NPASS Compound

Natural Product: NPC472711

Natural Product ID	NPC472711
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RLJNIUWDLJTFJV-DZUWHBGLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581697
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 70 73 0 0 0 0 0 0 0 0999 V2000 -1.9182 -4.6978 -1.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5949 -3.4402 -0.7178 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9151 -3.8046 -0.1479 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3790 -2.9288 0.9736 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2810 -2.3775 1.8139 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2585 -1.7387 0.8156 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7274 -2.8489 0.1890 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3123 -1.1672 1.6196 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2170 0.2113 1.5816 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8053 0.8157 0.3413 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5490 0.5460 -0.2414 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3932 1.3852 -1.5121 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6987 2.2270 -1.3326 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9549 2.2420 0.0778 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0990 3.2624 0.5935 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1246 4.4780 -0.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6229 5.5678 0.2117 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4505 5.4747 1.3187 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5172 4.3188 2.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7305 3.2225 1.6727 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2402 6.5564 1.7145 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5917 6.7603 -0.5011 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2646 6.8215 -1.6257 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7098 -0.9008 -0.5400 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0498 -1.2299 -1.1129 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0961 -1.5124 -0.2606 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3573 -1.8328 -0.7134 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5125 -1.8545 -2.0835 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4939 -1.5791 -2.9558 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2447 -1.2623 -2.4689 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7976 -2.1808 -2.5552 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4205 -2.1196 0.1470 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1934 -2.0794 1.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7777 -1.4258 2.6681 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2319 -3.6663 1.8085 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8684 -3.6977 -1.1850 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7016 -5.4579 -1.3926 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4431 -4.5031 -2.2046 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1592 -5.0614 -0.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6881 -2.7203 -1.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9865 -4.8728 0.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9632 -2.0669 0.5503 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7004 -3.1760 2.3156 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8223 -1.0526 0.1615 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4413 0.4064 2.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2217 0.5610 1.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4992 0.3350 -0.4749 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3768 0.9465 0.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0726 0.6647 -2.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3110 1.8662 -1.8326 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0198 2.5639 0.1578 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7649 4.5965 -1.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1348 4.1838 2.9191 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7740 2.3261 2.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2631 6.4914 1.6580 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0731 6.1363 -2.4359 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2814 6.5543 -1.2537 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3030 7.8794 -1.9952 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6121 -1.4792 0.3962 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0954 -1.2571 -1.2371 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9453 -1.4880 0.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6491 -1.6049 -4.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4280 -1.0471 -3.1770 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2107 -1.4613 -3.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1506 -2.2754 2.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4950 -2.8878 1.8371 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7308 -1.1199 1.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2247 -1.3097 3.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1648 -3.4035 2.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2889 -2.8110 -1.2070 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 1 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 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 18 21 1 0 17 22 1 0 22 23 1 0 11 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 28 31 1 0 27 32 1 0 32 33 1 0 5 34 1 0 4 35 1 0 3 36 1 0 7 2 1 0 14 10 1 0 20 15 1 0 30 25 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 3 41 1 0 4 42 1 0 5 43 1 0 6 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 14 51 1 0 16 52 1 0 19 53 1 0 20 54 1 0 21 55 1 0 23 56 1 0 23 57 1 0 23 58 1 0 24 59 1 0 24 60 1 0 26 61 1 0 29 62 1 0 30 63 1 0 31 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 34 68 1 0 35 69 1 0 36 70 1 0 M END

Standard InCHIKey	RLJNIUWDLJTFJV-DZUWHBGLSA-N
Standard InCHI	InChI=1S/C26H34O10/c1-13-22(29)23(30)24(31)26(36-13)35-12-17-16(8-14-4-6-18(27)20(9-14)32-2)11-34-25(17)15-5-7-19(28)21(10-15)33-3/h4-7,9-10,13,16-17,22-31H,8,11-12H2,1-3H3/t13-,16+,17+,22-,23+,24+,25-,26+/m0/s1
SMILES	CC1C(C(C(C(O1)OCC2C(COC2C3=CC(=C(C=C3)O)OC)CC4=CC(=C(C=C4)O)OC)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	506.22	Volume:	496.11 ? Van der Waals volume.
Dense:	1.02	LogP:	0.6 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.24 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.889 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	23.0
TPSA:	147.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.357	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.37	Fsp³:	0.538
MCE-18:	89.7 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.134	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.725 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.106	Promiscuous compounds:	0.281

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.204	MDCK Permeability:	-5.261
Pgp-inhibitor:	0.001	Pgp-substrate:	0.851
PAMPA:	0.343 ? 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):	0.058
20% Bioavailability (F20%):	0.506	30% Bioavailability (F30%):	0.636
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.99
Plasma Protein Binding (PPB):	69.957%	Volume Distribution (VD):	-0.415
Fu:	29.957% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.941
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.087
BSEP inhibitor:	0.42

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.862	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.961	CYP2D6-substrate:	0.967
CYP3A4-inhibitor:	0.184	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.754
HLM stability:	0.08 ? 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):

4.464

Half-life (T1/2):

2.443

ADMET: Toxicity

hERG Blockers:	0.159	hERG Blockers (10um):	0.684
Human Hepatotoxicity (H-HT):	0.525	Drug-induced Liver Injury (DILI):	0.469
AMES Toxicity:	0.639	Rat Oral Acute Toxicity:	0.355
Maximum Recommended Daily Dose:	0.373	Skin Sensitization:	0.326
Carcinogencity:	0.139	Eye Corrosion:	0.0
Eye Irritation:	0.061	Respiratory Toxicity:	0.156
Drug-induced Neurotoxicity:	0.58	Ototoxicity:	0.956
Hematotoxicity:	0.056	Drug-induced Nephrotoxicity:	0.18
Genotoxicity:	0.109	RPMI-8226 Immunitoxicity:	0.147
A549 Cytotoxicity:	0.176	Hek293 Cytotoxicity:	0.834
BCF:	0.905 ? 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:	3.46 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.186 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.226 ? 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
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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
IC50	5

Activity Type	# Activity
Cell line	5
Non-molecular	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
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	144.31	%	PMID[26341134]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	DrugMatrix in vivo data: Pathology
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[19015349]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	Open TG-GATES in vivo data: Hematology
NPT148	Cell line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	179700.0	nM	PMID[25894905]

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 NPC472711 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	14046
0.1-0.2	30422
0.2-0.3	4555
0.3-0.4	636
0.4-0.5	165
0.5-0.6	25
0.6-0.7	8
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	Natural Product ID
0.7826	Intermediate Similarity	NPC472713
0.6714	Remote Similarity	NPC278961
0.6714	Remote Similarity	NPC113680
0.6667	Remote Similarity	NPC67247
0.6622	Remote Similarity	NPC606627
0.6216	Remote Similarity	NPC281780
0.6	Remote Similarity	NPC187998
0.6	Remote Similarity	NPC257582
0.6	Remote Similarity	NPC241522
0.5904	Remote Similarity	NPC486545
0.5823	Remote Similarity	NPC67467
0.5789	Remote Similarity	NPC267091
0.5733	Remote Similarity	NPC472714
0.5584	Remote Similarity	NPC473046
0.5581	Remote Similarity	NPC185307
0.5581	Remote Similarity	NPC470950
0.5467	Remote Similarity	NPC42300
0.5405	Remote Similarity	NPC486558
0.5405	Remote Similarity	NPC282833
0.5405	Remote Similarity	NPC145144
0.5395	Remote Similarity	NPC64201
0.5244	Remote Similarity	NPC51328
0.5244	Remote Similarity	NPC252402
0.5244	Remote Similarity	NPC102934
0.5244	Remote Similarity	NPC55158
0.5233	Remote Similarity	NPC286245
0.5181	Remote Similarity	NPC38041
0.5181	Remote Similarity	NPC22150
0.5152	Remote Similarity	NPC115207
0.5152	Remote Similarity	NPC158079
0.5152	Remote Similarity	NPC228346
0.5152	Remote Similarity	NPC40432
0.5152	Remote Similarity	NPC161557
0.5111	Remote Similarity	NPC15956

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472711 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4190
0.1-0.2	4812
0.2-0.3	142
0.3-0.4	6
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