Natural Product: NPC74458

Natural Product IDNPC74458
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Benzylacetone
IUPAC Name 4-phenylbutan-2-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1490851
PubChem CID 17355
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted 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 AKGGYBADQZYZPD-UHFFFAOYSA-N
Standard InCHI InChI=1S/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
SMILES CC(=O)CCc1ccccc1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   148.09 Volume:   171.204
?
Van der Waals volume.
Dense:   0.865 LogP:   2.008
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.972
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.771
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   7.0
TPSA:   17.07
?
Topological Polar Surface Area.
 H-Bond Acceptor:   1.0
H-Bond Donor:   0.0 Rings:   1.0
Heavy Atoms:   1.0

MedChem Properties

QED Drug-Likeness Score:   0.642 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.363 Fsp3:   0.3
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:   0.032 Fluc inhibitor:   0.01
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.054
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.004
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.998 Promiscuous compounds:   0.089

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.475 MDCK Permeability:   -4.429
Pgp-inhibitor:   0.994 Pgp-substrate:   0.175
PAMPA:   0.075
?
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):   0.008
20% Bioavailability (F20%):   0.111 30% Bioavailability (F30%):   0.369
50% Bioavailability (F50%):   0.826

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.605 MRP1:   0.246
Plasma Protein Binding (PPB):   97.409% Volume Distribution (VD):   -0.366
Fu: 1.998%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.374
OATP1B3 inhibitor:   0.588 BCRP inhibitor:   0.379
BSEP inhibitor:   0.994

ADMET: Metabolism

CYP1A2-inhibitor:   0.56 CYP1A2-substrate:   0.419
CYP2C19-inhibitor:   0.296 CYP2C19-substrate:   0.154
CYP2C9-inhibitor:   0.835 CYP2C9-substrate:   0.017
CYP2D6-inhibitor:   0.3 CYP2D6-substrate:   0.004
CYP3A4-inhibitor:   0.05 CYP3A4-substrate:   0.048
CYP2B6-substrate:   0.868 CYP2C8-inhibitor:   0.736
HLM stability:   0.444
?
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):  8.753 Half-life (T1/2):  1.747

ADMET: Toxicity

hERG Blockers:  0.141 hERG Blockers (10um):  0.573
Human Hepatotoxicity (H-HT):  0.511 Drug-induced Liver Injury (DILI):  0.052
AMES Toxicity:  0.209 Rat Oral Acute Toxicity:  0.094
Maximum Recommended Daily Dose:  0.226 Skin Sensitization:  0.943
Carcinogencity:  0.372 Eye Corrosion:  0.952
Eye Irritation:  0.992 Respiratory Toxicity:  0.417
Drug-induced Neurotoxicity:  0.732 Ototoxicity:  0.345
Hematotoxicity:  0.391 Drug-induced Nephrotoxicity:  0.63
Genotoxicity:  0.007 RPMI-8226 Immunitoxicity:  0.025
A549 Cytotoxicity:  0.011 Hek293 Cytotoxicity:  0.063
BCF:   0.332
?
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:   2.556
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   3.79
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   2.896
?
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
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. whole plant n.a. DOI[10.1007/BF02329610]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. DOI[10.3390/plants9101397]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[15270561]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. PMID[16499335]
NPO18673 Rhododendron anthopogonoides Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[20586436]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[27128895]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota Resinous Wood n.a. n.a. PMID[29227647]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota Aerial Parts n.a. n.a. PMID[32991171]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[36903911]
NPO10730 Alpinia calcarata Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[37715949]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[38792158]
NPO19438 Alpinia nutans Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[39692462]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. rhizome n.a. PMID[7714541]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. PMID[7760071]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. rhizome n.a. PMID[7798964]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. PMID[7964801]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4711 Goniothalamus thwaitesii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18673 Rhododendron anthopogonoides Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10730 Alpinia calcarata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17388 Schefferomitra subaequalis n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO979 Salvinia imbricata Species Salviniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5646 Phoma violacea Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO51 Petalonia fascia Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6605 Neodiprion sertifer Species Diprionidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12265 Aquilaria agallochum Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18673 Rhododendron anthopogonoides Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4711 Goniothalamus thwaitesii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18673 Rhododendron anthopogonoides Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12265 Aquilaria agallochum Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18673 Rhododendron anthopogonoides Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12265 Aquilaria agallochum Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4711 Goniothalamus thwaitesii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1903 Cyperus haspan Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17388 Schefferomitra subaequalis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO979 Salvinia imbricata Species Salviniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6605 Neodiprion sertifer Species Diprionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO51 Petalonia fascia Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5646 Phoma violacea Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12265 Aquilaria agallochum Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19438 Alpinia nutans Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18673 Rhododendron anthopogonoides Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10730 Alpinia calcarata Species Zingiberaceae 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
NPO10398 Myrica gale Oil Leaves 0.78 ± 1.13 n.a. n.a. % PMID[36903911]
NPO10730 Alpinia calcarata n.a. Leaves 0.43 n.a. n.a. % PMID[37715949]
NPO14558 Aquilaria sinensis CO2 extract n.a. 0.20 n.a. n.a. % PMID[38792158]
NPO19438 Alpinia nutans Oil n.a. 0.17 n.a. n.a. % PMID[39692462]
NPO19438 Alpinia nutans Oil n.a. 0.20 n.a. n.a. % PMID[39692462]
NPO19438 Alpinia nutans Oil n.a. 0.11 n.a. n.a. % PMID[39692462]
NPO19438 Alpinia nutans Oil n.a. 0.07 n.a. n.a. % PMID[39692462]
NPO19438 Alpinia nutans Oil n.a. 0.06 n.a. n.a. % PMID[39692462]
NPO19438 Alpinia nutans Oil n.a. 0.12 n.a. n.a. % PMID[39692462]

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. 389 nM PubChem BioAssay data set
NPT29645 Single protein HTH-type transcriptional regulator LuxR Vibrio harveyi Inhibition = 13.0 % PMID[32871343]
NPT791 Individual protein Cruzipain Trypanosoma cruzi Potency = 5011.9 nM PubChem BioAssay data set
NPT94 Individual protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 25118.9 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT80 Cell line Raji Homo sapiens IC50 = 222.0 molar ratio PMID[26796952]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9285.0 nM PubChem BioAssay data set
NPT724 Organism Corticium Corticium GI = 100.0 % DOI[10.1584/jpestics.19.4_299]
NPT724 Organism Corticium Corticium GI = 30.5 % DOI[10.1584/jpestics.19.4_299]
NPT723 Organism Pythium Pythium GI = 100.0 % DOI[10.1584/jpestics.19.4_299]
NPT723 Organism Pythium Pythium GI = 24.5 % DOI[10.1584/jpestics.19.4_299]
NPT2 Others Unspecified n.a. Potency n.a. 2775.1 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 54.9 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 489.7 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 69707.2 nM PubChem BioAssay data set
NPT29131 Unknown Molecular identity unknown n.a. Activity = 109.0 nmol/min/mg PMID[36966660]
NPT29131 Unknown Molecular identity unknown n.a. Activity = 95.7 nmol/min/mg PMID[36966660]
NPT29131 Unknown Molecular identity unknown n.a. Activity = 364.0 nmol/min/mg PMID[36966660]

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 NPC74458 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

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC74458 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

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