NPASS Compound

Natural Product: NPC525352

Natural Product ID	NPC525352
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	octadeca-9,17-dienoic acid
IUPAC Name	octadeca-9,17-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 52 51 0 0 0 0 0 0 0 0999 V2000 9.1899 0.4911 -0.3276 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0777 0.3051 -1.0215 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 0.6086 -0.4305 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9484 -0.6797 -0.4396 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5565 -0.5000 0.1418 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7685 0.5035 -0.6362 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3954 0.6638 -0.0415 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6359 -0.6334 -0.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3039 -0.4135 0.5384 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7827 -0.6466 -0.1721 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1751 -0.4192 0.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8884 -1.7174 0.4119 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2040 -1.8954 1.0150 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3157 -1.0458 0.5569 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2067 0.3765 0.9211 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3878 1.2008 0.4115 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5402 1.1793 -1.0660 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4063 1.7087 -1.8208 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4913 1.6557 -3.0896 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2686 2.2531 -1.2933 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1428 0.8685 0.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1344 0.2689 -0.7665 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1234 -0.0755 -2.0428 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8474 0.9371 0.6127 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2657 1.3883 -1.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8752 -1.0404 -1.4836 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5020 -1.4189 0.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5918 -0.1698 1.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1112 -1.5174 0.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2989 1.4801 -0.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6362 0.2415 -1.7058 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4494 1.0201 1.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8341 1.3799 -0.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1231 -1.4303 0.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5761 -0.9562 -1.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1969 -0.0620 1.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7436 -0.9995 -1.1922 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6175 0.3214 -0.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1223 0.0413 1.4128 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8718 -2.0946 -0.6810 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1305 -2.4659 0.8687 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1463 -1.9139 2.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5185 -2.9852 0.7773 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3592 -1.1875 -0.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2998 -1.4323 0.9689 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3759 0.4068 2.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3064 0.9332 0.7854 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3266 0.8509 0.8844 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1899 2.2481 0.7357 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7307 0.1302 -1.3721 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4328 1.7801 -1.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4808 2.4577 -1.8970 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 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 2 3 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 0 18 20 1 0 1 21 1 0 1 22 1 0 2 23 1 0 3 24 1 0 3 25 1 0 4 26 1 0 4 27 1 0 5 28 1 0 5 29 1 0 6 30 1 0 6 31 1 0 7 32 1 0 7 33 1 0 8 34 1 0 8 35 1 0 9 36 1 0 10 37 1 0 11 38 1 0 11 39 1 0 12 40 1 0 12 41 1 0 13 42 1 0 13 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 15 47 1 0 16 48 1 0 16 49 1 0 17 50 1 0 17 51 1 0 20 52 1 0 M END

Standard InCHIKey	OHEMCNXPXOGQHX-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2,9-10H,1,3-8,11-17H2,(H,19,20)
SMILES	C=CCCCCCCC=CCCCCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	280.24	Volume:	329.555 ? Van der Waals volume.
Dense:	0.85	LogP:	6.54 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.514 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.49 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	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:	0.3	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.254	Fsp³:	0.722
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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.075	Fluc inhibitor:	0.223 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.995	Promiscuous compounds:	0.823

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.078	MDCK Permeability:	-4.698
Pgp-inhibitor:	0.002	Pgp-substrate:	0.001
PAMPA:	0.049 ? 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):	0.297
20% Bioavailability (F20%):	0.486	30% Bioavailability (F30%):	0.903
50% Bioavailability (F50%):	0.432

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101	MRP1:	0.959
Plasma Protein Binding (PPB):	98.187%	Volume Distribution (VD):	-0.605
Fu:	0.81% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.475
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.343
BSEP inhibitor:	0.429

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.766	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.831	CYP2C8-inhibitor:	1.0
HLM stability:	0.003 ? 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):

3.778

Half-life (T1/2):

0.734

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.249
Human Hepatotoxicity (H-HT):	0.134	Drug-induced Liver Injury (DILI):	0.005
AMES Toxicity:	0.153	Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.16	Skin Sensitization:	1.0
Carcinogencity:	0.24	Eye Corrosion:	0.999
Eye Irritation:	0.999	Respiratory Toxicity:	0.601
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.169
Hematotoxicity:	0.035	Drug-induced Nephrotoxicity:	0.134
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.063	Hek293 Cytotoxicity:	0.024
BCF:	1.204 ? 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:	3.896 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.416 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.447 ? 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
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	Lamiaceae	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 NPC525352 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	41378
0.1-0.2	7154
0.2-0.3	1003
0.3-0.4	169
0.4-0.5	62
0.5-0.6	46
0.6-0.7	15
0.7-0.8	4
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8846	High Similarity	NPC180534
0.8846	High Similarity	NPC611531
0.8214	Intermediate Similarity	NPC281245
0.7931	Intermediate Similarity	NPC424
0.7931	Intermediate Similarity	NPC36061
0.7931	Intermediate Similarity	NPC69510
0.7931	Intermediate Similarity	NPC77272
0.7931	Intermediate Similarity	NPC290563
0.7931	Intermediate Similarity	NPC139029
0.7931	Intermediate Similarity	NPC281972
0.7931	Intermediate Similarity	NPC261831
0.7931	Intermediate Similarity	NPC87564
0.7333	Intermediate Similarity	NPC92114
0.7188	Intermediate Similarity	NPC52955
0.7188	Intermediate Similarity	NPC88966
0.7188	Intermediate Similarity	NPC25417
0.7188	Intermediate Similarity	NPC1813
0.7188	Intermediate Similarity	NPC154245
0.7188	Intermediate Similarity	NPC85813
0.7188	Intermediate Similarity	NPC223697
0.7188	Intermediate Similarity	NPC6095
0.7097	Intermediate Similarity	NPC95145
0.7097	Intermediate Similarity	NPC325642
0.7097	Intermediate Similarity	NPC207292
0.7097	Intermediate Similarity	NPC65174
0.6875	Remote Similarity	NPC321062
0.6875	Remote Similarity	NPC70387
0.6538	Remote Similarity	NPC214610
0.6538	Remote Similarity	NPC118968
0.6538	Remote Similarity	NPC183424
0.6538	Remote Similarity	NPC294085
0.6452	Remote Similarity	NPC34416
0.6389	Remote Similarity	NPC606120
0.6364	Remote Similarity	NPC5413
0.6176	Remote Similarity	NPC59051
0.6154	Remote Similarity	NPC268826
0.6061	Remote Similarity	NPC149821
0.6053	Remote Similarity	NPC477201
0.6	Remote Similarity	NPC68343
0.6	Remote Similarity	NPC328089
0.5946	Remote Similarity	NPC225929
0.5882	Remote Similarity	NPC91495
0.5862	Remote Similarity	NPC171736
0.5862	Remote Similarity	NPC301585
0.5862	Remote Similarity	NPC261080
0.5862	Remote Similarity	NPC132565
0.5862	Remote Similarity	NPC209970
0.5862	Remote Similarity	NPC216630
0.5862	Remote Similarity	NPC201844
0.5862	Remote Similarity	NPC301696
0.5862	Remote Similarity	NPC196924
0.5862	Remote Similarity	NPC307783
0.5862	Remote Similarity	NPC154186
0.5862	Remote Similarity	NPC149184
0.5862	Remote Similarity	NPC279026
0.5862	Remote Similarity	NPC113928
0.5862	Remote Similarity	NPC14227
0.575	Remote Similarity	NPC243532
0.5714	Remote Similarity	NPC174560
0.5714	Remote Similarity	NPC125312
0.5676	Remote Similarity	NPC18357
0.5667	Remote Similarity	NPC604140
0.5641	Remote Similarity	NPC106851
0.5641	Remote Similarity	NPC282788
0.5641	Remote Similarity	NPC274927
0.5556	Remote Similarity	NPC134782
0.5526	Remote Similarity	NPC487561
0.5517	Remote Similarity	NPC155263
0.55	Remote Similarity	NPC179764
0.5429	Remote Similarity	NPC48162
0.5366	Remote Similarity	NPC251042
0.5366	Remote Similarity	NPC255863
0.5366	Remote Similarity	NPC473863
0.5366	Remote Similarity	NPC174447
0.5366	Remote Similarity	NPC136164
0.5366	Remote Similarity	NPC122521
0.5366	Remote Similarity	NPC245947
0.5312	Remote Similarity	NPC55023
0.5312	Remote Similarity	NPC21844
0.5238	Remote Similarity	NPC54766
0.5238	Remote Similarity	NPC318420
0.5238	Remote Similarity	NPC326268
0.5172	Remote Similarity	NPC175342
0.5152	Remote Similarity	NPC50457
0.5152	Remote Similarity	NPC604910
0.5122	Remote Similarity	NPC485704

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC525352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7269
0.1-0.2	1652
0.2-0.3	176
0.3-0.4	33
0.4-0.5	7
0.5-0.6	4
0.6-0.7	3
0.7-0.8	4
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD622	Pre-clinical
0.7931	Intermediate Similarity	NPD3195	Phase 2
0.7931	Intermediate Similarity	NPD3196	Approved
0.7188	Intermediate Similarity	NPD3172	Approved
0.7188	Intermediate Similarity	NPD4266	Phase 2
0.6538	Remote Similarity	NPD9655	Phase 4
0.6389	Remote Similarity	NPD3194	Phase 4
0.6364	Remote Similarity	NPD3173	Phase 4
0.5862	Remote Similarity	NPD2270	Pre-clinical
0.5862	Remote Similarity	NPD633	Phase 3
0.5862	Remote Similarity	NPD9448	Phase 2
0.561	Remote Similarity	NPD39	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