Natural Product: NPC243532

Natural Product IDNPC243532
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (Z,12R)-12-Hydroxyoctadec-9-Enoic Acid
IUPAC Name (Z,12R)-12-hydroxyoctadec-9-enoic acid
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL3186422
PubChem CID 643684
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000262] Fatty acids and conjugates
          • [CHEMONTID:0002949] Long-chain fatty acids

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 WBHHMMIMDMUBKC-QJWNTBNXSA-N
Standard InCHI InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1
SMILES CCCCCC[C@H](C/C=CCCCCCCCC(=O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   298.25 Volume:   340.982
?
Van der Waals volume.
Dense:   0.875 LogP:   4.923
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.156
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.942
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   15.0 Rigid Bonds:   2.0
TPSA:   57.53
?
Topological Polar Surface Area.
 H-Bond Acceptor:   3.0
H-Bond Donor:   2.0 Rings:   0.0
Heavy Atoms:   3.0

MedChem Properties

QED Drug-Likeness Score:   0.327 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.699 Fsp3:   0.833
MCE-18:   2.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.042 Fluc inhibitor:   0.008
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.003
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.001
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.987 Promiscuous compounds:   0.821

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.128 MDCK Permeability:   -4.753
Pgp-inhibitor:   0.0 Pgp-substrate:   0.008
PAMPA:   0.775
?
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%):   0.075 30% Bioavailability (F30%):   0.268
50% Bioavailability (F50%):   0.535

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.004 MRP1:   0.834
Plasma Protein Binding (PPB):   93.695% Volume Distribution (VD):   0.011
Fu: 4.691%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.025
OATP1B3 inhibitor:   0.799 BCRP inhibitor:   0.186
BSEP inhibitor:   0.982

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.066
CYP2C19-inhibitor:   0.001 CYP2C19-substrate:   0.197
CYP2C9-inhibitor:   1.0 CYP2C9-substrate:   0.13
CYP2D6-inhibitor:   0.748 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.982
CYP2B6-substrate:   0.33 CYP2C8-inhibitor:   0.993
HLM stability:   0.001
?
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):  4.129 Half-life (T1/2):  0.777

ADMET: Toxicity

hERG Blockers:  0.054 hERG Blockers (10um):  0.172
Human Hepatotoxicity (H-HT):  0.37 Drug-induced Liver Injury (DILI):  0.011
AMES Toxicity:  0.053 Rat Oral Acute Toxicity:  0.031
Maximum Recommended Daily Dose:  0.238 Skin Sensitization:  0.985
Carcinogencity:  0.16 Eye Corrosion:  0.985
Eye Irritation:  0.998 Respiratory Toxicity:  0.695
Drug-induced Neurotoxicity:  0.009 Ototoxicity:  0.496
Hematotoxicity:  0.096 Drug-induced Nephrotoxicity:  0.579
Genotoxicity:  0.0 RPMI-8226 Immunitoxicity:  0.028
A549 Cytotoxicity:  0.091 Hek293 Cytotoxicity:  0.03
BCF:   1.092
?
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:   3.969
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.284
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   2.935
?
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
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2005.10.025]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4039(01)00209-X]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[10575373]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[11520245]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[12045343]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[14695801]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. leaf n.a. PMID[15467205]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. whole plant n.a. PMID[16808005]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[1791484]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. spore n.a. PMID[18827358]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies Nagano, Japan 2008-MAY PMID[20039640]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[20384295]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies n.a. n.a. PMID[20702092]
NPO30686 Citrus hystrix Species Rutaceae Eukaryota n.a. exocarp n.a. PMID[20964319]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies n.a. n.a. PMID[21924611]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[22014750]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[22044278]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting body n.a. n.a. PMID[22047696]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23102654]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[26222905]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[26509914]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[31096694]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[31103896]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[31766491]
NPO30686 Citrus hystrix Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[38067483]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[38067483]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[38474459]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[9635497]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30686 Citrus hystrix Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25269 Ganoderma lucidum Species Ganodermataceae 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
NPO28928 Piper nigrum CO2 extract n.a. 0.231 n.a. n.a. % PMID[38067483]
NPO30686 Citrus hystrix CO2 extract n.a. 0.06 n.a. n.a. % PMID[38067483]

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
NPT106 Individual protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 43641.2 nM PubChem BioAssay data set
NPT153 Individual protein Androgen Receptor Homo sapiens Potency n.a. 19493.8 nM PubChem BioAssay data set
NPT153 Individual protein Androgen Receptor Homo sapiens Potency n.a. 30106.5 nM PubChem BioAssay data set
NPT162 Individual protein Heat shock protein beta-1 Homo sapiens Potency n.a. 54941 nM PubChem BioAssay data set
NPT869 Individual protein Free fatty acid receptor 1 Homo sapiens EC50 = 11481.54 nM PMID[30108848]
NPT4003 Individual protein G-protein coupled receptor 120 Homo sapiens EC50 = 1318.26 nM PMID[30108848]
NPT74 Individual protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 4896.6 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified n.a. Potency n.a. 54941 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 38895.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 48966.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 33491.5 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 26832.5 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 27535.7 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 43641.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 30106.5 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 48557.7 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 12.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 15484.5 nM PubChem BioAssay data set

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 NPC243532 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
0.7949 Intermediate Similarity NPC606120
0.7105 Intermediate Similarity NPC324004
0.7105 Intermediate Similarity NPC328497
0.7027 Intermediate Similarity NPC424
0.7027 Intermediate Similarity NPC36061
0.7027 Intermediate Similarity NPC69510
0.7027 Intermediate Similarity NPC77272
0.7027 Intermediate Similarity NPC290563
0.7027 Intermediate Similarity NPC139029
0.7027 Intermediate Similarity NPC281972
0.7027 Intermediate Similarity NPC261831
0.7027 Intermediate Similarity NPC87564
0.6818 Remote Similarity NPC255863
0.6818 Remote Similarity NPC136164
0.6818 Remote Similarity NPC245947
0.6757 Remote Similarity NPC281245
0.6579 Remote Similarity NPC92114
0.65 Remote Similarity NPC154245
0.65 Remote Similarity NPC85813
0.65 Remote Similarity NPC223697
0.65 Remote Similarity NPC6095
0.641 Remote Similarity NPC95145
0.641 Remote Similarity NPC325642
0.641 Remote Similarity NPC65174
0.6383 Remote Similarity NPC49863
0.625 Remote Similarity NPC321062
0.5957 Remote Similarity NPC321838
0.5854 Remote Similarity NPC5413
0.58 Remote Similarity NPC605544
0.58 Remote Similarity NPC607260
0.5745 Remote Similarity NPC99619
0.5714 Remote Similarity NPC52955
0.5714 Remote Similarity NPC88966
0.5714 Remote Similarity NPC25417
0.5714 Remote Similarity NPC323045
0.5714 Remote Similarity NPC26500
0.5714 Remote Similarity NPC1813
0.5714 Remote Similarity NPC317881
0.5714 Remote Similarity NPC59051
0.5652 Remote Similarity NPC477201
0.5625 Remote Similarity NPC323477
0.551 Remote Similarity NPC470320
0.551 Remote Similarity NPC327112
0.5476 Remote Similarity NPC91495
0.5476 Remote Similarity NPC70387
0.5417 Remote Similarity NPC251042
0.5417 Remote Similarity NPC174447
0.5417 Remote Similarity NPC122521
0.5405 Remote Similarity NPC171736
0.5405 Remote Similarity NPC301585
0.5405 Remote Similarity NPC261080
0.5405 Remote Similarity NPC132565
0.5405 Remote Similarity NPC209970
0.5405 Remote Similarity NPC216630
0.5405 Remote Similarity NPC201844
0.5405 Remote Similarity NPC301696
0.5405 Remote Similarity NPC196924
0.5405 Remote Similarity NPC307783
0.5405 Remote Similarity NPC154186
0.5405 Remote Similarity NPC149184
0.5405 Remote Similarity NPC279026
0.5405 Remote Similarity NPC113928
0.5405 Remote Similarity NPC14227
0.5319 Remote Similarity NPC106851
0.5319 Remote Similarity NPC282788
0.5319 Remote Similarity NPC274927
0.5306 Remote Similarity NPC68343
0.5306 Remote Similarity NPC318420
0.5306 Remote Similarity NPC326268
0.5306 Remote Similarity NPC328089
0.5217 Remote Similarity NPC225929
0.5208 Remote Similarity NPC179764
0.5192 Remote Similarity NPC328653
0.5172 Remote Similarity NPC318766
0.5135 Remote Similarity NPC155263
0.5102 Remote Similarity NPC473863

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC243532 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
0.7027 Intermediate Similarity NPD3195 Phase 2
0.7027 Intermediate Similarity NPD3196 Approved
0.6667 Remote Similarity NPD3194 Phase 4
0.65 Remote Similarity NPD4266 Phase 2
0.6383 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5854 Remote Similarity NPD3173 Phase 4
0.5714 Remote Similarity NPD3172 Approved
0.551 Remote Similarity NPD4246 Phase 2
0.5405 Remote Similarity NPD2270 Pre-clinical
0.5405 Remote Similarity NPD633 Phase 3
0.5405 Remote Similarity NPD9448 Phase 2
0.5306 Remote Similarity NPD39 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