NPASS Compound

Natural Product: NPC473082

Natural Product ID	NPC473082
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JDRNXTHXRJQQBJ-YBXHDGJPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3609586
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 83 86 0 0 0 0 0 0 0 0999 V2000 6.3374 5.0130 2.1637 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7347 3.7744 2.7696 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3265 2.7763 1.6764 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3260 3.4725 0.8214 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7866 2.6802 -0.3252 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0785 1.4416 0.0629 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9720 1.1752 1.2830 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5294 0.5656 -0.8606 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8726 -0.5871 -0.4578 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4409 -1.8284 -1.0821 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7436 -3.0737 -0.6958 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3910 -2.9827 -0.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5443 -3.8455 -0.9899 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6172 -4.1347 0.0718 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3648 -2.8653 0.3033 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7312 -1.6474 -0.3476 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2441 -1.6337 -0.0555 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3980 -0.5964 -0.9159 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3326 -0.8710 -2.3034 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1444 0.0892 -3.1835 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5178 1.2069 -2.7445 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2276 -0.1725 -4.6588 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1292 -1.1131 1.3872 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3697 -0.5274 0.2359 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1270 0.3487 -0.5226 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2216 0.1004 -1.7522 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8014 1.5209 0.0458 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5007 2.3024 -0.7368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1884 3.4823 -0.2058 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9165 4.2688 -1.0966 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5677 5.3676 -0.6552 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5122 5.7106 0.6739 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8049 4.9600 1.5815 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1379 3.8307 1.1178 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6649 -4.4542 1.2258 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3617 -3.5446 1.1341 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0986 -5.8288 0.9231 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3504 -4.5036 2.5459 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7873 -4.0048 -1.9229 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8262 4.8005 1.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0416 5.5176 2.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5180 5.7298 1.9598 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8202 3.9738 3.3619 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4826 3.3119 3.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9396 1.9025 2.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2612 2.5112 1.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8335 4.3844 0.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4962 3.8125 1.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6184 2.4217 -1.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0647 3.3307 -0.8646 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8688 -0.6747 0.6476 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3585 -1.6761 -2.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5542 -1.8956 -0.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4340 -3.6045 0.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9324 -3.3211 -1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0903 -4.8351 -1.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2389 -4.9833 -0.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 -2.9790 -0.1647 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5489 -2.6258 1.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9626 -1.6135 -1.4384 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0261 0.3988 -0.6787 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7503 0.0981 -5.0899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0207 0.4596 -5.0724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4964 -1.2323 -4.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6430 -1.7117 1.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0722 -1.2718 1.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0903 -0.0437 1.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6749 1.6669 1.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5684 2.0706 -1.7850 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9500 3.9843 -2.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1473 6.0037 -1.3339 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0568 6.6125 0.9890 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7526 5.2188 2.6343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5708 3.2300 1.8484 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9235 -5.7483 0.4944 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1088 -6.4647 1.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7018 -6.3705 0.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9927 -5.3765 3.1673 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0757 -3.6022 3.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4498 -4.6363 2.4686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 -3.7741 -2.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9703 -3.8084 -2.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8948 -5.0630 -1.6118 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 2 0 6 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 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 17 23 1 0 16 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 3 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 14 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 11 39 1 0 18 9 1 0 17 12 1 0 36 12 1 0 34 29 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 4 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 9 51 1 0 10 52 1 0 10 53 1 0 11 54 1 0 13 55 1 0 13 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 18 61 1 0 22 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 27 68 1 0 28 69 1 0 30 70 1 0 31 71 1 0 32 72 1 0 33 73 1 0 34 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 M END

Standard InCHIKey	JDRNXTHXRJQQBJ-YBXHDGJPSA-N
Standard InCHI	InChI=1S/C32H44O7/c1-7-8-10-15-27(34)37-25-18-21(2)32-20-24(30(4,5)39-32)19-26(31(32,6)29(25)36-22(3)33)38-28(35)17-16-23-13-11-9-12-14-23/h9,11-14,16-17,21,24-26,29H,7-8,10,15,18-20H2,1-6H3/b17-16+/t21-,24-,25+,26+,29+,31-,32+/m1/s1
SMILES	CCCCCC(=O)OC1CC(C23CC(CC(C2(C1OC(=O)C)C)OC(=O)C=CC4=CC=CC=C4)C(O3)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	540.31	Volume:	570.879 ? Van der Waals volume.
Dense:	0.946	LogP:	5.216 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.076 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.429 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	24.0
TPSA:	88.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.163	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.691	Fsp³:	0.656
MCE-18:	132.453 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.947	Fluc inhibitor:	0.328 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.05 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.572 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.183	Promiscuous compounds:	0.008

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.88	MDCK Permeability:	-4.607
Pgp-inhibitor:	0.907	Pgp-substrate:	0.103
PAMPA:	0.207 ? 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):	0.006
20% Bioavailability (F20%):	0.196	30% Bioavailability (F30%):	0.56
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.397	MRP1:	0.997
Plasma Protein Binding (PPB):	95.343%	Volume Distribution (VD):	0.162
Fu:	3.878% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.117
OATP1B3 inhibitor:	0.621	BCRP inhibitor:	0.009
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.256	CYP2C19-substrate:	0.138
CYP2C9-inhibitor:	0.362	CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.25
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	1.0
HLM stability:	0.51 ? 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):

2.585

Half-life (T1/2):

0.858

ADMET: Toxicity

hERG Blockers:	0.213	hERG Blockers (10um):	0.702
Human Hepatotoxicity (H-HT):	0.397	Drug-induced Liver Injury (DILI):	0.281
AMES Toxicity:	0.271	Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.713	Skin Sensitization:	0.996
Carcinogencity:	0.198	Eye Corrosion:	0.004
Eye Irritation:	0.127	Respiratory Toxicity:	0.122
Drug-induced Neurotoxicity:	0.717	Ototoxicity:	0.659
Hematotoxicity:	0.037	Drug-induced Nephrotoxicity:	0.525
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.086
A549 Cytotoxicity:	0.223	Hek293 Cytotoxicity:	0.518
BCF:	1.257 ? 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:	4.472 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.09 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.709 ? 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
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	seeds	Jilin, China	n.a.	PMID[26295746]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11250	Celastrus flagellaris	Species	Celastraceae	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

Activity Type	# Activity
Cell line	1

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
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	85.0	%	DrugMatrix in vivo data: Hematology

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 NPC473082 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	13239
0.1-0.2	33958
0.2-0.3	2389
0.3-0.4	209
0.4-0.5	45
0.5-0.6	11
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8594	High Similarity	NPC37641
0.8594	High Similarity	NPC114927
0.75	Intermediate Similarity	NPC214550
0.7297	Intermediate Similarity	NPC473083
0.6857	Remote Similarity	NPC84129
0.6757	Remote Similarity	NPC473110
0.6528	Remote Similarity	NPC473860
0.5976	Remote Similarity	NPC473109
0.5921	Remote Similarity	NPC475933
0.5789	Remote Similarity	NPC70973
0.5789	Remote Similarity	NPC473111
0.5333	Remote Similarity	NPC481066
0.5325	Remote Similarity	NPC473869
0.5294	Remote Similarity	NPC483878
0.5244	Remote Similarity	NPC488918
0.5244	Remote Similarity	NPC488913
0.5119	Remote Similarity	NPC473085
0.5057	Remote Similarity	NPC25768

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473082 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3895
0.1-0.2	5148
0.2-0.3	106
0.3-0.4	1
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