NPASS Compound

Natural Product: NPC124155

Natural Product ID	NPC124155
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4'-O-Glucosylaciculatin
IUPAC Name	8-[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5-hydroxy-7-methoxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms	4'-O-Glucosylaciculatin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2011653
PubChem CID	57332648
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-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 73 77 0 0 0 0 0 0 0 0999 V2000 -6.2868 3.3942 -0.1641 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3490 2.3072 -0.5961 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9693 1.4793 -1.6904 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0548 0.2878 -1.9396 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7533 0.4499 -1.2311 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9270 0.6951 0.2383 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1063 -0.6267 0.9115 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3610 -1.1028 1.2453 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4682 -2.3354 1.8473 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3499 -3.0990 2.1216 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1241 -2.6004 1.7802 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9895 -3.3352 2.0409 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0164 -4.4696 2.5888 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7697 -2.7596 1.6643 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6699 -1.5302 1.0647 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5989 -0.9329 0.6738 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7956 -1.5469 0.8818 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0136 -0.9825 0.5114 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0657 0.2442 -0.0935 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8399 0.8816 -0.3110 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6496 0.3133 0.0597 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2370 0.8584 -0.4844 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5402 0.3849 -0.3447 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2080 0.1444 -1.6878 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2776 1.1574 -1.9998 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3064 1.0758 -0.8909 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6586 0.8460 0.4529 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4589 1.5303 1.5196 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7826 1.0697 1.4078 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3224 1.2187 0.4601 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1575 0.0095 -1.1698 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7963 2.4304 -2.1885 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8115 -1.1062 -1.6385 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8117 -0.8779 0.8440 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9637 -1.3796 1.1796 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4515 -4.3415 2.7274 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4667 -0.3152 0.9615 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7801 -0.7171 1.2672 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0852 1.4685 0.4881 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8182 0.1246 -3.3067 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0673 2.1775 -2.8880 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0255 3.5450 -0.9968 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7403 4.3435 -0.0114 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8302 3.0737 0.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4037 2.7968 -0.9513 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9721 1.1738 -1.3519 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5545 -0.6253 -1.5808 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1989 -0.5263 -1.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0855 1.2012 -1.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0974 1.2622 0.6677 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4263 -2.7471 2.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1400 -3.3352 1.8656 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8572 -2.5179 1.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9121 -1.5407 0.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8504 1.8655 -0.7926 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3085 0.8053 -0.1070 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5161 -0.5835 0.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4004 0.1613 -2.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7795 0.8266 -2.9241 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9056 2.0127 -0.8045 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6922 -0.2444 0.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1179 1.3318 2.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5284 2.6284 1.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0478 0.5473 2.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9356 -0.8087 -0.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9654 2.9725 -1.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2585 -1.3381 -2.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2485 -5.1534 2.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2355 -1.2890 0.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8247 -1.2998 2.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4440 0.1826 1.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2364 -0.6865 -3.6456 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1554 1.4761 -3.6026 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 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 24 33 1 0 15 34 1 0 34 35 1 0 10 36 1 0 8 37 1 0 37 38 1 0 6 39 1 0 4 40 1 0 3 41 1 0 39 2 1 0 35 7 1 0 35 11 2 0 21 16 1 0 30 23 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 6 3 46 1 1 4 47 1 1 5 48 1 0 5 49 1 0 6 50 1 1 9 51 1 0 14 52 1 0 17 53 1 0 18 54 1 0 20 55 1 0 21 56 1 0 23 57 1 1 24 58 1 6 25 59 1 6 26 60 1 1 27 61 1 1 28 62 1 0 28 63 1 0 29 64 1 0 31 65 1 0 32 66 1 0 33 67 1 0 36 68 1 0 38 69 1 0 38 70 1 0 38 71 1 0 40 72 1 0 41 73 1 0 M END

Standard InCHIKey	ZULIRTBISMVOJB-YZWJOIRQSA-N
Standard InCHI	InChI=1S/C28H32O13/c1-11-23(33)16(32)9-19(38-11)22-18(37-2)8-15(31)21-14(30)7-17(40-27(21)22)12-3-5-13(6-4-12)39-28-26(36)25(35)24(34)20(10-29)41-28/h3-8,11,16,19-20,23-26,28-29,31-36H,9-10H2,1-2H3/t11-,16+,19-,20-,23-,24-,25+,26-,28-/m1/s1
SMILES	C[C@@H]1[C@H]([C@H](C[C@H](c2c(cc(c3c(=O)cc(c4ccc(cc4)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)oc23)O)OC)O1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.18	Volume:	543.243 ? Van der Waals volume.
Dense:	1.061	LogP:	0.729 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.323 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.403 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	208.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.205	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.682	Fsp³:	0.464
MCE-18:	115.098 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.614	Fluc inhibitor:	0.151 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.929 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.644 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.082	Promiscuous compounds:	0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.287	MDCK Permeability:	-5.301
Pgp-inhibitor:	0.0	Pgp-substrate:	0.752
PAMPA:	0.961 ? 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):	0.062
20% Bioavailability (F20%):	0.055	30% Bioavailability (F30%):	0.959
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.636
Plasma Protein Binding (PPB):	88.715%	Volume Distribution (VD):	-0.047
Fu:	10.732% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.11
BSEP inhibitor:	0.072

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:	0.286
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.966
HLM stability:	0.005 ? 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):

2.366

Half-life (T1/2):

4.515

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.09
Human Hepatotoxicity (H-HT):	0.838	Drug-induced Liver Injury (DILI):	0.993
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.184	Skin Sensitization:	0.996
Carcinogencity:	0.273	Eye Corrosion:	0.0
Eye Irritation:	0.079	Respiratory Toxicity:	0.081
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.925
Hematotoxicity:	0.63	Drug-induced Nephrotoxicity:	0.853
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.333
A549 Cytotoxicity:	0.784	Hek293 Cytotoxicity:	0.539
BCF:	0.496 ? 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:	3.297 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.908 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.993 ? 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
NPO32718	chrysopogon aciculatis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22272829]

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	4

Activity Type	# Activity
Cell line	4

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
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[8021914]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	>	100000.0	nM	DrugMatrix in vitro pharmacology data
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	100000.0	nM	PMID[16933875]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	>	100000.0	nM	PMID[8699183]

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 NPC124155 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	11857
0.1-0.2	33123
0.2-0.3	3726
0.3-0.4	892
0.4-0.5	210
0.5-0.6	38
0.6-0.7	6
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
0.7059	Intermediate Similarity	NPC607327
0.6292	Remote Similarity	NPC95090
0.6292	Remote Similarity	NPC27408
0.6044	Remote Similarity	NPC186807
0.604	Remote Similarity	NPC256760
0.6	Remote Similarity	NPC58053
0.6	Remote Similarity	NPC150767
0.5934	Remote Similarity	NPC111341
0.5824	Remote Similarity	NPC143851
0.58	Remote Similarity	NPC606547
0.5789	Remote Similarity	NPC607707
0.5684	Remote Similarity	NPC22832
0.5684	Remote Similarity	NPC243930
0.5556	Remote Similarity	NPC603300
0.5545	Remote Similarity	NPC106700
0.5545	Remote Similarity	NPC131745
0.5484	Remote Similarity	NPC39360
0.5484	Remote Similarity	NPC29763
0.5484	Remote Similarity	NPC210003
0.5417	Remote Similarity	NPC609451
0.5368	Remote Similarity	NPC105025
0.5333	Remote Similarity	NPC5319
0.5319	Remote Similarity	NPC261866
0.5306	Remote Similarity	NPC88023
0.5306	Remote Similarity	NPC311830
0.5306	Remote Similarity	NPC309025
0.5263	Remote Similarity	NPC189142
0.5263	Remote Similarity	NPC77660
0.5208	Remote Similarity	NPC181712
0.5204	Remote Similarity	NPC605067
0.5158	Remote Similarity	NPC289667
0.5155	Remote Similarity	NPC201292
0.5152	Remote Similarity	NPC220169
0.514	Remote Similarity	NPC475382
0.5104	Remote Similarity	NPC93337
0.5096	Remote Similarity	NPC606373
0.5088	Remote Similarity	NPC132111
0.5054	Remote Similarity	NPC56232
0.5054	Remote Similarity	NPC150123
0.5054	Remote Similarity	NPC608009
0.5051	Remote Similarity	NPC148710
0.5051	Remote Similarity	NPC80188
0.5051	Remote Similarity	NPC486578
0.5051	Remote Similarity	NPC601144
0.505	Remote Similarity	NPC211594

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC124155 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3591
0.1-0.2	5442
0.2-0.3	100
0.3-0.4	15
0.4-0.5	1
0.5-0.6	1
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
0.5333	Remote Similarity	NPD7804	Clinical (unspecified phase)

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