Natural Product: NPC7013

Natural Product IDNPC7013
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 7-Hydroxy-3-(4-Hydroxyphenyl)-5-Methoxychromen-4-One
IUPAC Name 7-hydroxy-3-(4-hydroxyphenyl)-5-methoxychromen-4-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1479463
PubChem CID 5748551
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 YSINCDVRUMTOPK-UHFFFAOYSA-N
Standard InCHI InChI=1S/C16H12O5/c1-20-13-6-11(18)7-14-15(13)16(19)12(8-21-14)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
SMILES COc1cc(O)cc2c1c(=O)c(co2)c1ccc(cc1)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   284.07 Volume:   282.482
?
Van der Waals volume.
Dense:   1.006 LogP:   1.953
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.107
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.066
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   18.0
TPSA:   79.9
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   2.0 Rings:   3.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.756 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.277 Fsp3:   0.062
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:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.301 Fluc inhibitor:   0.964
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.891
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.655
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.52 Promiscuous compounds:   0.768

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.781 MDCK Permeability:   -4.794
Pgp-inhibitor:   0.006 Pgp-substrate:   0.145
PAMPA:   0.765
?
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):   0.007
20% Bioavailability (F20%):   0.437 30% Bioavailability (F30%):   0.311
50% Bioavailability (F50%):   0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.078 MRP1:   0.509
Plasma Protein Binding (PPB):   93.623% Volume Distribution (VD):   -0.114
Fu: 7.735%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.638
OATP1B3 inhibitor:   0.538 BCRP inhibitor:   0.551
BSEP inhibitor:   0.773

ADMET: Metabolism

CYP1A2-inhibitor:   0.992 CYP1A2-substrate:   0.89
CYP2C19-inhibitor:   0.001 CYP2C19-substrate:   0.791
CYP2C9-inhibitor:   0.115 CYP2C9-substrate:   0.95
CYP2D6-inhibitor:   0.987 CYP2D6-substrate:   0.963
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.908
CYP2B6-substrate:   0.002 CYP2C8-inhibitor:   1.0
HLM stability:   0.011
?
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):  8.412 Half-life (T1/2):  1.036

ADMET: Toxicity

hERG Blockers:  0.205 hERG Blockers (10um):  0.592
Human Hepatotoxicity (H-HT):  0.51 Drug-induced Liver Injury (DILI):  0.607
AMES Toxicity:  0.537 Rat Oral Acute Toxicity:  0.519
Maximum Recommended Daily Dose:  0.781 Skin Sensitization:  0.481
Carcinogencity:  0.762 Eye Corrosion:  0.15
Eye Irritation:  0.987 Respiratory Toxicity:  0.687
Drug-induced Neurotoxicity:  0.512 Ototoxicity:  0.187
Hematotoxicity:  0.123 Drug-induced Nephrotoxicity:  0.171
Genotoxicity:  0.898 RPMI-8226 Immunitoxicity:  0.053
A549 Cytotoxicity:  0.179 Hek293 Cytotoxicity:  0.616
BCF:   1.277
?
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:   3.767
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.431
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.066
?
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
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0003-9861(62)90112-1]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(74)80113-5]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)94679-X]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. whole plant n.a. PMID[10361686]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[11035032]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[12902239]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[13835567]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14389294]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[1449509]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14607989]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15375647]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15744050]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[16724839]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[16850348]
NPO24639 Streptomyces filamentosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17284073]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[17439666]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19113969]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[22031445]
NPO546 Candida albicans Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. PMID[23902158]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2405251]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24305546]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24678285]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota leaves Bobai, Guangxi Province, China 2005-Dec PMID[24679044]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24733517]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota Barks n.a. n.a. PMID[24754786]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24831709]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24981409]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2687322]
NPO16444 Apios americana Species Fabaceae Eukaryota Tubers n.a. n.a. PMID[29932657]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[30199256]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[3289762]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4266242]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4616942]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[5764336]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[6306574]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[767332]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[7929110]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8017107]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8798704]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8852895]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8971708]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[9748245]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1154 Neomeris annulata Species Dasycladaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6060 Amaranthus spinosus Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO546 Candida albicans Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12152 Nicotiana raimondii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6679 Tephrosia watsoniana Species Geometridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26341 Trifolium resupinatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15242 Setosphaeria holmii Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9298 Piper wightii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20657 Garuga pinnata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2812 Lecanora kukunorensis Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6948 Davidsoniella virescens Species Ceratocystidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10228 Ascochyta viciae Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4061 Trollius europaeus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1468 Crassostrea virginica Species Ostreidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1468 Crassostrea virginica Species Ostreidae Eukaryota n.a. n.a. Database[FooDB]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1154 Neomeris annulata Species Dasycladaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2812 Lecanora kukunorensis Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26341 Trifolium resupinatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4061 Trollius europaeus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6679 Tephrosia watsoniana Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9298 Piper wightii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7011 Chamomilla recutita n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15242 Setosphaeria holmii Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20657 Garuga pinnata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6948 Davidsoniella virescens Species Ceratocystidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9830 Arum maximum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24639 Streptomyces filamentosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2419 Macrocentrus cingulum Species Braconidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1468 Crassostrea virginica Species Ostreidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16444 Apios americana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14912 Linostoma pauciflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6060 Amaranthus spinosus Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1077 Piper dilatatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26656 Heliotropium hirsutissimum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10228 Ascochyta viciae Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12152 Nicotiana raimondii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15875 Scolopia chinensis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2610 Chionodoxa gigantea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO11127 Inulanthera calva Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO546 Candida albicans Species Debaryomycetaceae 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
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 32642.7 nM PubChem BioAssay data set
NPT101 Individual protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 3162.3 nM PubChem BioAssay data set
NPT48 Individual protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PubChem BioAssay data set
NPT484 Individual protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 16944.1 nM PubChem BioAssay data set
NPT59 Individual protein DNA polymerase beta Homo sapiens Potency = 70794.6 nM PubChem BioAssay data set
NPT8 Individual protein DNA polymerase iota Homo sapiens Potency n.a. 50118.7 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 16353.5 nM PubChem BioAssay data set

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 IC50 > 1000.0 nM PMID[29932657]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 10417.9 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 13115.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 6309.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 11220.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 562.3 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 NPC7013 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
0.7963 Intermediate Similarity NPC109187
0.7593 Intermediate Similarity NPC121527
0.7222 Intermediate Similarity NPC162680
0.6429 Remote Similarity NPC269451
0.6316 Remote Similarity NPC303644
0.6316 Remote Similarity NPC100971
0.625 Remote Similarity NPC166036
0.625 Remote Similarity NPC605229
0.6034 Remote Similarity NPC181124
0.6034 Remote Similarity NPC216769
0.5968 Remote Similarity NPC62518
0.5926 Remote Similarity NPC234560
0.5862 Remote Similarity NPC131266
0.5818 Remote Similarity NPC39426
0.5763 Remote Similarity NPC124714
0.5763 Remote Similarity NPC209560
0.5763 Remote Similarity NPC490700
0.569 Remote Similarity NPC47815
0.5536 Remote Similarity NPC218490
0.55 Remote Similarity NPC294409
0.55 Remote Similarity NPC490701
0.5484 Remote Similarity NPC139364
0.5455 Remote Similarity NPC219917
0.541 Remote Similarity NPC483565
0.5397 Remote Similarity NPC254702
0.5345 Remote Similarity NPC223354
0.5345 Remote Similarity NPC608360
0.5323 Remote Similarity NPC309154
0.5323 Remote Similarity NPC12377
0.527 Remote Similarity NPC100720
0.5246 Remote Similarity NPC245382
0.5246 Remote Similarity NPC203747
0.5246 Remote Similarity NPC609386
0.5238 Remote Similarity NPC80710
0.5238 Remote Similarity NPC191741
0.52 Remote Similarity NPC479401
0.5156 Remote Similarity NPC285973
0.5082 Remote Similarity NPC10467
0.5082 Remote Similarity NPC116632
0.5082 Remote Similarity NPC35763
0.5082 Remote Similarity NPC149127
0.5082 Remote Similarity NPC78341
0.5082 Remote Similarity NPC270465
0.5079 Remote Similarity NPC200316
0.5077 Remote Similarity NPC259166
0.5075 Remote Similarity NPC97716

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC7013 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
0.5818 Remote Similarity NPD1510 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