Natural Product: NPC182869

Natural Product IDNPC182869
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Norstaminone A
IUPAC Name [(1R,2S,3S,4aS,6R,8R,8aS)-8-[(1E)-2-acetylbuta-1,3-dienyl]-2,6-diacetyloxy-3-hydroxy-4,4,8a-trimethyl-7-oxo-2,3,4a,5,6,8-hexahydro-1H-naphthalen-1-yl] benzoate
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL472848
PubChem CID 10414921
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001564] Bicyclic monoterpenoids

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 PHXNLVUWPCOMGG-HSGILHHISA-N
Standard InCHI InChI=1S/C30H36O9/c1-8-19(16(2)31)14-21-24(34)22(37-17(3)32)15-23-29(5,6)26(35)25(38-18(4)33)27(30(21,23)7)39-28(36)20-12-10-9-11-13-20/h8-14,21-23,25-27,35H,1,15H2,2-7H3/b19-14+/t21-,22+,23-,25-,26+,27-,30+/m0/s1
SMILES C=C/C(=C[C@H]1C(=O)[C@H](OC(=O)C)C[C@@H]2[C@]1(C)[C@@H](OC(=O)c1ccccc1)[C@@H](OC(=O)C)[C@H](C2(C)C)O)/C(=O)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   540.24 Volume:   554.514
?
Van der Waals volume.
Dense:   0.974 LogP:   2.748
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.805
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.695
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   10.0 Rigid Bonds:   24.0
TPSA:   133.27
?
Topological Polar Surface Area.
 H-Bond Acceptor:   9.0
H-Bond Donor:   1.0 Rings:   3.0
Heavy Atoms:   9.0

MedChem Properties

QED Drug-Likeness Score:   0.239 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.872 Fsp3:   0.5
MCE-18:   95.2
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.549 Fluc inhibitor:   0.124
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.041
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.173
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.206 Promiscuous compounds:   0.3

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.204 MDCK Permeability:   -4.785
Pgp-inhibitor:   0.364 Pgp-substrate:   0.226
PAMPA:   0.807
?
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):   0.0
20% Bioavailability (F20%):   0.007 30% Bioavailability (F30%):   0.029
50% Bioavailability (F50%):   0.684

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.005 MRP1:   0.999
Plasma Protein Binding (PPB):   79.232% Volume Distribution (VD):   -0.028
Fu: 19.617%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.922
OATP1B3 inhibitor:   0.594 BCRP inhibitor:   0.0
BSEP inhibitor:   0.416

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.247
CYP2C19-inhibitor:   0.025 CYP2C19-substrate:   0.259
CYP2C9-inhibitor:   0.001 CYP2C9-substrate:   0.053
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.012
CYP3A4-inhibitor:   0.029 CYP3A4-substrate:   0.561
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.999
?
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):  5.842 Half-life (T1/2):  0.553

ADMET: Toxicity

hERG Blockers:  0.014 hERG Blockers (10um):  0.262
Human Hepatotoxicity (H-HT):  0.356 Drug-induced Liver Injury (DILI):  0.961
AMES Toxicity:  0.927 Rat Oral Acute Toxicity:  0.368
Maximum Recommended Daily Dose:  0.525 Skin Sensitization:  0.999
Carcinogencity:  0.647 Eye Corrosion:  0.001
Eye Irritation:  0.349 Respiratory Toxicity:  0.184
Drug-induced Neurotoxicity:  0.635 Ototoxicity:  0.247
Hematotoxicity:  0.622 Drug-induced Nephrotoxicity:  0.781
Genotoxicity:  0.992 RPMI-8226 Immunitoxicity:  0.167
A549 Cytotoxicity:  0.618 Hek293 Cytotoxicity:  0.505
BCF:   0.618
?
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:   3.541
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.295
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.73
?
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
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[11374950]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[11473439]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[12141863]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. Indonesia n.a. PMID[12467611]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota aerial parts Bangdung, Indonesia 2000-Aug PMID[12608860]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. Taiwan n.a. PMID[15104497]
NPO21944 Laurencia mariannensis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[18076141]
NPO5877 Morus yunnanensis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[22165973]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[26473275]
NPO23000 Zephyranthes carinata Species Amaryllidaceae Eukaryota Whole Plants n.a. n.a. PMID[28898076]
NPO3549 Euonymus maackii Species Celastraceae Eukaryota Seeds n.a. n.a. PMID[31713425]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[32933154]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[33081385]
NPO23183 Pinus halepensis Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[34847783]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36671383]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36840093]
NPO23183 Pinus halepensis Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[38202742]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14529 Asterias rubens Species Asteriidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23183 Pinus halepensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22911 Enterococcus faecalis Species Enterococcaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22773 Teucrium alyssifolium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22071 Gentiana olivieri Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23141 Angelica ursina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22395 Ardisia macrocarpa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22462 Chlorophytum malayense Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22015 Clausena indica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20100 Ephedra lomatolepis Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22197 Eriogaster lanestris Species Lasiocampidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3549 Euonymus maackii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22518 Gnetum cleistostachyum Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21140 Igernella notabilis Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23101 Ircinia aruensis Species Irciniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21944 Laurencia mariannensis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21545 Maytenus guianensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23062 Melibe leonina Species Dendronotidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5877 Morus yunnanensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7320 Nicotiana gossei Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20726 Ophioplocus japonicus Species Ophiolepididae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21745 Phleum africanum Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20964 Picradeniopsis oppositifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22717 Pinus thunbergii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16275 Pterocaulon rugosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10353 Rauvolfia tetraphylla Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21680 Saussurea triangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22952 Senecio grandiflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21881 Stephania succifera Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14664 Stevia salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21384 Tetraria capillaris Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22137 Vernonia serratuloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23000 Zephyranthes carinata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23226 Satureja montana Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23141 Angelica ursina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22462 Chlorophytum malayense Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23141 Angelica ursina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22071 Gentiana olivieri Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3549 Euonymus maackii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21881 Stephania succifera Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21545 Maytenus guianensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19152 Empetrum nigrum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20726 Ophioplocus japonicus Species Ophiolepididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21384 Tetraria capillaris Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22462 Chlorophytum malayense Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21881 Stephania succifera Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22900 Orthosiphon stamineus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21140 Igernella notabilis Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21680 Saussurea triangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22518 Gnetum cleistostachyum Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22952 Senecio grandiflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22717 Pinus thunbergii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23000 Zephyranthes carinata Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5877 Morus yunnanensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16275 Pterocaulon rugosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19451 Salvia prionitis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23141 Angelica ursina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23101 Ircinia aruensis Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14664 Stevia salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20100 Ephedra lomatolepis Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22773 Teucrium alyssifolium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20964 Picradeniopsis oppositifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21944 Laurencia mariannensis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7320 Nicotiana gossei Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21745 Phleum africanum Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19929 Jateorhiza palmata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22197 Eriogaster lanestris Species Lasiocampidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23183 Pinus halepensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22911 Enterococcus faecalis Species Enterococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10353 Rauvolfia tetraphylla Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22137 Vernonia serratuloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22015 Clausena indica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22395 Ardisia macrocarpa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3549 Euonymus maackii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14529 Asterias rubens Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22071 Gentiana olivieri Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23062 Melibe leonina Species Dendronotidae 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
NPT453 Cell line HT-1080 Homo sapiens ED50 = 23.2 ug ml-1 PMID[11374950]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. ED50 = 12.8 ug ml-1 PMID[11374950]

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 NPC182869 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
0.5769 Remote Similarity NPC60509
0.5769 Remote Similarity NPC257213
0.5769 Remote Similarity NPC478502
0.5696 Remote Similarity NPC198455
0.5696 Remote Similarity NPC228204
0.5625 Remote Similarity NPC256142
0.5443 Remote Similarity NPC304876

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC182869 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