Natural Product: NPC152506

Natural Product IDNPC152506
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 NMJUQUGTCLZQRB-ORQKVXKBSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 16038718
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

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 NMJUQUGTCLZQRB-ORQKVXKBSA-N
Standard InCHI InChI=1S/C20H30O3/c1-13-12-16(21)17-19(2,3)9-5-10-20(17,4)15(13)7-6-14-8-11-23-18(14)22/h6,15-17,21H,1,5,7-12H2,2-4H3/b14-6+/t15-,16+,17-,20+/m0/s1
SMILES C=C1C[C@H]([C@H]2C(C)(C)CCC[C@]2(C)[C@H]1C/C=C/1CCOC1=O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   318.22 Volume:   347.268
?
Van der Waals volume.
Dense:   0.916 LogP:   3.393
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.356
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.445
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   19.0
TPSA:   46.53
?
Topological Polar Surface Area.
 H-Bond Acceptor:   3.0
H-Bond Donor:   1.0 Rings:   3.0
Heavy Atoms:   3.0

MedChem Properties

QED Drug-Likeness Score:   0.475 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.506 Fsp3:   0.75
MCE-18:   55.2
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.518 Fluc inhibitor:   0.017
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.008
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.002
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.574 Promiscuous compounds:   0.146

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.548 MDCK Permeability:   -4.808
Pgp-inhibitor:   0.722 Pgp-substrate:   0.0
PAMPA:   0.072
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.004
20% Bioavailability (F20%):   0.057 30% Bioavailability (F30%):   0.056
50% Bioavailability (F50%):   0.573

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.005 MRP1:   0.075
Plasma Protein Binding (PPB):   97.888% Volume Distribution (VD):   0.315
Fu: 2.878%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.998
OATP1B3 inhibitor:   0.992 BCRP inhibitor:   0.003
BSEP inhibitor:   0.999

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.535
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.217
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.085
CYP2D6-inhibitor:   0.01 CYP2D6-substrate:   0.944
CYP3A4-inhibitor:   1.0 CYP3A4-substrate:   0.998
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.636
HLM stability:   0.711
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  11.3 Half-life (T1/2):  0.903

ADMET: Toxicity

hERG Blockers:  0.082 hERG Blockers (10um):  0.328
Human Hepatotoxicity (H-HT):  0.695 Drug-induced Liver Injury (DILI):  0.408
AMES Toxicity:  0.273 Rat Oral Acute Toxicity:  0.457
Maximum Recommended Daily Dose:  0.846 Skin Sensitization:  0.725
Carcinogencity:  0.703 Eye Corrosion:  0.005
Eye Irritation:  0.53 Respiratory Toxicity:  0.579
Drug-induced Neurotoxicity:  0.295 Ototoxicity:  0.706
Hematotoxicity:  0.284 Drug-induced Nephrotoxicity:  0.674
Genotoxicity:  0.281 RPMI-8226 Immunitoxicity:  0.099
A549 Cytotoxicity:  0.054 Hek293 Cytotoxicity:  0.314
BCF:   1.97
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   4.423
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.035
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.433
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[1517742]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[21106458]
NPO21639 Prunus mahaleb Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[34382873]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[37514241]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[39317685]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21639 Prunus mahaleb Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26208 Brombya platynema Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25906 Acacia linarioides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25582 Aquilegia viridiflora Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26079 Asterococcus muratae Species Cerococcidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26481 Astragalus kabadianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24733 Celastrus dispermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26524 Chondria californica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26816 Clinopodium gracile Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25393 Coelogyne flavida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26676 Daphne arisanensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24608 Gaertnera morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15693 Guadua angustifolia Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26846 Guettarda noumeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24829 Gyrostroma missouriense n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26554 Hexagonia speciosa Species Carabidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29093 Homalium longifolium Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10372 Kiggelaria africana Species Achariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26743 Lippia adoensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22353 Lucilia caesar Species Calliphoridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24894 Parmelia tinctina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23589 Pecten irradians Species Pectinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13051 Perymenium jelskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19916 Phenax angustifolius Species Urticaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26392 Piptadenia colubrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14283 Ponera metallica Species Formicidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23410 Potentilla candicans Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26306 Pyrobaculum organotrophum Species Thermoproteaceae Archaea n.a. n.a. n.a. Database[COCONUT]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13072 Rhamnus formosana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25768 Senecio ruwenzoriensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17771 Senna didymobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26175 Spongionella gracilis Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25996 Stenolobium stans n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO25575 Streptomyces pseudovenezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26357 Trachyrhamphus serratus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25732 Trichilia havanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7465 Vachellia leucophloea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28819 Veronica liwanensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25086 Viburnum betulifolium Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota Leaves n.a. Database[FooDB]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26816 Clinopodium gracile Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26306 Pyrobaculum organotrophum Species Thermoproteaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO24894 Parmelia tinctina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25906 Acacia linarioides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7465 Vachellia leucophloea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13072 Rhamnus formosana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24608 Gaertnera morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26676 Daphne arisanensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26208 Brombya platynema Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25732 Trichilia havanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14283 Ponera metallica Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26392 Piptadenia colubrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25582 Aquilegia viridiflora Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19916 Phenax angustifolius Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25575 Streptomyces pseudovenezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26743 Lippia adoensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24829 Gyrostroma missouriense n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23589 Pecten irradians Species Pectinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10372 Kiggelaria africana Species Achariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25768 Senecio ruwenzoriensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26846 Guettarda noumeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21639 Prunus mahaleb Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29093 Homalium longifolium Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26357 Trachyrhamphus serratus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26481 Astragalus kabadianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15693 Guadua angustifolia Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23410 Potentilla candicans Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26524 Chondria californica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25086 Viburnum betulifolium Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26079 Asterococcus muratae Species Cerococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28819 Veronica liwanensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26175 Spongionella gracilis Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13051 Perymenium jelskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17771 Senna didymobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24733 Celastrus dispermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25996 Stenolobium stans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26554 Hexagonia speciosa Species Carabidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25393 Coelogyne flavida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22353 Lucilia caesar Species Calliphoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26610 Spiraea formosana Species Rosaceae 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

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 NPC152506 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
0.6964 Remote Similarity NPC473154
0.6727 Remote Similarity NPC50488
0.6727 Remote Similarity NPC474396
0.6364 Remote Similarity NPC12170
0.5862 Remote Similarity NPC472812
0.5593 Remote Similarity NPC472811
0.55 Remote Similarity NPC478375
0.5333 Remote Similarity NPC57117
0.5246 Remote Similarity NPC478369
0.5238 Remote Similarity NPC72845
0.5161 Remote Similarity NPC474343
0.5082 Remote Similarity NPC79027

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC152506 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