Natural Product: NPC206876

Natural Product IDNPC206876
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 1,2-Dimethoxybenzene
IUPAC Name 1,2-dimethoxybenzene
Synonyms 1,2-Dimethoxybenzene
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1668603
PubChem CID 7043
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0004113] Methoxybenzenes
          • [CHEMONTID:0004111] Dimethoxybenzenes

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 ABDKAPXRBAPSQN-UHFFFAOYSA-N
Standard InCHI InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
SMILES COc1ccccc1OC

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   138.07 Volume:   148.039
?
Van der Waals volume.
Dense:   0.933 LogP:   1.704
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.764
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.564
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   6.0
TPSA:   18.46
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   0.0 Rings:   1.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.619 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.07 Fsp3:   0.25
MCE-18:   5.0
?
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:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.037 Fluc inhibitor:   0.133
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.032
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.009
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   1.0 Promiscuous compounds:   0.707

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.455 MDCK Permeability:   -4.659
Pgp-inhibitor:   0.462 Pgp-substrate:   0.181
PAMPA:   0.077
?
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):   0.069
20% Bioavailability (F20%):   0.273 30% Bioavailability (F30%):   0.208
50% Bioavailability (F50%):   0.735

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.901 MRP1:   0.826
Plasma Protein Binding (PPB):   79.549% Volume Distribution (VD):   -0.081
Fu: 16.924%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.744
OATP1B3 inhibitor:   0.923 BCRP inhibitor:   0.612
BSEP inhibitor:   0.699

ADMET: Metabolism

CYP1A2-inhibitor:   0.85 CYP1A2-substrate:   0.869
CYP2C19-inhibitor:   0.989 CYP2C19-substrate:   0.26
CYP2C9-inhibitor:   0.871 CYP2C9-substrate:   0.097
CYP2D6-inhibitor:   0.532 CYP2D6-substrate:   0.657
CYP3A4-inhibitor:   0.982 CYP3A4-substrate:   0.329
CYP2B6-substrate:   0.943 CYP2C8-inhibitor:   0.429
HLM stability:   0.711
?
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):  5.679 Half-life (T1/2):  2.198

ADMET: Toxicity

hERG Blockers:  0.148 hERG Blockers (10um):  0.576
Human Hepatotoxicity (H-HT):  0.424 Drug-induced Liver Injury (DILI):  0.417
AMES Toxicity:  0.463 Rat Oral Acute Toxicity:  0.242
Maximum Recommended Daily Dose:  0.181 Skin Sensitization:  0.692
Carcinogencity:  0.845 Eye Corrosion:  0.985
Eye Irritation:  0.995 Respiratory Toxicity:  0.494
Drug-induced Neurotoxicity:  0.712 Ototoxicity:  0.169
Hematotoxicity:  0.268 Drug-induced Nephrotoxicity:  0.259
Genotoxicity:  0.014 RPMI-8226 Immunitoxicity:  0.079
A549 Cytotoxicity:  0.053 Hek293 Cytotoxicity:  0.075
BCF:   0.978
?
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:   2.743
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   3.622
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.226
?
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
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[12662092]
NPO1396 Cladogynos orientalis n.a. n.a. n.a. n.a. n.a. n.a. PMID[15679308]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. Caribbean n.a. PMID[1686898]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. stem n.a. PMID[21226514]
NPO31242 Silene latifolia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. PMID[22937972]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[26281591]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[3404159]
NPO10561 Mentha suaveolens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36432812]
NPO10561 Mentha suaveolens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37836777]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[37988956]
NPO10561 Mentha suaveolens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38560258]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7793 Matricaria matricarioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1049 Tethya amamensis Species Tethyidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO117 Acacia armata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5166 Adonis sutchuenensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO643 Astragalus ernestii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19991 Mantella aurantiaca Species Mantellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10561 Mentha suaveolens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5949 Pericarpium arecae n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO2008 Streptomyces ehimensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO8950 Stilpnopappus pickelii n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO1203 Solanum pseudoquina Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4836 Sideritis arborescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2323 Plantago lundborgii Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8306 Berneuxia thibetica Species Diapensiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13682 Lonchocarpus laxiflorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5339 Isophysis tasmanica Species Iridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8132 Fritillaria meleagris Species Liliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1706 Eragrostis curvula Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17179 Elizabethkingia meningoseptica Species Flavobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO3445 Dumoria heckeli n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO1541 Clusia ellipticifolia Species Clusiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1396 Cladogynos orientalis n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO21493 Bunodosoma caissarum Species Actiniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8433 Bongardia chrysogonum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota Pt n.a. n.a. Database[FooDB]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5166 Adonis sutchuenensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5949 Pericarpium arecae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO8306 Berneuxia thibetica Species Diapensiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5166 Adonis sutchuenensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10561 Mentha suaveolens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5949 Pericarpium arecae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO8306 Berneuxia thibetica Species Diapensiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10980 Petasites japonicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2323 Plantago lundborgii Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19991 Mantella aurantiaca Species Mantellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7793 Matricaria matricarioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1049 Tethya amamensis Species Tethyidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21493 Bunodosoma caissarum Species Actiniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8950 Stilpnopappus pickelii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO1706 Eragrostis curvula Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13682 Lonchocarpus laxiflorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17179 Elizabethkingia meningoseptica Species Flavobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5166 Adonis sutchuenensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1541 Clusia ellipticifolia Species Clusiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5339 Isophysis tasmanica Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1203 Solanum pseudoquina Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8433 Bongardia chrysogonum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO117 Acacia armata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8132 Fritillaria meleagris Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2008 Streptomyces ehimensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO1396 Cladogynos orientalis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4836 Sideritis arborescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO643 Astragalus ernestii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8306 Berneuxia thibetica Species Diapensiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3445 Dumoria heckeli n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10561 Mentha suaveolens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10980 Petasites japonicus Species Asteraceae 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
NPO10561 Mentha suaveolens Oil n.a. 0.5 n.a. n.a. % PMID[37836777]

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
NPT233 Individual protein Carbonic anhydrase II Homo sapiens Ki = 500.0 nM PMID[22245047]
NPT1062 Individual protein Carbonic anhydrase IV Homo sapiens Ki = 14320.0 nM PMID[22245047]
NPT1063 Individual protein Carbonic anhydrase VI Homo sapiens Ki = 234700.0 nM PMID[22245047]
NPT3965 Individual protein Carbonic anhydrase 3 Bos taurus Ki = 4240.0 nM PMID[22245047]
NPT955 Individual protein Carbonic anhydrase VII Homo sapiens Ki = 7250.0 nM PMID[22668600]
NPT948 Individual protein Carbonic anhydrase IX Homo sapiens Ki = 8630.0 nM PMID[21282059]
NPT949 Individual protein Carbonic anhydrase XII Homo sapiens Ki = 8360.0 nM PMID[21282059]
NPT947 Individual protein Carbonic anhydrase I Homo sapiens Ki = 10400.0 nM PMID[22245047]
NPT954 Individual protein Carbonic anhydrase XIV Homo sapiens Ki = 6830.0 nM PMID[22668600]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1365 Organism Trichoplusia ni Trichoplusia ni Activity = 26.0 % PMID[18020407]
NPT2 Others Unspecified n.a. Potency n.a. 21872.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 54941 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 2433.7 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 8707.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. FC = 2.0 n.a. PMID[26986086]
NPT2 Others Unspecified n.a. FC = 1.0 n.a. PMID[26986086]

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
- Rattus norvegicus LD50 ~ 1360.0 mg/kg ToxVal
- Rattus norvegicus LD50 = 890.0 mg/kg ToxVal
- Mus musculus LD50 ~ 2020.0 mg/kg ToxVal
- Mus musculus LD50 = 700.0 mg/kg ToxVal
- Homo sapiens PAC-3 = 180.0 mg/m3 ToxVal
- Homo sapiens PAC-2 = 29.0 mg/m3 ToxVal
- Homo sapiens PAC-1 = 2.7 mg/m3 ToxVal
- Homo sapiens MEG = 10.0 mg/m3 ToxVal
- Homo sapiens MEG = 75.0 mg/m3 ToxVal
- Homo sapiens MEG = 400.0 mg/m3 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 NPC206876 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
0.6471 Remote Similarity NPC124576
0.55 Remote Similarity NPC601908
0.5294 Remote Similarity NPC23837
0.5238 Remote Similarity NPC227308

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC206876 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
0.56 Remote Similarity NPD291 Phase 4

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