NPASS Compound

Natural Product: NPC4543

Natural Product ID	NPC4543
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FPYNOEOJFQHIMK-ARUCPLGTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14138152
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:0001770] Guaianolides 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

RDKit 3D 60 63 0 0 0 0 0 0 0 0999 V2000 1.9262 2.9283 1.9712 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8463 1.7377 1.3951 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4834 1.1803 1.5083 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1799 0.0921 0.5037 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1827 -0.9918 0.7658 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6881 -2.3852 0.6410 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7864 -3.1185 1.9896 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7259 -3.0314 -0.2143 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6487 -4.2169 -0.6109 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7184 -2.1313 -0.4657 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2772 -0.8006 -0.2669 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3625 -0.0008 0.3194 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4014 0.2061 -0.7521 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1050 -0.7434 -1.3324 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5370 1.6477 -1.0761 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4159 2.2931 -0.3424 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1237 1.3324 0.8226 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4105 1.8867 -2.4468 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1353 -0.2618 0.6399 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9185 0.0629 -0.4680 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4754 -1.1543 -1.0678 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8281 -1.0356 -1.7076 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6954 -0.2919 -0.7125 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0460 1.0426 -0.4889 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9061 1.7997 0.5135 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7881 1.1322 1.7382 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7785 1.0374 -0.0760 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9748 -0.0589 -1.2367 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3714 -2.2877 -1.9028 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6152 -1.6577 -2.0538 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0397 3.3437 2.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8697 3.4670 1.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2552 2.0032 1.4332 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3749 0.7420 2.5205 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2964 0.5441 -0.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6514 -0.8808 1.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2879 -2.5281 0.1832 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5806 -2.6142 2.6133 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1456 -3.0704 2.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1619 -4.1588 1.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8824 -0.4235 -1.2309 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8876 -0.6388 1.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9448 -1.7660 -1.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8411 -0.5488 -2.0982 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5127 2.0587 -0.7156 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 2.3344 -0.9760 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6640 3.3073 0.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9222 1.5881 1.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5670 2.8520 -2.5777 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2148 0.5425 -1.2101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5698 -1.9714 -0.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8107 -0.4160 -2.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7534 -0.8951 0.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1298 1.6239 -1.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9656 1.8107 0.2051 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4840 2.8137 0.6163 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4205 1.4743 2.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6255 -0.0617 -0.5022 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3598 -2.2846 -1.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9910 -2.4587 -2.4852 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 4 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 22 29 1 0 21 30 1 0 17 2 1 0 27 20 1 0 11 5 1 0 17 12 1 0 1 31 1 0 1 32 1 0 3 33 1 0 3 34 1 0 4 35 1 6 5 36 1 1 6 37 1 6 7 38 1 0 7 39 1 0 7 40 1 0 11 41 1 6 12 42 1 1 14 43 1 0 14 44 1 0 15 45 1 1 16 46 1 0 16 47 1 0 17 48 1 1 18 49 1 0 20 50 1 6 21 51 1 1 22 52 1 6 23 53 1 1 24 54 1 6 25 55 1 0 25 56 1 0 26 57 1 0 28 58 1 0 29 59 1 0 30 60 1 0 M END

Standard InCHIKey	FPYNOEOJFQHIMK-ARUCPLGTSA-N
Standard InCHI	InChI=1S/C21H30O9/c1-7-4-12(28-21-18(26)17(25)16(24)13(6-22)29-21)15-9(3)20(27)30-19(15)14-8(2)11(23)5-10(7)14/h9-19,21-26H,1-2,4-6H2,3H3/t9-,10-,11-,12-,13+,14-,15+,16+,17-,18+,19+,21+/m0/s1
SMILES	C=C1C[C@@H]([C@H]2[C@H](C)C(=O)O[C@@H]2[C@H]2C(=C)[C@H](C[C@@H]12)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.19	Volume:	408.749 ? Van der Waals volume.
Dense:	1.043	LogP:	-0.521 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.088 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.257 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	145.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.279	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.176	Fsp³:	0.762
MCE-18:	74.432 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.654	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? 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:	0.345	Promiscuous compounds:	0.31

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.879	MDCK Permeability:	-5.12
Pgp-inhibitor:	0.003	Pgp-substrate:	0.867
PAMPA:	0.864 ? 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):	0.029
20% Bioavailability (F20%):	0.046	30% Bioavailability (F30%):	0.957
50% Bioavailability (F50%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.201
Plasma Protein Binding (PPB):	62.142%	Volume Distribution (VD):	-0.385
Fu:	35.339% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.19
BSEP inhibitor:	0.066

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.145
HLM stability:	0.006 ? 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):

1.56

Half-life (T1/2):

2.901

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.622	Drug-induced Liver Injury (DILI):	0.933
AMES Toxicity:	0.947	Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.03	Skin Sensitization:	1.0
Carcinogencity:	0.341	Eye Corrosion:	0.0
Eye Irritation:	0.256	Respiratory Toxicity:	0.049
Drug-induced Neurotoxicity:	0.195	Ototoxicity:	0.969
Hematotoxicity:	0.843	Drug-induced Nephrotoxicity:	0.956
Genotoxicity:	0.636	RPMI-8226 Immunitoxicity:	0.226
A549 Cytotoxicity:	0.908	Hek293 Cytotoxicity:	0.358
BCF:	0.405 ? 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:	3.018 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.371 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.539 ? 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
NPO10471	Scorzonera radiata	Species	Asteraceae	Eukaryota	n.a.	Mongolian	n.a.	PMID[19271716]
NPO750	Emericellopsis salmosynnemata	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6394	Shorea robusta	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18273	Merendera sobolifera	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11001	Ceanothus papillosus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11433	Candelaria concolor	Species	Candelariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9427	Lemna minor	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9427	Lemna minor	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21021	Hemisteptia lyrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9427	Lemna minor	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4480	Phlojodicarpus villosus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10193	Agave tequilana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11433	Candelaria concolor	Species	Candelariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9427	Lemna minor	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5721	Psorothamnus spinosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10471	Scorzonera radiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO750	Emericellopsis salmosynnemata	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21021	Hemisteptia lyrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16819	Preussia aemulans	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18273	Merendera sobolifera	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6394	Shorea robusta	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18861	Pyxine coccifera	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5142	Garcinia pedunculata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11001	Ceanothus papillosus	Species	Rhamnaceae	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

Activity Type	# Activity
IC50	3
CC50	3

Activity Type	# Activity
Cell line	6

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
NPT23110	Cell line	Microglia	n.a.	IC50	=	44500.0	nM	PMID[35179378]
NPT23110	Cell line	Microglia	n.a.	CC50	>	100000.0	nM	PMID[35179378]

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 NPC4543 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	20817
0.1-0.2	24510
0.2-0.3	4073
0.3-0.4	426
0.4-0.5	19
0.5-0.6	4
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474297
0.7419	Intermediate Similarity	NPC263674
0.7419	Intermediate Similarity	NPC261372
0.6721	Remote Similarity	NPC475788
0.6667	Remote Similarity	NPC19087
0.661	Remote Similarity	NPC217983
0.625	Remote Similarity	NPC475925
0.5652	Remote Similarity	NPC67296
0.5429	Remote Similarity	NPC58267
0.5211	Remote Similarity	NPC304445
0.5139	Remote Similarity	NPC236580

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC4543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7057
0.1-0.2	2012
0.2-0.3	62
0.3-0.4	19
0.4-0.5	0
0.5-0.6	0
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
		NPD

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