NPASS Compound

Natural Product: NPC275053

Natural Product ID	NPC275053
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-[2-(4-Hydroxyphenyl)Ethenyl]Benzene-1,3-Diol
IUPAC Name	5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
Synonyms	(Cis-Trans)-Resveratrol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2019155
PubChem CID	5056
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

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 29 30 0 0 0 0 0 0 0 0999 V2000 0.4878 -0.3733 -0.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3696 0.4266 0.2420 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8066 0.3282 0.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6028 1.2535 0.7500 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9599 1.1552 0.5853 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5375 0.1900 -0.2124 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7730 -0.7351 -0.8921 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 -0.6306 -0.7209 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3417 -1.7120 -1.6985 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7749 2.0620 1.2473 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9294 -0.3044 -0.1861 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5242 0.6522 0.6058 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9206 0.7017 0.7345 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6946 -0.1995 0.0742 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1301 -1.1611 -0.7197 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7692 -1.1983 -0.8364 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0882 -0.1155 0.2299 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1063 -1.1567 -0.9747 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0424 1.1998 0.8776 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1635 2.0159 1.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6233 0.1451 -0.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8296 -1.3727 -1.2696 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9750 -2.6771 -1.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5071 2.4800 2.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9757 1.3862 1.1489 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3602 1.4489 1.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8013 -1.8470 -1.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3005 -1.9606 -1.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5248 -0.0013 1.1168 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 3 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 5 10 1 0 1 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 14 17 1 0 8 3 1 0 16 11 1 0 1 18 1 0 2 19 1 0 4 20 1 0 6 21 1 0 8 22 1 0 9 23 1 0 10 24 1 0 12 25 1 0 13 26 1 0 15 27 1 0 16 28 1 0 17 29 1 0 M END

Standard InCHIKey	LUKBXSAWLPMMSZ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H
SMILES	C(=Cc1cc(cc(c1)O)O)c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	228.08	Volume:	241.503 ? Van der Waals volume.
Dense:	0.944	LogP:	2.798 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.803 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.352 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	13.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.692	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.112	Fsp³:	0.0
MCE-18:	11.0 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.679	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.026 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.992	Promiscuous compounds:	0.845

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.942	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.001	Pgp-substrate:	0.011
PAMPA:	0.405 ? 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):	0.0
20% Bioavailability (F20%):	0.329	30% Bioavailability (F30%):	0.24
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.452
Plasma Protein Binding (PPB):	88.141%	Volume Distribution (VD):	0.16
Fu:	14.409% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.381
BSEP inhibitor:	0.095

ADMET: Metabolism

CYP1A2-inhibitor:	0.011	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.777	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.184
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.057 ? 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):

9.967

Half-life (T1/2):

1.536

ADMET: Toxicity

hERG Blockers:	0.487	hERG Blockers (10um):	0.735
Human Hepatotoxicity (H-HT):	0.841	Drug-induced Liver Injury (DILI):	0.011
AMES Toxicity:	0.814	Rat Oral Acute Toxicity:	0.316
Maximum Recommended Daily Dose:	0.688	Skin Sensitization:	1.0
Carcinogencity:	0.263	Eye Corrosion:	0.187
Eye Irritation:	0.998	Respiratory Toxicity:	0.278
Drug-induced Neurotoxicity:	0.908	Ototoxicity:	0.553
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.307
Genotoxicity:	0.228	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.78	Hek293 Cytotoxicity:	0.809
BCF:	1.14 ? 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:	3.346 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.15 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.917 ? 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
NPO5650	Eupatorium glutinosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027751]
NPO1782	Piper caninum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270572]
NPO98	Leucosceptrum canum	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15524427]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16441071]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[16441071]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17286431]
NPO11541	Curcuma xanthorrhiza	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409552]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1782	Piper caninum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11541	Curcuma xanthorrhiza	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11736	Bulla striata	Species	Bullidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9406	Cotula filicula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5650	Eupatorium glutinosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10915	Heliotropium hirsutum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO98	Leucosceptrum canum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14439	Marasmius oreades	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11202	Maytenus imbricata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13334	Senecio toluccanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15640	Sideritis chamaedryfolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14697	Ustilago esculenta	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10915	Heliotropium hirsutum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11541	Curcuma xanthorrhiza	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11541	Curcuma xanthorrhiza	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10915	Heliotropium hirsutum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14439	Marasmius oreades	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11736	Bulla striata	Species	Bullidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14697	Ustilago esculenta	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9406	Cotula filicula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO98	Leucosceptrum canum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15640	Sideritis chamaedryfolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5650	Eupatorium glutinosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1782	Piper caninum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10915	Heliotropium hirsutum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11202	Maytenus imbricata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11541	Curcuma xanthorrhiza	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13334	Senecio toluccanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	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
Ki	13

Activity Type	# Activity
Individual protein	13

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	=	1750.0	nM	PMID[22487176]
NPT1146	Individual protein	Carbonic anhydrase III	Homo sapiens	Ki	=	6750.0	nM	PMID[22487176]
NPT1062	Individual protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	4010.0	nM	PMID[22487176]
NPT1144	Individual protein	Carbonic anhydrase VB	Homo sapiens	Ki	=	3240.0	nM	PMID[22487176]
NPT1063	Individual protein	Carbonic anhydrase VI	Homo sapiens	Ki	=	8630.0	nM	PMID[22487176]
NPT3101	Individual protein	Carbonic anhydrase XIII	Homo sapiens	Ki	=	8250.0	nM	PMID[22487176]
NPT1147	Individual protein	Carbonic anhydrase 15	Mus musculus	Ki	=	2570.0	nM	PMID[22487176]
NPT1143	Individual protein	Carbonic anhydrase VA	Homo sapiens	Ki	=	2860.0	nM	PMID[22487176]
NPT955	Individual protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	8980.0	nM	PMID[22487176]
NPT948	Individual protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	9530.0	nM	PMID[22487176]
NPT949	Individual protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	8130.0	nM	PMID[22487176]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	=	2180.0	nM	PMID[22487176]
NPT954	Individual protein	Carbonic anhydrase XIV	Homo sapiens	Ki	=	1950.0	nM	PMID[22487176]

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 NPC275053 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	34527
0.1-0.2	13044
0.2-0.3	1923
0.3-0.4	287
0.4-0.5	50
0.5-0.6	13
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC248573
1.0	High Similarity	NPC161571
0.7241	Intermediate Similarity	NPC34864
0.7241	Intermediate Similarity	NPC105727
0.7241	Intermediate Similarity	NPC58427
0.7143	Intermediate Similarity	NPC291789
0.6774	Remote Similarity	NPC292452
0.6364	Remote Similarity	NPC478886
0.6207	Remote Similarity	NPC114392
0.5882	Remote Similarity	NPC296920
0.5882	Remote Similarity	NPC90520
0.5676	Remote Similarity	NPC10932
0.5556	Remote Similarity	NPC265146
0.5526	Remote Similarity	NPC203113
0.5405	Remote Similarity	NPC280606
0.5294	Remote Similarity	NPC61516
0.525	Remote Similarity	NPC165770
0.525	Remote Similarity	NPC223451
0.5172	Remote Similarity	NPC223393
0.5143	Remote Similarity	NPC261343
0.5135	Remote Similarity	NPC232084
0.5135	Remote Similarity	NPC247364

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC275053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7337
0.1-0.2	1653
0.2-0.3	141
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1242	Phase 3

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