Natural Product: NPC479067

Natural Product IDNPC479067
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 SFBODOKJTYAUCM-UHFFFAOYSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 3747
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002901] Isoflav-2-enes
          • [CHEMONTID:0000494] Isoflavones

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 SFBODOKJTYAUCM-UHFFFAOYSA-N
Standard InCHI InChI=1S/C18H16O3/c1-12(2)21-14-8-9-15-17(10-14)20-11-16(18(15)19)13-6-4-3-5-7-13/h3-12H,1-2H3
SMILES CC(C)Oc1ccc2c(c1)occ(c1ccccc1)c2=O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   280.11 Volume:   299.494
?
Van der Waals volume.
Dense:   0.935 LogP:   3.648
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.464
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.594
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   18.0
TPSA:   39.44
?
Topological Polar Surface Area.
 H-Bond Acceptor:   3.0
H-Bond Donor:   0.0 Rings:   3.0
Heavy Atoms:   3.0

MedChem Properties

QED Drug-Likeness Score:   0.72 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.956 Fsp3:   0.167
MCE-18:   16.0
?
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:   0.512 Fluc inhibitor:   0.997
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.916
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.816
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.601 Promiscuous compounds:   0.631

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.626 MDCK Permeability:   -4.635
Pgp-inhibitor:   0.886 Pgp-substrate:   0.023
PAMPA:   0.008
?
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):   0.016
20% Bioavailability (F20%):   0.017 30% Bioavailability (F30%):   0.155
50% Bioavailability (F50%):   0.512

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.005 MRP1:   0.905
Plasma Protein Binding (PPB):   98.482% Volume Distribution (VD):   0.233
Fu: 1.083%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.996
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.857
BSEP inhibitor:   1.0

ADMET: Metabolism

CYP1A2-inhibitor:   0.017 CYP1A2-substrate:   1.0
CYP2C19-inhibitor:   0.012 CYP2C19-substrate:   0.985
CYP2C9-inhibitor:   0.001 CYP2C9-substrate:   0.032
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.002
CYP3A4-inhibitor:   0.053 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.024 CYP2C8-inhibitor:   1.0
HLM stability:   0.0
?
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):  7.755 Half-life (T1/2):  0.849

ADMET: Toxicity

hERG Blockers:  0.302 hERG Blockers (10um):  0.656
Human Hepatotoxicity (H-HT):  0.57 Drug-induced Liver Injury (DILI):  0.883
AMES Toxicity:  0.266 Rat Oral Acute Toxicity:  0.469
Maximum Recommended Daily Dose:  0.588 Skin Sensitization:  0.159
Carcinogencity:  0.774 Eye Corrosion:  0.043
Eye Irritation:  0.837 Respiratory Toxicity:  0.636
Drug-induced Neurotoxicity:  0.698 Ototoxicity:  0.452
Hematotoxicity:  0.242 Drug-induced Nephrotoxicity:  0.754
Genotoxicity:  0.175 RPMI-8226 Immunitoxicity:  0.042
A549 Cytotoxicity:  0.084 Hek293 Cytotoxicity:  0.538
BCF:   1.777
?
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:   4.262
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.463
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.067
?
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
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. DOI[10.1002/ejlt.201100207]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. DOI[10.5219/332]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. PMID[24417583]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. n.a. PMID[26923696]
NPO12298 Epilobium parviflorum Species Onagraceae Eukaryota n.a. n.a. n.a. PMID[37111814]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12298 Epilobium parviflorum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25114 Linum usitatissimum Species Linaceae 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
NPO12298 Epilobium parviflorum n.a. n.a. 1.35 ± 0.03 n.a. n.a. μg/g PMID[37111814]
NPO12298 Epilobium parviflorum n.a. n.a. 27.82 ± 0.12 n.a. n.a. μg/g PMID[37111814]
NPO12298 Epilobium parviflorum n.a. n.a. 40.10 ± 0.67 n.a. n.a. μg/g PMID[37111814]

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
NPT292 Individual protein Serotonin 2c (5-HT2c) receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT264 Individual protein Muscarinic acetylcholine receptor M3 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT145 Individual protein Mu opioid receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT1250 Individual protein Macrophage migration inhibitory factor Homo sapiens IC50 = 255000.0 nM PMID[34758374]
NPT242 Individual protein Dopamine D1 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT1250 Individual protein Macrophage migration inhibitory factor Homo sapiens Ratio IC50 = 2.46 n.a. PMID[34758374]
NPT1250 Individual protein Macrophage migration inhibitory factor Homo sapiens Inhibition n.a. n.a. % PMID[34758374]
NPT246 Individual protein Dopamine transporter Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT153 Individual protein Androgen Receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT299 Individual protein Androgen Receptor Rattus norvegicus AC50 > 30000.0 nM PMID[37468498]
NPT272 Individual protein Kappa opioid receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT271 Individual protein Delta opioid receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT2879 Individual protein Equilibrative nucleoside transporter 1 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT222 Individual protein Alpha-2a adrenergic receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT263 Individual protein Muscarinic acetylcholine receptor M2 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT30 Individual protein Cyclooxygenase-1 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT249 Individual protein Glucocorticoid receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT217 Individual protein Adenosine A2a receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT267 Individual protein Neuropeptide Y receptor type 1 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT2761 Individual protein Phosphodiesterase 4A Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT291 Individual protein Serotonin 2b (5-HT2b) receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT204 Individual protein Acetylcholinesterase Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT2719 Individual protein Voltage-gated L-type calcium channel alpha-1C subunit Rattus norvegicus AC50 > 30000.0 nM PMID[37468498]
NPT216 Individual protein Adenosine A1 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT1163 Individual protein Glutamate (NMDA) receptor subunit zeta 1 Rattus norvegicus AC50 > 30000.0 nM PMID[37468498]
NPT244 Individual protein Dopamine D3 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT1647 Individual protein Vasopressin V2 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT262 Individual protein Muscarinic acetylcholine receptor M1 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT1788 Individual protein Alpha-1a adrenergic receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT2769 Individual protein Thromboxane A2 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT224 Individual protein Alpha-2c adrenergic receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT252 Individual protein Histamine H2 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT108 Individual protein Estrogen receptor alpha Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT226 Individual protein Beta-2 adrenergic receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT1410 Individual protein GABA receptor alpha-1 subunit Rattus norvegicus AC50 > 30000.0 nM PMID[37468498]
NPT230 Individual protein Bradykinin B2 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT225 Individual protein Beta-1 adrenergic receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT31 Individual protein Cyclooxygenase-2 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT295 Individual protein Serotonin transporter Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT259 Individual protein Melanocortin receptor 4 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT228 Individual protein Norepinephrine transporter Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT228 Individual protein Norepinephrine transporter Homo sapiens AC50 = 7059.9 nM PMID[37468498]
NPT239 Individual protein Cholecystokinin A receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT261 Individual protein Monoamine oxidase A Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT251 Individual protein Histamine H1 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT290 Individual protein Serotonin 2a (5-HT2a) receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT1464 Individual protein Phosphodiesterase 4D Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT243 Individual protein Dopamine D2 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT232 Individual protein Cannabinoid CB1 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT303 Individual protein Vasopressin V1a receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT223 Individual protein Alpha-2b adrenergic receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT72 Individual protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 84.86 % PMID[23571415]
NPT5301 Individual protein Motilin receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT987 Individual protein Histamine H3 receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT73 Individual protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 137.71 % PMID[23571415]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 12.52 % DOI[10.6019/CHEMBL4495564]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 16.29 % DOI[10.6019/CHEMBL4495564]
NPT542 Individual protein Progesterone receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT29430 Single protein Neuronal acetylcholine receptor protein alpha-4 subunit Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT692 Individual protein Histone deacetylase 6 Homo sapiens IC50 = 920.4 nM HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = 95.18 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = -8.43 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = 96.99 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT4358 Individual protein Type-1 angiotensin II receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT98 Individual protein HERG Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT4729 Individual protein Cholecystokinin B receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT5975 Individual protein Cyclooxygenase-1 Rattus norvegicus AC50 > 30000.0 nM PMID[37468498]
NPT92 Individual protein Serotonin 1a (5-HT1a) receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT5104 Individual protein Phosphodiesterase 3A Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT28814 Single protein Ghrelin receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT425 Individual protein Serotonin 3a (5-HT3a) receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT543 Individual protein Pregnane X receptor Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT30151 Single protein Melanocortin receptor 3 Homo sapiens AC50 > 30000.0 nM PMID[37468498]
NPT670 Individual protein Thrombin Homo sapiens AC50 > 30000.0 nM PMID[37468498]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell line RAW264.7 Mus musculus Inhibition = 31.0 % PMID[19339083]
NPT113 Cell line RAW264.7 Mus musculus Inhibition = 31.0 % PMID[21456521]
NPT113 Cell line RAW264.7 Mus musculus Activity n.a. n.a. n.a. PMID[34758374]
NPT21723 Cell line Bone marrow cell n.a. IC50 = 17200.0 nM PMID[26923696]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 5.86 % DOI[10.21203/rs.3.rs-23951/v1]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.34 % DOI[10.6019/CHEMBL4495565]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.9 % DOI[10.6019/CHEMBL4495565]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM DOI[10.6019/CHEMBL4651402]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM DOI[10.6019/CHEMBL4651402]
NPT21334 Cell line MC3T3-E1 Mus musculus Activity = 4.09 % PMID[28427808]
NPT20 Organism Candida albicans Candida albicans Inhibition = 3.92 % DOI[10.6019/CHEMBL4296181]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 12.22 % DOI[10.6019/CHEMBL4296181]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = 2.68 % DOI[10.6019/CHEMBL4296181]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 5.9 % DOI[10.6019/CHEMBL4296181]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 14.52 % DOI[10.6019/CHEMBL4296181]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = 16.93 % DOI[10.6019/CHEMBL4296181]
NPT2645 Organism Giardia intestinalis Giardia intestinalis IC50 = 25.0 nM PMID[33360795]
NPT2645 Organism Giardia intestinalis Giardia intestinalis IC50 = 34.0 nM PMID[33360795]
NPT2645 Organism Giardia intestinalis Giardia intestinalis IC50 = 510.0 nM PMID[33360795]
NPT2645 Organism Giardia intestinalis Giardia intestinalis IC50 = 14.0 nM PMID[33360795]
NPT2645 Organism Giardia intestinalis Giardia intestinalis IC50 = 45.0 nM PMID[33360795]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 25.6 % DOI[10.6019/CHEMBL4296181]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell line RAW264.7 Mus musculus Survival = 102.0 % PMID[21456521]





 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 NPC479067 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
0.6923 Remote Similarity NPC182428
0.6607 Remote Similarity NPC136095
0.6491 Remote Similarity NPC471590
0.6333 Remote Similarity NPC254741
0.6316 Remote Similarity NPC181124
0.625 Remote Similarity NPC185607
0.5781 Remote Similarity NPC185401
0.5769 Remote Similarity NPC201284
0.5738 Remote Similarity NPC602183
0.5714 Remote Similarity NPC120924
0.5614 Remote Similarity NPC608360
0.5593 Remote Similarity NPC216314
0.5588 Remote Similarity NPC25547
0.55 Remote Similarity NPC186507
0.5429 Remote Similarity NPC487214
0.5333 Remote Similarity NPC603503
0.5278 Remote Similarity NPC478528
0.5278 Remote Similarity NPC211014
0.5167 Remote Similarity NPC103001
0.5167 Remote Similarity NPC474264
0.5139 Remote Similarity NPC45165
0.5085 Remote Similarity NPC195919

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC479067 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
1.0 High Similarity NPD2796 Phase 2

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