NPASS Compound

Natural Product: NPC132652

Natural Product ID	NPC132652
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Euphodendriane A
IUPAC Name	n.a.
Synonyms	Euphodendriane A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1821797
PubChem CID	53388139
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 76 80 0 0 0 0 0 0 0 0999 V2000 -5.0841 -2.6841 1.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6049 -2.8988 1.1194 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9320 -1.7625 0.4244 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5747 -0.7709 0.0057 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5788 -1.7701 0.2217 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7971 -0.7672 -0.4031 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7649 0.5417 0.2611 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8126 1.4472 -0.0030 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6212 2.0456 0.9418 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4188 1.7684 2.1496 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6897 2.9741 0.6279 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4757 3.5514 1.5943 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4917 4.4370 1.2651 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7201 4.7473 -0.0664 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9373 4.1740 -1.0455 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9280 3.2912 -0.6851 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5587 1.2965 0.0981 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5586 2.4475 1.0800 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6299 0.2743 0.4126 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6859 -0.5583 -0.8694 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4065 -1.2945 -1.0608 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7024 -0.8701 -1.9113 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 0.3710 -2.7531 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5650 -1.9723 -2.5493 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8970 -1.4224 -0.8892 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7299 -1.7846 0.0655 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8243 -2.6743 -0.4054 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7289 -1.4421 1.4892 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7473 0.0456 1.7434 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9620 0.8423 0.7271 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9013 0.9335 -0.4100 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1449 0.7409 -0.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1492 0.5013 1.4417 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0850 0.6360 2.2635 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4030 0.7459 -0.8105 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8817 -1.9639 2.0780 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1166 -0.5143 1.4627 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3463 -4.2092 0.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3126 -2.1062 2.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4227 -2.1832 0.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5543 -3.6890 1.3512 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1814 -2.9565 2.1350 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7752 0.3710 1.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3328 3.3373 2.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1051 4.8844 2.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5193 5.4468 -0.3568 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1043 4.4085 -2.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3456 2.8732 -1.5092 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6709 1.7330 -0.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5246 2.1428 2.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3737 3.0399 0.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3790 3.1745 0.8437 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8473 0.1983 -1.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5850 -2.4123 -1.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2379 1.1605 -2.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3688 0.6817 -3.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1863 0.2505 -3.7453 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6223 -1.7020 -2.5711 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3359 -2.9514 -2.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2273 -2.0001 -3.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1167 -1.8151 -1.8778 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4399 -3.4764 -1.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3382 -3.1590 0.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5587 -2.0235 -0.9373 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8764 -1.9356 2.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4341 0.2740 2.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9078 1.8798 1.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6199 1.1312 -1.4266 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0965 0.4918 -1.8662 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8338 1.7757 -0.8921 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1506 0.0280 -0.4623 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7111 -1.6053 1.7259 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3396 -0.0278 2.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3770 -5.0082 1.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1558 -4.4165 -0.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3369 -4.2682 -0.0290 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 3 5 1 0 6 5 1 1 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 20 25 1 0 25 26 2 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 32 35 1 0 28 36 1 0 19 37 1 1 2 38 1 0 21 6 1 0 33 29 1 0 22 6 1 0 16 11 1 0 30 19 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 7 43 1 1 12 44 1 0 13 45 1 0 14 46 1 0 15 47 1 0 16 48 1 0 17 49 1 6 18 50 1 0 18 51 1 0 18 52 1 0 20 53 1 6 21 54 1 1 23 55 1 0 23 56 1 0 23 57 1 0 24 58 1 0 24 59 1 0 24 60 1 0 25 61 1 0 27 62 1 0 27 63 1 0 27 64 1 0 28 65 1 1 29 66 1 1 30 67 1 1 31 68 1 0 35 69 1 0 35 70 1 0 35 71 1 0 36 72 1 0 37 73 1 0 38 74 1 0 38 75 1 0 38 76 1 0 M END

Standard InCHIKey	TUYMOSZNDXCMQM-GLPNJXFDSA-N
Standard InCHI	InChI=1S/C31H38O7/c1-15(2)27(34)38-31-25(29(31,6)7)21-14-17(4)24(33)22-20(13-16(3)23(22)32)30(21,36)18(5)26(31)37-28(35)19-11-9-8-10-12-19/h8-15,18,20-22,24-26,33,36H,1-7H3/t18-,20-,21+,22-,24-,25-,26-,30+,31-/m1/s1
SMILES	CC(C(=O)O[C@@]12[C@H](OC(=O)c3ccccc3)[C@@H](C)[C@]3([C@H]([C@@H]1C2(C)C)C=C(C)[C@H]([C@@H]1[C@H]3C=C(C1=O)C)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	522.26	Volume:	542.39 ? Van der Waals volume.
Dense:	0.963	LogP:	3.337 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.363 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.892 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	27.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.456	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.015	Fsp³:	0.581
MCE-18:	129.51 ? 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:	0.682	Fluc inhibitor:	0.071 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? 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:	0.209	Promiscuous compounds:	0.156

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.371	MDCK Permeability:	-4.938
Pgp-inhibitor:	0.999	Pgp-substrate:	0.786
PAMPA:	0.801 ? 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):	0.004
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.999
Plasma Protein Binding (PPB):	93.234%	Volume Distribution (VD):	0.163
Fu:	5.621% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.389	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.26
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.928	CYP3A4-substrate:	0.624
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

9.724

Half-life (T1/2):

0.649

ADMET: Toxicity

hERG Blockers:	0.037	hERG Blockers (10um):	0.464
Human Hepatotoxicity (H-HT):	0.172	Drug-induced Liver Injury (DILI):	0.777
AMES Toxicity:	0.58	Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.132	Skin Sensitization:	0.993
Carcinogencity:	0.546	Eye Corrosion:	0.01
Eye Irritation:	0.759	Respiratory Toxicity:	0.467
Drug-induced Neurotoxicity:	0.578	Ototoxicity:	0.373
Hematotoxicity:	0.592	Drug-induced Nephrotoxicity:	0.795
Genotoxicity:	0.851	RPMI-8226 Immunitoxicity:	0.139
A549 Cytotoxicity:	0.597	Hek293 Cytotoxicity:	0.434
BCF:	0.784 ? 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:	3.588 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.061 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.531 ? 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
NPO4	Euphorbia dendroides	Species	Euphorbiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21707046]
NPO4	Euphorbia dendroides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29498278]
NPO4	Euphorbia dendroides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	4
IC30	4
Inhibition	1

Activity Type	# Activity
Cell line	7
Non-molecular	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
NPT579	Cell line	DLD-1	Homo sapiens	IC50	=	27400.0	nM	PMID[21707046]
NPT579	Cell line	DLD-1	Homo sapiens	IC30	=	13.3	uM	PMID[21707046]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	26000.0	nM	PMID[21707046]
NPT397	Cell line	NCI-H460	Homo sapiens	IC30	=	15.7	uM	PMID[21707046]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	14300.0	nM	PMID[21707046]
NPT397	Cell line	NCI-H460	Homo sapiens	IC30	=	7.0	uM	PMID[21707046]
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	>	50.0	%	PMID[30707022]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	60100.0	nM	PMID[21707046]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC30	=	33.2	uM	PMID[21707046]

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 NPC132652 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	8930
0.1-0.2	38641
0.2-0.3	1826
0.3-0.4	397
0.4-0.5	39
0.5-0.6	20
0.6-0.7	5
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
0.6875	Remote Similarity	NPC90358
0.6875	Remote Similarity	NPC107828
0.6582	Remote Similarity	NPC481523
0.6081	Remote Similarity	NPC600179
0.6081	Remote Similarity	NPC602150
0.593	Remote Similarity	NPC176371
0.593	Remote Similarity	NPC136573
0.5833	Remote Similarity	NPC472398
0.5833	Remote Similarity	NPC600915
0.5632	Remote Similarity	NPC11410
0.5632	Remote Similarity	NPC600144
0.5393	Remote Similarity	NPC486559
0.5385	Remote Similarity	NPC600480
0.5385	Remote Similarity	NPC603807
0.5341	Remote Similarity	NPC138641
0.5341	Remote Similarity	NPC611243
0.5287	Remote Similarity	NPC611138
0.5233	Remote Similarity	NPC605733
0.5169	Remote Similarity	NPC21483
0.5169	Remote Similarity	NPC198205
0.5169	Remote Similarity	NPC486562
0.5165	Remote Similarity	NPC601392
0.5109	Remote Similarity	NPC601559
0.5054	Remote Similarity	NPC283875
0.5054	Remote Similarity	NPC22571

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC132652 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3645
0.1-0.2	5407
0.2-0.3	98
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