NPASS Compound

Natural Product: NPC559837

Natural Product ID	NPC559837
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2~{R},3~{S},4~{S},5~{R},6~{S})-6-[(2~{S})-2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-chroman-7-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl (~{E})-3-(4-hydroxyphenyl)prop-2-enoate
IUPAC Name	[(2~{R},3~{S},4~{S},5~{R},6~{S})-6-[(2~{S})-2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-chroman-7-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl (~{E})-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 71 75 0 0 0 0 0 0 0 0999 V2000 2.7533 0.5535 -0.2637 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8573 -0.0205 -0.3640 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0960 0.6901 0.0132 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2746 0.1147 -0.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5224 0.7733 0.2799 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6261 2.0576 0.7511 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8696 2.6169 1.0749 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0388 1.9031 0.9345 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2865 2.4301 1.2471 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9432 0.6081 0.4602 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7191 0.0599 0.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9081 -1.3115 -0.8261 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8226 -2.0813 -1.2033 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8210 -2.3985 -0.1268 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2059 -1.3350 0.4537 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1670 -1.4171 0.6016 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7746 -1.4149 -0.6360 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6701 -0.5136 -1.1184 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1287 -0.7535 -2.4246 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0358 0.1058 -2.9942 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5469 -0.0567 -4.2944 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4781 1.1915 -2.2644 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4342 2.1448 -2.7935 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3887 2.3752 -4.0389 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4031 2.7983 -1.8962 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8614 2.9831 -0.5194 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7959 2.3102 0.4440 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7249 0.9507 0.7112 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5887 0.3389 1.5970 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5601 1.0626 2.2526 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4472 0.4690 3.1541 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6362 2.4147 1.9916 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6012 3.1628 2.6359 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7673 3.0298 1.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5383 2.5659 -0.3155 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0241 1.4275 -0.9743 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1186 0.5719 -0.4026 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4421 -2.7229 1.3700 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3191 -2.7284 2.5168 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0596 -3.9137 0.5182 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2150 -4.4523 -0.0782 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8677 -3.5025 -0.5849 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6673 -4.6295 -0.8921 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0174 1.6933 0.3673 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2787 -0.9154 -0.4506 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7167 2.6376 0.8692 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8966 3.6355 1.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1420 2.1698 0.8098 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8660 0.0328 0.3452 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6433 -0.9673 -0.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2171 -3.0611 -1.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3053 -1.5272 -2.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4187 -2.9030 0.7001 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4695 -0.5708 1.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7809 -1.6044 -2.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3078 -0.9458 -4.7402 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3540 2.1962 -1.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6972 3.8210 -2.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8752 4.0710 -0.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9524 0.3996 0.1840 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5253 -0.7188 1.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6327 -0.5137 3.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5773 3.0433 2.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8210 4.1037 0.8879 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7735 0.7784 0.6202 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4979 -2.8149 1.6264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9895 -1.9965 2.5283 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4356 -4.7019 1.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0060 -5.4059 -0.2577 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3748 -3.2351 -1.5187 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7785 -5.1587 -0.0673 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 6 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 2 0 2 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 20 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 2 0 26 35 1 0 35 36 1 0 36 37 2 0 16 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 11 5 1 0 42 14 1 0 37 18 1 0 36 22 1 0 34 27 1 0 3 44 1 0 4 45 1 0 6 46 1 0 7 47 1 0 9 48 1 0 10 49 1 0 11 50 1 0 13 51 1 0 13 52 1 0 14 53 1 1 16 54 1 1 19 55 1 0 21 56 1 0 25 57 1 0 25 58 1 0 26 59 1 1 28 60 1 0 29 61 1 0 31 62 1 0 33 63 1 0 34 64 1 0 37 65 1 0 38 66 1 1 39 67 1 0 40 68 1 1 41 69 1 0 42 70 1 6 43 71 1 0 M END

Standard InCHIKey	OGVBUVNWHBXNFL-KRYLVGRBSA-N
Standard InCHI	InChI=1S/C30H28O13/c31-16-5-1-14(2-6-16)3-8-25(36)40-13-24-27(37)28(38)29(39)30(43-24)41-17-10-20(34)26-21(35)12-22(42-23(26)11-17)15-4-7-18(32)19(33)9-15/h1-11,22,24,27-34,37-39H,12-13H2/b8-3+/t22-,24+,27+,28-,29+,30+/m0/s1
SMILES	O=C(/C=C/C1=CC=C(O)C=C1)OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C[C@@H](C4=CC=C(O)C(O)=C4)OC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.15	Volume:	567.289 ? Van der Waals volume.
Dense:	1.051	LogP:	1.625 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.802 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.128 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	212.67 ? 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:	0.118	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.351	Fsp³:	0.267
MCE-18:	107.789 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.835	Fluc inhibitor:	0.669 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.333 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.951 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.2	Promiscuous compounds:	0.376

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.483	MDCK Permeability:	-5.256
Pgp-inhibitor:	0.003	Pgp-substrate:	0.003
PAMPA:	0.923 ? 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%):	0.955	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.011
Plasma Protein Binding (PPB):	88.76%	Volume Distribution (VD):	-0.135
Fu:	10.597% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.313
BSEP inhibitor:	0.483

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.812 ? 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):

3.234

Half-life (T1/2):

3.346

ADMET: Toxicity

hERG Blockers:	0.103	hERG Blockers (10um):	0.543
Human Hepatotoxicity (H-HT):	0.754	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.923	Rat Oral Acute Toxicity:	0.2
Maximum Recommended Daily Dose:	0.698	Skin Sensitization:	0.999
Carcinogencity:	0.062	Eye Corrosion:	0.0
Eye Irritation:	0.614	Respiratory Toxicity:	0.115
Drug-induced Neurotoxicity:	0.085	Ototoxicity:	0.888
Hematotoxicity:	0.033	Drug-induced Nephrotoxicity:	0.899
Genotoxicity:	0.996	RPMI-8226 Immunitoxicity:	0.16
A549 Cytotoxicity:	0.98	Hek293 Cytotoxicity:	0.783
BCF:	0.926 ? 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:	3.808 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.063 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.636 ? 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
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754604]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	Roots	Simao city, Yunnan Province, China	2007-MAY	PMID[19374435]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	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

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

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 NPC559837 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	14289
0.1-0.2	30120
0.2-0.3	4325
0.3-0.4	942
0.4-0.5	142
0.5-0.6	28
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9036	High Similarity	NPC67134
0.7273	Intermediate Similarity	NPC472876
0.7191	Intermediate Similarity	NPC43587
0.6778	Remote Similarity	NPC271270
0.6706	Remote Similarity	NPC29830
0.6279	Remote Similarity	NPC39351
0.6211	Remote Similarity	NPC44328
0.6211	Remote Similarity	NPC79056
0.6163	Remote Similarity	NPC291153
0.602	Remote Similarity	NPC47140
0.5909	Remote Similarity	NPC157898
0.5816	Remote Similarity	NPC293629
0.5741	Remote Similarity	NPC469371
0.5638	Remote Similarity	NPC204937
0.5625	Remote Similarity	NPC105283
0.5591	Remote Similarity	NPC10205
0.5591	Remote Similarity	NPC236934
0.5532	Remote Similarity	NPC476867
0.5444	Remote Similarity	NPC97052
0.5417	Remote Similarity	NPC476866
0.54	Remote Similarity	NPC291124
0.54	Remote Similarity	NPC131157
0.5385	Remote Similarity	NPC219163
0.5278	Remote Similarity	NPC321916
0.5275	Remote Similarity	NPC163191
0.5263	Remote Similarity	NPC291296
0.5258	Remote Similarity	NPC476869
0.5234	Remote Similarity	NPC318119
0.5155	Remote Similarity	NPC157816
0.5155	Remote Similarity	NPC476864
0.5152	Remote Similarity	NPC476870
0.5054	Remote Similarity	NPC34293
0.5051	Remote Similarity	NPC476868
0.505	Remote Similarity	NPC142860
0.505	Remote Similarity	NPC152538
0.505	Remote Similarity	NPC246469
0.505	Remote Similarity	NPC89088
0.5047	Remote Similarity	NPC80068

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC559837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4644
0.1-0.2	4434
0.2-0.3	61
0.3-0.4	10
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
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
0.6211	Remote Similarity	NPD7074	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