NPASS Compound

Natural Product: NPC478055

Natural Product ID	NPC478055
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3R,3aR,6R,6aS)-6-(4-hydroxy-3-methoxyphenyl)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,3a,6,6a-tetrahydro-1H-furo[3,4-c]furan-4-one
IUPAC Name	(3R,3aR,6R,6aS)-6-(4-hydroxy-3-methoxyphenyl)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,3a,6,6a-tetrahydro-1H-furo[3,4-c]furan-4-one
Synonyms	(-)-Pinoresinol Glucoside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44575735
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 68 72 0 0 0 0 0 0 0 0999 V2000 9.6587 1.0104 1.6644 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3561 -0.1563 0.9628 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1872 -0.4883 0.3359 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1529 -1.7273 -0.2998 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0058 -2.1165 -0.9484 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9114 -1.2650 -0.9533 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9412 -0.0446 -0.3279 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0946 0.3401 0.3209 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7419 0.8346 -0.3432 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4690 0.0968 -0.6049 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0996 0.2398 -2.0382 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0806 1.1341 -2.0947 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5215 1.3638 -0.8642 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4337 0.8399 0.1904 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2105 1.8884 0.9050 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7087 2.9276 1.3714 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5276 1.4414 0.9148 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1483 0.7870 -0.7207 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8820 1.4874 -0.1416 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1463 0.9055 -0.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4259 -0.3564 -0.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3608 -1.0646 -1.0572 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1153 -0.4862 -1.1705 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6343 -0.9232 -0.3568 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8555 -0.5969 0.1393 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9753 -0.6895 -0.9190 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1402 0.0589 -0.3517 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5503 -0.6507 0.9237 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3870 -0.9924 1.8043 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3099 -1.5139 1.1325 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8816 -2.0891 2.7605 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2549 -3.2267 2.0282 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3622 0.2591 1.6391 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2229 0.1400 -1.2009 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5585 -0.2326 -2.1446 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1317 1.6692 0.5680 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9254 2.9734 1.0467 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2675 -2.5753 -0.2851 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6653 0.7550 2.7479 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9590 1.8115 1.3904 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7214 1.2924 1.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9469 -3.0751 -1.4519 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0110 -1.5916 -1.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0928 1.3127 0.8110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8821 1.6260 -1.0815 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5293 -0.9775 -0.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9800 0.6431 -2.5980 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8801 -0.7328 -2.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4012 2.4901 -0.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9000 0.1764 0.9050 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6935 2.4992 0.2210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5705 -2.0731 -1.4140 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7054 -1.0396 -1.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9805 0.3866 0.6336 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2484 -1.7489 -1.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7823 1.0766 -0.0301 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1649 -1.5161 0.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1203 -0.1108 2.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1590 -2.3204 3.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8171 -1.7043 3.2141 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5828 -3.4935 1.3623 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1576 0.4020 1.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8846 -0.1570 -2.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6176 0.0041 -2.0918 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8268 3.6486 0.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8568 3.2622 1.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0627 3.0062 1.7119 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4538 -3.0536 -1.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 13 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 28 33 1 0 27 34 1 0 26 35 1 0 20 36 1 0 36 37 1 0 4 38 1 0 8 3 1 0 17 9 1 0 14 10 1 0 23 18 1 0 30 25 1 0 1 39 1 0 1 40 1 0 1 41 1 0 5 42 1 0 6 43 1 0 8 44 1 0 9 45 1 6 10 46 1 1 11 47 1 0 11 48 1 0 13 49 1 1 14 50 1 1 19 51 1 0 22 52 1 0 23 53 1 0 25 54 1 1 26 55 1 6 27 56 1 1 28 57 1 6 29 58 1 1 31 59 1 0 31 60 1 0 32 61 1 0 33 62 1 0 34 63 1 0 35 64 1 0 37 65 1 0 37 66 1 0 37 67 1 0 38 68 1 0 M END

Standard InCHIKey	REJREAKEHPGNCH-KVDZAEMRSA-N
Standard InCHI	InChI=1S/C26H30O12/c1-33-16-7-11(3-5-14(16)28)23-13-10-35-24(19(13)25(32)38-23)12-4-6-15(17(8-12)34-2)36-26-22(31)21(30)20(29)18(9-27)37-26/h3-8,13,18-24,26-31H,9-10H2,1-2H3/t13-,18-,19-,20-,21+,22-,23+,24+,26-/m1/s1
SMILES	COC1=C(C=CC(=C1)[C@H]2[C@@H]3CO[C@H]([C@@H]3C(=O)O2)C4=CC(=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.17	Volume:	502.497 ? Van der Waals volume.
Dense:	1.063	LogP:	0.01 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.626 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.447 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	28.0
TPSA:	173.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.306	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.499	Fsp³:	0.5
MCE-18:	108.897 ? 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:	0.612	Fluc inhibitor:	0.33 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.044 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.139 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.08	Promiscuous compounds:	0.313

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.155	MDCK Permeability:	-5.297
Pgp-inhibitor:	0.005	Pgp-substrate:	0.405
PAMPA:	0.33 ? 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):	0.05
20% Bioavailability (F20%):	0.019	30% Bioavailability (F30%):	0.926
50% Bioavailability (F50%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.451
Plasma Protein Binding (PPB):	69.305%	Volume Distribution (VD):	-0.385
Fu:	30.886% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.538
BSEP inhibitor:	0.011

ADMET: Metabolism

CYP1A2-inhibitor:	0.374	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.084	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? 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):

2.893

Half-life (T1/2):

4.378

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.12
Human Hepatotoxicity (H-HT):	0.859	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.964	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.037	Skin Sensitization:	0.999
Carcinogencity:	0.295	Eye Corrosion:	0.0
Eye Irritation:	0.261	Respiratory Toxicity:	0.014
Drug-induced Neurotoxicity:	0.046	Ototoxicity:	0.899
Hematotoxicity:	0.516	Drug-induced Nephrotoxicity:	0.951
Genotoxicity:	0.977	RPMI-8226 Immunitoxicity:	0.186
A549 Cytotoxicity:	0.518	Hek293 Cytotoxicity:	0.216
BCF:	0.559 ? 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:	3.21 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.807 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.901 ? 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
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	n.a.	bark	n.a.	PMID[15577246]
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[15620237]
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

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
Inhibition	1

Activity Type	# Activity
Cell line	1
Others	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
NPT71	Cell line	HEK293	Homo sapiens	Inhibition	=	23.2	%	PMID[24018191]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	260000	nM	PMID[15620237]

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 NPC478055 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	13357
0.1-0.2	31533
0.2-0.3	3797
0.3-0.4	931
0.4-0.5	184
0.5-0.6	34
0.6-0.7	10
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC38041
0.8333	Intermediate Similarity	NPC22150
0.7922	Intermediate Similarity	NPC186316
0.7237	Intermediate Similarity	NPC286235
0.7143	Intermediate Similarity	NPC279298
0.7083	Intermediate Similarity	NPC276753
0.7083	Intermediate Similarity	NPC205796
0.7013	Intermediate Similarity	NPC51328
0.7013	Intermediate Similarity	NPC55158
0.6986	Remote Similarity	NPC246947
0.6786	Remote Similarity	NPC112861
0.6709	Remote Similarity	NPC18979
0.6667	Remote Similarity	NPC185307
0.6667	Remote Similarity	NPC470950
0.6429	Remote Similarity	NPC223185
0.6292	Remote Similarity	NPC11411
0.6207	Remote Similarity	NPC129417
0.6207	Remote Similarity	NPC470235
0.6023	Remote Similarity	NPC283995
0.5909	Remote Similarity	NPC46092
0.5875	Remote Similarity	NPC216129
0.5875	Remote Similarity	NPC130449
0.5875	Remote Similarity	NPC248132
0.5833	Remote Similarity	NPC471063
0.5686	Remote Similarity	NPC475224
0.5682	Remote Similarity	NPC299706
0.5682	Remote Similarity	NPC115466
0.5682	Remote Similarity	NPC39657
0.5682	Remote Similarity	NPC61604
0.5584	Remote Similarity	NPC95392
0.5584	Remote Similarity	NPC84013
0.5584	Remote Similarity	NPC55715
0.5584	Remote Similarity	NPC35877
0.5556	Remote Similarity	NPC163635
0.5543	Remote Similarity	NPC486097
0.5495	Remote Similarity	NPC486549
0.5495	Remote Similarity	NPC486548
0.5479	Remote Similarity	NPC27843
0.5479	Remote Similarity	NPC7171
0.5455	Remote Similarity	NPC469586
0.5435	Remote Similarity	NPC486546
0.5417	Remote Similarity	NPC149873
0.5333	Remote Similarity	NPC486098
0.5333	Remote Similarity	NPC486545
0.5238	Remote Similarity	NPC486102
0.5165	Remote Similarity	NPC245615
0.5122	Remote Similarity	NPC486107
0.5114	Remote Similarity	NPC84181
0.5114	Remote Similarity	NPC486106
0.5102	Remote Similarity	NPC7191
0.5059	Remote Similarity	NPC486104
0.5057	Remote Similarity	NPC114119
0.5057	Remote Similarity	NPC471415

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4143
0.1-0.2	4878
0.2-0.3	116
0.3-0.4	13
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