NPASS Compound

Natural Product: NPC543069

Natural Product ID	NPC543069
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2-octadeca-9,12-dienoyloxy-3-tetradeca-9,12-dienoyloxy-propyl) octadeca-9,12-dienoate
IUPAC Name	(2-octadeca-9,12-dienoyloxy-3-tetradeca-9,12-dienoyloxy-propyl) octadeca-9,12-dienoate
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

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0 0 0 0 0 0 19.4856 -14.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.1865 -15.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 20.7846 -15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.0836 -15.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.3827 -16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 24.6817 -17.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 25.9808 -18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 27.2798 -18.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 28.5788 -19.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 29.8779 -20.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 31.1769 -19.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 32.4760 -20.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 33.7750 -21.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 33.7750 -22.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 35.0740 -23.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 36.3731 -24.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 37.6721 -24.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 38.9711 -25.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 40.2702 -26.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.6375 -9.9510 0.0000 O 0 0 0 0 0 0 0 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29.8779 -21.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 31.1769 -18.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 33.2260 -18.9510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 31.7260 -21.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 35.0740 -20.2500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 32.4760 -23.2500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 34.3240 -24.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 35.8240 -21.9510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 37.1231 -22.7010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 35.6231 -25.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 36.9221 -26.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 38.4221 -23.4510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 39.7211 -24.2010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 38.2211 -26.7990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 41.5692 -27.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 39.5202 -27.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 41.0202 -24.9510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.1865 -9.4019 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.5885 -7.9019 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 19.3385 -6.6029 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.9365 -8.1029 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.6865 -6.8038 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.0885 -5.3038 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.8385 -4.0048 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 23.4365 -5.5048 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 24.1865 -4.2058 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.5885 -2.7058 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.3385 -1.4067 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 24.9365 -2.9067 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 23.0885 -0.1077 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 25.6865 -1.6077 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 26.6375 0.4413 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.8875 1.7404 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 23.8385 3.7894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 26.4365 2.2894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 25.1375 5.6375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 28.1375 3.0394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 29.4365 4.8875 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 26.8385 6.3875 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 27.5885 7.6865 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 30.1865 6.1865 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 30.9365 7.4856 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 28.3385 8.9856 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 29.0885 10.2846 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 31.6865 8.7846 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 31.8875 12.1327 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 32.4365 10.0836 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 29.8385 11.5836 0.0000 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 3 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 2 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 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 3 31 32 1 0 32 33 1 0 33 34 2 3 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 18 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 2 3 51 52 1 0 52 53 1 0 53 54 2 3 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 1 60 1 0 1 61 1 0 1 62 1 0 2 63 1 0 3 64 1 0 4 65 1 0 4 66 1 0 5 67 1 0 6 68 1 0 7 69 1 0 7 70 1 0 8 71 1 0 8 72 1 0 9 73 1 0 9 74 1 0 10 75 1 0 10 76 1 0 11 77 1 0 11 78 1 0 12 79 1 0 12 80 1 0 13 81 1 0 13 82 1 0 17 83 1 0 17 84 1 0 18 85 1 0 19 86 1 0 19 87 1 0 23 88 1 0 23 89 1 0 24 90 1 0 24 91 1 0 25 92 1 0 25 93 1 0 26 94 1 0 26 95 1 0 27 96 1 0 27 97 1 0 28 98 1 0 28 99 1 0 29100 1 0 29101 1 0 30102 1 0 31103 1 0 32104 1 0 32105 1 0 33106 1 0 34107 1 0 35108 1 0 35109 1 0 36110 1 0 36111 1 0 37112 1 0 37113 1 0 38114 1 0 38115 1 0 39116 1 0 39117 1 0 39118 1 0 43119 1 0 43120 1 0 44121 1 0 44122 1 0 45123 1 0 45124 1 0 46125 1 0 46126 1 0 47127 1 0 47128 1 0 48129 1 0 48130 1 0 49131 1 0 49132 1 0 50133 1 0 51134 1 0 52135 1 0 52136 1 0 53137 1 0 54138 1 0 55139 1 0 55140 1 0 56141 1 0 56142 1 0 57143 1 0 57144 1 0 58145 1 0 58146 1 0 59147 1 0 59148 1 0 59149 1 0 M END

Standard InCHIKey	ZTGYARIMLPBWEI-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C53H90O6/c1-4-7-10-13-16-19-22-24-26-28-31-34-37-40-43-46-52(55)58-49-50(48-57-51(54)45-42-39-36-33-30-21-18-15-12-9-6-3)59-53(56)47-44-41-38-35-32-29-27-25-23-20-17-14-11-8-5-2/h6,9,15-20,24-27,50H,4-5,7-8,10-14,21-23,28-49H2,1-3H3
SMILES	CC=CCC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	822.67	Volume:	954.257 ? Van der Waals volume.
Dense:	0.862	LogP:	13.725 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.444 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-10.703 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	46.0	Rigid Bonds:	9.0
TPSA:	78.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.026	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.85	Fsp³:	0.717
MCE-18:	4.0 ? 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:	0.665	Fluc inhibitor:	0.269 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.012 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.688	Promiscuous compounds:	0.336

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002	MDCK Permeability:	-4.759
Pgp-inhibitor:	0.367	Pgp-substrate:	0.007
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):	0.052
20% Bioavailability (F20%):	0.986	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	98.725%	Volume Distribution (VD):	0.011
Fu:	0.424% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.377
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.248
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.005	CYP2C8-inhibitor:	1.0
HLM stability:	0.494 ? 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):

4.717

Half-life (T1/2):

1.116

ADMET: Toxicity

hERG Blockers:	0.779	hERG Blockers (10um):	0.782
Human Hepatotoxicity (H-HT):	0.008	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.747	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.01	Skin Sensitization:	1.0
Carcinogencity:	0.232	Eye Corrosion:	0.879
Eye Irritation:	0.796	Respiratory Toxicity:	0.073
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.065
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.773
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.051
A549 Cytotoxicity:	0.953	Hek293 Cytotoxicity:	0.152
BCF:	-0.909 ? 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:	4.441 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.307 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.806 ? 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
NPO46697	Araliaceae	Family	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC543069 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	24751
0.1-0.2	22745
0.2-0.3	2045
0.3-0.4	218
0.4-0.5	54
0.5-0.6	30
0.6-0.7	14
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC54925
0.7105	Intermediate Similarity	NPC55678
0.6957	Remote Similarity	NPC473559
0.6957	Remote Similarity	NPC324981
0.6792	Remote Similarity	NPC489083
0.675	Remote Similarity	NPC28779
0.6316	Remote Similarity	NPC21693
0.6304	Remote Similarity	NPC48218
0.6304	Remote Similarity	NPC141481
0.6304	Remote Similarity	NPC464342
0.6222	Remote Similarity	NPC330426
0.6222	Remote Similarity	NPC127091
0.6222	Remote Similarity	NPC22101
0.6	Remote Similarity	NPC475443
0.6	Remote Similarity	NPC128061
0.6	Remote Similarity	NPC473829
0.5952	Remote Similarity	NPC10316
0.5952	Remote Similarity	NPC200845
0.5854	Remote Similarity	NPC39633
0.5789	Remote Similarity	NPC488689
0.5778	Remote Similarity	NPC602940
0.5763	Remote Similarity	NPC236649
0.5714	Remote Similarity	NPC488692
0.5652	Remote Similarity	NPC321919
0.5625	Remote Similarity	NPC470313
0.5625	Remote Similarity	NPC473500
0.5625	Remote Similarity	NPC611497
0.5593	Remote Similarity	NPC478995
0.5581	Remote Similarity	NPC223677
0.5574	Remote Similarity	NPC110813
0.5556	Remote Similarity	NPC104537
0.5538	Remote Similarity	NPC488691
0.5532	Remote Similarity	NPC271921
0.5435	Remote Similarity	NPC81896
0.5333	Remote Similarity	NPC277597
0.5333	Remote Similarity	NPC148192
0.5323	Remote Similarity	NPC156089
0.5312	Remote Similarity	NPC38295
0.5238	Remote Similarity	NPC488694
0.5217	Remote Similarity	NPC22558
0.5122	Remote Similarity	NPC309606
0.5116	Remote Similarity	NPC139545
0.5094	Remote Similarity	NPC224700
0.5094	Remote Similarity	NPC320663
0.5079	Remote Similarity	NPC133377
0.5079	Remote Similarity	NPC39290

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC543069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7000
0.1-0.2	2025
0.2-0.3	99
0.3-0.4	16
0.4-0.5	6
0.5-0.6	2
0.6-0.7	0
0.7-0.8	1
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
0.7105	Intermediate Similarity	NPD6125	Phase 4
0.5116	Remote Similarity	NPD5343	Phase 4
0.5094	Remote Similarity	NPD8278	Phase 4

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