NPASS Compound

Natural Product: NPC319749

Natural Product ID	NPC319749
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ananolignan K
IUPAC Name	n.a.
Synonyms	Ananolignan K
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1782119
PubChem CID	53355457
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 76 80 0 0 0 0 0 0 0 0999 V2000 0.6129 3.5633 -0.5667 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2270 2.1251 -0.2135 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2197 1.1995 -0.8230 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7728 0.1460 0.1502 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9711 -1.0705 -0.1234 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7584 -2.1087 -0.4762 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1866 -3.3225 -0.8319 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2102 -3.4808 -0.8318 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0262 -2.4337 -0.4779 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4235 -1.2565 -0.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5435 -0.4098 0.2680 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3120 -1.2349 1.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4962 -0.7269 1.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8988 0.5731 1.2274 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1017 1.3876 0.4435 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9203 0.9165 -0.0453 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2022 1.9687 -0.7914 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8946 3.1860 -0.7156 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2681 3.8822 -1.8785 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9497 3.3570 -2.9599 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0075 5.1822 -1.7998 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0923 1.0890 1.7012 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5162 2.4001 1.4148 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3180 -1.5050 2.3066 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3003 -2.2946 1.6723 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8353 -2.4884 1.3137 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0324 -2.8048 2.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3952 -2.4887 -0.4737 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1969 -2.1834 -1.5998 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4549 -4.7938 -1.2307 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7265 -5.3984 -1.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7303 -4.5325 -1.2256 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1310 -0.0900 -0.0424 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9979 0.1856 1.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5315 0.6326 2.0955 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4375 -0.0405 0.8784 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9642 -0.5293 -0.2966 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3480 -0.7248 -0.3679 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1753 -0.4392 0.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6409 0.0491 1.8757 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2791 0.2313 1.9173 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4370 1.9150 -1.3733 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5557 3.8694 -0.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2468 4.1870 -0.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5693 3.6324 -1.6658 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1435 1.9878 0.8832 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7341 0.7154 -1.7033 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5418 0.5393 1.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8377 -1.9739 -0.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4302 2.3932 0.2288 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0420 1.7215 -1.8614 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6863 5.1775 -0.9461 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6245 5.2503 -2.7162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2800 6.0214 -1.7965 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6891 3.1285 1.6530 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3662 2.7189 2.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8026 2.4496 0.3387 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1516 -1.6045 1.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9203 -2.8173 0.7820 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7041 -3.0634 2.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1041 -3.8668 2.7336 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0020 -2.5809 2.1866 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3210 -2.1010 3.2562 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8816 -3.0202 -1.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8004 -1.3130 -1.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5040 -1.9280 -2.4281 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 -6.4349 -1.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7672 -5.3356 -2.8368 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3320 -0.7584 -1.1461 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7768 -1.1033 -1.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2447 -0.5798 0.6788 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2643 0.2740 2.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8721 0.6223 2.8622 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9791 2.4977 -0.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2037 2.5529 -2.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1308 1.1099 -1.7350 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 2 0 6 7 1 0 7 8 2 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 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 14 22 1 0 22 23 1 0 13 24 1 0 24 25 1 0 12 26 1 0 26 27 1 0 9 28 1 0 28 29 1 0 8 30 1 0 30 31 1 0 31 32 1 0 4 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 3 42 1 0 17 2 1 0 10 5 1 0 32 7 1 0 16 11 1 0 41 36 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 3 47 1 0 4 48 1 0 6 49 1 0 15 50 1 0 17 51 1 0 21 52 1 0 21 53 1 0 21 54 1 0 23 55 1 0 23 56 1 0 23 57 1 0 25 58 1 0 25 59 1 0 25 60 1 0 27 61 1 0 27 62 1 0 27 63 1 0 29 64 1 0 29 65 1 0 29 66 1 0 31 67 1 0 31 68 1 0 37 69 1 0 38 70 1 0 39 71 1 0 40 72 1 0 41 73 1 0 42 74 1 0 42 75 1 0 42 76 1 0 M END

Standard InCHIKey	GXKNDJXUIKGIKK-WDJHCCQWSA-N
Standard InCHI	InChI=1S/C32H34O10/c1-16-17(2)27(42-32(34)19-11-9-8-10-12-19)21-14-23-29(40-15-39-23)31(38-7)25(21)24-20(26(16)41-18(3)33)13-22(35-4)28(36-5)30(24)37-6/h8-14,16-17,26-27H,15H2,1-7H3/t16-,17+,26+,27+/m0/s1
SMILES	CC1C(C(C2=CC3=C(C(=C2C4=C(C(=C(C=C4C1OC(=O)C)OC)OC)OC)OC)OCO3)OC(=O)C5=CC=CC=C5)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.22	Volume:	578.147 ? Van der Waals volume.
Dense:	1.0	LogP:	4.59 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.78 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.133 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	107.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.314	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.093	Fsp³:	0.375
MCE-18:	103.273 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.58	Fluc inhibitor:	0.114 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.394 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.639 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.108	Promiscuous compounds:	0.086

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002	MDCK Permeability:	-4.762
Pgp-inhibitor:	0.985	Pgp-substrate:	0.03
PAMPA:	0.046 ? 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):	0.0
20% Bioavailability (F20%):	0.017	30% Bioavailability (F30%):	0.003
50% Bioavailability (F50%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.652	MRP1:	1.0
Plasma Protein Binding (PPB):	98.571%	Volume Distribution (VD):	-0.372
Fu:	1.343% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.385
OATP1B3 inhibitor:	0.96	BCRP inhibitor:	0.036
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.019	CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.941	CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.127	CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.972
CYP3A4-inhibitor:	0.188	CYP3A4-substrate:	0.019
CYP2B6-substrate:	0.703	CYP2C8-inhibitor:	1.0
HLM stability:	0.988 ? 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):

3.437

Half-life (T1/2):

0.726

ADMET: Toxicity

hERG Blockers:	0.2	hERG Blockers (10um):	0.747
Human Hepatotoxicity (H-HT):	0.203	Drug-induced Liver Injury (DILI):	0.907
AMES Toxicity:	0.234	Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.576	Skin Sensitization:	0.424
Carcinogencity:	0.868	Eye Corrosion:	0.0
Eye Irritation:	0.037	Respiratory Toxicity:	0.165
Drug-induced Neurotoxicity:	0.897	Ototoxicity:	0.54
Hematotoxicity:	0.214	Drug-induced Nephrotoxicity:	0.728
Genotoxicity:	0.207	RPMI-8226 Immunitoxicity:	0.252
A549 Cytotoxicity:	0.31	Hek293 Cytotoxicity:	0.639
BCF:	1.496 ? 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:	4.151 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.365 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.246 ? 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
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165154]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[20025236]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	seed	n.a.	PMID[21381710]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27599	Kadsura ananosma	Species	Schisandraceae	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
Activity	2

Activity Type	# Activity
Cell line	2

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
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	68.9	%	PMID[21381710]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	71.4	%	PMID[21381710]

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 NPC319749 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	20166
0.1-0.2	26675
0.2-0.3	2734
0.3-0.4	192
0.4-0.5	47
0.5-0.6	15
0.6-0.7	20
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
0.7727	Intermediate Similarity	NPC483405
0.7593	Intermediate Similarity	NPC326144
0.7241	Intermediate Similarity	NPC318286
0.7188	Intermediate Similarity	NPC191352
0.7069	Intermediate Similarity	NPC327651
0.7	Intermediate Similarity	NPC321958
0.7	Intermediate Similarity	NPC321696
0.697	Remote Similarity	NPC473445
0.6857	Remote Similarity	NPC477884
0.6721	Remote Similarity	NPC327352
0.6721	Remote Similarity	NPC198129
0.6721	Remote Similarity	NPC252281
0.6508	Remote Similarity	NPC325122
0.625	Remote Similarity	NPC76415
0.625	Remote Similarity	NPC218510
0.6197	Remote Similarity	NPC280778
0.614	Remote Similarity	NPC216434
0.614	Remote Similarity	NPC103448
0.614	Remote Similarity	NPC606558
0.6133	Remote Similarity	NPC477880
0.6111	Remote Similarity	NPC83049
0.6111	Remote Similarity	NPC320471
0.6111	Remote Similarity	NPC118162
0.6061	Remote Similarity	NPC316989
0.6061	Remote Similarity	NPC325720
0.6061	Remote Similarity	NPC316676
0.6	Remote Similarity	NPC322426
0.5921	Remote Similarity	NPC311912
0.5915	Remote Similarity	NPC258322
0.5833	Remote Similarity	NPC79322
0.5823	Remote Similarity	NPC477882
0.5811	Remote Similarity	NPC475229
0.5789	Remote Similarity	NPC474295
0.5758	Remote Similarity	NPC473989
0.5395	Remote Similarity	NPC291977
0.5342	Remote Similarity	NPC477380
0.5278	Remote Similarity	NPC308739
0.5205	Remote Similarity	NPC24562
0.5156	Remote Similarity	NPC865
0.507	Remote Similarity	NPC85141
0.5067	Remote Similarity	NPC477885
0.506	Remote Similarity	NPC477883

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC319749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3888
0.1-0.2	5101
0.2-0.3	160
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