NPASS Compound

Natural Product: NPC482405

Natural Product ID	NPC482405
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OBNLKIYUNMSGTC-ZOTBZMMGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	134754487
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

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 74 77 0 0 0 0 0 0 0 0999 V2000 -3.7789 5.1705 -0.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4009 3.8838 -0.0409 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3811 3.1523 -0.4531 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5976 3.6502 -1.5961 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0909 1.9036 0.2433 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7636 1.4958 1.2127 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0622 1.0462 -0.0801 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7330 -0.1470 0.5343 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5961 -0.2322 1.1981 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5073 -1.2682 2.3004 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7389 -0.6366 0.2955 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0241 0.0917 0.6205 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0661 0.5742 2.0029 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6794 1.7354 2.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9256 2.5582 3.2978 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0929 2.1308 0.7130 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9405 2.9874 0.4060 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2740 1.2801 -0.2252 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1233 1.0349 -1.4361 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7117 -0.2420 -2.0644 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 -0.8397 -1.9420 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3472 -0.4508 -1.1792 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2322 -1.4415 -1.4017 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0858 -1.0466 -1.9031 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3575 0.2820 -2.5239 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8331 -2.1705 -2.6455 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8976 -1.2740 -0.4568 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4165 -2.4967 0.0582 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6722 -2.5260 0.6170 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3451 -1.4744 0.6600 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2509 -3.7996 1.1772 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6178 -3.5047 1.7070 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3638 -4.2612 2.2951 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6999 -0.9014 -2.9053 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3833 -1.9855 -3.4530 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0129 -2.0056 0.4078 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9652 4.9245 -1.7647 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7225 5.5348 -0.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0082 5.9421 -0.5978 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9818 3.5127 0.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0826 3.2836 -2.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6000 4.7721 -1.6359 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5388 3.3109 -1.5605 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4774 -0.3129 1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9130 0.7047 1.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3541 -1.9286 2.2336 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4452 -0.7832 3.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4174 -1.9006 2.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9115 -0.5921 0.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6656 0.0849 2.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0337 2.4204 3.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7918 2.1238 3.8606 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1518 3.5965 3.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3751 1.8911 -0.4409 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8835 1.8379 -2.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2077 1.0378 -1.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4645 -1.7596 -2.4857 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0636 0.5893 -1.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6164 -2.4661 -1.5915 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6017 1.0492 -2.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4069 0.6530 -2.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3558 0.1371 -3.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9218 -1.9141 -2.5557 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7020 -3.1337 -2.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5169 -2.2154 -3.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3243 -4.5788 0.3936 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2128 -2.9227 0.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1024 -4.4697 1.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5034 -2.8767 2.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2836 -4.1361 2.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5557 -5.3461 2.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5774 -3.7235 3.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6636 -0.4297 -3.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9339 -2.1897 0.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 14 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 27 28 1 1 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 31 33 1 0 20 34 1 0 34 35 2 0 11 36 1 6 27 8 1 0 22 11 1 0 27 23 1 0 18 12 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 4 41 1 0 4 42 1 0 4 43 1 0 8 44 1 1 9 45 1 1 10 46 1 0 10 47 1 0 10 48 1 0 12 49 1 1 13 50 1 0 15 51 1 0 15 52 1 0 15 53 1 0 18 54 1 6 19 55 1 0 19 56 1 0 21 57 1 0 22 58 1 1 23 59 1 6 25 60 1 0 25 61 1 0 25 62 1 0 26 63 1 0 26 64 1 0 26 65 1 0 31 66 1 0 32 67 1 0 32 68 1 0 32 69 1 0 33 70 1 0 33 71 1 0 33 72 1 0 34 73 1 0 36 74 1 0 M END

Standard InCHIKey	OBNLKIYUNMSGTC-ZOTBZMMGSA-N
Standard InCHI	InChI=1S/C29H38O7/c1-9-15(4)26(33)35-24-17(6)28(34)20-10-16(5)22(31)19(20)11-18(13-30)12-21(28)23-27(7,8)29(23,24)36-25(32)14(2)3/h9-10,12-14,17,19-21,23-24,34H,11H2,1-8H3/b15-9+/t17-,19+,20-,21+,23-,24-,28+,29-/m1/s1
SMILES	C/C=C(C)/C(=O)O[C@@H]1[C@@H](C)[C@@]2([C@@H]3C=C(C)C(=O)[C@H]3CC(=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(=O)C(C)C)C=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.26	Volume:	518.991 ? Van der Waals volume.
Dense:	0.96	LogP:	3.23 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.262 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.391 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	23.0
TPSA:	106.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.349	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.37	Fsp³:	0.655
MCE-18:	82.167 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.388	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.347	Promiscuous compounds:	0.096

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.209	MDCK Permeability:	-4.911
Pgp-inhibitor:	0.998	Pgp-substrate:	0.293
PAMPA:	0.916 ? 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):	0.128
20% Bioavailability (F20%):	0.973	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.99
Plasma Protein Binding (PPB):	89.444%	Volume Distribution (VD):	0.118
Fu:	13.907% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.726	BCRP inhibitor:	0.003
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.667	CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.112	CYP2C19-substrate:	0.184
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.731
CYP3A4-inhibitor:	0.974	CYP3A4-substrate:	0.323
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.909
HLM stability:	0.948 ? 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):

8.83

Half-life (T1/2):

0.718

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.287
Human Hepatotoxicity (H-HT):	0.621	Drug-induced Liver Injury (DILI):	0.705
AMES Toxicity:	0.748	Rat Oral Acute Toxicity:	0.566
Maximum Recommended Daily Dose:	0.546	Skin Sensitization:	0.983
Carcinogencity:	0.815	Eye Corrosion:	0.104
Eye Irritation:	0.643	Respiratory Toxicity:	0.656
Drug-induced Neurotoxicity:	0.528	Ototoxicity:	0.444
Hematotoxicity:	0.697	Drug-induced Nephrotoxicity:	0.822
Genotoxicity:	0.953	RPMI-8226 Immunitoxicity:	0.262
A549 Cytotoxicity:	0.356	Hek293 Cytotoxicity:	0.555
BCF:	1.276 ? 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:	4.004 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.489 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.092 ? 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
NPO21274	Euphorbia semiperfoliata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28925702]
NPO21274	Euphorbia semiperfoliata	Species	Euphorbiaceae	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	2
CC50	2
Ratio CC50/EC50	2

Activity Type	# Activity
Cell line	2
Organism	2
Others	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
NPT460	Cell line	MT2	Homo sapiens	CC50	>	50000.0	nM	PMID[28925702]
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	=	154000.0	nM	PMID[28925702]
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	EC50	=	2560.0	nM	PMID[28925702]
NPT20632	Organism	Chikungunya virus	Chikungunya virus	EC50	=	51100.0	nM	PMID[28925702]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	>	20.0	n.a.	PMID[28925702]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	3.0	n.a.	PMID[28925702]

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 NPC482405 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	19631
0.1-0.2	28342
0.2-0.3	1760
0.3-0.4	58
0.4-0.5	30
0.5-0.6	21
0.6-0.7	7
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC481528
0.8154	Intermediate Similarity	NPC234858
0.8154	Intermediate Similarity	NPC179207
0.7391	Intermediate Similarity	NPC471127
0.7391	Intermediate Similarity	NPC481525
0.7391	Intermediate Similarity	NPC481531
0.7313	Intermediate Similarity	NPC154363
0.7015	Intermediate Similarity	NPC482406
0.7	Intermediate Similarity	NPC485734
0.6714	Remote Similarity	NPC481520
0.6622	Remote Similarity	NPC10721
0.6338	Remote Similarity	NPC472757
0.6338	Remote Similarity	NPC481522
0.6111	Remote Similarity	NPC606275
0.6049	Remote Similarity	NPC140021
0.6026	Remote Similarity	NPC482221
0.5949	Remote Similarity	NPC482220
0.5875	Remote Similarity	NPC482222
0.5867	Remote Similarity	NPC145182
0.5857	Remote Similarity	NPC481529
0.5802	Remote Similarity	NPC482219
0.5802	Remote Similarity	NPC611138
0.5714	Remote Similarity	NPC90814
0.5714	Remote Similarity	NPC189393
0.5658	Remote Similarity	NPC485737
0.5584	Remote Similarity	NPC476111
0.5513	Remote Similarity	NPC608501
0.5488	Remote Similarity	NPC329080
0.5375	Remote Similarity	NPC236918
0.5375	Remote Similarity	NPC156745
0.5316	Remote Similarity	NPC471126
0.527	Remote Similarity	NPC481527
0.5244	Remote Similarity	NPC472759
0.52	Remote Similarity	NPC600179
0.52	Remote Similarity	NPC602150
0.5195	Remote Similarity	NPC157252
0.5181	Remote Similarity	NPC481523

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6977
0.1-0.2	2141
0.2-0.3	32
0.3-0.4	0
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