Natural Product: NPC275519

Natural Product IDNPC275519
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Benzyl Caffeate
IUPAC Name benzyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms Benzyl 3-(3,4-Dihydroxyphenyl)Acrylate; Benzyl Caffeate; Phenylmethyl 1-(3',4'-Dihydroxyphenyl)Propenate
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL133714
PubChem CID 5919576
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric acids 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 WWVKQTNONPWVEL-VQHVLOKHSA-N
Standard InCHI InChI=1S/C16H14O4/c17-14-8-6-12(10-15(14)18)7-9-16(19)20-11-13-4-2-1-3-5-13/h1-10,17-18H,11H2/b9-7+
SMILES c1ccc(cc1)COC(=O)/C=C/c1ccc(c(c1)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   270.09 Volume:   282.249
?
Van der Waals volume.
Dense:   0.957 LogP:   3.115
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.019
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.074
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   14.0
TPSA:   66.76
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   2.0 Rings:   2.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.509 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.884 Fsp3:   0.062
MCE-18:   11.0
?
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:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.944 Fluc inhibitor:   0.999
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.201
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.852
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.967 Promiscuous compounds:   0.93

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.164 MDCK Permeability:   -4.716
Pgp-inhibitor:   0.278 Pgp-substrate:   0.0
PAMPA:   0.44
?
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):   0.379
20% Bioavailability (F20%):   0.987 30% Bioavailability (F30%):   1.0
50% Bioavailability (F50%):   0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.064 MRP1:   0.165
Plasma Protein Binding (PPB):   96.605% Volume Distribution (VD):   -0.547
Fu: 3.175%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.99
OATP1B3 inhibitor:   0.999 BCRP inhibitor:   0.001
BSEP inhibitor:   0.87

ADMET: Metabolism

CYP1A2-inhibitor:   0.001 CYP1A2-substrate:   0.07
CYP2C19-inhibitor:   0.002 CYP2C19-substrate:   0.101
CYP2C9-inhibitor:   0.016 CYP2C9-substrate:   0.005
CYP2D6-inhibitor:   0.158 CYP2D6-substrate:   0.853
CYP3A4-inhibitor:   0.001 CYP3A4-substrate:   0.999
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.225
?
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):  14.752 Half-life (T1/2):  1.241

ADMET: Toxicity

hERG Blockers:  0.241 hERG Blockers (10um):  0.795
Human Hepatotoxicity (H-HT):  0.224 Drug-induced Liver Injury (DILI):  0.436
AMES Toxicity:  0.521 Rat Oral Acute Toxicity:  0.077
Maximum Recommended Daily Dose:  0.489 Skin Sensitization:  0.989
Carcinogencity:  0.328 Eye Corrosion:  0.119
Eye Irritation:  0.982 Respiratory Toxicity:  0.18
Drug-induced Neurotoxicity:  0.14 Ototoxicity:  0.226
Hematotoxicity:  0.02 Drug-induced Nephrotoxicity:  0.044
Genotoxicity:  0.331 RPMI-8226 Immunitoxicity:  0.017
A549 Cytotoxicity:  0.403 Hek293 Cytotoxicity:  0.377
BCF:   1.01
?
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:   4.325
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.353
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.135
?
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
NPO32948 propolis Genus Rhytismataceae Eukaryota n.a. n.a. n.a. PMID[10757720]
NPO32539 chinese propolis Species Rhytismataceae Eukaryota n.a. n.a. n.a. PMID[12027739]
NPO32948 propolis Genus Rhytismataceae Eukaryota n.a. n.a. n.a. PMID[1593279]
NPO32948 propolis Genus Rhytismataceae Eukaryota n.a. China n.a. PMID[19278239]
NPO32948 propolis Genus Rhytismataceae Eukaryota n.a. Ywar Taw village, Shan State of Myanmar 2006-Dec PMID[19572611]
NPO33094 korean propolis Species n.a. n.a. n.a. n.a. n.a. PMID[24928402]
NPO32539 chinese propolis Species Rhytismataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO33094 korean propolis Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO32948 propolis Genus Rhytismataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]

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
NPT12 Individual protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 9000.0 nM PMID[18490501]
NPT12 Individual protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 8912.51 nM PMID[22037378]
NPT12 Individual protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 > 100000.0 nM PMID[18952420]
NPT1270 Individual protein Aldo-keto reductase family 1 member B10 Homo sapiens IC50 = 210.0 nM PubChem BioAssay data set
NPT41 Individual protein Aldose reductase Homo sapiens IC50 = 400.0 nM PMID[16792405]
NPT77 Individual protein Transthyretin Homo sapiens EC50 = 16000.0 nM PMID[17846127]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell line RAW264.7 Mus musculus EC50 = 38800.0 nM PMID[20499851]
NPT113 Cell line RAW264.7 Mus musculus EC50 = 347.0 nM PMID[17488817]
NPT113 Cell line RAW264.7 Mus musculus Ratio EC50 = 111.82 n.a. PMID[19653640]
NPT181 Cell line Bel-7402 Homo sapiens IC50 = 17400.0 nM PMID[19854643]
NPT83 Cell line MCF7 Homo sapiens IC50 = 14100.0 nM PMID[22123322]
NPT81 Cell line A549 Homo sapiens IC50 = 27300.0 nM PMID[20058933]
NPT453 Cell line HT-1080 Homo sapiens EC50 = 9740.0 nM PMID[16309323]
NPT81 Cell line A549 Homo sapiens EC50 = 35000.0 nM PMID[21534539]
NPT165 Cell line HeLa Homo sapiens EC50 = 2330.0 nM PMID[23806110]
NPT368 Cell line SN12C Homo sapiens GI50 n.a. 11561.12 nM PMID[1965654]
NPT367 Cell line MDA-N Homo sapiens GI50 n.a. 4395.42 nM DOI[10.6019/CHEMBL1201861]
NPT369 Cell line ACHN Homo sapiens GI50 n.a. 11803.21 nM PMID[11325227]
NPT370 Cell line NCI-H23 Homo sapiens GI50 n.a. 14825.18 nM PMID[24631899]
NPT371 Cell line UO-31 Homo sapiens GI50 n.a. 13740.42 nM PMID[20855208]
NPT372 Cell line HOP-92 Homo sapiens GI50 n.a. 16218.1 nM DrugMatrix in vivo data: Pathology
NPT90 Cell line DU-145 Homo sapiens GI50 n.a. 15135.61 nM PMID[18163582]
NPT116 Cell line HL-60 Homo sapiens GI50 n.a. 937.56 nM PMID[24035341]
NPT373 Cell line SK-MEL-5 Homo sapiens GI50 n.a. 9727.47 nM PMID[19715320]
NPT374 Cell line SF-539 Homo sapiens GI50 n.a. 7063.18 nM PMID[15730238]
NPT375 Cell line Malme-3M Homo sapiens GI50 n.a. 11776.06 nM PMID[15974612]
NPT376 Cell line A498 Homo sapiens GI50 n.a. 20511.62 nM PMID[18183025]
NPT111 Cell line K562 Homo sapiens GI50 n.a. 9840.11 nM PMID[15387645]
NPT377 Cell line OVCAR-3 Homo sapiens GI50 n.a. 10990.06 nM PMID[10075754]
NPT112 Cell line MOLT-4 Homo sapiens GI50 n.a. 2280.34 nM PMID[12444692]
NPT378 Cell line NCI/ADR-RES Homo sapiens GI50 n.a. 15776.11 nM PMID[16724853]
NPT379 Cell line HOP-62 Homo sapiens GI50 n.a. 25585.86 nM PubChem BioAssay data set
NPT380 Cell line U-251 Homo sapiens GI50 n.a. 14454.4 nM PMID[26000707]
NPT382 Cell line OVCAR-5 Homo sapiens GI50 n.a. 29512.09 nM PMID[19604701]
NPT383 Cell line SNB-19 Homo sapiens GI50 n.a. 27605.78 nM PMID[27025343]
NPT82 Cell line MDA-MB-231 Homo sapiens GI50 n.a. 21577.44 nM PMID[20853878]
NPT384 Cell line TK-10 Homo sapiens GI50 n.a. 15381.55 nM DrugMatrix in vivo data: Hematology
NPT385 Cell line SR Homo sapiens GI50 n.a. 3741.11 nM PMID[15620268]
NPT323 Cell line SW-620 Homo sapiens GI50 n.a. 17418.07 nM PMID[23252603]
NPT386 Cell line KM12 Homo sapiens GI50 n.a. 8452.79 nM PMID[19874044]
NPT455 Cell line NCI-H522 Homo sapiens GI50 n.a. 809.1 nM DrugMatrix in vivo data: Pathology
NPT387 Cell line M14 Homo sapiens GI50 n.a. 11091.75 nM PMID[17850214]
NPT388 Cell line NCI-H322M Homo sapiens GI50 n.a. 30549.21 nM PMID[18154272]
NPT389 Cell line RPMI-8226 Homo sapiens GI50 n.a. 10592.54 nM PMID[17432904]
NPT456 Cell line OVCAR-4 Homo sapiens GI50 n.a. 8974.29 nM PMID[24195447]
NPT390 Cell line LOX IMVI Homo sapiens GI50 n.a. 15452.54 nM PMID[17993275]
NPT147 Cell line SK-MEL-2 Homo sapiens GI50 n.a. 13427.65 nM PMID[24893224]
NPT391 Cell line HCC 2998 Homo sapiens GI50 n.a. 36559.48 nM PMID[17428663]
NPT81 Cell line A549 Homo sapiens GI50 n.a. 19230.92 nM DrugMatrix in vivo data: Pathology
NPT148 Cell line HCT-15 Homo sapiens GI50 n.a. 5395.11 nM PMID[22429052]
NPT393 Cell line HCT-116 Homo sapiens GI50 n.a. 13427.65 nM PMID[17638695]
NPT394 Cell line EKVX Homo sapiens GI50 n.a. 29716.66 nM PMID[19391605]
NPT395 Cell line SF-268 Homo sapiens GI50 n.a. 10864.26 nM PMID[20192239]
NPT306 Cell line PC-3 Homo sapiens GI50 n.a. 17988.71 nM PMID[24491225]
NPT83 Cell line MCF7 Homo sapiens GI50 n.a. 7798.3 nM PMID[20155971]
NPT146 Cell line SK-OV-3 Homo sapiens GI50 n.a. 18281.0 nM PMID[17958396]
NPT396 Cell line T47D Homo sapiens GI50 n.a. 12078.14 nM PMID[17698848]
NPT397 Cell line NCI-H460 Homo sapiens GI50 n.a. 12823.31 nM PMID[26331334]
NPT308 Cell line CAKI-1 Homo sapiens GI50 n.a. 26977.39 nM PMID[18180352]
NPT398 Cell line UACC-62 Homo sapiens GI50 n.a. 6576.58 nM PMID[11430019]
NPT400 Cell line MDA-MB-435 Homo sapiens GI50 n.a. 6266.14 nM DOI[10.6019/CHEMBL1201861]
NPT399 Cell line SF-295 Homo sapiens GI50 n.a. 11194.38 nM PMID[25437914]
NPT458 Cell line IGROV-1 Homo sapiens GI50 n.a. 3380.65 nM PMID[24345446]
NPT401 Cell line 786-0 Homo sapiens GI50 n.a. 14723.13 nM PMID[9090867]
NPT402 Cell line Hs-578T Homo sapiens GI50 n.a. 9705.1 nM PMID[15026054]
NPT403 Cell line UACC-257 Homo sapiens GI50 n.a. 21232.44 nM PMID[26042639]
NPT139 Cell line HT-29 Homo sapiens GI50 n.a. 32284.94 nM PMID[14640515]
NPT405 Cell line NCI-H226 Homo sapiens GI50 n.a. 31332.86 nM PMID[23738539]
NPT170 Cell line SK-MEL-28 Homo sapiens GI50 n.a. 6367.96 nM PMID[15711537]
NPT406 Cell line RXF 393 Homo sapiens GI50 n.a. 16826.74 nM DOI[10.6019/CHEMBL1201861]
NPT407 Cell line COLO 205 Homo sapiens GI50 n.a. 22438.82 nM DOI[10.1039/C5MD00247H]
NPT858 Cell line LNCaP Homo sapiens IC50 = 45600.0 nM PMID[25310730]
NPT2245 Cell line SiHa Homo sapiens IC50 = 74270.0 nM PMID[12762798]
NPT165 Cell line HeLa Homo sapiens IC50 = 23480.0 nM PMID[19651906]
NPT2609 Cell line BeWo Homo sapiens IC50 = 28220.0 nM PMID[16933888]
NPT65 Cell line HepG2 Homo sapiens IC50 = 85640.0 nM PMID[22037378]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 48100.0 nM PMID[18952420]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. EC50 = 9780.0 nM PMID[12027739]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. EC50 = 1010.0 nM PMID[12027739]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 8000.0 nM PMID[25160837]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 70450.0 nM PMID[25160837]
NPT339 Organism Influenza A virus H3N2 Influenza A virus H3N2 MIC = 25.0 ug.mL-1 PMID[1593279]
NPT1453 Organism Influenza A virus (A/PR/8/34(H1N1)) Influenza A virus (A/Puerto Rico/8/1934(H1N1)) MIC > 50.0 ug.mL-1 PMID[23414843]
NPT1 Others Radical scavenging activity n.a. IC50 = 15300.0 nM PMID[19651906]
NPT2 Others Unspecified n.a. Ratio IC50 = 2.0 n.a. PMID[12713401]
NPT2 Others Unspecified n.a. Ratio IC50 = 3.42 n.a. PMID[8576915]
NPT2 Others Unspecified n.a. Ratio IC50 = 3.86 n.a. PMID[8576915]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT32 Organism Mus musculus Mus musculus Inhibition = 8.8 % PMID[22435669]





 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 NPC275519 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
0.7857 Intermediate Similarity NPC206341
0.7 Intermediate Similarity NPC119631
0.7 Intermediate Similarity NPC603212
0.6875 Remote Similarity NPC289459
0.6585 Remote Similarity NPC226250
0.6512 Remote Similarity NPC95381
0.6122 Remote Similarity NPC263386
0.6122 Remote Similarity NPC141791
0.5833 Remote Similarity NPC217052
0.5833 Remote Similarity NPC329344
0.5833 Remote Similarity NPC237506
0.5833 Remote Similarity NPC32626
0.5745 Remote Similarity NPC217472
0.5745 Remote Similarity NPC150610
0.551 Remote Similarity NPC233669
0.551 Remote Similarity NPC261453
0.551 Remote Similarity NPC474967
0.551 Remote Similarity NPC33749
0.54 Remote Similarity NPC147654
0.54 Remote Similarity NPC281277
0.5397 Remote Similarity NPC186406
0.5294 Remote Similarity NPC328593
0.5294 Remote Similarity NPC474275
0.5294 Remote Similarity NPC147192
0.5294 Remote Similarity NPC309434
0.5294 Remote Similarity NPC224208
0.5294 Remote Similarity NPC41661
0.5217 Remote Similarity NPC94343
0.5208 Remote Similarity NPC14908
0.5094 Remote Similarity NPC203124
0.5094 Remote Similarity NPC607366
0.5085 Remote Similarity NPC147250

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC275519 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