Natural Product: NPC25389

Natural Product IDNPC25389
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 DEUNVKAEJOZXBQ-UVNCQSPWSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL3604317
PubChem CID NA
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic glycosides

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 DEUNVKAEJOZXBQ-UVNCQSPWSA-N
Standard InCHI InChI=1S/C20H22O12/c1-29-13-6-9(2-3-10(13)21)31-20-18(27)17(26)16(25)14(32-20)7-30-19(28)8-4-11(22)15(24)12(23)5-8/h2-6,14,16-18,20-27H,7H2,1H3/t14-,16-,17+,18-,20-/m1/s1
SMILES COc1cc(ccc1O)O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   454.11 Volume:   415.834
?
Van der Waals volume.
Dense:   1.092 LogP:   0.605
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.071
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.258
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   7.0 Rigid Bonds:   19.0
TPSA:   195.6
?
Topological Polar Surface Area.
 H-Bond Acceptor:   12.0
H-Bond Donor:   7.0 Rings:   3.0
Heavy Atoms:   12.0

MedChem Properties

QED Drug-Likeness Score:   0.22 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.774 Fsp3:   0.35
MCE-18:   74.148
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Accepted
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.529 Fluc inhibitor:   0.371
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.181
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.489
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.156 Promiscuous compounds:   0.889

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.322 MDCK Permeability:   -5.352
Pgp-inhibitor:   0.0 Pgp-substrate:   0.005
PAMPA:   0.954
?
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):   0.029
20% Bioavailability (F20%):   0.9 30% Bioavailability (F30%):   0.974
50% Bioavailability (F50%):   0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.993
Plasma Protein Binding (PPB):   68.58% Volume Distribution (VD):   -0.5
Fu: 31.573%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.547
BSEP inhibitor:   0.011

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.001
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.053
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.991
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.996
HLM stability:   0.247
?
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):  4.024 Half-life (T1/2):  3.846

ADMET: Toxicity

hERG Blockers:  0.039 hERG Blockers (10um):  0.719
Human Hepatotoxicity (H-HT):  0.136 Drug-induced Liver Injury (DILI):  0.89
AMES Toxicity:  0.851 Rat Oral Acute Toxicity:  0.021
Maximum Recommended Daily Dose:  0.142 Skin Sensitization:  1.0
Carcinogencity:  0.299 Eye Corrosion:  0.0
Eye Irritation:  0.696 Respiratory Toxicity:  0.017
Drug-induced Neurotoxicity:  0.001 Ototoxicity:  0.97
Hematotoxicity:  0.009 Drug-induced Nephrotoxicity:  0.052
Genotoxicity:  0.681 RPMI-8226 Immunitoxicity:  0.019
A549 Cytotoxicity:  0.95 Hek293 Cytotoxicity:  0.283
BCF:   0.418
?
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:   3.133
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.345
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.757
?
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
NPO18142 Elysia ornata Species Placobranchidae Eukaryota n.a. n.a. n.a. PMID[10650101]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10757709]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. leaf n.a. PMID[10830513]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. twig n.a. PMID[10830513]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. PMID[10830513]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[12193039]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. leaf n.a. PMID[17685627]
NPO18584 Streptoalloteichus hindustanus Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[21210656]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota rhizomes n.a. n.a. PMID[21353549]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21510636]
NPO25715 Senna siamea Species Fabaceae Eukaryota Stems n.a. n.a. PMID[23078294]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[23210623]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23513740]
NPO5755.1 Bauhinia glauca Under-species n.a. n.a. n.a. n.a. n.a. PMID[26096681]
NPO18584 Streptoalloteichus hindustanus Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[29792433]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[30379546]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[31596079]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[32092041]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14615 Streptomyces paulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO6179 Aframomum amaniense Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14504 Alectoria divergens Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14200 Aristolochia zollingeriana Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1661 Bartramia pomiformis Species Bartramiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7752 Beilschmiedia anacardioides Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13076 Cephalaria grossheimii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12754 Cerinthe minor Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21498 Coccus ilicis Species Coccidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12585 Craspidospermum verticillatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9669 Dictyopteris acrostichoides Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12069 Isaria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12910 Ixeris stolonifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12061 Justicia paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12234 Khaya ivorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10389 Larix cajanderi Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3458 Lupinus verbasciformis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13701 Melaleuca rhaphiophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7169 Nama hispidum Species Namaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12414 Penicillium paxilli Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14289 Pieris napi Species Pieridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10865 Sextonia rubra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10012 Triaenophora rupestris Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18827 Aspidosperma olivaceum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17726 Helichrysum cymosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18584 Streptoalloteichus hindustanus Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO18142 Elysia ornata Species Placobranchidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19558 Meryta lanceolata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17566 Magnolia biloba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18827 Aspidosperma olivaceum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17566 Magnolia biloba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18827 Aspidosperma olivaceum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17566 Magnolia biloba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21498 Coccus ilicis Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9669 Dictyopteris acrostichoides Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13701 Melaleuca rhaphiophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12069 Isaria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1661 Bartramia pomiformis Species Bartramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12910 Ixeris stolonifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14200 Aristolochia zollingeriana Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18408 Litsea lancifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14504 Alectoria divergens Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17195 Felicia wrightii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12754 Cerinthe minor Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14289 Pieris napi Species Pieridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10012 Triaenophora rupestris Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7169 Nama hispidum Species Namaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17726 Helichrysum cymosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7752 Beilschmiedia anacardioides Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12414 Penicillium paxilli Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10389 Larix cajanderi Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10865 Sextonia rubra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3458 Lupinus verbasciformis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14615 Streptomyces paulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12234 Khaya ivorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13076 Cephalaria grossheimii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18142 Elysia ornata Species Placobranchidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12061 Justicia paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17566 Magnolia biloba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12585 Craspidospermum verticillatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16492 Mentha gattefossei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6179 Aframomum amaniense Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19558 Meryta lanceolata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18584 Streptoalloteichus hindustanus Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18827 Aspidosperma olivaceum Species Apocynaceae 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
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 22.13 % PMID[26096681]

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 NPC25389 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
0.7937 Intermediate Similarity NPC472859
0.7778 Intermediate Similarity NPC166277
0.7188 Intermediate Similarity NPC484156
0.7042 Intermediate Similarity NPC5786
0.7015 Intermediate Similarity NPC1913
0.6714 Remote Similarity NPC160780
0.662 Remote Similarity NPC311803
0.6579 Remote Similarity NPC33298
0.6429 Remote Similarity NPC119125
0.6324 Remote Similarity NPC37074
0.6267 Remote Similarity NPC472860
0.6267 Remote Similarity NPC289346
0.6267 Remote Similarity NPC484816
0.6232 Remote Similarity NPC287780
0.6232 Remote Similarity NPC60982
0.6119 Remote Similarity NPC65833
0.6032 Remote Similarity NPC92117
0.5946 Remote Similarity NPC327032
0.5873 Remote Similarity NPC221090
0.5823 Remote Similarity NPC479375
0.5682 Remote Similarity NPC486577
0.5634 Remote Similarity NPC4013
0.5422 Remote Similarity NPC105591
0.5412 Remote Similarity NPC479369
0.5393 Remote Similarity NPC37668
0.5393 Remote Similarity NPC270448
0.5385 Remote Similarity NPC102851
0.5333 Remote Similarity NPC215811
0.5333 Remote Similarity NPC4958
0.5333 Remote Similarity NPC90905
0.5325 Remote Similarity NPC197708
0.5269 Remote Similarity NPC67629
0.5269 Remote Similarity NPC79736
0.5231 Remote Similarity NPC229036
0.5213 Remote Similarity NPC267549
0.52 Remote Similarity NPC140151
0.5156 Remote Similarity NPC225036
0.5075 Remote Similarity NPC44260
0.5067 Remote Similarity NPC111785
0.5067 Remote Similarity NPC95421
0.506 Remote Similarity NPC485743

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC25389 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