NPASS Compound

Natural Product: NPC228907

Natural Product ID	NPC228907
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pyrocatechol-O-Beta-D-Diglucopyranoside
IUPAC Name	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL512797
PubChem CID	44577197
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 56 58 0 0 0 0 0 0 0 0999 V2000 -0.8260 -3.3607 -2.1832 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5317 -3.3677 -2.3733 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2704 -2.3564 -1.7514 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6880 -1.3859 -0.9785 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7129 -1.4147 -0.8082 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4594 -2.4032 -1.4127 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2285 -0.4157 -0.0240 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5619 -0.2619 0.2674 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8445 -0.3241 1.7751 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3492 -0.4112 1.9225 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9634 0.8206 1.2740 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4573 0.8729 -0.1380 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1238 1.9499 -0.9605 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7993 3.1863 -0.4564 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0694 0.9922 -0.1477 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3417 0.6880 1.2520 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7386 -0.5505 3.2403 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3216 -1.5452 2.2352 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3665 -0.3762 -0.3496 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7277 -0.2034 -0.4116 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1131 1.1611 -1.0181 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6003 1.0952 -1.2301 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2701 0.8820 0.0854 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6035 -0.1530 0.9493 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0002 0.1613 2.3799 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4823 1.4242 2.6654 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2335 -0.1373 0.8902 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5757 0.4385 -0.1597 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1117 2.2677 -1.7893 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3967 1.4256 -2.1602 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4248 -4.1238 -2.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0412 -4.1100 -2.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3436 -2.3735 -1.9100 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5470 -2.4436 -1.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2475 -1.0060 -0.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4066 0.5268 2.3007 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6806 -1.2767 1.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6390 1.6973 1.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6729 -0.1351 -0.5972 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2026 1.7489 -0.9661 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7692 1.7970 -2.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1519 3.8814 -1.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7462 1.5922 1.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5979 -1.0760 3.2522 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9955 -2.0851 2.7007 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3063 -0.9298 -1.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9321 1.9350 -0.2242 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7799 0.2220 -1.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3021 1.8694 0.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0135 -1.1668 0.6920 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0991 0.1179 2.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4741 -0.5547 3.0691 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9995 1.8972 3.3616 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8299 0.5509 -1.1200 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6826 2.3640 -2.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1041 2.3826 -2.1069 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 5 7 1 0 7 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 12 15 1 0 11 16 1 0 10 17 1 0 9 18 1 0 4 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 22 29 1 0 21 30 1 0 6 1 1 0 15 8 1 0 27 20 1 0 1 31 1 0 2 32 1 0 3 33 1 0 6 34 1 0 8 35 1 6 9 36 1 1 10 37 1 6 11 38 1 1 12 39 1 6 13 40 1 0 13 41 1 0 14 42 1 0 16 43 1 0 17 44 1 0 18 45 1 0 20 46 1 6 21 47 1 1 22 48 1 6 23 49 1 1 24 50 1 6 25 51 1 0 25 52 1 0 26 53 1 0 28 54 1 0 29 55 1 0 30 56 1 0 M END

Standard InCHIKey	QWZXKMQLRBUBMH-NNUBVHJDSA-N
Standard InCHI	InChI=1S/C18H26O12/c19-5-9-11(21)13(23)15(25)17(29-9)27-7-3-1-2-4-8(7)28-18-16(26)14(24)12(22)10(6-20)30-18/h1-4,9-26H,5-6H2/t9-,10-,11-,12-,13+,14+,15-,16-,17-,18-/m1/s1
SMILES	c1ccc(c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	434.14	Volume:	391.788 ? Van der Waals volume.
Dense:	1.108	LogP:	-1.664 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.834 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.622 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	18.0
TPSA:	198.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	8.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.216	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.149	Fsp³:	0.667
MCE-18:	77.0 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.419	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.059 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.02 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.421	Promiscuous compounds:	0.05

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.827	MDCK Permeability:	-4.921
Pgp-inhibitor:	0.0	Pgp-substrate:	0.402
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):	0.991
20% Bioavailability (F20%):	0.238	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.692	MRP1:	0.007
Plasma Protein Binding (PPB):	55.129%	Volume Distribution (VD):	-0.423
Fu:	45.245% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.026
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:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.093
HLM stability:	0.008 ? 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):

0.933

Half-life (T1/2):

3.346

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.735	Drug-induced Liver Injury (DILI):	0.895
AMES Toxicity:	0.95	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.05	Eye Corrosion:	0.0
Eye Irritation:	0.049	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.985
Hematotoxicity:	0.274	Drug-induced Nephrotoxicity:	0.918
Genotoxicity:	0.06	RPMI-8226 Immunitoxicity:	0.146
A549 Cytotoxicity:	0.239	Hek293 Cytotoxicity:	0.051
BCF:	0.318 ? 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:	2.418 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.892 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.011 ? 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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9317	Itoa orientalis	Species	Salicaceae	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
Inhibition	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
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	54.3	%	PubChem BioAssay data set

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 NPC228907 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	15079
0.1-0.2	31125
0.2-0.3	2532
0.3-0.4	663
0.4-0.5	352
0.5-0.6	66
0.6-0.7	26
0.7-0.8	1
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
0.7381	Intermediate Similarity	NPC25817
0.7045	Intermediate Similarity	NPC226712
0.6977	Remote Similarity	NPC9248
0.6744	Remote Similarity	NPC153149
0.6739	Remote Similarity	NPC166040
0.6667	Remote Similarity	NPC276195
0.6667	Remote Similarity	NPC212729
0.6667	Remote Similarity	NPC142319
0.6667	Remote Similarity	NPC604498
0.6667	Remote Similarity	NPC608788
0.6596	Remote Similarity	NPC9912
0.6512	Remote Similarity	NPC217854
0.6512	Remote Similarity	NPC269242
0.6364	Remote Similarity	NPC294470
0.6327	Remote Similarity	NPC472024
0.6327	Remote Similarity	NPC270849
0.6222	Remote Similarity	NPC152722
0.62	Remote Similarity	NPC26653
0.62	Remote Similarity	NPC80600
0.617	Remote Similarity	NPC145900
0.6136	Remote Similarity	NPC484157
0.6087	Remote Similarity	NPC299144
0.6087	Remote Similarity	NPC60589
0.6087	Remote Similarity	NPC469708
0.6087	Remote Similarity	NPC604439
0.6087	Remote Similarity	NPC609376
0.6078	Remote Similarity	NPC248355
0.6	Remote Similarity	NPC192810
0.5962	Remote Similarity	NPC55040
0.5957	Remote Similarity	NPC200092
0.5849	Remote Similarity	NPC302378
0.5849	Remote Similarity	NPC247146
0.5833	Remote Similarity	NPC221090
0.5833	Remote Similarity	NPC69513
0.5833	Remote Similarity	NPC80098
0.5769	Remote Similarity	NPC479029
0.5714	Remote Similarity	NPC48863
0.5714	Remote Similarity	NPC166168
0.5714	Remote Similarity	NPC214454
0.5714	Remote Similarity	NPC95292
0.5714	Remote Similarity	NPC251981
0.5714	Remote Similarity	NPC13745
0.5686	Remote Similarity	NPC606892
0.5636	Remote Similarity	NPC276753
0.5636	Remote Similarity	NPC205796
0.5625	Remote Similarity	NPC12308
0.56	Remote Similarity	NPC40377
0.56	Remote Similarity	NPC310661
0.56	Remote Similarity	NPC215833
0.5577	Remote Similarity	NPC164599
0.5577	Remote Similarity	NPC210478
0.5556	Remote Similarity	NPC34456
0.5536	Remote Similarity	NPC37468
0.5536	Remote Similarity	NPC246947
0.5536	Remote Similarity	NPC604095
0.549	Remote Similarity	NPC218685
0.549	Remote Similarity	NPC49074
0.5455	Remote Similarity	NPC99515
0.5455	Remote Similarity	NPC146540
0.5455	Remote Similarity	NPC52740
0.5455	Remote Similarity	NPC269421
0.54	Remote Similarity	NPC604209
0.5385	Remote Similarity	NPC251102
0.5385	Remote Similarity	NPC162093
0.5385	Remote Similarity	NPC479028
0.5385	Remote Similarity	NPC485268
0.5385	Remote Similarity	NPC83975
0.5385	Remote Similarity	NPC205054
0.5385	Remote Similarity	NPC210298
0.5385	Remote Similarity	NPC23084
0.5385	Remote Similarity	NPC479031
0.5385	Remote Similarity	NPC19470
0.5385	Remote Similarity	NPC604356
0.537	Remote Similarity	NPC222455
0.537	Remote Similarity	NPC104167
0.5283	Remote Similarity	NPC26080
0.5283	Remote Similarity	NPC165686
0.5283	Remote Similarity	NPC481303
0.5273	Remote Similarity	NPC604162
0.5192	Remote Similarity	NPC265442
0.5185	Remote Similarity	NPC105827
0.5185	Remote Similarity	NPC288349
0.5179	Remote Similarity	NPC190714
0.5179	Remote Similarity	NPC600105
0.5172	Remote Similarity	NPC60756
0.5172	Remote Similarity	NPC175976
0.5091	Remote Similarity	NPC95392
0.5091	Remote Similarity	NPC84013
0.5091	Remote Similarity	NPC55715
0.5091	Remote Similarity	NPC106025
0.5091	Remote Similarity	NPC35877
0.5091	Remote Similarity	NPC25292
0.5091	Remote Similarity	NPC599943
0.5088	Remote Similarity	NPC96294

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC228907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4611
0.1-0.2	4334
0.2-0.3	167
0.3-0.4	31
0.4-0.5	6
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7045	Intermediate Similarity	NPD1091	Pre-clinical

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