NPASS Compound

Natural Product: NPC169733

Natural Product ID	NPC169733
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Rhodiosin
IUPAC Name	7-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5,8-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms	Rhodiosin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL596218
PubChem CID	46226585
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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 73 77 0 0 0 0 0 0 0 0999 V2000 -2.8445 2.7053 -2.0229 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4137 3.5618 -0.8710 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3495 3.4597 0.3101 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0414 2.1765 1.1150 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5727 2.3259 1.4561 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8458 2.1591 0.1205 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0951 3.3406 -0.5844 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5021 1.9279 0.2581 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2572 0.8498 -0.0927 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7447 -0.2795 -0.6943 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5485 -1.3576 -1.0362 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8913 -1.3182 -0.7770 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7226 -2.3621 -1.0985 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3017 -3.4059 -1.6451 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0855 -2.2113 -0.7854 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5921 -1.0892 -0.1880 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9732 -0.8539 0.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0004 -1.7157 -0.0381 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3155 -1.3813 0.3494 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6141 -0.1800 0.9457 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5816 0.6978 1.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3094 0.3614 0.7758 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9125 0.1302 1.3191 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7097 -0.1431 0.0801 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4351 -0.2032 -0.1762 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6112 0.8732 0.1614 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1564 1.9957 0.7659 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9161 -3.2608 -1.1095 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 -2.5036 -1.6454 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1655 1.4430 2.4188 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1486 1.0706 0.2749 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1047 0.1567 0.6385 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4589 -1.2012 0.7597 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4764 -2.2954 1.0121 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5490 -2.2090 -0.0223 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0575 -0.7812 -0.1959 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9264 -0.7773 -1.4368 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1281 -1.2082 -2.4959 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0082 0.0833 -0.4267 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6257 -3.0372 0.2645 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7912 -3.5149 0.8158 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4008 -1.2558 1.6319 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1315 4.5214 1.1675 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4675 1.6830 -2.0083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4457 3.1868 -2.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9689 2.6274 -2.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4872 4.6293 -1.2238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3796 3.4853 -0.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7159 2.1762 1.9661 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3589 3.3788 1.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3291 1.2869 -0.3638 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3061 -0.3709 -0.9245 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8287 -2.6706 -0.5002 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0992 -2.0994 0.1661 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7876 1.6398 1.6191 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4814 1.0552 0.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4625 -0.4408 1.9219 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9206 2.9132 0.4274 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0078 -3.5722 -2.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8841 -3.3297 -1.0709 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4143 0.8789 2.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6027 0.4814 1.5721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0409 -1.4262 -0.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8613 -2.2909 2.0405 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1317 -2.5070 -1.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6784 -0.4945 0.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2226 0.2662 -1.6701 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8041 -1.4497 -1.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3106 -0.7145 -3.3215 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1013 -3.2340 -0.5978 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1275 -3.6566 1.5374 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5716 -1.0027 1.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2286 4.2770 2.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 16 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 15 28 1 0 11 29 1 0 5 30 1 0 4 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 3 43 1 0 7 2 1 0 26 9 1 0 39 32 1 0 25 12 1 0 22 17 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 3 48 1 6 4 49 1 1 5 50 1 1 6 51 1 6 10 52 1 0 18 53 1 0 19 54 1 0 21 55 1 0 22 56 1 0 23 57 1 0 27 58 1 0 28 59 1 0 29 60 1 0 30 61 1 0 32 62 1 1 33 63 1 6 34 64 1 1 35 65 1 6 36 66 1 1 37 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	WXBBQBYCUTXTJQ-FUIZFARNSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-8-15(31)25(43-26-21(37)19(35)16(32)13(7-28)41-26)22(38)27(39-8)40-12-6-11(30)14-18(34)20(36)23(42-24(14)17(12)33)9-2-4-10(29)5-3-9/h2-6,8,13,15-16,19,21-22,25-33,35-38H,7H2,1H3/t8-,13-,15-,16-,19+,21-,22+,25+,26+,27-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc(c2c(=O)c(c(c3ccc(cc3)O)oc2c1O)O)O)O)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.058 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.912 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.74 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.14	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.823	Fsp³:	0.444
MCE-18:	122.949 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.634	Fluc inhibitor:	0.284 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.694 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.613 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.268	Promiscuous compounds:	0.613

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.78	MDCK Permeability:	-4.932
Pgp-inhibitor:	0.0	Pgp-substrate:	0.318
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):	0.976
20% Bioavailability (F20%):	0.366	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.106
Plasma Protein Binding (PPB):	86.813%	Volume Distribution (VD):	-0.126
Fu:	10.071% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.535
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.437
HLM stability:	0.295 ? 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):

1.485

Half-life (T1/2):

4.89

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.115
Human Hepatotoxicity (H-HT):	0.429	Drug-induced Liver Injury (DILI):	0.975
AMES Toxicity:	0.771	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.019	Skin Sensitization:	0.986
Carcinogencity:	0.055	Eye Corrosion:	0.0
Eye Irritation:	0.408	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.895
Hematotoxicity:	0.128	Drug-induced Nephrotoxicity:	0.511
Genotoxicity:	0.692	RPMI-8226 Immunitoxicity:	0.163
A549 Cytotoxicity:	0.557	Hek293 Cytotoxicity:	0.322
BCF:	0.296 ? 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:	2.775 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.191 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.642 ? 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
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	roots	n.a.	n.a.	PMID[19729316]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16239	Rhodiola rosea	Species	Crassulaceae	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	1
IC50	2
EC50	2
Ratio CC50/EC50	2
CC50	1

Activity Type	# Activity
Individual protein	3
Cell line	1
Organism	2
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT344	Individual protein	Sialidase	Clostridium perfringens	IC50	=	56900.0	nM	PubChem BioAssay data set
NPT493	Individual protein	Neuraminidase	Influenza A virus	Ki	=	64100.0	nM	Open TG-GATES in vivo data: Hematology
NPT493	Individual protein	Neuraminidase	Influenza A virus	IC50	=	56500.0	nM	Open TG-GATES in vivo data: Hematology

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell line	MDCK	Canis lupus familiaris	CC50	=	297300.0	nM	DOI[10.1007/s00044-011-9811-1]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	EC50	=	81900.0	nM	PMID[10425121]
NPT742	Organism	Influenza A virus	Influenza A virus	EC50	=	35100.0	nM	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	3.63	n.a.	PMID[20346682]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	8.47	n.a.	PMID[10757708]

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 NPC169733 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	22705
0.1-0.2	23221
0.2-0.3	3106
0.3-0.4	610
0.4-0.5	191
0.5-0.6	19
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	Natural Product ID
0.7407	Intermediate Similarity	NPC476405
0.5955	Remote Similarity	NPC323593
0.5955	Remote Similarity	NPC203500
0.5714	Remote Similarity	NPC84265
0.5667	Remote Similarity	NPC108831
0.5667	Remote Similarity	NPC182634
0.5524	Remote Similarity	NPC203145
0.5472	Remote Similarity	NPC189564
0.5455	Remote Similarity	NPC183672
0.5269	Remote Similarity	NPC277205
0.5269	Remote Similarity	NPC37919
0.5258	Remote Similarity	NPC601586
0.5208	Remote Similarity	NPC197285
0.5149	Remote Similarity	NPC3583
0.5138	Remote Similarity	NPC292019
0.5138	Remote Similarity	NPC202908
0.5106	Remote Similarity	NPC609879
0.5104	Remote Similarity	NPC285197
0.5053	Remote Similarity	NPC245014
0.5052	Remote Similarity	NPC486578

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC169733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5792
0.1-0.2	3294
0.2-0.3	54
0.3-0.4	10
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