NPASS Compound

Natural Product: NPC204937

Natural Product ID	NPC204937
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2R,3S,4S,5R,6S)-6-[2,3-Dihydroxy-4-[(E)-3-(4-Hydroxyphenyl)Prop-2-Enoyl]Phenoxy]-3,4,5-Trihydroxyoxan-2-Yl]Methyl (E)-3-(4-Hydroxyphenyl)Prop-2-Enoate
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[2,3-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL454585
PubChem CID	10460858
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 70 73 0 0 0 0 0 0 0 0999 V2000 2.9187 0.0916 2.8714 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8848 -0.1582 2.1097 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6049 -0.4489 0.8047 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3453 -0.5047 0.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5776 -0.8637 -1.2643 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4358 -0.9600 -2.0065 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7810 0.2408 -2.2659 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1858 0.4170 -1.3057 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5352 0.4731 -1.4350 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1695 0.3527 -2.6448 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5351 0.4060 -2.7869 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3679 0.5948 -1.6417 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7283 0.7160 -0.4528 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3200 0.6588 -0.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7430 0.7863 0.9287 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4309 0.9181 0.7029 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7820 0.5176 -1.8648 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1342 0.7005 -3.1627 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9408 0.2941 -1.0928 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1668 -0.0123 0.1492 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5151 -0.1745 0.6760 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6793 -0.5038 2.0187 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9088 -0.6807 2.6108 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0235 -0.5191 1.8157 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9223 -0.1937 0.4825 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6387 -0.0252 -0.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2986 -0.6901 2.3775 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7432 1.4213 -2.3695 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0458 0.8677 -2.9029 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6775 -0.0376 -1.8805 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6080 -0.8457 -2.5677 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8936 1.8643 -3.3585 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2757 2.3196 -3.3569 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2758 -0.1478 2.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2509 -0.4146 1.7423 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6615 -0.4281 2.1070 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1292 -0.1619 3.3580 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4907 -0.1884 3.6583 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4138 -0.4896 2.6804 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9532 -0.7596 1.4153 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6064 -0.7304 1.1309 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7729 -0.5256 2.9396 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8295 0.4410 0.3495 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7670 -1.3643 0.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9951 -1.9177 -1.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3852 0.1324 -3.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5504 0.2079 -3.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9843 0.3042 -3.7550 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8021 0.0683 1.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2100 0.6062 1.6187 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9058 0.4097 -1.6858 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3191 -0.2103 0.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7861 -0.6226 2.6127 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9836 -0.9350 3.6524 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8153 -0.0758 -0.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6399 0.2282 -1.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9864 -1.1489 1.7955 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8353 2.0027 -1.4571 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7591 0.2050 -3.7710 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2485 0.5510 -1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8689 -1.5575 -1.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6092 1.4190 -3.8810 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3303 2.0999 -3.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4912 0.0831 3.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9617 -0.6395 0.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4460 0.0767 4.1479 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8141 0.0340 4.6832 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6797 -0.9976 0.6414 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2618 -0.9479 0.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3802 0.2684 2.8642 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 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 14 15 1 0 13 16 1 0 12 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 7 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 2 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 30 5 1 0 41 36 1 0 14 9 1 0 26 21 1 0 4 43 1 0 4 44 1 0 5 45 1 1 7 46 1 6 10 47 1 0 11 48 1 0 15 49 1 0 16 50 1 0 19 51 1 0 20 52 1 0 22 53 1 0 23 54 1 0 25 55 1 0 26 56 1 0 27 57 1 0 28 58 1 1 29 59 1 6 30 60 1 1 31 61 1 0 32 62 1 0 33 63 1 0 34 64 1 0 35 65 1 0 37 66 1 0 38 67 1 0 40 68 1 0 41 69 1 0 42 70 1 0 M END

Standard InCHIKey	MXLIDYXKRCYRPL-SVQBVAIGSA-N
Standard InCHI	InChI=1S/C30H28O12/c31-18-7-1-16(2-8-18)5-12-21(33)20-11-13-22(26(36)25(20)35)41-30-29(39)28(38)27(37)23(42-30)15-40-24(34)14-6-17-3-9-19(32)10-4-17/h1-14,23,27-32,35-39H,15H2/b12-5+,14-6+/t23-,27-,28+,29-,30-/m1/s1
SMILES	O=C(OC[C@H]1O[C@@H](Oc2ccc(c(c2O)O)C(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O)/C=C/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.16	Volume:	564.419 ? Van der Waals volume.
Dense:	1.028	LogP:	1.64 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.744 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.776 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	28.0
TPSA:	203.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.084	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.088	Fsp³:	0.2
MCE-18:	88.5 ? 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:	0.778	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.398 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.974 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.435	Promiscuous compounds:	0.577

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.321	MDCK Permeability:	-5.174
Pgp-inhibitor:	0.002	Pgp-substrate:	0.003
PAMPA:	0.94 ? 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):	0.033
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	88.972%	Volume Distribution (VD):	-0.116
Fu:	8.328% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.021
BSEP inhibitor:	0.844

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.774
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.527
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.024 ? 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):

2.579

Half-life (T1/2):

2.961

ADMET: Toxicity

hERG Blockers:	0.129	hERG Blockers (10um):	0.468
Human Hepatotoxicity (H-HT):	0.548	Drug-induced Liver Injury (DILI):	0.831
AMES Toxicity:	0.63	Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.504	Skin Sensitization:	0.995
Carcinogencity:	0.033	Eye Corrosion:	0.0
Eye Irritation:	0.737	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.128	Ototoxicity:	0.525
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	0.669
Genotoxicity:	0.837	RPMI-8226 Immunitoxicity:	0.169
A549 Cytotoxicity:	0.55	Hek293 Cytotoxicity:	0.848
BCF:	0.94 ? 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:	3.963 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.103 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.79 ? 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
NPO19496	Bidens leucantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090869]
NPO19496	Bidens leucantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19496	Bidens leucantha	Species	Asteraceae	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
EC50	1
TC50	1

Activity Type	# Activity
Cell line	1
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
NPT1452	Cell line	C8166	Homo sapiens	TC50	=	250.0	ug ml-1	PMID[23030848]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50.0	ug.mL-1	PMID[23030848]

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 NPC204937 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	14791
0.1-0.2	30319
0.2-0.3	3707
0.3-0.4	856
0.4-0.5	130
0.5-0.6	42
0.6-0.7	7
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
0.7143	Intermediate Similarity	NPC175230
0.7108	Intermediate Similarity	NPC172033
0.7037	Intermediate Similarity	NPC88560
0.6842	Remote Similarity	NPC291153
0.6341	Remote Similarity	NPC10205
0.631	Remote Similarity	NPC476869
0.631	Remote Similarity	NPC476866
0.6282	Remote Similarity	NPC88043
0.622	Remote Similarity	NPC149011
0.6125	Remote Similarity	NPC157898
0.5952	Remote Similarity	NPC291296
0.5854	Remote Similarity	NPC310064
0.5843	Remote Similarity	NPC472876
0.5814	Remote Similarity	NPC476864
0.5698	Remote Similarity	NPC471405
0.5698	Remote Similarity	NPC476867
0.5682	Remote Similarity	NPC476868
0.5579	Remote Similarity	NPC476620
0.5506	Remote Similarity	NPC488082
0.5484	Remote Similarity	NPC133984
0.5455	Remote Similarity	NPC157816
0.5435	Remote Similarity	NPC488081
0.5432	Remote Similarity	NPC479473
0.5432	Remote Similarity	NPC275721
0.5432	Remote Similarity	NPC288416
0.5432	Remote Similarity	NPC479468
0.5432	Remote Similarity	NPC479474
0.5432	Remote Similarity	NPC57587
0.5385	Remote Similarity	NPC476865
0.5361	Remote Similarity	NPC270675
0.5361	Remote Similarity	NPC195685
0.5357	Remote Similarity	NPC34293
0.5306	Remote Similarity	NPC80068
0.5281	Remote Similarity	NPC116745
0.5275	Remote Similarity	NPC476870
0.5263	Remote Similarity	NPC476872
0.5263	Remote Similarity	NPC476871
0.5248	Remote Similarity	NPC599948
0.5233	Remote Similarity	NPC137813
0.52	Remote Similarity	NPC223426
0.5161	Remote Similarity	NPC479767
0.5152	Remote Similarity	NPC85751
0.5152	Remote Similarity	NPC19240
0.5152	Remote Similarity	NPC477629
0.5122	Remote Similarity	NPC470572
0.51	Remote Similarity	NPC36138
0.5094	Remote Similarity	NPC484988
0.5059	Remote Similarity	NPC199977
0.5057	Remote Similarity	NPC252114
0.5053	Remote Similarity	NPC11411
0.5053	Remote Similarity	NPC300262
0.505	Remote Similarity	NPC472994

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC204937 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4776
0.1-0.2	4305
0.2-0.3	61
0.3-0.4	7
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