Natural Product: NPC161957

Natural Product IDNPC161957
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Aromaticin
IUPAC Name (3aS,5R,5aR,8aS,9aR)-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
Synonyms Aromaticin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL494255
PubChem CID 282529
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0002046] Ambrosanolides and secoambrosanolides

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 OSSDUQKWVVZIGP-SCGWIAOYSA-N
Standard InCHI InChI=1S/C15H18O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h4-5,8,10-12H,2,6-7H2,1,3H3/t8-,10-,11+,12+,15+/m1/s1
SMILES C[C@@H]1C[C@H]2[C@H](C[C@@]3(C)[C@H]1C=CC3=O)C(=C)C(=O)O2

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   246.13 Volume:   258.152
?
Van der Waals volume.
Dense:   0.953 LogP:   1.355
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.466
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.437
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   0.0 Rigid Bonds:   18.0
TPSA:   43.37
?
Topological Polar Surface Area.
 H-Bond Acceptor:   3.0
H-Bond Donor:   0.0 Rings:   3.0
Heavy Atoms:   3.0

MedChem Properties

QED Drug-Likeness Score:   0.486 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.676 Fsp3:   0.6
MCE-18:   49.083
?
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:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.455 Fluc inhibitor:   0.026
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.031
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.0
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.783 Promiscuous compounds:   0.228

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.73 MDCK Permeability:   -4.649
Pgp-inhibitor:   0.821 Pgp-substrate:   0.143
PAMPA:   0.743
?
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):   0.037
20% Bioavailability (F20%):   0.58 30% Bioavailability (F30%):   0.886
50% Bioavailability (F50%):   0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.068 MRP1:   0.696
Plasma Protein Binding (PPB):   83.626% Volume Distribution (VD):   0.003
Fu: 17.856%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   0.999 BCRP inhibitor:   0.07
BSEP inhibitor:   0.994

ADMET: Metabolism

CYP1A2-inhibitor:   0.049 CYP1A2-substrate:   0.004
CYP2C19-inhibitor:   0.037 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.001 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.004
CYP3A4-inhibitor:   0.26 CYP3A4-substrate:   0.003
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.175
HLM stability:   0.261
?
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):  6.053 Half-life (T1/2):  1.426

ADMET: Toxicity

hERG Blockers:  0.039 hERG Blockers (10um):  0.166
Human Hepatotoxicity (H-HT):  0.776 Drug-induced Liver Injury (DILI):  0.907
AMES Toxicity:  0.727 Rat Oral Acute Toxicity:  0.366
Maximum Recommended Daily Dose:  0.596 Skin Sensitization:  0.967
Carcinogencity:  0.845 Eye Corrosion:  0.606
Eye Irritation:  0.972 Respiratory Toxicity:  0.582
Drug-induced Neurotoxicity:  0.481 Ototoxicity:  0.496
Hematotoxicity:  0.734 Drug-induced Nephrotoxicity:  0.852
Genotoxicity:  0.754 RPMI-8226 Immunitoxicity:  0.116
A549 Cytotoxicity:  0.187 Hek293 Cytotoxicity:  0.217
BCF:   1.013
?
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:   3.726
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.057
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.67
?
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
NPO33469 Asteraceae Family Asteraceae Eukaryota n.a. n.a. n.a. PMID[18329753]
NPO4280 Inula hupehensis Species Asteraceae Eukaryota aerial parts n.a. n.a. PMID[21894898]
NPO4280 Inula hupehensis Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[21894898]
NPO17502 Senecio jacquemontianus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO33469 Asteraceae Family Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21499 Halimeda tuna Species Halimedaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9681 Toxicodendron diversilobum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11615 Kopsia deverrei Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10732 Erysimum allionii Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19131 Callilepis salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16482 Hypoestes forskalei Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28309 Artocarpus nitidus Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15631 Baccharis neaei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18249 Eucalyptus deglupta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18577 Lathyrus roseus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17192 Licaria macrophylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16848 Nasutitermes nigriceps Species Termitoidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15114 Oxalis pes-caprae Species Oxalidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8509 Senecio discolor Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18249 Eucalyptus deglupta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18577 Lathyrus roseus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19131 Callilepis salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15631 Baccharis neaei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15114 Oxalis pes-caprae Species Oxalidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9681 Toxicodendron diversilobum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4280 Inula hupehensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17502 Senecio jacquemontianus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21499 Halimeda tuna Species Halimedaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8509 Senecio discolor Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16482 Hypoestes forskalei Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10732 Erysimum allionii Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28309 Artocarpus nitidus Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11615 Kopsia deverrei Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17192 Licaria macrophylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16848 Nasutitermes nigriceps Species Termitoidae 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
NPT1197 Individual protein Huntingtin Homo sapiens Potency = 5623.4 nM PubChem BioAssay data set
NPT3 Individual protein Thioredoxin glutathione reductase Schistosoma mansoni Potency = 35481.3 nM PubChem BioAssay data set
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 20596.2 nM PubChem BioAssay data set
NPT2892 Individual protein X-box-binding protein 1 Homo sapiens IC50 = 5710.0 nM PubChem BioAssay data set
NPT2893 Individual protein DNA damage-inducible transcript 3 protein Mus musculus IC50 = 10000.0 nM PubChem BioAssay data set
NPT154 Individual protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 4466.8 nM PubChem BioAssay data set
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 2909.3 nM PubChem BioAssay data set
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 1458.1 nM PubChem BioAssay data set
NPT101 Individual protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 10000.0 nM PubChem BioAssay data set
NPT537 Individual protein Ras-related protein Rab-9A Homo sapiens Potency = 2511.9 nM PubChem BioAssay data set
NPT531 Individual protein Nuclear receptor ROR-gamma Mus musculus Potency = 10000.0 nM PubChem BioAssay data set
NPT531 Individual protein Nuclear receptor ROR-gamma Mus musculus Potency = 6309.6 nM PubChem BioAssay data set
NPT538 Individual protein Niemann-Pick C1 protein Homo sapiens Potency = 3548.1 nM PubChem BioAssay data set
NPT477 Individual protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 3162.3 nM PubChem BioAssay data set
NPT444 Individual protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 35481.3 nM PubChem BioAssay data set
NPT51 Individual protein Microtubule-associated protein tau Homo sapiens Potency = 17782.8 nM PubChem BioAssay data set
NPT51 Individual protein Microtubule-associated protein tau Homo sapiens Potency = 14125.4 nM PubChem BioAssay data set
NPT8 Individual protein DNA polymerase iota Homo sapiens Potency n.a. 17782.8 nM PubChem BioAssay data set
NPT478 Individual protein Ataxin-2 Homo sapiens Potency n.a. 7943.3 nM PubChem BioAssay data set
NPT861 Individual protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 12995.3 nM PubChem BioAssay data set
NPT535 Individual protein Parathyroid hormone receptor Homo sapiens Potency n.a. 70794.6 nM PubChem BioAssay data set
NPT3728 Individual protein p53-binding protein Mdm-2 Homo sapiens EC50 = 590.0 nM PubChem BioAssay data set
NPT536 Nucleic acid microRNA 21 Homo sapiens Potency = 4645.1 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 3661.1 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 32629.4 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell line KB Homo sapiens pED50 = 5.86 n.a. PMID[17336532]
NPT91 Cell line KB Homo sapiens ED50 = 0.34 ug ml-1 PMID[17336532]
NPT91 Cell line KB Homo sapiens ED50 = 1.38 umol/L PMID[18329753]
NPT91 Cell line KB Homo sapiens ED50 = 2.0 ug ml-1 DOI[10.1021/np50005a002]
NPT1397 Cell line INS1 Rattus norvegicus AC50 = 7821.0 nM PubChem BioAssay data set
NPT65 Cell line HepG2 Homo sapiens Potency n.a. 7943.3 nM PubChem BioAssay data set
NPT113 Cell line RAW264.7 Mus musculus IC50 = 8200.0 nM PMID[21894898]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 8275.3 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 5221.3 nM PubChem BioAssay data set
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Potency = 11220.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency = 18356.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 18356.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 1584.9 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. IC50 = 5840.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. IC50 > 80000.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. IC50 = 1260.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. IC50 = 1250.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 12589.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 1995.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 22.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 10000.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 8199.5 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 2238.7 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 25118.9 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 NPC161957 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
0.6 Remote Similarity NPC193645
0.6 Remote Similarity NPC48803
0.6 Remote Similarity NPC275960
0.5918 Remote Similarity NPC293418
0.5918 Remote Similarity NPC290508
0.5918 Remote Similarity NPC73052
0.5769 Remote Similarity NPC607377
0.5686 Remote Similarity NPC123177
0.5686 Remote Similarity NPC200237
0.5686 Remote Similarity NPC70595
0.5686 Remote Similarity NPC150978
0.5472 Remote Similarity NPC74103
0.5472 Remote Similarity NPC604741
0.5455 Remote Similarity NPC141191
0.5283 Remote Similarity NPC611056
0.5273 Remote Similarity NPC610944
0.52 Remote Similarity NPC39588
0.5192 Remote Similarity NPC24728
0.5098 Remote Similarity NPC21471
0.5098 Remote Similarity NPC33570
0.5088 Remote Similarity NPC169205

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC161957 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
0.6 Remote Similarity NPD1698 Clinical (unspecified phase)

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