Natural Product: NPC216752

Natural Product IDNPC216752
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Nepodin-8-O-Beta-D-Glucopyranoside
IUPAC Name 1-[1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-2-yl]ethanone
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL2204399
PubChem CID 5319972
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 FZUPKYUANHOYBD-JZXZQAMYSA-N
Standard InCHI InChI=1S/C19H22O8/c1-8-6-10-4-3-5-11(14(10)16(23)13(8)9(2)21)26-19-18(25)17(24)15(22)12(7-20)27-19/h3-6,12,15,17-20,22-25H,7H2,1-2H3/t12-,15-,17+,18-,19-/m1/s1
SMILES Cc1cc2cccc(c2c(c1C(=O)C)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   378.13 Volume:   366.014
?
Van der Waals volume.
Dense:   1.033 LogP:   1.127
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.804
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.841
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   18.0
TPSA:   136.68
?
Topological Polar Surface Area.
 H-Bond Acceptor:   8.0
H-Bond Donor:   5.0 Rings:   3.0
Heavy Atoms:   8.0

MedChem Properties

QED Drug-Likeness Score:   0.477 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.769 Fsp3:   0.421
MCE-18:   70.778
?
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:   0.414 Fluc inhibitor:   0.117
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.214
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.444
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.133 Promiscuous compounds:   0.189

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.929 MDCK Permeability:   -5.152
Pgp-inhibitor:   0.001 Pgp-substrate:   0.146
PAMPA:   0.952
?
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):   0.302
20% Bioavailability (F20%):   0.086 30% Bioavailability (F30%):   0.876
50% Bioavailability (F50%):   0.901

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.207 MRP1:   0.662
Plasma Protein Binding (PPB):   84.065% Volume Distribution (VD):   -0.364
Fu: 12.804%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.009
BSEP inhibitor:   0.009

ADMET: Metabolism

CYP1A2-inhibitor:   0.022 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.001 CYP2C19-substrate:   0.002
CYP2C9-inhibitor:   0.002 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.356
HLM stability:   0.644
?
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):  2.489 Half-life (T1/2):  3.018

ADMET: Toxicity

hERG Blockers:  0.021 hERG Blockers (10um):  0.117
Human Hepatotoxicity (H-HT):  0.74 Drug-induced Liver Injury (DILI):  0.91
AMES Toxicity:  0.907 Rat Oral Acute Toxicity:  0.02
Maximum Recommended Daily Dose:  0.031 Skin Sensitization:  0.996
Carcinogencity:  0.247 Eye Corrosion:  0.0
Eye Irritation:  0.624 Respiratory Toxicity:  0.108
Drug-induced Neurotoxicity:  0.021 Ototoxicity:  0.916
Hematotoxicity:  0.53 Drug-induced Nephrotoxicity:  0.799
Genotoxicity:  0.383 RPMI-8226 Immunitoxicity:  0.135
A549 Cytotoxicity:  0.276 Hek293 Cytotoxicity:  0.214
BCF:   0.372
?
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:   3.074
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.3
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.564
?
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
NPO21244 Delphinium nuttallianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[10978210]
NPO21244 Delphinium nuttallianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[19012276]
NPO19996 Caulerpa peltata Species Caulerpaceae Eukaryota n.a. n.a. n.a. PMID[25593390]
NPO19037 Senecio praecox Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10359 Chaiturus marrubiastrum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19818 Jacquemontia paniculata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14248 Mandragora autumnalis Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20223 Rosa pomifera Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28769 Albizzia anthelmintica n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO11580 Onobrychis arenaria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22675 Helichrysum chionosphaerum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18144 Metrodorea nigra Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20422 Albizia myriophylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21244 Delphinium nuttallianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26393.1 Petunia integrifolia subsp. inflata Subspecies Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17018 Salvia greggii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20753 Grangea maderaspatana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21691 Dillenia indica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13454 Amphorogyne spicata Species Amphorogynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26917 Quercus rubra Species Fagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16142 Verbascum thapsiforme Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15422 Carduus tenuiflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20144 Lespedeza tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18287 Penicillium bilaiae Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO20144 Lespedeza tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26917 Quercus rubra Species Fagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28769 Albizzia anthelmintica n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO20144 Lespedeza tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17018 Salvia greggii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13754 Tanacetum coccineum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21691 Dillenia indica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2228 Photinia serratifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26917 Quercus rubra Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28769 Albizzia anthelmintica n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10359 Chaiturus marrubiastrum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26917 Quercus rubra Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17018 Salvia greggii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21564 Senecio behnii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14932.1 Dalbergia lanceolaria subsp. paniculata Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19996 Caulerpa peltata Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18144 Metrodorea nigra Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17856 Anaphalis lactea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11580 Onobrychis arenaria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19037 Senecio praecox Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14800 Oophaga granulifera Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18867 Stephanitis takeyai Species Tingidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21376 Lupinus corymbosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20625 Delphinium virgatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2228 Photinia serratifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19818 Jacquemontia paniculata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20560 Polyporus betulinus Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13454 Amphorogyne spicata Species Amphorogynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21244 Delphinium nuttallianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20144 Lespedeza tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21691 Dillenia indica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16572 Rhododendron dahuricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19512 Gleichenia quadripartita Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13754 Tanacetum coccineum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12108 Aizopsis selskiana Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20223 Rosa pomifera Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27737 Penicillium shearii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20422 Albizia myriophylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20947 Tagetes filifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20353 Degenia velebitica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10216 Leptocereus quadricostatus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21112 Chaetomium carinthiacum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18287 Penicillium bilaiae Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24407 Bipolaris heveae Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16142 Verbascum thapsiforme Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20753 Grangea maderaspatana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19913 Rhynchophorus ferrugineus Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19395 Nepeta granatensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15422 Carduus tenuiflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22675 Helichrysum chionosphaerum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19671 Dipsacus azureus Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19232 Anchusa azurea Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17568 Balanophora laxiflora Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20844 Sphaerella rosigena n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26393.1 Petunia integrifolia subsp. inflata Subspecies Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13246 Pinalia stricta Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14248 Mandragora autumnalis Species Solanaceae 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
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 26600.0 nM PMID[22280816]

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 NPC216752 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
0.5965 Remote Similarity NPC603021
0.5775 Remote Similarity NPC178851
0.527 Remote Similarity NPC478798
0.5224 Remote Similarity NPC23084
0.5161 Remote Similarity NPC294470

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC216752 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