NPASS Compound

Natural Product: NPC72840

Natural Product ID	NPC72840
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OVPHXTVCLYBRDV-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321169
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 64 66 0 0 0 0 0 0 0 0999 V2000 -1.6032 3.8283 -1.7880 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9999 2.5678 -1.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0586 1.4894 -1.3537 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7509 0.2916 -0.5402 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8992 -0.4200 -0.3464 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9140 -1.5796 0.4256 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7193 -2.0028 1.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5378 -1.3239 0.8458 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5790 -0.1974 0.0733 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8070 0.2463 0.0294 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3917 1.5110 0.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8860 2.8858 0.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6315 2.8296 0.2437 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1501 4.1560 0.7607 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7667 1.5435 0.1878 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5181 0.4131 -0.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8738 -0.8052 -0.2476 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5051 -0.9055 -0.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7746 -2.0584 -0.4243 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3542 -2.4548 -1.6963 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6646 -1.7189 -2.6664 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4335 -3.7103 -1.8697 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5956 -1.9695 -0.4887 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9328 -2.3679 -1.7916 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9077 0.4415 -0.0936 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6547 1.6160 0.0946 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6709 -1.6689 1.4073 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0909 -1.2024 2.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7243 -3.1524 1.7750 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9729 -3.1173 3.1821 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0688 -2.3181 0.6318 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2571 -1.8487 0.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 4.5485 -2.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1774 3.5120 -2.6976 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3656 4.2638 -1.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1241 2.2973 -1.8053 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0178 1.9057 -0.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1035 1.2340 -2.4135 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8137 -0.0691 -0.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2993 3.5171 -0.3652 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1355 3.2719 1.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1034 2.0548 0.8822 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8627 4.9961 0.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6101 4.3423 1.7260 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2228 4.1346 1.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2753 2.5002 0.3423 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0353 -4.5158 -1.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4887 -3.5267 -1.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4207 -4.0467 -2.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6292 -1.5809 -2.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3989 -3.3049 -2.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0324 -2.4951 -1.8870 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1897 2.5079 -0.3631 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6778 1.4825 -0.3213 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8042 1.8379 1.1825 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0631 -0.7218 2.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1733 -2.1366 3.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2848 -0.5531 3.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8335 -2.0642 3.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2280 -3.7922 3.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0048 -3.4327 3.4114 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0963 -2.5717 0.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1256 -1.7122 -1.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5796 -0.8805 0.4339 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 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 11 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 17 23 1 0 23 24 1 0 16 25 1 0 25 26 1 0 8 27 1 0 27 28 1 0 7 29 1 0 29 30 1 0 6 31 1 0 31 32 1 0 13 2 1 0 9 4 1 0 18 10 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 3 37 1 0 3 38 1 0 5 39 1 0 12 40 1 0 12 41 1 0 13 42 1 0 14 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 22 47 1 0 22 48 1 0 22 49 1 0 24 50 1 0 24 51 1 0 24 52 1 0 26 53 1 0 26 54 1 0 26 55 1 0 28 56 1 0 28 57 1 0 28 58 1 0 30 59 1 0 30 60 1 0 30 61 1 0 32 62 1 0 32 63 1 0 32 64 1 0 M END

Standard InCHIKey	OVPHXTVCLYBRDV-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C25H32O7/c1-13-9-16-11-18(27-4)22(29-6)24(31-8)20(16)21-17(10-14(13)2)12-19(28-5)23(30-7)25(21)32-15(3)26/h11-14H,9-10H2,1-8H3
SMILES	CC1Cc2cc(c(c(c2-c2c(CC1C)cc(c(c2OC(=O)C)OC)OC)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	444.21	Volume:	458.363 ? Van der Waals volume.
Dense:	0.969	LogP:	2.877 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.071 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.282 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	19.0
TPSA:	72.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.473	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.463	Fsp³:	0.48
MCE-18:	70.757 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.417	Fluc inhibitor:	0.324 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.457 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.705 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.312	Promiscuous compounds:	0.061

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.633	MDCK Permeability:	-4.624
Pgp-inhibitor:	0.549	Pgp-substrate:	0.054
PAMPA:	0.001 ? 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%):	0.001	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.119

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.887	MRP1:	1.0
Plasma Protein Binding (PPB):	95.776%	Volume Distribution (VD):	0.234
Fu:	3.77% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.878
OATP1B3 inhibitor:	0.953	BCRP inhibitor:	0.011
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.854	CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.874	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.025	CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	0.684
CYP2B6-substrate:	0.343	CYP2C8-inhibitor:	1.0
HLM stability:	0.989 ? 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):

4.763

Half-life (T1/2):

0.596

ADMET: Toxicity

hERG Blockers:	0.134	hERG Blockers (10um):	0.628
Human Hepatotoxicity (H-HT):	0.532	Drug-induced Liver Injury (DILI):	0.679
AMES Toxicity:	0.305	Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.472	Skin Sensitization:	0.798
Carcinogencity:	0.52	Eye Corrosion:	0.008
Eye Irritation:	0.27	Respiratory Toxicity:	0.812
Drug-induced Neurotoxicity:	0.649	Ototoxicity:	0.587
Hematotoxicity:	0.567	Drug-induced Nephrotoxicity:	0.112
Genotoxicity:	0.056	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.769	Hek293 Cytotoxicity:	0.474
BCF:	2.329 ? 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:	4.303 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.587 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.061 ? 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
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24804	Schisandra rubriflora	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

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

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 NPC72840 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	22266
0.1-0.2	25168
0.2-0.3	2180
0.3-0.4	163
0.4-0.5	49
0.5-0.6	20
0.6-0.7	10
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8286	Intermediate Similarity	NPC283114
0.8286	Intermediate Similarity	NPC207702
0.8286	Intermediate Similarity	NPC149008
0.6744	Remote Similarity	NPC145722
0.6744	Remote Similarity	NPC256776
0.6744	Remote Similarity	NPC185680
0.6279	Remote Similarity	NPC32189
0.625	Remote Similarity	NPC865
0.6078	Remote Similarity	NPC137352
0.6078	Remote Similarity	NPC183083
0.6078	Remote Similarity	NPC485503
0.6038	Remote Similarity	NPC477381
0.6	Remote Similarity	NPC471182
0.5957	Remote Similarity	NPC206737
0.5957	Remote Similarity	NPC289258
0.5957	Remote Similarity	NPC611061
0.5926	Remote Similarity	NPC477879
0.5714	Remote Similarity	NPC141493
0.5652	Remote Similarity	NPC102256
0.549	Remote Similarity	NPC184928
0.5472	Remote Similarity	NPC220577
0.5455	Remote Similarity	NPC76415
0.5455	Remote Similarity	NPC218510
0.5283	Remote Similarity	NPC184684
0.5283	Remote Similarity	NPC184641
0.5246	Remote Similarity	NPC473323
0.5167	Remote Similarity	NPC149735
0.5161	Remote Similarity	NPC473425
0.5091	Remote Similarity	NPC230538
0.5091	Remote Similarity	NPC229172
0.5091	Remote Similarity	NPC103637
0.5091	Remote Similarity	NPC301765
0.5091	Remote Similarity	NPC36531

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC72840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4316
0.1-0.2	4631
0.2-0.3	198
0.3-0.4	4
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