NPASS Compound

Natural Product: NPC506429

Natural Product ID	NPC506429
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	25-methyl-5,9-hexacosadienoic acid
IUPAC Name	25-methylhexacosa-5,9-dienoic acid
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

RDKit 3D 79 78 0 0 0 0 0 0 0 0999 V2000 -10.6101 1.4695 0.5558 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6906 0.2477 0.6956 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4643 -1.0258 0.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7712 0.2709 -0.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8190 -0.8912 -0.4713 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9865 -0.8393 0.7767 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1694 0.4030 0.9137 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1967 0.6144 -0.2051 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1846 -0.5070 -0.3506 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3976 -0.6234 0.9119 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3961 -1.7204 0.8293 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4136 -1.5007 -0.2875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7038 -0.1943 -0.0359 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3233 0.0906 -1.1434 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9494 1.4228 -0.7569 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9901 1.8956 -1.7169 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1593 0.9557 -1.8730 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7926 0.8020 -0.5532 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0458 1.1231 -0.2981 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0252 1.6770 -1.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2258 0.7483 -1.3685 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9164 0.5480 -0.0659 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0078 -0.6655 0.4267 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6865 -0.9119 1.7172 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8345 -1.8587 1.6055 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8986 -1.3413 0.6903 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4400 -0.0793 1.2306 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9502 1.0346 0.9841 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5503 -0.1284 2.0556 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0097 2.3409 0.8574 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8124 1.5700 -0.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5400 1.3449 1.1379 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0839 0.3949 1.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0384 -1.6842 1.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5270 -0.8897 1.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4134 -1.6458 -0.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2305 1.2393 -0.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3499 0.2581 -1.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1435 -0.8811 -1.3760 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3650 -1.8608 -0.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6022 -0.9547 1.6916 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3369 -1.7549 0.7564 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8432 1.2798 0.9472 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6788 0.3764 1.9097 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6096 1.5366 0.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6579 0.7877 -1.1738 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6065 -1.4345 -0.7326 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4723 -0.1259 -1.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9780 0.3741 1.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0640 -0.8509 1.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9815 -2.6591 0.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8516 -1.8630 1.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6976 -2.3477 -0.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9647 -1.4259 -1.2395 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4105 0.6577 -0.0991 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1119 -0.2126 0.9019 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1325 0.1131 -2.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1339 -0.6738 -1.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1651 2.2260 -0.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3739 1.3891 0.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3056 2.9061 -1.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5371 2.0449 -2.7306 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8053 1.2652 -2.6892 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7163 -0.0372 -2.1670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1601 0.3963 0.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4181 0.9647 0.7340 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3701 2.6787 -0.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6682 1.8761 -2.2537 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9820 1.2357 -2.0413 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8924 -0.2144 -1.7517 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3356 1.4085 0.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5882 -1.5130 -0.1009 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9442 -1.2778 2.4695 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0735 0.0768 2.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2531 -1.9864 2.6284 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4798 -2.8402 1.2127 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4924 -1.2096 -0.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7184 -2.1042 0.6892 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1081 0.6901 2.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 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 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 3 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 3 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 13 55 1 0 13 56 1 0 14 57 1 0 14 58 1 0 15 59 1 0 15 60 1 0 16 61 1 0 16 62 1 0 17 63 1 0 17 64 1 0 18 65 1 0 19 66 1 0 20 67 1 0 20 68 1 0 21 69 1 0 21 70 1 0 22 71 1 0 23 72 1 0 24 73 1 0 24 74 1 0 25 75 1 0 25 76 1 0 26 77 1 0 26 78 1 0 29 79 1 0 M END

Standard InCHIKey	DNEGLXLXJLONIP-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C27H50O2/c1-26(2)24-22-20-18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-21-23-25-27(28)29/h9,11,17,19,26H,3-8,10,12-16,18,20-25H2,1-2H3,(H,28,29)
SMILES	CC(C)CCCCCCCCCCCCCCC=CCCC=CCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	406.38	Volume:	485.219 ? Van der Waals volume.
Dense:	0.838	LogP:	10.544 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.988 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-9.047 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	22.0	Rigid Bonds:	3.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.144	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.456	Fsp³:	0.815
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.609	Fluc inhibitor:	0.327 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.982	Promiscuous compounds:	0.762

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.094	MDCK Permeability:	-4.716
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.004 ? 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):	0.173
20% Bioavailability (F20%):	0.087	30% Bioavailability (F30%):	0.887
50% Bioavailability (F50%):	0.591

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.993
Plasma Protein Binding (PPB):	98.426%	Volume Distribution (VD):	-0.189
Fu:	0.527% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.333
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.085
BSEP inhibitor:	0.139

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.232
CYP2C19-inhibitor:	0.954	CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.273
CYP2D6-inhibitor:	0.173	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.848
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.109 ? 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):

5.237

Half-life (T1/2):

0.72

ADMET: Toxicity

hERG Blockers:	0.211	hERG Blockers (10um):	0.452
Human Hepatotoxicity (H-HT):	0.373	Drug-induced Liver Injury (DILI):	0.002
AMES Toxicity:	0.071	Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.235	Skin Sensitization:	1.0
Carcinogencity:	0.117	Eye Corrosion:	0.994
Eye Irritation:	0.996	Respiratory Toxicity:	0.847
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.301
Hematotoxicity:	0.066	Drug-induced Nephrotoxicity:	0.221
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.429	Hek293 Cytotoxicity:	0.051
BCF:	0.686 ? 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:	4.056 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.05 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.145 ? 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
NPO9919	Jaspis stellifera	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9919	Jaspis stellifera	Species	Ancorinidae	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

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 NPC506429 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	32835
0.1-0.2	15276
0.2-0.3	1433
0.3-0.4	185
0.4-0.5	84
0.5-0.6	26
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.871	High Similarity	NPC48162
0.6857	Remote Similarity	NPC59051
0.6667	Remote Similarity	NPC281245
0.6571	Remote Similarity	NPC91495
0.6562	Remote Similarity	NPC55023
0.6562	Remote Similarity	NPC21844
0.6471	Remote Similarity	NPC424
0.6471	Remote Similarity	NPC36061
0.6471	Remote Similarity	NPC69510
0.6471	Remote Similarity	NPC77272
0.6471	Remote Similarity	NPC290563
0.6471	Remote Similarity	NPC139029
0.6471	Remote Similarity	NPC281972
0.6471	Remote Similarity	NPC92114
0.6471	Remote Similarity	NPC261831
0.6471	Remote Similarity	NPC87564
0.5946	Remote Similarity	NPC52955
0.5946	Remote Similarity	NPC88966
0.5946	Remote Similarity	NPC25417
0.5946	Remote Similarity	NPC1813
0.5946	Remote Similarity	NPC154245
0.5946	Remote Similarity	NPC85813
0.5946	Remote Similarity	NPC223697
0.5946	Remote Similarity	NPC6095
0.5833	Remote Similarity	NPC95145
0.5833	Remote Similarity	NPC325642
0.5833	Remote Similarity	NPC65174
0.5714	Remote Similarity	NPC117572
0.5676	Remote Similarity	NPC321062
0.5676	Remote Similarity	NPC5413
0.5676	Remote Similarity	NPC70387
0.5526	Remote Similarity	NPC174560
0.5526	Remote Similarity	NPC125312
0.5405	Remote Similarity	NPC149821
0.5366	Remote Similarity	NPC606120
0.5278	Remote Similarity	NPC314679
0.5227	Remote Similarity	NPC323597
0.5227	Remote Similarity	NPC211752
0.5227	Remote Similarity	NPC323498
0.5143	Remote Similarity	NPC180534
0.5143	Remote Similarity	NPC611531
0.5116	Remote Similarity	NPC477201

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC506429 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6423
0.1-0.2	2471
0.2-0.3	198
0.3-0.4	36
0.4-0.5	13
0.5-0.6	7
0.6-0.7	2
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
0.6471	Remote Similarity	NPD3195	Phase 2
0.6471	Remote Similarity	NPD3196	Approved
0.5946	Remote Similarity	NPD3172	Approved
0.5946	Remote Similarity	NPD4266	Phase 2
0.5714	Remote Similarity	NPD4222	Phase 3
0.5676	Remote Similarity	NPD3173	Phase 4
0.5455	Remote Similarity	NPD39	Phase 4
0.5366	Remote Similarity	NPD3194	Phase 4
0.5143	Remote Similarity	NPD622	Pre-clinical

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