NPASS Compound

Natural Product: NPC470878

Natural Product ID	NPC470878
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	APUZDLZWOPKUBG-RRPNDCTPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL227443
PubChem CID	44423090
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids

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 74 79 0 0 0 0 0 0 0 0999 V2000 -7.4948 0.7813 -0.0813 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0880 0.4352 0.0927 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3940 -0.4064 -0.6742 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0598 -1.0740 -1.8137 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9572 -0.6981 -0.4088 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2220 0.4612 0.1936 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1000 1.4092 0.6636 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2728 1.0349 1.2105 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9530 2.2306 1.5562 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1226 0.1328 1.1320 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.6148 0.7612 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1608 -0.7101 1.9743 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0116 -2.0088 0.2816 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3562 -2.3080 -0.3720 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1207 -1.1045 -0.0459 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0597 -0.0045 -0.1920 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4517 0.1284 -1.5838 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6771 1.2608 0.2412 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0759 1.1770 0.7957 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0300 0.3173 0.0948 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3392 -0.7567 -0.7752 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3324 -1.8636 -0.9447 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7598 -1.5034 -0.8845 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2037 -0.1520 -0.7823 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0743 0.9004 -0.7698 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6631 1.0015 -2.2525 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5854 2.2249 -0.4282 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8406 3.2247 -0.5240 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9451 2.4815 0.0304 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7338 1.4828 0.3632 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2337 0.1210 0.2694 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2467 -0.8256 0.0938 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4401 -0.8873 -1.9064 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6874 -0.5135 2.4171 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6903 0.9560 -1.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1951 -0.0205 0.2669 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7679 1.7051 0.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3441 -1.6056 -2.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7878 -1.8516 -1.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6785 -0.3601 -2.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5480 -1.0573 -1.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9310 -1.5816 0.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7899 1.0001 -0.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2530 0.3783 2.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0381 2.8314 0.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7687 1.1469 1.5285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2536 0.1435 2.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0760 -2.7298 1.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8081 -2.3077 -0.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2227 -2.5195 -1.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -3.1985 0.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3666 -1.1414 1.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3159 -0.5224 -1.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3211 -0.0679 -2.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6749 1.2257 -1.7438 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0758 1.7982 1.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7430 1.9953 -0.6167 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3990 2.2358 0.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9303 0.8372 1.8715 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5417 -0.3159 0.8878 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1428 -0.3655 -1.7655 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1452 -2.3533 -1.9465 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0836 -2.6811 -0.2199 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3967 -2.3115 -0.4072 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3997 1.7058 -2.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8280 0.0468 -2.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6946 1.4731 -2.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3333 3.5109 0.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7555 1.6799 0.7058 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7141 -0.0931 1.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6279 -1.0120 0.9950 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1034 0.2836 3.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4910 -1.2146 2.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8313 -1.0166 2.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 6 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 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 1 0 25 26 1 6 25 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 24 33 1 6 10 34 1 0 8 2 1 0 16 11 1 0 25 20 1 0 21 15 1 0 33 23 1 0 31 24 1 0 1 35 1 0 1 36 1 0 1 37 1 0 4 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 6 8 44 1 0 9 45 1 0 10 46 1 1 12 47 1 0 13 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 1 17 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 1 21 61 1 6 22 62 1 0 22 63 1 0 23 64 1 1 26 65 1 0 26 66 1 0 26 67 1 0 29 68 1 0 30 69 1 0 31 70 1 1 32 71 1 0 34 72 1 0 34 73 1 0 34 74 1 0 M END

Standard InCHIKey	APUZDLZWOPKUBG-RRPNDCTPSA-N
Standard InCHI	InChI=1S/C28H40O6/c1-14-12-20(33-24(31)15(14)2)16(3)27(32)11-9-18-17-13-23-28(34-23)22(30)7-6-21(29)26(28,5)19(17)8-10-25(18,27)4/h6-7,16-20,22-24,30-32H,8-13H2,1-5H3/t16-,17+,18+,19+,20-,22+,23-,24?,25+,26+,27+,28-/m1/s1
SMILES	CC1=C(C)C[C@@H](OC1O)[C@H]([C@@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C=C[C@@H]3O)O2)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.28	Volume:	486.337 ? Van der Waals volume.
Dense:	0.971	LogP:	2.434 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.782 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.998 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	29.0
TPSA:	99.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.421	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.069	Fsp³:	0.821
MCE-18:	150.333 ? 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:	0.667	Fluc inhibitor:	0.05 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? 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:	0.14	Promiscuous compounds:	0.359

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.851	MDCK Permeability:	-4.638
Pgp-inhibitor:	0.004	Pgp-substrate:	0.67
PAMPA:	0.978 ? 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):	0.001
20% Bioavailability (F20%):	0.181	30% Bioavailability (F30%):	0.639
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.18
Plasma Protein Binding (PPB):	79.807%	Volume Distribution (VD):	0.019
Fu:	19.442% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.076
BSEP inhibitor:	0.942

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.024	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.012	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.313
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.254
HLM stability:	0.236 ? 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):

9.182

Half-life (T1/2):

3.101

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.466
Human Hepatotoxicity (H-HT):	0.534	Drug-induced Liver Injury (DILI):	0.368
AMES Toxicity:	0.628	Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.882	Skin Sensitization:	0.92
Carcinogencity:	0.885	Eye Corrosion:	0.002
Eye Irritation:	0.322	Respiratory Toxicity:	0.776
Drug-induced Neurotoxicity:	0.229	Ototoxicity:	0.544
Hematotoxicity:	0.193	Drug-induced Nephrotoxicity:	0.36
Genotoxicity:	0.931	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.088	Hek293 Cytotoxicity:	0.566
BCF:	0.667 ? 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:	3.424 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.241 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.378 ? 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
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	stems, roots, and leaves	Da-Han Mountain, Kaohsiung, Taiwan	2004-OCT	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	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	5

Activity Type	# Activity
Cell line	5

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
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	0.64	ug.mL-1	Open TG-GATES in vivo data: Hematology
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	1.98	ug.mL-1	PMID[19441846]
NPT81	Cell line	A549	Homo sapiens	IC50	=	0.88	ug.mL-1	PMID[24487236]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	0.99	ug.mL-1	PMID[24411199]
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	0.81	ug.mL-1	PMID[12932129]

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 NPC470878 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	20159
0.1-0.2	27502
0.2-0.3	2067
0.3-0.4	77
0.4-0.5	24
0.5-0.6	24
0.6-0.7	3
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
0.7778	Intermediate Similarity	NPC264954
0.7397	Intermediate Similarity	NPC473256
0.6494	Remote Similarity	NPC473253
0.6447	Remote Similarity	NPC473274
0.6053	Remote Similarity	NPC473270
0.5844	Remote Similarity	NPC286528
0.575	Remote Similarity	NPC329736
0.575	Remote Similarity	NPC88326
0.575	Remote Similarity	NPC599946
0.5696	Remote Similarity	NPC140055
0.5696	Remote Similarity	NPC167606
0.5556	Remote Similarity	NPC183580
0.5556	Remote Similarity	NPC474370
0.5476	Remote Similarity	NPC470880
0.5476	Remote Similarity	NPC470494
0.5432	Remote Similarity	NPC609580
0.5422	Remote Similarity	NPC312824
0.5422	Remote Similarity	NPC20302
0.5357	Remote Similarity	NPC609769
0.5357	Remote Similarity	NPC610140
0.5301	Remote Similarity	NPC153700
0.5238	Remote Similarity	NPC67569
0.506	Remote Similarity	NPC125794
0.506	Remote Similarity	NPC171401
0.5059	Remote Similarity	NPC470492
0.5059	Remote Similarity	NPC8369
0.5059	Remote Similarity	NPC608655
0.5057	Remote Similarity	NPC23786
0.5056	Remote Similarity	NPC3381

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6901
0.1-0.2	2091
0.2-0.3	155
0.3-0.4	2
0.4-0.5	0
0.5-0.6	1
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
0.5696	Remote Similarity	NPD7115	Discovery

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