NPASS Compound

Natural Product: NPC168358

Natural Product ID	NPC168358
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HEZGCCGUQRUGNI-NOAXIPAFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321882
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene 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 72 75 0 0 0 0 0 0 0 0999 V2000 -3.4296 -0.4802 -1.4348 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6332 -1.1106 -0.6255 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9198 -2.4438 -0.0914 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0553 -3.1312 -0.4316 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3468 -4.3990 0.0611 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4447 -4.9622 0.9208 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2906 -4.3068 1.2897 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0264 -3.0537 0.7887 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8543 -2.4322 1.1878 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7476 -1.5671 2.3168 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1431 -2.1289 3.3647 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6026 -1.8484 3.2439 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7998 -0.4605 2.6210 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5225 0.3011 2.7140 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6657 1.7520 2.3693 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9259 2.0386 1.0998 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0239 1.7789 0.4162 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7764 1.0451 -0.9171 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1313 0.6822 -1.4483 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2464 1.5561 -1.0122 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8881 2.8617 -0.4083 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2264 3.9605 -1.4260 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4070 3.8385 -2.5460 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5778 3.0221 -0.0574 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0032 0.8369 -0.0566 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0373 0.6886 -2.8596 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9939 -0.0678 -0.7872 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4476 -0.2804 1.9456 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8310 0.2034 3.3007 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3020 -2.8148 2.5531 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3214 -1.7663 4.6508 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4647 -4.9981 2.1671 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5007 -5.0703 -0.2987 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2305 0.8359 -2.0103 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1401 1.5790 -1.7167 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9674 2.8389 -2.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8936 3.3561 -3.1517 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0133 2.6122 -3.4633 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1604 1.3506 -2.8782 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7427 4.6122 -3.7314 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3621 -0.9875 -1.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7103 -0.5955 -0.3616 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7993 -2.7255 -1.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6684 -5.9504 1.3068 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8169 -1.5083 2.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0712 -3.2650 3.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0317 -1.7982 4.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0995 -0.6606 1.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1782 0.2906 3.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4835 2.1242 3.0845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2735 2.3202 2.6842 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8843 1.2886 0.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3454 1.8121 -1.5972 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3389 -0.3928 -1.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9758 1.7010 -1.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5053 3.0750 0.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1442 4.9649 -0.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2731 3.8666 -1.7723 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9232 3.7585 -3.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9621 1.0177 -0.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5769 -0.1519 -3.1309 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5710 -0.8718 -0.7593 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4322 0.5486 4.1359 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5165 -2.5502 1.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2602 -2.0167 4.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7849 -5.5070 2.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5466 -6.0822 -0.2568 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3743 1.2441 -1.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0969 3.4099 -2.0387 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7455 3.0052 -4.1404 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0540 0.7845 -3.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2933 5.4234 -3.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 20 25 1 0 19 26 1 0 18 27 1 0 14 28 1 0 13 29 1 0 12 30 1 0 11 31 1 0 7 32 1 0 5 33 1 0 1 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 8 3 1 0 28 10 1 0 39 34 1 0 24 17 1 0 1 41 1 0 2 42 1 0 4 43 1 0 6 44 1 0 10 45 1 1 11 46 1 1 12 47 1 1 13 48 1 6 14 49 1 1 15 50 1 0 15 51 1 0 17 52 1 1 18 53 1 6 19 54 1 1 20 55 1 6 21 56 1 1 22 57 1 0 22 58 1 0 23 59 1 0 25 60 1 0 26 61 1 0 27 62 1 0 29 63 1 0 30 64 1 0 31 65 1 0 32 66 1 0 33 67 1 0 35 68 1 0 36 69 1 0 38 70 1 0 39 71 1 0 40 72 1 0 M END

Standard InCHIKey	HEZGCCGUQRUGNI-NOAXIPAFSA-N
Standard InCHI	InChI=1S/C26H32O14/c27-9-16-18(31)20(33)22(35)25(38-16)37-10-17-19(32)21(34)23(36)26(39-17)40-24-12(7-14(29)8-15(24)30)4-1-11-2-5-13(28)6-3-11/h1-8,16-23,25-36H,9-10H2/b4-1+/t16-,17-,18-,19-,20+,21+,22-,23-,25-,26+/m1/s1
SMILES	C(=Cc1cc(cc(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O)O)O)/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.18	Volume:	528.634 ? Van der Waals volume.
Dense:	1.075	LogP:	0.513 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.906 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.747 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	25.0
TPSA:	239.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	10.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.155	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.647	Fsp³:	0.462
MCE-18:	98.737 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.603	Fluc inhibitor:	0.659 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.25 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.452 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.44	Promiscuous compounds:	0.344

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.653	MDCK Permeability:	-5.009
Pgp-inhibitor:	0.0	Pgp-substrate:	0.088
PAMPA:	0.999 ? 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):	0.348
20% Bioavailability (F20%):	0.898	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016	MRP1:	0.003
Plasma Protein Binding (PPB):	79.95%	Volume Distribution (VD):	-0.093
Fu:	19.935% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.036
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.342
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.04 ? 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):

1.026

Half-life (T1/2):

3.757

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.17
Human Hepatotoxicity (H-HT):	0.584	Drug-induced Liver Injury (DILI):	0.359
AMES Toxicity:	0.758	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.026	Skin Sensitization:	0.996
Carcinogencity:	0.033	Eye Corrosion:	0.0
Eye Irritation:	0.735	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.881
Hematotoxicity:	0.027	Drug-induced Nephrotoxicity:	0.711
Genotoxicity:	0.283	RPMI-8226 Immunitoxicity:	0.21
A549 Cytotoxicity:	0.543	Hek293 Cytotoxicity:	0.466
BCF:	0.444 ? 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:	2.897 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.637 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.745 ? 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
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	50000.0	nM	PMID[31944695]

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 NPC168358 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	22159
0.1-0.2	22941
0.2-0.3	3470
0.3-0.4	1061
0.4-0.5	181
0.5-0.6	34
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC252169
0.7714	Intermediate Similarity	NPC199977
0.7571	Intermediate Similarity	NPC478884
0.6812	Remote Similarity	NPC478888
0.6429	Remote Similarity	NPC74374
0.6154	Remote Similarity	NPC40664
0.6154	Remote Similarity	NPC197723
0.6143	Remote Similarity	NPC57751
0.6081	Remote Similarity	NPC87696
0.6026	Remote Similarity	NPC130496
0.5949	Remote Similarity	NPC3293
0.5897	Remote Similarity	NPC478882
0.5867	Remote Similarity	NPC260681
0.5647	Remote Similarity	NPC476866
0.5618	Remote Similarity	NPC478880
0.5618	Remote Similarity	NPC478878
0.5581	Remote Similarity	NPC100936
0.5581	Remote Similarity	NPC1253
0.5556	Remote Similarity	NPC214910
0.5541	Remote Similarity	NPC85799
0.5541	Remote Similarity	NPC303422
0.5526	Remote Similarity	NPC37074
0.5467	Remote Similarity	NPC478871
0.5467	Remote Similarity	NPC478870
0.5467	Remote Similarity	NPC478872
0.5467	Remote Similarity	NPC478873
0.5465	Remote Similarity	NPC476869
0.5455	Remote Similarity	NPC60756
0.5455	Remote Similarity	NPC287780
0.5455	Remote Similarity	NPC60982
0.5405	Remote Similarity	NPC189589
0.5395	Remote Similarity	NPC65530
0.5357	Remote Similarity	NPC70804
0.5342	Remote Similarity	NPC26080
0.5342	Remote Similarity	NPC165686
0.5333	Remote Similarity	NPC208769
0.5258	Remote Similarity	NPC484979
0.5233	Remote Similarity	NPC476867
0.5172	Remote Similarity	NPC476864
0.5165	Remote Similarity	NPC478877
0.5132	Remote Similarity	NPC59324
0.5111	Remote Similarity	NPC478883
0.5056	Remote Similarity	NPC478887
0.5056	Remote Similarity	NPC476868

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC168358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5952
0.1-0.2	3108
0.2-0.3	72
0.3-0.4	18
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