NPASS Compound

Natural Product: NPC471405

Natural Product ID	NPC471405
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Scroneoside A
IUPAC Name	[(2R,3S,4S,5R,6S)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2436435
PubChem CID	73347939
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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 64 66 0 0 0 0 0 0 0 0999 V2000 -3.6092 3.0273 -1.6906 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5376 1.7360 -1.1184 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6327 1.2503 -0.4190 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7781 2.0012 -0.2755 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8571 1.5103 0.4192 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7420 0.2517 0.9573 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5780 -0.5204 0.8158 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4945 -0.0362 0.1222 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3194 -0.7246 -0.0634 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0035 -1.9953 0.3929 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9107 -2.0637 1.2143 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6751 -2.1526 0.6812 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2225 -1.0169 1.2151 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5178 -1.1667 0.6140 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5110 -0.2591 0.9400 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2853 0.6724 1.7415 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8288 -0.4401 0.3068 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8337 0.3707 0.5549 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1643 0.2661 -0.0242 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5533 -0.7017 -0.9173 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8238 -0.7855 -1.4573 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7444 0.1586 -1.0723 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4014 1.1567 -0.1730 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1204 1.1965 0.3369 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3810 2.0626 0.1605 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1787 3.1262 1.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0288 0.0766 -1.6160 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5131 -2.3322 -0.7750 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7339 -2.2822 -1.6187 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8575 -2.9461 -0.8117 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4124 -4.1514 -0.3252 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1448 -0.9934 -1.9366 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1184 -3.5653 -1.0720 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0680 2.3063 0.5700 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1315 3.4549 0.0621 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2575 1.8175 1.3102 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3666 2.9807 -2.5255 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9793 3.7825 -0.9901 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6369 3.3330 -2.1155 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8556 2.9946 -0.7061 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5836 -0.1508 1.5087 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5577 -1.4955 1.2625 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8493 -2.4264 0.9614 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2005 -3.0609 1.1739 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3873 -1.1270 2.3068 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2128 -0.0359 1.0352 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9929 -1.2540 -0.3821 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5986 1.1775 1.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8239 -1.4400 -1.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1063 -1.5586 -2.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9086 2.0042 1.0401 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4763 3.8564 0.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7183 2.7723 1.9937 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1448 3.6091 1.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6227 -0.7390 -1.4201 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2547 -1.5749 -1.1243 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5531 -2.8117 -2.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7975 -2.9726 -1.3578 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5020 -4.8903 -0.9553 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3908 -0.4064 -2.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6844 -3.8736 -0.3406 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1396 1.9253 2.4066 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3916 0.7133 1.1401 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1586 2.3600 0.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 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 2 0 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 22 27 1 0 12 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 5 34 1 0 34 35 2 0 34 36 1 0 8 3 1 0 30 10 1 0 24 19 1 0 1 37 1 0 1 38 1 0 1 39 1 0 4 40 1 0 6 41 1 0 7 42 1 0 10 43 1 1 12 44 1 1 13 45 1 0 13 46 1 0 17 47 1 0 18 48 1 0 20 49 1 0 21 50 1 0 24 51 1 0 26 52 1 0 26 53 1 0 26 54 1 0 27 55 1 0 28 56 1 6 29 57 1 6 30 58 1 6 31 59 1 0 32 60 1 0 33 61 1 0 36 62 1 0 36 63 1 0 36 64 1 0 M END

Standard InCHIKey	MHPWKMWQIOIJHD-WDOAYHAPSA-N
Standard InCHI	InChI=1S/C25H28O11/c1-13(26)15-6-8-17(19(11-15)33-3)35-25-24(31)23(30)22(29)20(36-25)12-34-21(28)9-5-14-4-7-16(27)18(10-14)32-2/h4-11,20,22-25,27,29-31H,12H2,1-3H3/b9-5+/t20-,22-,23+,24-,25-/m1/s1
SMILES	COc1cc(ccc1O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O)C(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.16	Volume:	488.251 ? Van der Waals volume.
Dense:	1.033	LogP:	1.388 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.681 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.9 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	21.0
TPSA:	161.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.219	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.735	Fsp³:	0.36
MCE-18:	72.471 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.768	Fluc inhibitor:	0.987 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.324 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.819 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.114	Promiscuous compounds:	0.332

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.971	MDCK Permeability:	-5.143
Pgp-inhibitor:	0.085	Pgp-substrate:	0.127
PAMPA:	0.23 ? 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):	0.187
20% Bioavailability (F20%):	0.525	30% Bioavailability (F30%):	0.858
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.028
Plasma Protein Binding (PPB):	76.043%	Volume Distribution (VD):	-0.399
Fu:	22.516% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.184
BSEP inhibitor:	0.852

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.46 ? 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):

2.225

Half-life (T1/2):

2.476

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.378
Human Hepatotoxicity (H-HT):	0.463	Drug-induced Liver Injury (DILI):	0.854
AMES Toxicity:	0.814	Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.1	Skin Sensitization:	0.97
Carcinogencity:	0.2	Eye Corrosion:	0.0
Eye Irritation:	0.513	Respiratory Toxicity:	0.059
Drug-induced Neurotoxicity:	0.111	Ototoxicity:	0.63
Hematotoxicity:	0.231	Drug-induced Nephrotoxicity:	0.819
Genotoxicity:	0.283	RPMI-8226 Immunitoxicity:	0.286
A549 Cytotoxicity:	0.244	Hek293 Cytotoxicity:	0.274
BCF:	0.51 ? 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:	3.223 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.593 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.997 ? 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
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	root	n.a.	PMID[15133218]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	root	n.a.	PMID[15706916]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24035096]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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
IC50	1

Activity Type	# Activity
Organism	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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	25000.0	nM	PMID[19226152]

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 NPC471405 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	9458
0.1-0.2	33742
0.2-0.3	5250
0.3-0.4	1080
0.4-0.5	262
0.5-0.6	44
0.6-0.7	10
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8732	High Similarity	NPC10205
0.8056	Intermediate Similarity	NPC137813
0.7317	Intermediate Similarity	NPC11411
0.7089	Intermediate Similarity	NPC157816
0.6933	Remote Similarity	NPC291153
0.6842	Remote Similarity	NPC157898
0.6835	Remote Similarity	NPC291296
0.6667	Remote Similarity	NPC479767
0.6548	Remote Similarity	NPC476865
0.6386	Remote Similarity	NPC476869
0.631	Remote Similarity	NPC476868
0.6118	Remote Similarity	NPC488082
0.6023	Remote Similarity	NPC488081
0.6	Remote Similarity	NPC226005
0.5909	Remote Similarity	NPC83743
0.5889	Remote Similarity	NPC133984
0.5876	Remote Similarity	NPC470416
0.5825	Remote Similarity	NPC488078
0.5816	Remote Similarity	NPC480796
0.5816	Remote Similarity	NPC472993
0.5778	Remote Similarity	NPC300262
0.5698	Remote Similarity	NPC204937
0.5673	Remote Similarity	NPC488079
0.5618	Remote Similarity	NPC262182
0.561	Remote Similarity	NPC327032
0.5591	Remote Similarity	NPC7191
0.5591	Remote Similarity	NPC149873
0.5517	Remote Similarity	NPC134905
0.5517	Remote Similarity	NPC476864
0.5484	Remote Similarity	NPC125823
0.5484	Remote Similarity	NPC7145
0.5484	Remote Similarity	NPC143480
0.5474	Remote Similarity	NPC201148
0.5455	Remote Similarity	NPC289811
0.5455	Remote Similarity	NPC157554
0.5455	Remote Similarity	NPC476866
0.5402	Remote Similarity	NPC476867
0.5368	Remote Similarity	NPC472611
0.5362	Remote Similarity	NPC202474
0.5333	Remote Similarity	NPC476870
0.5288	Remote Similarity	NPC484988
0.5217	Remote Similarity	NPC472876
0.5208	Remote Similarity	NPC600370
0.5161	Remote Similarity	NPC216819
0.5161	Remote Similarity	NPC80732
0.5158	Remote Similarity	NPC287615
0.5158	Remote Similarity	NPC199311
0.5158	Remote Similarity	NPC476871
0.5152	Remote Similarity	NPC36138
0.5146	Remote Similarity	NPC217520
0.5114	Remote Similarity	NPC194095
0.5104	Remote Similarity	NPC3460
0.5059	Remote Similarity	NPC311803
0.5057	Remote Similarity	NPC5786
0.5056	Remote Similarity	NPC199928
0.5055	Remote Similarity	NPC21516
0.5049	Remote Similarity	NPC477895
0.5048	Remote Similarity	NPC139571

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3181
0.1-0.2	5760
0.2-0.3	193
0.3-0.4	15
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