NPASS Compound

Natural Product: NPC158523

Natural Product ID	NPC158523
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QSTFRCUXCBXJAW-CYZOKXGXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL528106
PubChem CID	107855
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 [CHEMONTID:0002906] Phorbol 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 64 67 0 0 0 0 0 0 0 0999 V2000 -4.4622 -3.6711 1.0137 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7726 -3.2690 -0.1461 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0458 -2.0066 0.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7301 -2.0126 0.1545 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7446 -0.9356 0.4670 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6434 -1.4026 0.1073 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6788 -0.3554 0.4661 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6575 -1.6644 1.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 -1.7982 2.6032 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6957 -2.6971 0.7248 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7453 -0.1639 -0.4376 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8017 0.6963 -0.2744 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8757 1.3931 0.7613 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8866 0.8449 -1.2896 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5903 -0.4977 -1.5037 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9351 1.7830 -0.7431 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9980 0.8512 1.0026 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1428 1.3676 0.1135 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9873 0.2778 -0.4438 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4245 0.5614 -0.6281 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2599 0.4531 0.6121 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9041 -0.8868 0.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6221 0.8600 1.7635 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3351 1.4606 0.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4731 1.5163 0.8371 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7890 2.3913 -0.6571 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7042 1.8789 -1.2034 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3925 3.7181 -0.9824 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4665 -0.1084 -1.7022 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4846 2.1536 -1.0009 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8670 -3.7032 1.8001 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0362 -4.0422 -0.4400 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5152 -3.0294 -0.9052 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3078 -2.9398 -0.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8147 -0.5892 1.4956 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7359 -1.7946 -0.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5132 -1.1065 2.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9395 -2.8648 2.7466 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1928 -1.6867 3.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1994 -2.3940 -0.2174 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4003 -2.9424 1.5324 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1109 -3.6154 0.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5047 1.2225 -2.2548 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0575 -1.1199 -2.2458 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6760 -0.9790 -0.5237 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6151 -0.2664 -1.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4789 2.7926 -0.6965 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2327 1.4095 0.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8652 1.7483 -1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6937 1.7042 1.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6272 0.7190 2.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7353 2.0696 0.7680 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8481 -0.1944 -1.3545 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7923 -0.8795 0.0142 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3435 -1.0840 1.7155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7998 1.8131 1.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1196 2.3636 -1.9596 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4522 3.7525 -0.6839 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3282 3.8827 -2.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7755 4.5045 -0.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1672 -0.7186 -2.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0137 3.1465 -1.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5501 2.4360 -0.7538 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5105 1.6474 -1.9646 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 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 7 11 1 6 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 14 16 1 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 1 21 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 26 28 1 0 19 29 1 6 18 30 1 0 22 3 1 0 19 5 1 0 27 20 1 0 8 6 1 0 1 31 1 0 2 32 1 0 2 33 1 0 4 34 1 0 5 35 1 1 6 36 1 6 9 37 1 0 9 38 1 0 9 39 1 0 10 40 1 0 10 41 1 0 10 42 1 0 14 43 1 0 15 44 1 0 15 45 1 0 15 46 1 0 16 47 1 0 16 48 1 0 16 49 1 0 17 50 1 0 17 51 1 0 18 52 1 1 20 53 1 6 22 54 1 0 22 55 1 0 23 56 1 0 27 57 1 0 28 58 1 0 28 59 1 0 28 60 1 0 29 61 1 0 30 62 1 0 30 63 1 0 30 64 1 0 M END

Standard InCHIKey	QSTFRCUXCBXJAW-CYZOKXGXSA-N
Standard InCHI	InChI=1S/C24H34O6/c1-12(2)20(27)30-23-9-14(4)24(29)16(18(23)21(23,5)6)8-15(11-25)10-22(28)17(24)7-13(3)19(22)26/h7-8,12,14,16-18,25,28-29H,9-11H2,1-6H3/t14-,16+,17-,18-,22-,23+,24-/m1/s1
SMILES	OCC1=C[C@H]2[C@H]3[C@@](C3(C)C)(OC(=O)C(C)C)C[C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	418.24	Volume:	431.63 ? Van der Waals volume.
Dense:	0.969	LogP:	1.596 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.876 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.02 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	20.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.479	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.033	Fsp³:	0.75
MCE-18:	81.714 ? 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:	0.09	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.299	Promiscuous compounds:	0.364

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953	MDCK Permeability:	-4.816
Pgp-inhibitor:	0.029	Pgp-substrate:	0.245
PAMPA:	0.88 ? 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):	0.092
20% Bioavailability (F20%):	0.93	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.995
Plasma Protein Binding (PPB):	72.215%	Volume Distribution (VD):	0.158
Fu:	31.131% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.943
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.002
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.057	CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.028	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.971	CYP3A4-substrate:	0.361
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.87
HLM stability:	0.201 ? 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):

8.719

Half-life (T1/2):

1.299

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.203
Human Hepatotoxicity (H-HT):	0.65	Drug-induced Liver Injury (DILI):	0.535
AMES Toxicity:	0.6	Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.3	Skin Sensitization:	0.959
Carcinogencity:	0.569	Eye Corrosion:	0.032
Eye Irritation:	0.818	Respiratory Toxicity:	0.718
Drug-induced Neurotoxicity:	0.344	Ototoxicity:	0.666
Hematotoxicity:	0.706	Drug-induced Nephrotoxicity:	0.721
Genotoxicity:	0.738	RPMI-8226 Immunitoxicity:	0.109
A549 Cytotoxicity:	0.244	Hek293 Cytotoxicity:	0.261
BCF:	0.603 ? 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:	3.077 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.356 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.756 ? 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
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25960	Euphorbia triangularis	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
Activity	2

Activity Type	# Activity
Organism	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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.53	nmol	PMID[17665951]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.9	/nmol	PMID[11754599]

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 NPC158523 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	16061
0.1-0.2	32390
0.2-0.3	1250
0.3-0.4	62
0.4-0.5	31
0.5-0.6	36
0.6-0.7	17
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
0.8929	High Similarity	NPC475937
0.8889	High Similarity	NPC153036
0.8276	Intermediate Similarity	NPC71889
0.7869	Intermediate Similarity	NPC485736
0.7869	Intermediate Similarity	NPC277477
0.7869	Intermediate Similarity	NPC479003
0.7869	Intermediate Similarity	NPC485735
0.7619	Intermediate Similarity	NPC482454
0.7541	Intermediate Similarity	NPC174471
0.7273	Intermediate Similarity	NPC485732
0.7	Intermediate Similarity	NPC91189
0.6866	Remote Similarity	NPC474872
0.6774	Remote Similarity	NPC96739
0.6769	Remote Similarity	NPC260786
0.6667	Remote Similarity	NPC472760
0.6615	Remote Similarity	NPC472397
0.6522	Remote Similarity	NPC477091
0.6324	Remote Similarity	NPC471125
0.6269	Remote Similarity	NPC474871
0.6269	Remote Similarity	NPC485733
0.6232	Remote Similarity	NPC145182
0.6094	Remote Similarity	NPC156252
0.6	Remote Similarity	NPC17138
0.6	Remote Similarity	NPC101825
0.6	Remote Similarity	NPC170212
0.6	Remote Similarity	NPC215643
0.6	Remote Similarity	NPC265499
0.6	Remote Similarity	NPC153651
0.5942	Remote Similarity	NPC472758
0.5915	Remote Similarity	NPC221511
0.5882	Remote Similarity	NPC171905
0.5833	Remote Similarity	NPC485731
0.5714	Remote Similarity	NPC157252
0.5676	Remote Similarity	NPC151216
0.5676	Remote Similarity	NPC183540
0.5676	Remote Similarity	NPC89227
0.5658	Remote Similarity	NPC222307
0.5652	Remote Similarity	NPC478681
0.5616	Remote Similarity	NPC471128
0.5616	Remote Similarity	NPC471126
0.56	Remote Similarity	NPC479000
0.5584	Remote Similarity	NPC159692
0.5556	Remote Similarity	NPC275696
0.5556	Remote Similarity	NPC255081
0.55	Remote Similarity	NPC180640
0.5479	Remote Similarity	NPC5991
0.5479	Remote Similarity	NPC196500
0.5479	Remote Similarity	NPC471108
0.5479	Remote Similarity	NPC5989
0.5467	Remote Similarity	NPC22628
0.5455	Remote Similarity	NPC602538
0.5443	Remote Similarity	NPC482199
0.5443	Remote Similarity	NPC482197
0.5432	Remote Similarity	NPC185876
0.5432	Remote Similarity	NPC19336
0.541	Remote Similarity	NPC453
0.5405	Remote Similarity	NPC475391
0.5333	Remote Similarity	NPC243902
0.5263	Remote Similarity	NPC478999
0.5263	Remote Similarity	NPC600005
0.5224	Remote Similarity	NPC478680
0.5195	Remote Similarity	NPC484333
0.5128	Remote Similarity	NPC145238
0.5065	Remote Similarity	NPC474937

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6477
0.1-0.2	2660
0.2-0.3	13
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