NPASS Compound

Natural Product: NPC303451

Natural Product ID	NPC303451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oleoside Dimethyl Ester
IUPAC Name	methyl (4S,5Z,6S)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms	Oleoside Dimethyl Ester
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1087778
PubChem CID	14038300
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

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 55 56 0 0 0 0 0 0 0 0999 V2000 -1.7767 0.0806 3.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9974 0.1727 1.8363 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2398 -0.1027 1.2955 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1633 -0.4359 2.0756 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5262 -0.0214 -0.1605 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3312 0.3850 -0.9413 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1888 -0.5903 -0.7742 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2734 -1.7485 -0.1779 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0886 -2.6155 -0.0754 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1318 -0.1857 -1.3547 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1655 0.5613 -2.5447 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4213 0.5548 -3.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5326 0.4701 -2.4029 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8325 0.4588 -3.0312 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8983 0.5337 -4.3086 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0418 0.3733 -2.3842 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2674 0.3694 -3.0924 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7338 0.6658 -0.4305 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0116 0.3151 -0.0782 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0859 0.0478 1.2721 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3182 -0.3919 1.6987 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3135 -0.3946 3.2192 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2757 -1.2780 3.5973 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4798 0.3549 1.1237 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1009 1.6036 0.3968 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9430 1.4133 -0.5168 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3822 1.1254 -1.8064 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8775 2.6846 1.2536 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2979 -0.4761 0.3603 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9999 -0.7135 3.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6737 -0.2508 3.7553 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4116 1.0557 3.6495 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2821 0.8101 -0.2547 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0216 -0.9368 -0.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9316 1.3563 -0.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2422 -2.0511 0.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4105 -3.5603 0.4541 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7369 -2.2192 0.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3250 -2.9149 -1.0685 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7551 -1.0182 -1.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5489 0.6193 -4.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3742 -0.6386 -3.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1265 0.6507 -2.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2119 1.1518 -3.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2905 -0.6064 -0.6287 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4158 -1.4545 1.3928 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2778 -0.8248 3.5356 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1239 0.6212 3.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5777 -2.2105 3.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1193 0.6742 1.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9833 1.8982 -0.2332 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4050 2.3906 -0.5891 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1401 1.7447 -2.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4522 2.5408 2.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4245 -0.0435 -0.5234 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 7 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 10 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 13 6 1 0 26 19 1 0 1 30 1 0 1 31 1 0 1 32 1 0 5 33 1 0 5 34 1 0 6 35 1 1 8 36 1 0 9 37 1 0 9 38 1 0 9 39 1 0 10 40 1 6 12 41 1 0 17 42 1 0 17 43 1 0 17 44 1 0 19 45 1 6 21 46 1 6 22 47 1 0 22 48 1 0 23 49 1 0 24 50 1 1 25 51 1 6 26 52 1 6 27 53 1 0 28 54 1 0 29 55 1 0 M END

Standard InCHIKey	KYVUMEGNMQDSHO-ISEXSMSQSA-N
Standard InCHI	InChI=1S/C18H26O11/c1-4-8-9(5-12(20)25-2)10(16(24)26-3)7-27-17(8)29-18-15(23)14(22)13(21)11(6-19)28-18/h4,7,9,11,13-15,17-19,21-23H,5-6H2,1-3H3/b8-4-/t9-,11+,13+,14-,15+,17-,18-/m0/s1
SMILES	COC(=O)C[C@H]1/C(=C/C)/[C@@H](OC=C1C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	418.15	Volume:	388.918 ? Van der Waals volume.
Dense:	1.075	LogP:	0.236 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.612 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.438 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	15.0
TPSA:	161.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.289	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.612	Fsp³:	0.667
MCE-18:	41.933 ? 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:	0.459	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.119 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.014 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.31	Promiscuous compounds:	0.113

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.631	MDCK Permeability:	-5.032
Pgp-inhibitor:	0.005	Pgp-substrate:	0.616
PAMPA:	0.849 ? 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):	0.632
20% Bioavailability (F20%):	0.36	30% Bioavailability (F30%):	0.97
50% Bioavailability (F50%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044	MRP1:	0.775
Plasma Protein Binding (PPB):	58.539%	Volume Distribution (VD):	-0.44
Fu:	41.418% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.228
BSEP inhibitor:	0.008

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.948
HLM stability:	0.583 ? 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):

2.291

Half-life (T1/2):

2.019

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.09
Human Hepatotoxicity (H-HT):	0.886	Drug-induced Liver Injury (DILI):	0.983
AMES Toxicity:	0.953	Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.208	Skin Sensitization:	1.0
Carcinogencity:	0.648	Eye Corrosion:	0.0
Eye Irritation:	0.033	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.51	Ototoxicity:	0.941
Hematotoxicity:	0.589	Drug-induced Nephrotoxicity:	0.965
Genotoxicity:	0.978	RPMI-8226 Immunitoxicity:	0.113
A549 Cytotoxicity:	0.15	Hek293 Cytotoxicity:	0.129
BCF:	0.249 ? 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:	2.601 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.478 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.444 ? 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
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11411539]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787443]
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000781]
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18340	Ligustrum lucidum	Species	Oleaceae	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
Activity	1
Inhibition	3

Activity Type	# Activity
Cell line	3
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT866	Individual protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	Activity	=	27.9	%	PMID[20000781]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	78.2	%	PMID[20000781]
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	-7.3	%	PMID[20000781]
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	-81.0	%	PMID[20000781]

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 NPC303451 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	17018
0.1-0.2	27844
0.2-0.3	4403
0.3-0.4	454
0.4-0.5	80
0.5-0.6	37
0.6-0.7	16
0.7-0.8	0
0.8-0.85	1
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	NPC72358
0.8475	Intermediate Similarity	NPC469543
0.7	Intermediate Similarity	NPC169398
0.6901	Remote Similarity	NPC296643
0.6901	Remote Similarity	NPC299576
0.6806	Remote Similarity	NPC600692
0.6667	Remote Similarity	NPC6414
0.6667	Remote Similarity	NPC610085
0.6533	Remote Similarity	NPC488384
0.6447	Remote Similarity	NPC488388
0.6447	Remote Similarity	NPC488383
0.6282	Remote Similarity	NPC469364
0.6282	Remote Similarity	NPC23677
0.6282	Remote Similarity	NPC609284
0.6203	Remote Similarity	NPC65262
0.6203	Remote Similarity	NPC84429
0.6203	Remote Similarity	NPC101686
0.6129	Remote Similarity	NPC117596
0.6125	Remote Similarity	NPC198577
0.5904	Remote Similarity	NPC246893
0.5802	Remote Similarity	NPC469367
0.5781	Remote Similarity	NPC35185
0.5781	Remote Similarity	NPC4899
0.5781	Remote Similarity	NPC177013
0.5781	Remote Similarity	NPC475928
0.5765	Remote Similarity	NPC488385
0.5692	Remote Similarity	NPC148270
0.5625	Remote Similarity	NPC474730
0.5625	Remote Similarity	NPC170432
0.5606	Remote Similarity	NPC27687
0.5606	Remote Similarity	NPC106668
0.5606	Remote Similarity	NPC37240
0.5538	Remote Similarity	NPC255677
0.5538	Remote Similarity	NPC22149
0.5538	Remote Similarity	NPC306344
0.5522	Remote Similarity	NPC231710
0.5522	Remote Similarity	NPC470573
0.5522	Remote Similarity	NPC120021
0.5522	Remote Similarity	NPC216826
0.5522	Remote Similarity	NPC270908
0.5522	Remote Similarity	NPC65665
0.5506	Remote Similarity	NPC488389
0.5506	Remote Similarity	NPC488387
0.5444	Remote Similarity	NPC488386
0.5373	Remote Similarity	NPC110701
0.5373	Remote Similarity	NPC61201
0.5362	Remote Similarity	NPC488472
0.5362	Remote Similarity	NPC257424
0.5303	Remote Similarity	NPC195510
0.5303	Remote Similarity	NPC298255
0.5303	Remote Similarity	NPC13171
0.5143	Remote Similarity	NPC222062
0.5143	Remote Similarity	NPC254538
0.5075	Remote Similarity	NPC307699
0.5072	Remote Similarity	NPC193741
0.507	Remote Similarity	NPC41681

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC303451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6591
0.1-0.2	2470
0.2-0.3	69
0.3-0.4	20
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