NPASS Compound

Natural Product: NPC278052

Natural Product ID	NPC278052
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Butyraxanthone A
IUPAC Name	2-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,3,6-trihydroxy-7-methoxy-8-(3-methylbut-2-enyl)xanthen-9-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL550835
PubChem CID	44138727
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

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 69 71 0 0 0 0 0 0 0 0999 V2000 -8.5497 -1.6567 -0.9569 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6454 -0.4910 -0.7593 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3455 -0.6474 -0.8302 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6787 -1.9471 -1.1035 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7565 -2.3642 0.0281 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6729 -1.3209 0.2352 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6106 -0.7468 1.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7172 0.2642 1.9259 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6798 0.8589 1.1098 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9754 1.8014 0.1555 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9672 2.3794 -0.5832 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3559 2.0372 -0.3936 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6677 1.0875 0.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3360 0.5069 1.3071 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0092 -0.4311 2.2528 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0152 0.7829 0.7112 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3015 -0.0591 1.5661 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0156 1.3688 -0.0376 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3450 1.0514 0.1260 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7719 0.0164 1.0743 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6721 -1.3704 0.5775 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7087 -2.1745 0.5951 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5362 -3.5739 0.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0157 -1.7089 1.1275 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2597 1.7254 -0.6936 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8732 2.6650 -1.6292 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5315 2.9445 -1.7542 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5865 2.3078 -0.9678 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3078 2.5925 -1.1012 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7955 3.3211 -2.4315 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5913 1.4050 -0.5235 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4473 2.0698 0.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2857 2.1517 -0.0442 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7538 -0.9970 -0.8533 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2402 0.8478 -0.4839 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6140 -1.3124 -1.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2638 -2.1332 -1.9197 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4444 -2.3514 -0.1191 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6922 0.2310 -0.6801 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0809 -1.9280 -2.0404 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4717 -2.7229 -1.1546 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3875 -2.4858 0.9261 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2376 -3.2958 -0.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3794 -1.0856 2.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 1.1402 2.2495 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2950 -0.0314 2.9587 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1816 3.1375 -1.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1204 -1.4021 1.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8988 0.1923 1.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4558 0.1647 2.1267 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7298 -1.7209 0.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9020 -3.5385 -0.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1101 -4.3089 0.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4535 -3.8011 0.0359 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5115 -0.9484 0.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6939 -2.6011 1.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8882 -1.2822 2.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1476 3.6721 -2.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3563 4.0648 -2.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0787 1.3437 0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9316 2.7240 1.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1629 2.6920 -0.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7046 2.2743 -0.9438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6969 -0.9327 -0.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8174 -1.8874 -1.5766 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1154 -0.1603 -1.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7460 1.3861 0.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3026 0.7410 -0.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1941 1.4700 -1.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 13 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 2 3 22 23 1 0 22 24 1 0 19 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 26 30 1 0 25 31 1 0 31 32 1 0 10 33 1 0 6 34 1 0 2 35 1 0 14 9 1 0 28 18 1 0 29 12 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 11 47 1 0 15 48 1 0 20 49 1 0 20 50 1 0 21 51 1 0 23 52 1 0 23 53 1 0 23 54 1 0 24 55 1 0 24 56 1 0 24 57 1 0 27 58 1 0 30 59 1 0 32 60 1 0 32 61 1 0 32 62 1 0 33 63 1 0 34 64 1 0 34 65 1 0 34 66 1 0 35 67 1 0 35 68 1 0 35 69 1 0 M END

Standard InCHIKey	ABFFWBKBJIQSFF-WOJGMQOQSA-N
Standard InCHI	InChI=1S/C29H34O6/c1-16(2)8-7-9-18(5)11-13-19-21(30)14-24-26(27(19)32)28(33)25-20(12-10-17(3)4)29(34-6)22(31)15-23(25)35-24/h8,10-11,14-15,30-32H,7,9,12-13H2,1-6H3/b18-11+
SMILES	CC(=CCC/C(=C/Cc1c(cc2c(c1O)c(=O)c1c(CC=C(C)C)c(c(cc1o2)O)OC)O)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	478.24	Volume:	510.847 ? Van der Waals volume.
Dense:	0.936	LogP:	7.489 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.846 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.969 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	20.0
TPSA:	100.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.243	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.335	Fsp³:	0.345
MCE-18:	23.0 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.996	Fluc inhibitor:	0.434 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.98 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.83 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.301	Promiscuous compounds:	0.174

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.029	MDCK Permeability:	-4.665
Pgp-inhibitor:	1.0	Pgp-substrate:	0.03
PAMPA:	0.004 ? 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%):	0.841	30% Bioavailability (F30%):	0.98
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.932
Plasma Protein Binding (PPB):	96.131%	Volume Distribution (VD):	0.147
Fu:	3.699% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.941
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.144	CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.985	CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.463	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

2.35

Half-life (T1/2):

1.349

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.585
Human Hepatotoxicity (H-HT):	0.66	Drug-induced Liver Injury (DILI):	0.846
AMES Toxicity:	0.308	Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.595	Skin Sensitization:	0.981
Carcinogencity:	0.496	Eye Corrosion:	0.0
Eye Irritation:	0.685	Respiratory Toxicity:	0.986
Drug-induced Neurotoxicity:	0.088	Ototoxicity:	0.37
Hematotoxicity:	0.163	Drug-induced Nephrotoxicity:	0.406
Genotoxicity:	0.931	RPMI-8226 Immunitoxicity:	0.099
A549 Cytotoxicity:	0.553	Hek293 Cytotoxicity:	0.642
BCF:	2.21 ? 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:	5.491 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.138 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.928 ? 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
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296616]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	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
IC50	2
Ratio IC50	1

Activity Type	# Activity
Cell line	1
Organism	1
Others	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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	3.5	ug.mL-1	PMID[22500574]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	3.0	ug.mL-1	PMID[19651906]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	1.17	n.a.	PMID[17070063]

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 NPC278052 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	19091
0.1-0.2	26906
0.2-0.3	3353
0.3-0.4	391
0.4-0.5	66
0.5-0.6	26
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC40491
0.9	High Similarity	NPC7483
0.9	High Similarity	NPC74766
0.8438	Intermediate Similarity	NPC228785
0.7703	Intermediate Similarity	NPC479155
0.75	Intermediate Similarity	NPC300727
0.7361	Intermediate Similarity	NPC310349
0.7361	Intermediate Similarity	NPC61010
0.726	Intermediate Similarity	NPC262286
0.7222	Intermediate Similarity	NPC236796
0.7105	Intermediate Similarity	NPC206153
0.7105	Intermediate Similarity	NPC271629
0.6986	Remote Similarity	NPC25152
0.6875	Remote Similarity	NPC39091
0.662	Remote Similarity	NPC602307
0.6447	Remote Similarity	NPC320359
0.6389	Remote Similarity	NPC14353
0.6351	Remote Similarity	NPC236132
0.625	Remote Similarity	NPC241904
0.6133	Remote Similarity	NPC68093
0.6071	Remote Similarity	NPC479158
0.6026	Remote Similarity	NPC189473
0.6	Remote Similarity	NPC217677
0.6	Remote Similarity	NPC476242
0.5949	Remote Similarity	NPC236521
0.5897	Remote Similarity	NPC227337
0.5833	Remote Similarity	NPC142339
0.5811	Remote Similarity	NPC488548
0.5789	Remote Similarity	NPC479160
0.575	Remote Similarity	NPC275780
0.5732	Remote Similarity	NPC133392
0.5714	Remote Similarity	NPC488441
0.5698	Remote Similarity	NPC479159
0.5679	Remote Similarity	NPC117854
0.5679	Remote Similarity	NPC170245
0.5641	Remote Similarity	NPC220313
0.5625	Remote Similarity	NPC248638
0.5568	Remote Similarity	NPC150977
0.5556	Remote Similarity	NPC152659
0.5309	Remote Similarity	NPC37684
0.5309	Remote Similarity	NPC212932
0.5301	Remote Similarity	NPC6588
0.5263	Remote Similarity	NPC119224
0.5238	Remote Similarity	NPC479164
0.5176	Remote Similarity	NPC39306
0.5132	Remote Similarity	NPC100123
0.5122	Remote Similarity	NPC488731
0.5114	Remote Similarity	NPC479157
0.5111	Remote Similarity	NPC479156
0.506	Remote Similarity	NPC133065

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC278052 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3638
0.1-0.2	5471
0.2-0.3	40
0.3-0.4	1
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