Natural Product: NPC309056

Natural Product IDNPC309056
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (1R,10S)-10-Hydroxy-1,6-Dimethyl-10-(2-Oxopropyl)-1,2-Dihydronaphtho[1,2-G][1]Benzofuran-11-One
IUPAC Name (1R,10S)-10-hydroxy-1,6-dimethyl-10-(2-oxopropyl)-1,2-dihydronaphtho[1,2-g][1]benzofuran-11-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL2261306
PubChem CID 3083514
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

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 WQYKPUPMMFGHQW-QKVFXAPYSA-N
Standard InCHI InChI=1S/C21H20O4/c1-11-5-4-6-15-14(11)7-8-16-18(15)21(24,9-13(3)22)20(23)17-12(2)10-25-19(16)17/h4-8,12,24H,9-10H2,1-3H3/t12-,21-/m0/s1
SMILES CC(=O)C[C@@]1(O)C(=O)C2=C(c3c1c1cccc(c1cc3)C)OC[C@@H]2C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   336.14 Volume:   351.616
?
Van der Waals volume.
Dense:   0.956 LogP:   2.78
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.738
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.032
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   22.0
TPSA:   63.6
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   1.0 Rings:   4.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.914 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.847 Fsp3:   0.333
MCE-18:   80.357
?
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:   0.096 Fluc inhibitor:   0.448
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.585
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.151
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.164 Promiscuous compounds:   0.214

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.717 MDCK Permeability:   -4.639
Pgp-inhibitor:   0.612 Pgp-substrate:   0.834
PAMPA:   0.5
?
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%):   0.017 30% Bioavailability (F30%):   0.052
50% Bioavailability (F50%):   0.78

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.852 MRP1:   0.979
Plasma Protein Binding (PPB):   95.571% Volume Distribution (VD):   0.058
Fu: 3.939%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.953
OATP1B3 inhibitor:   0.406 BCRP inhibitor:   0.189
BSEP inhibitor:   0.999

ADMET: Metabolism

CYP1A2-inhibitor:   0.632 CYP1A2-substrate:   0.892
CYP2C19-inhibitor:   0.848 CYP2C19-substrate:   0.338
CYP2C9-inhibitor:   0.173 CYP2C9-substrate:   0.016
CYP2D6-inhibitor:   0.037 CYP2D6-substrate:   0.707
CYP3A4-inhibitor:   0.998 CYP3A4-substrate:   0.622
CYP2B6-substrate:   0.002 CYP2C8-inhibitor:   0.859
HLM stability:   0.627
?
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):  3.687 Half-life (T1/2):  1.185

ADMET: Toxicity

hERG Blockers:  0.018 hERG Blockers (10um):  0.141
Human Hepatotoxicity (H-HT):  0.939 Drug-induced Liver Injury (DILI):  0.977
AMES Toxicity:  0.956 Rat Oral Acute Toxicity:  0.553
Maximum Recommended Daily Dose:  0.709 Skin Sensitization:  0.994
Carcinogencity:  0.974 Eye Corrosion:  0.001
Eye Irritation:  0.871 Respiratory Toxicity:  0.437
Drug-induced Neurotoxicity:  0.592 Ototoxicity:  0.514
Hematotoxicity:  0.86 Drug-induced Nephrotoxicity:  0.971
Genotoxicity:  1.0 RPMI-8226 Immunitoxicity:  0.13
A549 Cytotoxicity:  0.18 Hek293 Cytotoxicity:  0.501
BCF:   1.223
?
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:   4.072
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.053
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.775
?
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
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[ 17014425]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/bab.1236]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.indcrop.2010.09.006]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. root n.a. PMID[11374966]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[12880325]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[1567426]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[16038550]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[17217287]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17583950]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18855446]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20455578]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21775156]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23286284]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[24108414]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[27569393]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29185738]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30351923]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. root n.a. PMID[3655791]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[37570961]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota roots n.a. n.a. PMID[9834151]
NPO22016 Notholaena dealbata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO415 Deguelia hatschbachii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25212 Ritterella rubra n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26054 Palmaria palmata Species Palmariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12800 Glycine falcata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6321 Agathosma thymifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11487 Senecio madagascariensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24988 Viburnum sieboldi Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25974 Streptomyces lateritius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO10155 Stauntonia obovatifoliola Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23417 Rhabdia lycioides n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO26316 Pleurophycus gardneri Species Alariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6346 Phallusia fumigata Species Ascidiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22758 Picradeniopsis pringlei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10497 Hydrolithon reinboldii Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26087 Euphorbia retusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12476 Delphinium cyphoplectrum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25868 Decachaeta ovatifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO26223 Cladonia bellidiflora Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27437 Camptothecium lutescens Species Brachytheciaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23960 Artemisia siversiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4009 Allochromatium minutissimum Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26087 Euphorbia retusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25868 Decachaeta ovatifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11003 Euphorbia sancta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26223 Cladonia bellidiflora Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26054 Palmaria palmata Species Palmariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22016 Notholaena dealbata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14253 Bothriocline longipes Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4009 Allochromatium minutissimum Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO28189 Metzgeria pubescens Species Metzgeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24988 Viburnum sieboldi Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO415 Deguelia hatschbachii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25974 Streptomyces lateritius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6346 Phallusia fumigata Species Ascidiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23417 Rhabdia lycioides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO22758 Picradeniopsis pringlei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11814 Asphodeline tenuior Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13164 Iris hoogiana Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26316 Pleurophycus gardneri Species Alariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10155 Stauntonia obovatifoliola Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25212 Ritterella rubra n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27437 Camptothecium lutescens Species Brachytheciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11487 Senecio madagascariensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11985 Glycyrrhiza triphylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23960 Artemisia siversiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12800 Glycine falcata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10497 Hydrolithon reinboldii Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO191 Amaranthus hybr Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6321 Agathosma thymifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12476 Delphinium cyphoplectrum Species Ranunculaceae 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
NPT68 Individual protein Aldose reductase Rattus norvegicus IC50 = 100.0 nM DOI[10.1007/s00044-011-9681-6]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

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 NPC309056 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
0.6066 Remote Similarity NPC289432
0.6066 Remote Similarity NPC988
0.5312 Remote Similarity NPC144547

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC309056 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