NPASS Compound

Natural Product: NPC469543

Natural Product ID	NPC469543
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Excelside A
IUPAC Name	methyl (4S,5E)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1086876
PubChem CID	46881041
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 76 78 0 0 0 0 0 0 0 0999 V2000 -1.8101 1.1123 -0.9676 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2186 0.7525 -0.6688 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6377 -0.2759 -0.0125 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1138 -0.4808 0.1948 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4346 -1.7099 -0.5704 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5757 -2.7264 -0.4114 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4719 -2.6149 0.4139 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8045 -1.3622 0.5997 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4918 -1.3612 0.2712 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6199 -1.2202 1.3323 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1174 -2.5499 1.5680 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1648 -2.6058 0.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1060 -1.4018 0.7779 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3098 -0.1779 0.4863 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2020 -0.1596 1.3389 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0042 1.1322 0.7544 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1014 1.4878 0.1169 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3110 0.8928 0.2430 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7492 0.3225 -1.0641 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5310 1.2268 -1.9426 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6017 1.8854 -1.0892 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8038 2.6622 -0.0355 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1862 1.8090 0.8007 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8304 3.4547 0.7562 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5068 4.3586 -0.0684 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4191 0.9482 -0.4579 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0617 0.5175 -2.9953 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5394 -0.8266 -0.8405 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3608 -1.4900 2.1319 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9026 -3.7855 0.5061 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7803 -3.5871 1.5168 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5887 -1.8426 -1.4505 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3924 -0.8970 -1.6049 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8577 -3.0053 -2.1555 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9757 -3.1397 -3.0104 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9465 0.7008 -0.1051 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5160 1.8348 0.7754 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0602 2.9665 0.7188 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4992 1.6421 1.6728 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9974 2.6055 2.5513 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7467 1.9344 -1.7245 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3973 1.5429 -0.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2576 0.2456 -1.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9626 1.4651 -1.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2421 -0.7333 1.2771 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7851 -3.6296 -0.9541 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8824 -1.2021 1.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2655 -1.1350 2.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6475 -2.4792 2.5453 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7130 -2.3835 -0.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9961 -1.5584 0.1276 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.1630 -0.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2394 1.9818 0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1764 1.2193 1.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2680 0.0766 0.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8699 -0.0423 -1.6373 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8949 2.0373 -2.3312 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2568 2.5542 -1.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1669 3.3733 -0.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3226 4.0478 1.5647 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5694 2.8116 1.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2839 4.7474 0.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1563 0.8060 0.4858 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3253 1.1817 -3.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2855 -1.5728 -1.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9847 -2.2499 2.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8815 -4.1378 -0.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3703 -4.3616 1.0581 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0453 -2.2377 -3.6427 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9125 -3.3246 -2.4554 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7906 -4.0101 -3.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0262 0.4939 0.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8950 1.0087 -1.1565 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1565 2.1459 3.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5543 3.4619 1.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7401 2.9938 3.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 2 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 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 13 29 1 0 12 30 1 0 11 31 1 0 5 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 4 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 8 3 1 0 15 10 1 0 23 18 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 4 45 1 0 6 46 1 0 8 47 1 0 10 48 1 0 11 49 1 0 12 50 1 0 13 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 18 55 1 0 19 56 1 0 20 57 1 0 21 58 1 0 22 59 1 0 24 60 1 0 24 61 1 0 25 62 1 0 26 63 1 0 27 64 1 0 28 65 1 0 29 66 1 0 30 67 1 0 31 68 1 0 35 69 1 0 35 70 1 0 35 71 1 0 36 72 1 0 36 73 1 0 40 74 1 0 40 75 1 0 40 76 1 0 M END

Standard InCHIKey	KIYJRYWOZVDCRC-GLYOJDOWSA-N
Standard InCHI	InChI=1S/C24H36O16/c1-4-9-10(5-14(26)34-2)11(21(33)35-3)7-36-22(9)40-24-20(32)18(30)16(28)13(39-24)8-37-23-19(31)17(29)15(27)12(6-25)38-23/h4,7,10,12-13,15-20,22-25,27-32H,5-6,8H2,1-3H3/b9-4+/t10-,12+,13+,15+,16+,17-,18-,19+,20+,22?,23+,24-/m0/s1
SMILES	CC=C1C(C(=COC1OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O)C(=O)OC)CC(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.2	Volume:	528.089 ? Van der Waals volume.
Dense:	1.099	LogP:	-0.709 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.074 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.431 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	21.0
TPSA:	240.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	7.0	Rings:	3.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.102	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.166	Fsp³:	0.75
MCE-18:	64.286 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.001	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.064 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.281 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.393	Promiscuous compounds:	0.0

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.956	MDCK Permeability:	-5.309
Pgp-inhibitor:	0.0	Pgp-substrate:	0.986
PAMPA:	1.0 ? 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):	0.999
20% Bioavailability (F20%):	0.957	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.996
Plasma Protein Binding (PPB):	26.326%	Volume Distribution (VD):	-0.639
Fu:	71.77% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.217	BCRP inhibitor:	0.116
BSEP inhibitor:	0.013

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.198	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.021	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.542
HLM stability:	0.008 ? 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):

1.355

Half-life (T1/2):

2.043

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.403
Human Hepatotoxicity (H-HT):	0.378	Drug-induced Liver Injury (DILI):	0.825
AMES Toxicity:	0.687	Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.175	Skin Sensitization:	0.609
Carcinogencity:	0.133	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.654	Ototoxicity:	0.986
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.17
Genotoxicity:	0.881	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.003	Hek293 Cytotoxicity:	0.289
BCF:	0.141 ? 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:	2.176 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.47 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.061 ? 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
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]
NPO19884	Fraxinus excelsior	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
Inhibition	3

Activity Type	# Activity
Cell line	3

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
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	102.5	%	PMID[1517739]
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	30.9	%	PMID[18258441]
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	-16.6	%	PMID[11858756]

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 NPC469543 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	18346
0.1-0.2	26712
0.2-0.3	4019
0.3-0.4	647
0.4-0.5	92
0.5-0.6	18
0.6-0.7	16
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8475	Intermediate Similarity	NPC303451
0.8475	Intermediate Similarity	NPC72358
0.7436	Intermediate Similarity	NPC469364
0.7436	Intermediate Similarity	NPC609284
0.7273	Intermediate Similarity	NPC488384
0.7179	Intermediate Similarity	NPC488383
0.6914	Remote Similarity	NPC65262
0.6914	Remote Similarity	NPC84429
0.6914	Remote Similarity	NPC101686
0.6829	Remote Similarity	NPC198577
0.679	Remote Similarity	NPC23677
0.675	Remote Similarity	NPC488388
0.641	Remote Similarity	NPC169398
0.6329	Remote Similarity	NPC296643
0.6329	Remote Similarity	NPC299576
0.625	Remote Similarity	NPC600692
0.6207	Remote Similarity	NPC246893
0.6154	Remote Similarity	NPC488387
0.6087	Remote Similarity	NPC488386
0.6081	Remote Similarity	NPC197541
0.6081	Remote Similarity	NPC118761
0.6067	Remote Similarity	NPC488385
0.5833	Remote Similarity	NPC6414
0.5833	Remote Similarity	NPC610085
0.5714	Remote Similarity	NPC488456
0.5714	Remote Similarity	NPC488471
0.5714	Remote Similarity	NPC488466
0.5714	Remote Similarity	NPC488465
0.5714	Remote Similarity	NPC488460
0.5714	Remote Similarity	NPC488462
0.5584	Remote Similarity	NPC284929
0.5352	Remote Similarity	NPC117596
0.5238	Remote Similarity	NPC488467
0.5222	Remote Similarity	NPC469367
0.519	Remote Similarity	NPC267869
0.5155	Remote Similarity	NPC488389
0.5068	Remote Similarity	NPC35185
0.5068	Remote Similarity	NPC4899
0.5068	Remote Similarity	NPC177013
0.5068	Remote Similarity	NPC475928

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6672
0.1-0.2	2392
0.2-0.3	80
0.3-0.4	5
0.4-0.5	1
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