NPASS Compound

Natural Product: NPC517857

Natural Product ID	NPC517857
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	N-2,4-Eicosadienoylpyrrolidin
IUPAC Name	1-pyrrolidin-1-ylicosa-2,4-dien-1-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 69 69 0 0 0 0 0 0 0 0999 V2000 -7.8860 -2.3158 1.9840 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6882 -2.8011 1.2126 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7821 -1.5942 0.9972 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5160 -0.5313 0.2204 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5903 0.6418 0.0042 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1037 1.2794 1.2588 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2255 2.4475 0.9636 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9804 2.0471 0.1590 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1705 3.2842 -0.0636 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 3.1269 -0.7934 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9529 2.7041 -2.1908 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5340 1.4220 -2.6065 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9317 0.1945 -1.9626 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5424 0.1743 -2.3306 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1928 -1.0535 -1.6993 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6111 -1.0360 -2.0788 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5979 -0.9818 -1.1483 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9565 -0.9686 -1.6100 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9999 -0.9197 -0.8758 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0572 -0.8678 0.5504 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9620 -0.8671 1.2109 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2944 -0.8158 1.2795 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6003 -0.8135 0.7018 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3587 -1.7689 1.6370 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6770 -1.5744 2.9672 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4346 -0.7531 2.7065 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6290 -1.8387 1.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3845 -3.1274 2.5428 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5205 -1.5059 2.6778 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9452 -3.1800 0.2026 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1795 -3.6038 1.7513 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8957 -1.9569 0.4468 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5102 -1.1490 1.9902 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8114 -0.9828 -0.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4217 -0.2462 0.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7521 0.2243 -0.6256 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1509 1.4196 -0.5653 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0029 1.6114 1.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5539 0.5723 1.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8434 2.9280 1.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7969 3.1899 0.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3140 1.5670 -0.7388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3698 1.3902 0.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9594 3.6901 0.9750 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8644 4.0219 -0.5657 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2315 2.4326 -0.1856 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2855 4.1049 -0.7391 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4498 3.5025 -2.8428 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1097 2.7283 -2.6254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1523 1.2982 -3.7188 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6126 1.3282 -2.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4516 -0.7135 -2.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9916 0.2013 -0.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0749 1.0536 -1.9638 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6974 0.0815 -3.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0631 -1.0198 -0.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6836 -1.9601 -2.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8426 -1.0683 -3.1378 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2725 -0.9527 -0.1272 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1080 -1.0048 -2.7193 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9836 -0.9153 -1.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1062 0.1835 0.8535 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6709 -1.1502 -0.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1558 -2.7900 1.2390 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4299 -1.5347 1.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3485 -1.0474 3.6945 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3288 -2.5490 3.4044 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5465 -1.1715 3.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6341 0.2794 3.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 3 17 18 1 0 18 19 2 3 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 22 1 0 1 27 1 0 1 28 1 0 1 29 1 0 2 30 1 0 2 31 1 0 3 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 5 36 1 0 5 37 1 0 6 38 1 0 6 39 1 0 7 40 1 0 7 41 1 0 8 42 1 0 8 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 17 59 1 0 18 60 1 0 19 61 1 0 23 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 M END

Standard InCHIKey	RIDFJCCEYZWOSP-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C24H43NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21-24(26)25-22-19-20-23-25/h16-18,21H,2-15,19-20,22-23H2,1H3
SMILES	CCCCCCCCCCCCCCCC=CC=CC(=O)N1CCCC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	361.33	Volume:	426.981 ? Van der Waals volume.
Dense:	0.846	LogP:	7.509 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.568 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.73 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	8.0
TPSA:	20.31 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.162	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.336	Fsp³:	0.792
MCE-18:	5.93 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.543	Fluc inhibitor:	0.917 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.284 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.372	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.05	MDCK Permeability:	-4.762
Pgp-inhibitor:	0.029	Pgp-substrate:	0.103
PAMPA:	0.0 ? 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):	0.851
20% Bioavailability (F20%):	0.886	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127	MRP1:	0.921
Plasma Protein Binding (PPB):	100.135%	Volume Distribution (VD):	1.43
Fu:	0.755% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.557
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.745
BSEP inhibitor:	0.85

ADMET: Metabolism

CYP1A2-inhibitor:	0.069	CYP1A2-substrate:	0.309
CYP2C19-inhibitor:	0.398	CYP2C19-substrate:	0.518
CYP2C9-inhibitor:	0.987	CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.095	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.869	CYP2C8-inhibitor:	1.0
HLM stability:	0.064 ? 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):

5.183

Half-life (T1/2):

0.66

ADMET: Toxicity

hERG Blockers:	0.698	hERG Blockers (10um):	0.847
Human Hepatotoxicity (H-HT):	0.512	Drug-induced Liver Injury (DILI):	0.119
AMES Toxicity:	0.172	Rat Oral Acute Toxicity:	0.212
Maximum Recommended Daily Dose:	0.489	Skin Sensitization:	0.993
Carcinogencity:	0.245	Eye Corrosion:	0.709
Eye Irritation:	0.972	Respiratory Toxicity:	0.934
Drug-induced Neurotoxicity:	0.117	Ototoxicity:	0.184
Hematotoxicity:	0.14	Drug-induced Nephrotoxicity:	0.248
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.823	Hek293 Cytotoxicity:	0.468
BCF:	0.904 ? 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:	4.974 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.407 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.934 ? 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
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26213786]
NPO17517	Artemisia arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38592817]
NPO14795	Vitis coignetiae	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15369	Tabernaemontana rupicola	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2913	Tabebuia pentaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15893	Solandra guttata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16447	Potato virus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16048	Euphorbia serrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15734	Euchresta horsfeldii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21786	Culcitium serratifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17297	Caragana pygmaea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17517	Artemisia arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18069	Streptomyces coelicoflavus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14795	Vitis coignetiae	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17517	Artemisia arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15893	Solandra guttata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17297	Caragana pygmaea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15734	Euchresta horsfeldii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21786	Culcitium serratifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16048	Euphorbia serrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18069	Streptomyces coelicoflavus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2913	Tabebuia pentaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16447	Potato virus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14795	Vitis coignetiae	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15369	Tabernaemontana rupicola	Species	Apocynaceae	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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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

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 NPC517857 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	27032
0.1-0.2	21250
0.2-0.3	1375
0.3-0.4	159
0.4-0.5	35
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC252684
1.0	High Similarity	NPC206660
0.9655	High Similarity	NPC385
0.9355	High Similarity	NPC42477
0.9333	High Similarity	NPC133923
0.7222	Intermediate Similarity	NPC34672
0.5455	Remote Similarity	NPC209232

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC517857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6864
0.1-0.2	2185
0.2-0.3	93
0.3-0.4	7
0.4-0.5	0
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5667	Remote Similarity	NPD866	Clinical (unspecified phase)

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