NPASS Compound

Natural Product: NPC542450

Natural Product ID	NPC542450
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},3~{R},4~{S},5~{R})-2-(6-aminopurin-9-yl)-5-[[[[(2~{R},3~{S},4~{R},5~{R})-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl-methyl-amino]-methyl-amino]methyl]tetrahydrofuran-3,4-diol
IUPAC Name	(2~{R},3~{R},4~{S},5~{R})-2-(6-aminopurin-9-yl)-5-[[[[(2~{R},3~{S},4~{R},5~{R})-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl-methyl-amino]-methyl-amino]methyl]tetrahydrofuran-3,4-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 70 75 0 0 0 0 0 0 0 0999 V2000 0.4329 -1.0763 1.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5089 -1.9129 0.4610 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6712 -1.6197 -0.3310 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9934 -2.0104 0.1981 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9510 -1.6247 -0.7451 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0213 -1.0682 -0.1257 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2825 0.3077 -0.3889 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4275 1.2278 -0.8335 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0745 2.3911 -0.9436 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3619 2.2295 -0.5681 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4108 3.1251 -0.5097 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2768 4.4772 -0.8691 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6092 2.6422 -0.0812 N 0 0 0 0 0 0 0 0 0 0 0 0 8.7284 1.3562 0.2589 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7058 0.4861 0.2010 N 0 0 0 0 0 0 0 0 0 0 0 0 6.4931 0.9009 -0.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9239 -1.3309 1.3455 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6458 -2.4393 1.7308 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4210 -1.5306 1.5166 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3318 -2.5418 2.5143 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5593 -2.0645 -0.3232 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3924 -2.6942 -1.5769 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8717 -2.1277 0.1686 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7325 -1.2413 -0.7169 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0646 -1.2028 -0.3350 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5015 -0.0848 -1.0272 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8652 0.2624 -0.8615 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8791 -0.1351 -1.6666 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0428 0.3921 -1.2091 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.7969 1.1224 -0.1226 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6243 1.8611 0.7132 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0109 1.9202 0.4541 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.0288 2.4922 1.7442 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.6849 2.4038 1.9467 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8899 1.6812 1.1259 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.4240 1.0276 0.0783 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5175 0.9586 -0.5447 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4730 2.0894 -1.3258 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2115 0.1758 -0.7419 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6312 0.4896 -1.9694 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6234 -0.8250 1.9042 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8980 -1.4438 2.5228 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8276 -0.0455 1.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5666 -1.9729 -1.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6966 -0.4845 -0.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0904 -3.1479 0.2171 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9391 -1.6368 -0.4703 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 1.0654 -1.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9285 4.9151 -1.5427 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5155 5.0459 -0.4521 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6944 0.9770 0.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2627 -0.4878 1.9779 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1383 -3.1124 2.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0228 -0.5771 1.8742 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4004 -2.0301 3.3746 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3527 -3.2029 -1.8973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3368 -3.5567 -1.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1814 -1.9946 -2.4197 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0546 -1.9900 1.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2712 -3.1774 -0.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7042 -1.6935 -1.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2195 -0.2743 -2.1048 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7372 -0.7727 -2.5271 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4547 2.8399 0.2883 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5816 1.0660 0.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2877 2.9447 2.8044 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6049 1.1911 0.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1342 2.7541 -0.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4975 0.4187 0.0405 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0776 -0.1072 -2.6416 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 6 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 2 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 26 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 19 4 1 0 39 24 1 0 16 7 1 0 36 27 1 0 16 10 1 0 36 30 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 0 3 45 1 0 4 46 1 1 6 47 1 6 8 48 1 0 12 49 1 0 12 50 1 0 14 51 1 0 17 52 1 1 18 53 1 0 19 54 1 1 20 55 1 0 22 56 1 0 22 57 1 0 22 58 1 0 23 59 1 0 23 60 1 0 24 61 1 6 26 62 1 6 28 63 1 0 32 64 1 0 32 65 1 0 34 66 1 0 37 67 1 1 38 68 1 0 39 69 1 1 40 70 1 0 M END

Standard InCHIKey	DCGONHUNBJPIDK-LAMCKDNKSA-N
Standard InCHI	InChI=1S/C22H30N12O6/c1-31(3-9-13(35)15(37)21(39-9)33-7-29-11-17(23)25-5-27-19(11)33)32(2)4-10-14(36)16(38)22(40-10)34-8-30-12-18(24)26-6-28-20(12)34/h5-10,13-16,21-22,35-38H,3-4H2,1-2H3,(H2,23,25,27)(H2,24,26,28)/t9-,10-,13-,14-,15-,16-,21-,22-/m1/s1
SMILES	CN(C[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O)N(C)C[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	558.24	Volume:	501.34 ? Van der Waals volume.
Dense:	1.113	LogP:	-1.17 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.724 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.231 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	245.1 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.123	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.877	Fsp³:	0.545
MCE-18:	124.941 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.271	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.03 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.181 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.04	Promiscuous compounds:	0.282

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.113	MDCK Permeability:	-5.443
Pgp-inhibitor:	0.0	Pgp-substrate:	0.968
PAMPA:	1.0 ? 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):	0.025
20% Bioavailability (F20%):	0.008	30% Bioavailability (F30%):	0.37
50% Bioavailability (F50%):	0.613

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029	MRP1:	0.164
Plasma Protein Binding (PPB):	21.44%	Volume Distribution (VD):	-0.174
Fu:	75.796% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.463
HLM stability:	0.007 ? 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):

3.698

Half-life (T1/2):

3.36

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.112
Human Hepatotoxicity (H-HT):	0.885	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.273	Skin Sensitization:	0.989
Carcinogencity:	0.589	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.903
Drug-induced Neurotoxicity:	0.996	Ototoxicity:	0.97
Hematotoxicity:	0.971	Drug-induced Nephrotoxicity:	0.97
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.486
A549 Cytotoxicity:	0.521	Hek293 Cytotoxicity:	0.815
BCF:	-0.049 ? 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:	2.195 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.919 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.789 ? 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
NPO60433	Magallana rivularis	Genus	Ostreidae	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

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 NPC542450 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	37192
0.1-0.2	12481
0.2-0.3	70
0.3-0.4	37
0.4-0.5	32
0.5-0.6	23
0.6-0.7	12
0.7-0.8	5
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8246	Intermediate Similarity	NPC136349
0.8246	Intermediate Similarity	NPC219313
0.7368	Intermediate Similarity	NPC156461
0.7368	Intermediate Similarity	NPC107374
0.7368	Intermediate Similarity	NPC600382
0.7368	Intermediate Similarity	NPC612067
0.7321	Intermediate Similarity	NPC317821
0.7302	Intermediate Similarity	NPC185991
0.7302	Intermediate Similarity	NPC321814
0.7188	Intermediate Similarity	NPC328479
0.6866	Remote Similarity	NPC324198
0.6866	Remote Similarity	NPC326529
0.6866	Remote Similarity	NPC319100
0.6765	Remote Similarity	NPC130586
0.6667	Remote Similarity	NPC324484
0.6571	Remote Similarity	NPC174802
0.6479	Remote Similarity	NPC606410
0.6389	Remote Similarity	NPC316618
0.6389	Remote Similarity	NPC323091
0.6216	Remote Similarity	NPC484199
0.6133	Remote Similarity	NPC484196
0.6129	Remote Similarity	NPC229974
0.5915	Remote Similarity	NPC195140
0.5692	Remote Similarity	NPC309832
0.5625	Remote Similarity	NPC209525
0.5625	Remote Similarity	NPC161659
0.56	Remote Similarity	NPC325906
0.56	Remote Similarity	NPC606116
0.5538	Remote Similarity	NPC609472
0.5507	Remote Similarity	NPC85689
0.5469	Remote Similarity	NPC33996
0.5417	Remote Similarity	NPC164952
0.5342	Remote Similarity	NPC302778
0.5342	Remote Similarity	NPC329404
0.5342	Remote Similarity	NPC212551
0.5278	Remote Similarity	NPC121222
0.5224	Remote Similarity	NPC189068
0.5205	Remote Similarity	NPC472816
0.5205	Remote Similarity	NPC600171
0.5152	Remote Similarity	NPC609036
0.5143	Remote Similarity	NPC605318
0.5139	Remote Similarity	NPC239737
0.5111	Remote Similarity	NPC21461
0.5075	Remote Similarity	NPC164665
0.507	Remote Similarity	NPC211025

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC542450 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7050
0.1-0.2	1957
0.2-0.3	67
0.3-0.4	37
0.4-0.5	22
0.5-0.6	7
0.6-0.7	1
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8246	Intermediate Similarity	NPD548	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD249	Phase 4
0.7368	Intermediate Similarity	NPD250	Phase 4
0.7344	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD283	Phase 4
0.7121	Intermediate Similarity	NPD338	Approved
0.6571	Remote Similarity	NPD339	Phase 2
0.56	Remote Similarity	NPD1777	Phase 4
0.5455	Remote Similarity	NPD1776	Approved
0.5455	Remote Similarity	NPD193	Phase 2
0.5205	Remote Similarity	NPD1369	Phase 2
0.5205	Remote Similarity	NPD242	Phase 4
0.519	Remote Similarity	NPD1732	Phase 3
0.5075	Remote Similarity	NPD186	Phase 1

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