Natural Product: NPC192768

Natural Product IDNPC192768
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.
 JLYWCHLTLCGOMW-GJZGRUSLSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1494954
PubChem CID 12300156
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002793] Pavine alkaloids

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 JLYWCHLTLCGOMW-GJZGRUSLSA-N
Standard InCHI InChI=1S/C19H21NO4/c1-20-14-4-10-6-16(21)19(24-3)9-13(10)15(20)5-11-7-18(23-2)17(22)8-12(11)14/h6-9,14-15,21-22H,4-5H2,1-3H3/t14-,15-/m0/s1
SMILES CN1[C@H]2Cc3cc(c(cc3[C@@H]1Cc1cc(c(cc21)O)OC)OC)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
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(98)00534-2]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[12932146]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. twig n.a. PMID[16204994]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[17020288]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota leaves Lai-I, Pingtung County, Taiwan 2005-May PMID[20704331]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota aerial parts n.a. n.a. PMID[20949916]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[20949916]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[22624550]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota aerial parts Nanning, Guangxi Province, China 2014-OCT PMID[28753309]
NPO12301 Chenopodium quinoa Species Chenopodiaceae Eukaryota n.a. n.a. PMID[31861466]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[39064968]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15911 Streptomyces graminofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO13040 Veretillum cynomorium Species Veretillidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6615 Aplidium solidum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13929 Hypocrella bambusae Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7036 Davidsonia pruriens Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13631 Microglossa pyrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12296 Sphaerechinus granularis Species Toxopneustidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14086 Parthenium confertum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3521 Geranium collinum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14366 Youngia japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14485 Eriocephalus kingesii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12301 Chenopodium quinoa Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7878 Lysastrosoma anthosticta n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO12301 Chenopodium quinoa Species Chenopodiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13929 Hypocrella bambusae Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6615 Aplidium solidum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12301 Chenopodium quinoa Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14086 Parthenium confertum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8632 Aralia hispida Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2770 Pyropolyporus fomentarius n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12064 Lychnophora pinaster Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11277 Baeckea frutescens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14485 Eriocephalus kingesii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1202 Psathyrotes ramosissima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15311 Cryptocarya chinensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11607 Marrubium parviflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1946 Veronica stricta Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13755 Gonotheca helianthoides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20068 Fusarium striatum Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13241 Coprosma foetidissima Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3521 Geranium collinum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14223 Harpullia cupanioides Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13040 Veretillum cynomorium Species Veretillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26228 Phymatopteris hastata Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10936 Andira retusa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14996 Lobelia syphilitica Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6241 Girgensohnia oppositiflora Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14344 Trifolium diffusum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13631 Microglossa pyrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2075 Zanthoxylum ocumarense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5040 Polygonatum polyanthemum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12818 Lespedeza maximowiczi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7036 Davidsonia pruriens Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14885 Lilium rubrum Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7878 Lysastrosoma anthosticta n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15098 Cyttaria johowii Species Cyttariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16090 Panicum crus-galli Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16174 Scleropyrum wallichianum Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12296 Sphaerechinus granularis Species Toxopneustidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15911 Streptomyces graminofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14639 Balanophora polyandra Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14366 Youngia japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13929 Hypocrella bambusae Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11833 Dyssodia anthemidifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6229 Chenopodiastrum murale Species Chenopodiaceae 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
NPT100 Individual protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 35481.3 nM PubChem BioAssay data set
NPT444 Individual protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 251.2 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2936.2 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 14715.7 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency = 3662.6 nM PubChem BioAssay data set

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 NPC192768 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
0.8571 High Similarity NPC34559
0.766 Intermediate Similarity NPC111485
0.7447 Intermediate Similarity NPC185467
0.566 Remote Similarity NPC88249
0.566 Remote Similarity NPC220858
0.5455 Remote Similarity NPC147390
0.5455 Remote Similarity NPC428
0.5357 Remote Similarity NPC321505
0.5357 Remote Similarity NPC179825
0.5357 Remote Similarity NPC151895
0.5179 Remote Similarity NPC191376
0.5172 Remote Similarity NPC189266
0.5172 Remote Similarity NPC172765
0.5172 Remote Similarity NPC2413
0.5172 Remote Similarity NPC110416
0.5085 Remote Similarity NPC249797
0.5085 Remote Similarity NPC193949

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC192768 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