Natural Product: NPC293545

Natural Product IDNPC293545
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (9S,9's)-2,2',4,4',5,5'-Hexahydroxy-7,7'-Dimethyl-9,9'-Bianthracene-10,10'(9H,9'h)-Dione
IUPAC Name (10S)-1,3,8-trihydroxy-6-methyl-10-[(9S)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-10H-anthracen-9-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL464711
PubChem CID 12096290
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes

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 UUXPVUHOWQPCSC-ZEQRLZLVSA-N
Standard InCHI InChI=1S/C30H22O8/c1-11-3-15-23(17-7-13(31)9-21(35)27(17)29(37)25(15)19(33)5-11)24-16-4-12(2)6-20(34)26(16)30(38)28-18(24)8-14(32)10-22(28)36/h3-10,23-24,31-36H,1-2H3/t23-,24-/m0/s1
SMILES Cc1cc2[C@@H](c3cc(cc(c3C(=O)c2c(c1)O)O)O)[C@H]1c2cc(C)cc(c2C(=O)c2c1cc(cc2O)O)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
NPO27239 Maclura tinctoria Species Moraceae Eukaryota n.a. n.a. n.a. PMID[11087602]
NPO32935 rhamnus nepalensis Species Rhamnaceae Eukaryota Leaves Pa Co, Mai Chau, Hoa Binh Province, 150 km west of Hanoi, Vietnam 1995-Nov PMID[11575949]
NPO27239 Maclura tinctoria Species Moraceae Eukaryota n.a. stem n.a. PMID[12932124]
NPO27239 Maclura tinctoria Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12932124]
NPO27164 Aspergillus alliaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[29517220]
NPO27164 Aspergillus alliaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[3417561]
NPO27873 Ravenia spectabilis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[34570617]
NPO27140 Amanita phalloides Species Amanitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27164 Aspergillus alliaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27239 Maclura tinctoria Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27873 Ravenia spectabilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19050 Garcinia polyantha Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26972 Baccharis potosina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27140 Amanita phalloides Species Amanitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19050 Garcinia polyantha Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3980 Frangula purshiana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19050 Garcinia polyantha Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4132 Cranfillia fluviatilis Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27454 Turbo cornutus Species Turbinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27790 Delia arenicola Species Anthomyiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3980 Frangula purshiana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24629 Achromobacter denitrificans Species Alcaligenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27140 Amanita phalloides Species Amanitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10239 Magnolia figo Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27564 Stevia berlandieri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17822 Fridericia triplinervia Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27873 Ravenia spectabilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26972 Baccharis potosina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27164 Aspergillus alliaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27239 Maclura tinctoria Species Moraceae 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
NPT91 Cell line KB Homo sapiens IC50 = 2500.0 nM PMID[11575949]

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 NPC293545 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 NPC174905
0.8095 Intermediate Similarity NPC474203
0.8095 Intermediate Similarity NPC313047
0.8095 Intermediate Similarity NPC451542
0.8095 Intermediate Similarity NPC295712
0.6429 Remote Similarity NPC161964
0.6429 Remote Similarity NPC287604
0.6098 Remote Similarity NPC254847
0.5814 Remote Similarity NPC267205
0.5472 Remote Similarity NPC477221
0.5294 Remote Similarity NPC601142
0.5294 Remote Similarity NPC601530
0.5294 Remote Similarity NPC606267
0.5294 Remote Similarity NPC610829
0.5185 Remote Similarity NPC600622
0.5088 Remote Similarity NPC600612
0.5075 Remote Similarity NPC600427
0.5075 Remote Similarity NPC607712

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC293545 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
0.6098 Remote Similarity NPD1509 Clinical (unspecified phase)

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