NPASS Compound

Natural Product: NPC177839

Natural Product ID	NPC177839
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pentaacetylquercetin
IUPAC Name	[2-acetyloxy-4-(3,5,7-triacetyloxy-4-oxochromen-2-yl)phenyl] acetate
Synonyms	NSC-115919
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL19074
PubChem CID	14005
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

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 57 59 0 0 0 0 0 0 0 0999 V2000 -6.3925 5.0503 1.3454 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5500 3.8164 1.3637 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1059 3.3615 2.4245 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2340 3.1335 0.1862 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4430 1.9809 0.2335 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0112 0.7339 0.3804 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1950 -0.3683 0.4215 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8241 -0.2031 0.3149 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2329 1.0323 0.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0641 2.1303 0.1277 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9582 1.1458 0.0720 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0767 0.1379 0.1004 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3104 0.4794 -0.0211 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6437 1.8125 -0.2817 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9327 2.2721 -0.4024 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9893 1.3833 -0.2621 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7087 0.0577 -0.0040 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3915 -0.3514 0.1082 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6959 -0.8994 0.1510 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2724 -1.2172 1.3593 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8879 -0.6107 2.3828 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3187 -2.2600 1.3916 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3103 1.7790 -0.3718 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9691 1.7650 -1.5949 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3315 1.3816 -2.6051 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3884 2.1941 -1.6906 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6254 -1.0921 0.2428 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9870 -1.2812 0.3514 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4250 -2.4306 0.4806 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1756 -2.2007 0.2786 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2974 -3.0715 -0.8176 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3588 -2.7898 -1.8297 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1755 -4.2428 -0.7091 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6806 -1.6619 0.5669 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0228 -2.4669 -0.5072 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8839 -1.9960 -1.6620 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5429 -3.8495 -0.3840 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3189 5.5965 0.3888 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0102 5.7256 2.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4387 4.7848 1.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0809 0.6251 0.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6414 3.1075 0.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8665 2.5518 -0.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1551 3.2993 -0.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2250 -1.3710 0.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2432 -2.8339 2.3350 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2993 -1.7609 1.2731 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1652 -3.0025 0.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3694 3.2641 -2.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8491 2.1097 -0.6952 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8916 1.5912 -2.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5126 -4.3810 0.3363 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0531 -4.1643 -1.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5522 -5.1430 -0.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6490 -4.5281 -0.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1003 -4.1314 -1.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1281 -3.9940 0.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 16 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 12 27 2 0 27 28 1 0 28 29 2 0 27 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 7 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 10 5 1 0 18 13 1 0 28 8 1 0 1 38 1 0 1 39 1 0 1 40 1 0 6 41 1 0 10 42 1 0 14 43 1 0 15 44 1 0 18 45 1 0 22 46 1 0 22 47 1 0 22 48 1 0 26 49 1 0 26 50 1 0 26 51 1 0 33 52 1 0 33 53 1 0 33 54 1 0 37 55 1 0 37 56 1 0 37 57 1 0 M END

Standard InCHIKey	JQUHMSXLZZWRHU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C25H20O12/c1-11(26)32-17-9-20(35-14(4)29)22-21(10-17)37-24(25(23(22)31)36-15(5)30)16-6-7-18(33-12(2)27)19(8-16)34-13(3)28/h6-10H,1-5H3
SMILES	CC(=O)Oc1cc(c2c(c1)oc(c1ccc(c(c1)OC(=O)C)OC(=O)C)c(c2=O)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.1	Volume:	486.495 ? Van der Waals volume.
Dense:	1.053	LogP:	1.725 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.06 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.157 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	161.71 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.351	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.827	Fsp³:	0.2
MCE-18:	24.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.018	Fluc inhibitor:	0.422 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.996 ? 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:	0.356	Promiscuous compounds:	0.342

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.924	MDCK Permeability:	-4.516
Pgp-inhibitor:	0.998	Pgp-substrate:	0.02
PAMPA:	0.154 ? 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):	0.005
20% Bioavailability (F20%):	0.083	30% Bioavailability (F30%):	0.915
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	0.905
Plasma Protein Binding (PPB):	75.243%	Volume Distribution (VD):	-0.379
Fu:	23.312% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.174
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.972
HLM stability:	0.994 ? 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):

2.335

Half-life (T1/2):

0.383

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.26	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.458	Rat Oral Acute Toxicity:	0.785
Maximum Recommended Daily Dose:	0.131	Skin Sensitization:	0.976
Carcinogencity:	0.06	Eye Corrosion:	0.773
Eye Irritation:	0.881	Respiratory Toxicity:	0.065
Drug-induced Neurotoxicity:	0.069	Ototoxicity:	0.027
Hematotoxicity:	0.671	Drug-induced Nephrotoxicity:	0.004
Genotoxicity:	0.942	RPMI-8226 Immunitoxicity:	0.012
A549 Cytotoxicity:	0.924	Hek293 Cytotoxicity:	0.095
BCF:	0.706 ? 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:	3.633 ? 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:	4.491 ? 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
NPO28094	Consolida oliveriana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19489596]
NPO33509	byrsonima coccolobifolia	Species	Malpighiaceae	Eukaryota	leaves and stems	cerrado at the Federal University of So Carlos (UFSCar), So Carlos, SP, Brazil	2011-Jul	PMID[24521209]
NPO33118	Rhamnus	Genus	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350094]
NPO28094	Consolida oliveriana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28094	Consolida oliveriana	Species	Ranunculaceae	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	7
IC50	8
Ratio	1
Activity	7
Ratio IC50	2
Activation	4

Activity Type	# Activity
Individual protein	6
Cell line	6
Others	5
Organism	12

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1558	Individual protein	Aflatoxin B1 aldehyde reductase	Rattus norvegicus	Inhibition	=	6.7	%	PMID[27338658]
NPT1558	Individual protein	Aflatoxin B1 aldehyde reductase	Rattus norvegicus	Inhibition	=	12.8	%	PMID[27338658]
NPT1558	Individual protein	Aflatoxin B1 aldehyde reductase	Rattus norvegicus	Inhibition	=	18.0	%	PMID[27338658]
NPT1563	Individual protein	Phosphodiesterase 2A	Rattus norvegicus	IC50	=	275000.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT1310	Individual protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0.0	%	PMID[23013356]
NPT1662	Individual protein	Arginase	Leishmania amazonensis	IC50	=	120800.0	nM	PMID[22608855]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1597	Cell line	J774.2	n.a.	IC50	=	109230.0	nM	DOI[10.1016/j.cropro.2011.12.007]
NPT1597	Cell line	J774.2	n.a.	Ratio IC50	=	10.0	n.a.	PubChem BioAssay data set
NPT1596	Organism	Leishmania peruviana	Leishmania peruviana	IC50	=	11180.0	nM	PMID[19691312]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC50	=	46780.0	nM	PMID[16562830]
NPT1596	Organism	Leishmania peruviana	Leishmania peruviana	Activity	=	40.0	%	PMID[22194678]
NPT1596	Organism	Leishmania peruviana	Leishmania peruviana	Activity	=	72.0	%	PMID[22194678]
NPT1596	Organism	Leishmania peruviana	Leishmania peruviana	Inhibition	=	30.0	%	PMID[19124664]
NPT20967	Cell line	Platelet	n.a.	Activity	=	2.4	%	PMID[8350094]
NPT20967	Cell line	Platelet	n.a.	Activity	=	17.4	%	PMID[8350094]
NPT20967	Cell line	Platelet	n.a.	Activity	=	89.2	%	PMID[8350094]
NPT2	Others	Unspecified	n.a.	IC50	=	355000.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	IC50	=	126000.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	Ratio	=	0.46	n.a.	Open TG-GATES in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	IC50	=	6800.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Inhibition	=	90.0	%	PMID[10691710]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activation	=	7.1	%	PMID[12182864]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activation	=	13.3	%	PMID[12182864]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activation	=	25.0	%	PMID[12182864]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activation	=	37.0	%	PMID[12182864]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	2.25	n.a.	PMID[21546250]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	4.75	n.a.	PMID[21546250]

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 NPC177839 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	34597
0.1-0.2	13560
0.2-0.3	1473
0.3-0.4	174
0.4-0.5	26
0.5-0.6	13
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9245	High Similarity	NPC472535
0.9057	High Similarity	NPC474170
0.8704	High Similarity	NPC474388
0.7925	Intermediate Similarity	NPC474037
0.7321	Intermediate Similarity	NPC605569
0.6667	Remote Similarity	NPC310259
0.6533	Remote Similarity	NPC475214
0.6129	Remote Similarity	NPC34725
0.6129	Remote Similarity	NPC608137
0.6125	Remote Similarity	NPC476180
0.569	Remote Similarity	NPC72452
0.5593	Remote Similarity	NPC602291
0.5373	Remote Similarity	NPC122623
0.5349	Remote Similarity	NPC475434
0.5256	Remote Similarity	NPC117478
0.5217	Remote Similarity	NPC241774
0.519	Remote Similarity	NPC481404
0.5167	Remote Similarity	NPC61546
0.5161	Remote Similarity	NPC259058
0.5079	Remote Similarity	NPC90582
0.5079	Remote Similarity	NPC299923
0.5077	Remote Similarity	NPC153758
0.5077	Remote Similarity	NPC605582

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC177839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5779
0.1-0.2	3322
0.2-0.3	45
0.3-0.4	3
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