NPASS Compound

Natural Product: NPC103356

Natural Product ID	NPC103356
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Stipulin
IUPAC Name	(E)-1-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
Synonyms	Stipulin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1169874
PubChem CID	10069091
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

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 58 0 0 0 0 0 0 0 0999 V2000 -8.4444 -1.8862 -1.5427 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9505 -0.9681 -0.4454 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6878 -1.0849 -0.0929 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1435 -0.2068 0.9800 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9528 0.5027 0.4352 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6950 0.0626 0.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5292 0.6683 0.3243 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7029 1.7292 -0.5282 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9751 2.1792 -0.9003 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1167 1.5635 -0.4167 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3676 2.0406 -0.8102 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2455 0.1491 0.7585 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0615 0.6186 0.3562 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1734 0.0521 0.8312 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0820 -0.9204 1.6650 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4858 0.5063 0.4312 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5732 -0.1574 0.9977 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8688 0.1709 0.7022 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0130 -0.5857 1.3457 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6212 -1.5582 0.4043 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8927 -1.5585 0.0750 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8788 -0.5909 0.6015 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3971 -2.5962 -0.8891 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1071 1.1907 -0.1839 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0581 1.8672 -0.7615 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7394 1.5209 -0.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 2.2243 -1.0510 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3962 1.5636 -0.5184 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8949 -0.0231 0.1724 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6493 -1.9806 -2.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5788 -2.9061 -1.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3996 -1.5294 -1.9653 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0506 -1.8259 -0.5916 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8250 -0.8305 1.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8990 0.5108 1.2999 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5742 -0.7838 1.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8257 2.2277 -0.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0781 3.0183 -1.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6824 2.9927 -0.6299 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2113 -0.6697 1.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1242 1.4333 -0.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4115 -0.9851 1.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7428 0.1484 1.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5904 -1.1607 2.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9401 -2.2941 -0.0129 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8045 -0.5917 -0.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1427 -0.9495 1.6414 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5285 0.4281 0.7298 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3912 -2.3616 -1.2673 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4288 -3.5870 -0.4201 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7065 -2.6689 -1.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1927 2.6765 -1.4644 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7810 2.6584 -1.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5744 1.9900 -1.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8295 -0.0433 1.2897 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7882 0.9969 -0.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9335 -0.3866 -0.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 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 10 11 1 0 7 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 3 21 22 1 0 21 23 1 0 18 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 24 28 1 0 2 29 1 0 10 5 1 0 26 16 1 0 1 30 1 0 1 31 1 0 1 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 6 36 1 0 8 37 1 0 9 38 1 0 11 39 1 0 12 40 1 0 13 41 1 0 17 42 1 0 19 43 1 0 19 44 1 0 20 45 1 0 22 46 1 0 22 47 1 0 22 48 1 0 23 49 1 0 23 50 1 0 23 51 1 0 25 52 1 0 27 53 1 0 28 54 1 0 29 55 1 0 29 56 1 0 29 57 1 0 M END

Standard InCHIKey	UENVXGIVHQSJHZ-XYOKQWHBSA-N
Standard InCHI	InChI=1S/C25H28O4/c1-16(2)5-9-19-13-18(7-11-22(19)26)8-12-23(27)21-14-20(10-6-17(3)4)24(28)15-25(21)29/h5-8,11-15,26,28-29H,9-10H2,1-4H3/b12-8+
SMILES	CC(=CCc1cc(ccc1O)/C=C/C(=O)c1cc(CC=C(C)C)c(cc1O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	392.2	Volume:	432.639 ? Van der Waals volume.
Dense:	0.907	LogP:	6.019 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.977 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.85 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	16.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.32	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.865	Fsp³:	0.24
MCE-18:	16.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	0.99 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.669 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.578 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.665	Promiscuous compounds:	0.203

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.001	MDCK Permeability:	-4.73
Pgp-inhibitor:	0.41	Pgp-substrate:	0.004
PAMPA:	0.379 ? 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):	0.105
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.065
Plasma Protein Binding (PPB):	96.223%	Volume Distribution (VD):	0.273
Fu:	3.229% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.785
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	1.0
BSEP inhibitor:	0.834

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.59	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.046	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

6.106

Half-life (T1/2):

1.169

ADMET: Toxicity

hERG Blockers:	0.107	hERG Blockers (10um):	0.561
Human Hepatotoxicity (H-HT):	0.663	Drug-induced Liver Injury (DILI):	0.626
AMES Toxicity:	0.632	Rat Oral Acute Toxicity:	0.59
Maximum Recommended Daily Dose:	0.602	Skin Sensitization:	0.99
Carcinogencity:	0.173	Eye Corrosion:	0.0
Eye Irritation:	0.7	Respiratory Toxicity:	0.951
Drug-induced Neurotoxicity:	0.69	Ototoxicity:	0.534
Hematotoxicity:	0.15	Drug-induced Nephrotoxicity:	0.889
Genotoxicity:	0.922	RPMI-8226 Immunitoxicity:	0.124
A549 Cytotoxicity:	0.703	Hek293 Cytotoxicity:	0.759
BCF:	1.837 ? 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:	5.361 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.785 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.293 ? 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
NPO12044.1	Dorstenia barteri var. subtriangularis	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	Leaf; Twig	n.a.	n.a.	PMID[30835120]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO507	Diplophyllum taxifolium	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10832	Pseudocalymma elegans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7173	Armillaria matsutake	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3225	Streptomyces garyphalus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12044.1	Dorstenia barteri var. subtriangularis	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12044.1	Dorstenia barteri var. subtriangularis	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15399	Phyllanthus meghalayensis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12044.1	Dorstenia barteri var. subtriangularis	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7173	Armillaria matsutake	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16095	Euryspongia rosea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10832	Pseudocalymma elegans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12845	Podocarpus urbanii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12256	Meconopsis quintuplinervia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15399	Phyllanthus meghalayensis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3225	Streptomyces garyphalus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10520	Thunbergia fragrans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7173	Armillaria matsutake	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15426	Artemisia atrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO507	Diplophyllum taxifolium	Species	Scapaniaceae	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
IC50	1

Activity Type	# Activity
Organism	1

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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5130.0	nM	PMID[19299148]

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 NPC103356 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	20834
0.1-0.2	25115
0.2-0.3	3428
0.3-0.4	362
0.4-0.5	88
0.5-0.6	21
0.6-0.7	3
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8511	High Similarity	NPC30501
0.8302	Intermediate Similarity	NPC40524
0.8163	Intermediate Similarity	NPC194764
0.78	Intermediate Similarity	NPC169250
0.7308	Intermediate Similarity	NPC100067
0.6415	Remote Similarity	NPC190043
0.6129	Remote Similarity	NPC6118
0.6111	Remote Similarity	NPC221777
0.5965	Remote Similarity	NPC65005
0.5849	Remote Similarity	NPC471954
0.5849	Remote Similarity	NPC75272
0.5818	Remote Similarity	NPC72158
0.58	Remote Similarity	NPC128723
0.569	Remote Similarity	NPC269694
0.5614	Remote Similarity	NPC130899
0.5614	Remote Similarity	NPC59319
0.5536	Remote Similarity	NPC62952
0.5439	Remote Similarity	NPC98254
0.5439	Remote Similarity	NPC601405
0.5417	Remote Similarity	NPC242136
0.5333	Remote Similarity	NPC131039
0.5283	Remote Similarity	NPC165770
0.5098	Remote Similarity	NPC19174
0.5098	Remote Similarity	NPC115159
0.5091	Remote Similarity	NPC303141
0.5085	Remote Similarity	NPC162612
0.5085	Remote Similarity	NPC283590
0.5082	Remote Similarity	NPC485637
0.5082	Remote Similarity	NPC477244

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC103356 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4063
0.1-0.2	4985
0.2-0.3	101
0.3-0.4	1
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