Natural Product: NPC15819

Natural Product IDNPC15819
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Xanthotoxol
IUPAC Name 9-hydroxyfuro[3,2-g]chromen-7-one
Synonyms 8-Hydroxypsoralen; Xanthotoxol; Xanthoxol
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1192
PubChem CID 65090
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002569] Linear furanocoumarins
            • [CHEMONTID:0000202] Psoralens
              • [CHEMONTID:0002831] 8-hydroxypsoralens

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 JWVYQQGERKEAHW-UHFFFAOYSA-N
Standard InCHI InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H
SMILES O=c1ccc2c(o1)c(O)c1c(c2)cco1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   202.03 Volume:   192.485
?
Van der Waals volume.
Dense:   1.05 LogP:   1.314
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.326
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.268
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   0.0 Rigid Bonds:   16.0
TPSA:   63.58
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   1.0 Rings:   3.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.568 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.741 Fsp3:   0.0
MCE-18:   15.0
?
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:   0.588 Fluc inhibitor:   0.522
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.959
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.449
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.854 Promiscuous compounds:   0.774

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.92 MDCK Permeability:   -4.732
Pgp-inhibitor:   0.001 Pgp-substrate:   0.0
PAMPA:   0.643
?
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):   0.01
20% Bioavailability (F20%):   0.905 30% Bioavailability (F30%):   0.875
50% Bioavailability (F50%):   0.269

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.001 MRP1:   0.993
Plasma Protein Binding (PPB):   95.598% Volume Distribution (VD):   -0.574
Fu: 3.921%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.99
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.0
BSEP inhibitor:   0.878

ADMET: Metabolism

CYP1A2-inhibitor:   0.396 CYP1A2-substrate:   0.12
CYP2C19-inhibitor:   0.001 CYP2C19-substrate:   0.021
CYP2C9-inhibitor:   0.974 CYP2C9-substrate:   0.258
CYP2D6-inhibitor:   0.046 CYP2D6-substrate:   0.013
CYP3A4-inhibitor:   0.026 CYP3A4-substrate:   0.99
CYP2B6-substrate:   0.03 CYP2C8-inhibitor:   0.723
HLM stability:   0.683
?
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):  9.919 Half-life (T1/2):  0.843

ADMET: Toxicity

hERG Blockers:  0.084 hERG Blockers (10um):  0.317
Human Hepatotoxicity (H-HT):  0.475 Drug-induced Liver Injury (DILI):  0.901
AMES Toxicity:  0.609 Rat Oral Acute Toxicity:  0.715
Maximum Recommended Daily Dose:  0.863 Skin Sensitization:  0.072
Carcinogencity:  0.807 Eye Corrosion:  0.176
Eye Irritation:  0.985 Respiratory Toxicity:  0.77
Drug-induced Neurotoxicity:  0.121 Ototoxicity:  0.149
Hematotoxicity:  0.215 Drug-induced Nephrotoxicity:  0.183
Genotoxicity:  0.985 RPMI-8226 Immunitoxicity:  0.102
A549 Cytotoxicity:  0.124 Hek293 Cytotoxicity:  0.299
BCF:   0.664
?
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:   3.364
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.272
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.044
?
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
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. fruit n.a. PMID[10785419]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[1453177]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[17666859]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[17703773]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota fruits n.a. n.a. PMID[22932311]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. fruit n.a. PMID[23721280]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24813739]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[38830452]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO900 Cnidium monieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16614 Zanthoxylum spinosum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Root Essent. Oil n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30713 Angelica talwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO900 Cnidium monieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16614 Zanthoxylum spinosum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16696 Cryptodiscus didymus Species Stictidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO662 Angelica officinalis Species Apiaceae 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
NPO16755 Saposhnikovia divaricata n.a. Roots 175.03897, 147.04405 n.a. n.a. % PMID[38830452]
NPO16755 Saposhnikovia divaricata n.a. Roots 0.03 n.a. n.a. % PMID[38830452]
NPO16755 Saposhnikovia divaricata n.a. Roots 0.01 n.a. n.a. % PMID[38830452]

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
NPT156 Individual protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PubChem BioAssay data set
NPT740 Individual protein Beta-secretase 1 Homo sapiens IC50 > 500000.0 nM PMID[22222157]
NPT740 Individual protein Beta-secretase 1 Homo sapiens Inhibition = 32.8 % PMID[22222157]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT139 Cell line HT-29 Homo sapiens IC50 > 500000.0 nM PMID[19054677]
NPT520 Cell line 3T3-L1 Mus musculus IC50 > 500000.0 nM PMID[19054677]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 10300.0 nM PMID[20332056]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 188300.0 nM PMID[20332056]
NPT452 Organism Helicobacter pylori SS1 Helicobacter pylori SS1 MIC > 50.0 ug.mL-1 PMID[20832915]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 19.8 % PMID[15217285]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 10.5 % PMID[15217285]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 5.2 % PMID[15217285]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 0.7 % PMID[15217285]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 2.7 % PMID[15217285]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = -5.0 % PMID[15217285]
NPT1 Others Radical scavenging activity n.a. IC50 = 69600.0 nM PMID[20332056]
NPT1 Others Radical scavenging activity n.a. Activity = 25.0 % PMID[23291118]
NPT1 Others Radical scavenging activity n.a. Activity = 22.0 % PMID[23291118]
NPT2 Others Unspecified n.a. Potency n.a. 163.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 1000.0 nM PubChem BioAssay data set
NPT35 Others n.a. n.a. Inhibition = 5.0 % PMID[23291118]
NPT2 Others Unspecified n.a. IC50 = 89000.0 nM PMID[23291118]

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 = 480.0 mg/kg ToxVal
- Mus musculus LD50 = 2.635460117 mg/kg TOXRIC

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 NPC15819 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
0.5814 Remote Similarity NPC601991
0.56 Remote Similarity NPC281835
0.5333 Remote Similarity NPC51146
0.5227 Remote Similarity NPC73738

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC15819 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
0.5333 Remote Similarity NPD643 Phase 1

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