NPASS Compound

Natural Product: NPC321696

Natural Product ID	NPC321696
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ananolignan J
IUPAC Name	n.a.
Synonyms	Ananolignan J
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1782118
PubChem CID	53355456
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 78 81 0 0 0 0 0 0 0 0999 V2000 5.6299 -0.6075 -0.2508 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1208 0.0205 1.0195 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3320 1.2721 1.3658 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8899 1.0140 1.5599 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3949 1.2660 2.6874 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0756 0.5198 0.5814 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6937 0.2669 0.7441 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4966 -1.2217 0.6240 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8493 -1.7301 -0.7724 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2165 -1.7701 1.1273 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4218 -3.0421 1.9683 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7970 -2.1758 0.0645 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4513 -3.3668 0.3601 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4752 -4.3611 -0.6277 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9132 -4.1634 -1.7497 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1342 -5.6655 -0.4388 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7899 -1.0561 0.0902 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6069 0.3159 -0.1077 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4520 1.0871 -0.5636 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8964 1.0829 -0.1388 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7187 1.9889 -0.7042 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2405 2.8854 -1.6700 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8529 3.8979 -2.3940 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8338 4.7310 -2.9290 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2547 3.8470 -3.0201 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0966 2.8374 -2.0518 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9666 1.9271 -1.5010 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2862 1.8018 -1.8455 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7688 0.9849 -2.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5887 1.2562 0.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2482 2.5722 -0.1596 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8074 3.4106 0.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8334 0.7922 0.3830 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0498 -0.5848 0.5833 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0111 -1.4946 0.4331 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3165 -1.0150 0.9325 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5207 -2.3987 1.1305 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8551 1.7135 0.5288 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6488 2.0447 -0.5771 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9283 1.9971 2.5351 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5063 -0.6899 -0.9562 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1891 -1.6148 -0.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9158 0.0646 -0.7740 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1946 0.2384 0.9413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9659 -0.7349 1.8317 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4702 1.9520 0.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4461 0.5412 1.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3017 -1.6519 1.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3316 -1.1886 -1.5706 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5609 -2.8229 -0.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9468 -1.7260 -0.9199 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1970 -1.0338 1.8621 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8633 -3.8223 1.3135 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0472 -2.8122 2.8426 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5776 -3.3772 2.2636 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3548 -2.1501 -0.9539 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 -5.8154 0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9538 -5.7584 -1.2080 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3872 -6.4508 -0.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7794 2.0877 -0.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1746 5.0793 -3.9346 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6818 5.5556 -2.2271 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0401 0.2944 -3.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2020 1.7014 -3.6397 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6453 0.4303 -2.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0701 4.4447 0.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2656 3.0232 1.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7333 3.2825 1.0084 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1492 -2.5560 0.5835 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9355 -2.7770 2.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5778 -2.6311 1.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1679 -2.9994 0.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1238 3.0409 -0.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4156 1.2323 -0.6766 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0725 2.0898 -1.5228 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5588 1.3398 3.1819 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1375 2.5156 3.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6275 2.8192 2.2048 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 12 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 18 30 1 0 30 31 1 0 31 32 1 0 30 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 33 38 1 0 38 39 1 0 3 40 1 0 20 7 1 0 26 22 1 0 35 17 1 0 27 19 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 2 45 1 0 3 46 1 0 7 47 1 1 8 48 1 1 9 49 1 0 9 50 1 0 9 51 1 0 10 52 1 1 11 53 1 0 11 54 1 0 11 55 1 0 12 56 1 6 16 57 1 0 16 58 1 0 16 59 1 0 21 60 1 0 24 61 1 0 24 62 1 0 29 63 1 0 29 64 1 0 29 65 1 0 32 66 1 0 32 67 1 0 32 68 1 0 35 69 1 0 37 70 1 0 37 71 1 0 37 72 1 0 39 73 1 0 39 74 1 0 39 75 1 0 40 76 1 0 40 77 1 0 40 78 1 0 M END

Standard InCHIKey	CTOBKBWNSSDQMA-BTZGXSAMSA-N
Standard InCHI	InChI=1S/C30H38O10/c1-10-14(2)30(32)40-25-16(4)15(3)24(39-17(5)31)18-11-20(33-6)26(34-7)28(35-8)22(18)23-19(25)12-21-27(29(23)36-9)38-13-37-21/h11-12,14-16,24-25H,10,13H2,1-9H3/t14?,15-,16+,24+,25+/m0/s1
SMILES	CCC(C(=O)O[C@@H]1[C@H](C)[C@H](C)[C@@H](OC(=O)C)c2c(c3c1cc1OCOc1c3OC)c(OC)c(c(c2)OC)OC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	558.25	Volume:	560.021 ? Van der Waals volume.
Dense:	0.997	LogP:	3.87 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.375 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.189 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	24.0
TPSA:	107.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.378	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.364	Fsp³:	0.533
MCE-18:	93.304 ? 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:	0.615	Fluc inhibitor:	0.011 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.346 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.372 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.272	Promiscuous compounds:	0.119

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.994	MDCK Permeability:	-4.753
Pgp-inhibitor:	0.926	Pgp-substrate:	0.073
PAMPA:	0.069 ? 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):	0.001
20% Bioavailability (F20%):	0.454	30% Bioavailability (F30%):	0.028
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.381	MRP1:	0.995
Plasma Protein Binding (PPB):	95.856%	Volume Distribution (VD):	-0.113
Fu:	4.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.901
OATP1B3 inhibitor:	0.859	BCRP inhibitor:	0.032
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.829	CYP1A2-substrate:	0.185
CYP2C19-inhibitor:	0.99	CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.326
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.983	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.01	CYP2C8-inhibitor:	0.875
HLM stability:	0.947 ? 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):

4.552

Half-life (T1/2):

0.582

ADMET: Toxicity

hERG Blockers:	0.09	hERG Blockers (10um):	0.48
Human Hepatotoxicity (H-HT):	0.646	Drug-induced Liver Injury (DILI):	0.919
AMES Toxicity:	0.523	Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.514	Skin Sensitization:	0.813
Carcinogencity:	0.819	Eye Corrosion:	0.001
Eye Irritation:	0.036	Respiratory Toxicity:	0.465
Drug-induced Neurotoxicity:	0.633	Ototoxicity:	0.705
Hematotoxicity:	0.876	Drug-induced Nephrotoxicity:	0.881
Genotoxicity:	0.064	RPMI-8226 Immunitoxicity:	0.307
A549 Cytotoxicity:	0.616	Hek293 Cytotoxicity:	0.345
BCF:	1.503 ? 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:	3.857 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.031 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.024 ? 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	=	52.2	%	PMID[21381710]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	55.1	%	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 NPC321696 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	15261
0.1-0.2	32107
0.2-0.3	2149
0.3-0.4	224
0.4-0.5	84
0.5-0.6	12
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.86	High Similarity	NPC327651
0.8542	High Similarity	NPC326144
0.8077	Intermediate Similarity	NPC318286
0.7778	Intermediate Similarity	NPC321958
0.7455	Intermediate Similarity	NPC327352
0.7455	Intermediate Similarity	NPC198129
0.7455	Intermediate Similarity	NPC252281
0.7193	Intermediate Similarity	NPC322426
0.7193	Intermediate Similarity	NPC325122
0.7	Intermediate Similarity	NPC319749
0.6897	Remote Similarity	NPC76415
0.6897	Remote Similarity	NPC218510
0.6863	Remote Similarity	NPC216434
0.6863	Remote Similarity	NPC103448
0.6863	Remote Similarity	NPC606558
0.6667	Remote Similarity	NPC316989
0.6667	Remote Similarity	NPC325720
0.6667	Remote Similarity	NPC316676
0.6471	Remote Similarity	NPC474295
0.6333	Remote Similarity	NPC473989
0.6087	Remote Similarity	NPC474606
0.5821	Remote Similarity	NPC477380
0.5758	Remote Similarity	NPC471154
0.5758	Remote Similarity	NPC308739
0.569	Remote Similarity	NPC865
0.5672	Remote Similarity	NPC24562
0.5634	Remote Similarity	NPC475229
0.5538	Remote Similarity	NPC85141
0.5507	Remote Similarity	NPC477885
0.549	Remote Similarity	NPC475856
0.5417	Remote Similarity	NPC483405
0.5373	Remote Similarity	NPC312763
0.5205	Remote Similarity	NPC63061

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC321696 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4241
0.1-0.2	4784
0.2-0.3	120
0.3-0.4	5
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