NPASS Compound

Natural Product: NPC249836

Natural Product ID	NPC249836
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oncostemonol A
IUPAC Name	[3-[(Z)-16-(3-acetyloxy-5-hydroxyphenyl)hexadec-8-enyl]-5-hydroxyphenyl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL458521
PubChem CID	643740
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002319] Phenol esters

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 82 83 0 0 0 0 0 0 0 0999 V2000 5.7315 0.2411 5.0314 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4379 0.3161 3.7170 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5677 -0.2295 3.6475 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9271 0.9322 2.6179 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5297 1.0339 1.3727 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4106 0.0470 0.4177 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0092 0.1378 -0.8457 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9242 -0.9805 -1.7756 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6658 -1.2128 -2.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1270 -0.1863 -3.3578 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6829 1.0978 -2.7927 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5832 0.9724 -1.7403 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3985 0.2709 -2.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2608 0.1502 -1.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1426 -0.5488 -1.9795 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0705 -0.0289 -2.1486 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3673 1.3251 -1.7337 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3723 1.5036 -0.6826 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7655 1.1312 -0.9114 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1141 -0.2726 -1.2066 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6610 -0.3314 -1.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1342 -1.7259 -1.5432 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7715 -2.7233 -0.4901 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3926 -2.3564 0.7951 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6508 -2.8841 1.1113 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2980 -2.5853 2.2862 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5535 -3.1216 2.5838 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6952 -1.7399 3.1870 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4578 -1.1963 2.9215 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8378 -1.5220 1.7253 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8851 -0.3517 3.8475 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1333 0.9862 3.9521 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9627 1.5076 3.1329 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4958 1.8520 4.9596 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7574 1.2864 -1.1320 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8868 2.2811 -0.1910 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2752 2.1437 1.0421 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6379 3.4407 -0.4687 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3024 -0.7816 5.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5044 0.3759 5.8149 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9767 1.0414 5.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8389 -0.8513 0.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7976 -0.8916 -2.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2787 -1.9272 -1.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7856 -2.2188 -3.0290 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8503 -1.4916 -1.7070 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3233 -0.6755 -3.9966 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8884 0.0919 -4.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1303 1.6373 -3.6599 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5103 1.7259 -2.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2208 1.9752 -1.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8998 0.4299 -0.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6536 -0.7239 -2.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0629 0.9509 -3.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0874 1.0913 -0.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6955 -0.5244 -0.5656 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2872 -1.5891 -2.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8264 -0.6699 -2.6470 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8127 1.8695 -2.6759 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4509 1.9606 -1.5797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9654 0.9056 0.2336 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3255 2.5821 -0.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3709 1.5257 -0.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2202 1.7365 -1.7901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7529 -1.0227 -0.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8136 -0.5068 -2.2784 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0742 0.0114 -0.3046 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9654 0.3209 -2.1082 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2375 -1.6723 -1.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7087 -2.0188 -2.5365 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6806 -2.7762 -0.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0885 -3.7566 -0.8126 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1036 -3.5553 0.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1225 -3.3569 1.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1990 -1.4900 4.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8858 -1.0902 1.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1280 2.7976 4.5243 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6383 1.2932 5.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2243 2.0579 5.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2446 1.4190 -2.0869 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3543 2.9105 1.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5645 4.2210 0.1655 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 26 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 7 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 37 5 1 0 30 24 1 0 1 39 1 0 1 40 1 0 1 41 1 0 6 42 1 0 8 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 22 69 1 0 22 70 1 0 23 71 1 0 23 72 1 0 25 73 1 0 27 74 1 0 28 75 1 0 30 76 1 0 34 77 1 0 34 78 1 0 34 79 1 0 35 80 1 0 37 81 1 0 38 82 1 0 M END

Standard InCHIKey	KKAFTGMKZVJNPP-ARJAWSKDSA-N
Standard InCHI	InChI=1S/C32H44O6/c1-25(33)37-31-21-27(19-29(35)23-31)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-28-20-30(36)24-32(22-28)38-26(2)34/h3-4,19-24,35-36H,5-18H2,1-2H3/b4-3-
SMILES	CC(=O)Oc1cc(CCCCCCC/C=CCCCCCCCc2cc(O)cc(c2)OC(=O)C)cc(c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	524.31	Volume:	573.928 ? Van der Waals volume.
Dense:	0.914	LogP:	7.537 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.92 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.179 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	15.0
TPSA:	93.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.739	Fsp³:	0.5
MCE-18:	14.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.836	Fluc inhibitor:	0.385 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.441 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.612	Promiscuous compounds:	0.173

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.3	MDCK Permeability:	-4.695
Pgp-inhibitor:	0.998	Pgp-substrate:	0.001
PAMPA:	0.0 ? 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%):	0.972	30% Bioavailability (F30%):	0.983
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.982
Plasma Protein Binding (PPB):	97.878%	Volume Distribution (VD):	0.382
Fu:	1.58% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.672
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.974
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.998
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.434
CYP2D6-inhibitor:	0.266	CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.36 ? 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):

2.411

Half-life (T1/2):

1.073

ADMET: Toxicity

hERG Blockers:	0.416	hERG Blockers (10um):	0.714
Human Hepatotoxicity (H-HT):	0.314	Drug-induced Liver Injury (DILI):	0.026
AMES Toxicity:	0.188	Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.547	Skin Sensitization:	1.0
Carcinogencity:	0.032	Eye Corrosion:	0.824
Eye Irritation:	0.978	Respiratory Toxicity:	0.376
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.082
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.077
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.957	Hek293 Cytotoxicity:	0.882
BCF:	0.873 ? 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:	5.349 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.718 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.184 ? 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
NPO33313	oncostemon bojerianum	Species	n.a.	n.a.	leaves	Madagascar rainforest	n.a.	PMID[12444688]

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	1

Activity Type	# Activity
Cell line	1

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
NPT179	Cell line	A2780	Homo sapiens	IC50	=	9.4	ug.mL-1	PMID[22037378]

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 NPC249836 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	14063
0.1-0.2	31324
0.2-0.3	4182
0.3-0.4	195
0.4-0.5	50
0.5-0.6	33
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9149	High Similarity	NPC140521
0.8605	High Similarity	NPC78446
0.7826	Intermediate Similarity	NPC219070
0.72	Intermediate Similarity	NPC127894
0.72	Intermediate Similarity	NPC15860
0.72	Intermediate Similarity	NPC470759
0.6275	Remote Similarity	NPC471498
0.6275	Remote Similarity	NPC471503
0.617	Remote Similarity	NPC168657
0.6	Remote Similarity	NPC114064
0.6	Remote Similarity	NPC470699
0.5625	Remote Similarity	NPC53051
0.5625	Remote Similarity	NPC24404
0.5625	Remote Similarity	NPC313030
0.5577	Remote Similarity	NPC470161
0.5532	Remote Similarity	NPC470700
0.5532	Remote Similarity	NPC54844
0.5532	Remote Similarity	NPC39097
0.5532	Remote Similarity	NPC302681
0.5532	Remote Similarity	NPC118286
0.5532	Remote Similarity	NPC109691
0.551	Remote Similarity	NPC146798
0.551	Remote Similarity	NPC222522
0.551	Remote Similarity	NPC106396
0.551	Remote Similarity	NPC94351
0.551	Remote Similarity	NPC168303
0.549	Remote Similarity	NPC71002
0.549	Remote Similarity	NPC302219
0.549	Remote Similarity	NPC242342
0.549	Remote Similarity	NPC249828
0.549	Remote Similarity	NPC85479
0.5306	Remote Similarity	NPC39664
0.5294	Remote Similarity	NPC483454
0.5294	Remote Similarity	NPC162314
0.5246	Remote Similarity	NPC471504
0.5238	Remote Similarity	NPC470752
0.5192	Remote Similarity	NPC10588
0.5192	Remote Similarity	NPC94139
0.5192	Remote Similarity	NPC147284
0.5185	Remote Similarity	NPC210497
0.5161	Remote Similarity	NPC473290
0.5161	Remote Similarity	NPC29577
0.5094	Remote Similarity	NPC72947
0.5085	Remote Similarity	NPC473221

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC249836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3476
0.1-0.2	5444
0.2-0.3	223
0.3-0.4	7
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