50 = 52000.0 nM PMID[28818768]
NPT2 Others Unspecified n.a. Inhibition = 6.64 % PMID[23265871]

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 NPC77237 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 NPC126405
1.0 High Similarity NPC53669
1.0 High Similarity NPC297271
1.0 High Similarity NPC16791
1.0 High Similarity NPC217708
0.9661 High Similarity NPC198461
0.8814 High Similarity NPC295297
0.8154 Intermediate Similarity NPC224472
0.7606 Intermediate Similarity NPC485504
0.7463 Intermediate Similarity NPC470916
0.7424 Intermediate Similarity NPC308739
0.7324 Intermediate Similarity NPC29727
0.6806 Remote Similarity NPC83049
0.6806 Remote Similarity NPC320471
0.6806 Remote Similarity NPC118162
0.6716 Remote Similarity NPC85141
0.6528 Remote Similarity NPC79322
0.625 Remote Similarity NPC53722
0.625 Remote Similarity NPC201404
0.625 Remote Similarity NPC290714
0.6212 Remote Similarity NPC327352
0.6212 Remote Similarity NPC198129
0.6212 Remote Similarity NPC252281
0.6029 Remote Similarity NPC322426
0.6029 Remote Similarity NPC76415
0.6029 Remote Similarity NPC218510
0.5921 Remote Similarity NPC475592
0.589 Remote Similarity NPC24562
0.5857 Remote Similarity NPC316989
0.5616 Remote Similarity NPC312763
0.5513 Remote Similarity NPC476065
0.5507 Remote Similarity NPC304821
0.5484 Remote Similarity NPC145722
0.5484 Remote Similarity NPC256776
0.5484 Remote Similarity NPC185680
0.5443 Remote Similarity NPC63061
0.5432 Remote Similarity NPC348849
0.5432 Remote Similarity NPC178195
0.5395 Remote Similarity NPC473323
0.5385 Remote Similarity NPC326144
0.5325 Remote Similarity NPC477885
0.525 Remote Similarity NPC475229
0.5238 Remote Similarity NPC88557
0.5217 Remote Similarity NPC318286
0.5161 Remote Similarity NPC32189
0.5143 Remote Similarity NPC137352
0.5143 Remote Similarity NPC183083
0.5143 Remote Similarity NPC485503
0.5132 Remote Similarity NPC471154
0.5072 Remote Similarity NPC327651
0.507 Remote Similarity NPC321958
0.507 Remote Similarity NPC230538
0.507 Remote Similarity NPC229172
0.507 Remote Similarity NPC103637
0.507 Remote Similarity NPC36531

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC77237 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