Natural Product: NPC98028

Natural Product IDNPC98028
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Peucedanin
IUPAC Name 3-methoxy-2-propan-2-ylfuro[3,2-g]chromen-7-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1410943
PubChem CID 8616
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002569] Linear furanocoumarins
            • [CHEMONTID:0000202] Psoralens

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 YQBNJPACAUPNLV-UHFFFAOYSA-N
Standard InCHI InChI=1S/C15H14O4/c1-8(2)14-15(17-3)10-6-9-4-5-13(16)18-11(9)7-12(10)19-14/h4-8H,1-3H3
SMILES CC(C)c1c(c2cc3ccc(=O)oc3cc2o1)OC

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   258.09 Volume:   261.669
?
Van der Waals volume.
Dense:   0.986 LogP:   3.709
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.486
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.388
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   16.0
TPSA:   52.58
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   0.0 Rings:   3.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.658 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.602 Fsp3:   0.267
MCE-18:   17.0
?
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:   0.126 Fluc inhibitor:   0.412
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.993
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.625
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.472 Promiscuous compounds:   0.326

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.798 MDCK Permeability:   -4.782
Pgp-inhibitor:   0.034 Pgp-substrate:   0.0
PAMPA:   0.012
?
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%):   0.92 30% Bioavailability (F30%):   0.921
50% Bioavailability (F50%):   0.691

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.001 MRP1:   1.0
Plasma Protein Binding (PPB):   97.837% Volume Distribution (VD):   -0.177
Fu: 1.739%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.001
BSEP inhibitor:   0.999

ADMET: Metabolism

CYP1A2-inhibitor:   0.003 CYP1A2-substrate:   0.763
CYP2C19-inhibitor:   0.982 CYP2C19-substrate:   0.964
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.008
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.599
CYP3A4-inhibitor:   0.998 CYP3A4-substrate:   0.998
CYP2B6-substrate:   0.897 CYP2C8-inhibitor:   1.0
HLM stability:   0.755
?
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):  6.808 Half-life (T1/2):  0.746

ADMET: Toxicity

hERG Blockers:  0.109 hERG Blockers (10um):  0.389
Human Hepatotoxicity (H-HT):  0.515 Drug-induced Liver Injury (DILI):  0.953
AMES Toxicity:  0.583 Rat Oral Acute Toxicity:  0.552
Maximum Recommended Daily Dose:  0.726 Skin Sensitization:  0.123
Carcinogencity:  0.923 Eye Corrosion:  0.265
Eye Irritation:  0.954 Respiratory Toxicity:  0.629
Drug-induced Neurotoxicity:  0.192 Ototoxicity:  0.135
Hematotoxicity:  0.238 Drug-induced Nephrotoxicity:  0.182
Genotoxicity:  0.921 RPMI-8226 Immunitoxicity:  0.093
A549 Cytotoxicity:  0.084 Hek293 Cytotoxicity:  0.366
BCF:   1.263
?
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:   3.905
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.135
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.829
?
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
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. DOI[10.1016/0045-6535(91)90110-Y]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.abb.2017.09.009]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0885-5765(05)80069-4]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/jf980687v]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. exocarp n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. root n.a. PMID[21800857]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. root n.a. PMID[22784551]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[24459770]
NPO30569 Peucedanum tauricum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24660466]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. root n.a. PMID[25068578]
NPO31043 Opopanax hispidus Species Apiaceae Eukaryota n.a. aerial part n.a. PMID[25179742]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[35430270]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[36432786]
NPO31043 Opopanax hispidus Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[37049817]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[38977255]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4849 Peucedanum stenocarpum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30569 Peucedanum tauricum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24780 Oppopanax chironium n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO4849 Peucedanum stenocarpum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24559.1 Cotinus coggygria var. cinerea Varieties Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO11298 Peucedanum ruthenicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4849 Peucedanum stenocarpum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5201 Peucedanum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24559.1 Cotinus coggygria var. cinerea Varieties Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28932 Myrrhis odorata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24780 Oppopanax chironium n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6004 Peucedanum morisonii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5201 Peucedanum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6997 Anthriscus cerefolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28932 Myrrhis odorata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4934 Phaseolus vulgaris Species Fabaceae 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
NPT149 Individual protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 25118.9 nM PubChem BioAssay data set
NPT154 Individual protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 1412.5 nM PubChem BioAssay data set
NPT156 Individual protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PubChem BioAssay data set
NPT154 Individual protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 5173.5 nM PubChem BioAssay data set
NPT154 Individual protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 2310.9 nM PubChem BioAssay data set
NPT72 Individual protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 105.23 % PMID[23571415]
NPT48 Individual protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PubChem BioAssay data set
NPT94 Individual protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 39810.7 nM PubChem BioAssay data set
NPT538 Individual protein Niemann-Pick C1 protein Homo sapiens Potency = 2818.4 nM PubChem BioAssay data set
NPT444 Individual protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 31622.8 nM PubChem BioAssay data set
NPT73 Individual protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 101.26 % PMID[23571415]
NPT63 Individual protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 89125.1 nM PubChem BioAssay data set
NPT536 Nucleic acid microRNA 21 Homo sapiens Potency = 11668.1 nM PubChem BioAssay data set
NPT56 Individual protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 1995.3 nM PubChem BioAssay data set
NPT5 Individual protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 28183.8 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 29081.0 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell line HepG2 Homo sapiens Potency n.a. 398.1 nM PubChem BioAssay data set
NPT25 Cell line MT4 Homo sapiens CTD50 = 67.0 uM PMID[26079088]
NPT466 Cell line U-937 Homo sapiens CTD50 = 58.0 uM PMID[26079088]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2332.3 nM PubChem BioAssay data set
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. CTD50 = 81.0 uM PMID[26079088]
NPT2 Others Unspecified n.a. Potency n.a. 6309.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 1122.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 4610.9 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
- Mus musculus LD50 = 315.0 mg/kg ToxVal

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 NPC98028 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
0.6 Remote Similarity NPC254010

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC98028 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