Natural Product: NPC469981

Natural Product IDNPC469981
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.
 4-Hydroxysesamin
IUPAC Name (3R,3aR,6R,6aS)-3,6-bis(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-4-ol
Synonyms 4-Hydroxysesamin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1641633
PubChem CID 53321864
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans

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 AWLJZFUREZNLGG-RXABKWRFSA-N
Standard InCHI InChI=1S/C20H18O7/c21-20-17-12(18(27-20)10-1-3-13-15(5-10)25-8-23-13)7-22-19(17)11-2-4-14-16(6-11)26-9-24-14/h1-6,12,17-21H,7-9H2/t12-,17-,18+,19+,20?/m1/s1
SMILES C1C2C(C(O1)C3=CC4=C(C=C3)OCO4)C(OC2C5=CC6=C(C=C5)OCO6)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
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[15095145]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[17559265]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. mycelium n.a. PMID[17932820]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[21028898]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota fruiting body n.a. n.a. PMID[21028898]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota fruiting body n.a. n.a. PMID[21115251]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[23517145]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[31891260]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[8594142]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae 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
NPT1184 Cell line Daoy Homo sapiens ED50 > 20.0 ug ml-1 PMID[19734910]
NPT1171 Cell line HEp-2 Homo sapiens ED50 > 20.0 ug ml-1 PMID[12383020]
NPT83 Cell line MCF7 Homo sapiens ED50 > 20.0 ug ml-1 PMID[21907579]
NPT165 Cell line HeLa Homo sapiens ED50 > 20.0 ug ml-1 PMID[11678655]

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 NPC469981 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
0.7021 Intermediate Similarity NPC171928
0.7021 Intermediate Similarity NPC158526
0.7021 Intermediate Similarity NPC129687
0.7021 Intermediate Similarity NPC33611
0.7021 Intermediate Similarity NPC16830
0.7021 Intermediate Similarity NPC100223
0.6471 Remote Similarity NPC227160
0.6471 Remote Similarity NPC82111
0.6226 Remote Similarity NPC189474
0.5965 Remote Similarity NPC298317
0.5965 Remote Similarity NPC255566
0.5763 Remote Similarity NPC88640
0.5763 Remote Similarity NPC101153
0.5763 Remote Similarity NPC193666
0.5763 Remote Similarity NPC123526
0.5763 Remote Similarity NPC608725
0.5714 Remote Similarity NPC14022
0.5714 Remote Similarity NPC601703
0.5593 Remote Similarity NPC483653
0.55 Remote Similarity NPC47181
0.5424 Remote Similarity NPC101807
0.5294 Remote Similarity NPC271208
0.5294 Remote Similarity NPC233224
0.5294 Remote Similarity NPC610263
0.5185 Remote Similarity NPC137487
0.5179 Remote Similarity NPC487685
0.5156 Remote Similarity NPC483651
0.5156 Remote Similarity NPC600032
0.5098 Remote Similarity NPC121783
0.5098 Remote Similarity NPC34902
0.5098 Remote Similarity NPC18449
0.5082 Remote Similarity NPC474139

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469981 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