NPASS Compound

Natural Product: NPC249312

Natural Product ID	NPC249312
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	20-Epi-3-Dehydroxy-3-Oxo-5,6-Dihydro-4,5-Dehydroverazine
IUPAC Name	(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(1R)-1-[(3S)-3-methyl-2,3,4,5-tetrahydropyridin-6-yl]ethyl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL514438
PubChem CID	10572798
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002732] 22,26-epiminocholestanes [CHEMONTID:0002735] 3-oxo-22,26-epiminocholestanes

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 74 0 0 0 0 0 0 0 0999 V2000 5.2462 1.4229 2.1575 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5225 0.8878 0.7655 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8348 -0.4516 0.5955 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6031 -0.6221 -0.8878 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6546 0.3894 -1.3849 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0219 1.6095 -1.0507 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2006 1.8759 -0.2994 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4362 0.2340 -2.1518 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9190 1.6033 -2.6367 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3172 -0.5636 -1.7205 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5264 -2.0350 -1.4867 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1924 -2.5225 -0.8780 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6175 -1.2830 -0.8356 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7824 -1.2643 0.0420 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8480 -2.1480 -0.5682 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1339 -1.4593 -0.8778 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5982 -0.5326 0.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8678 -0.3130 0.3644 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2457 0.6189 1.4237 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3208 0.4947 2.0716 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3465 1.7439 1.7521 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9371 1.5728 1.2960 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5617 0.1407 0.9958 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4226 -0.6273 2.2732 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3189 0.1280 0.1470 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2669 1.0825 0.5768 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1842 1.0964 -0.5163 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4680 -0.2265 -0.5450 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0207 -0.5780 0.7920 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0913 1.2266 2.8359 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0888 2.5253 2.0840 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3596 0.9026 2.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6242 0.6691 0.7174 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5039 -1.2780 0.9357 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8710 -0.4274 1.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6161 -0.2905 -1.3425 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4682 -1.6407 -1.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0417 1.9396 -1.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1072 2.9150 0.0952 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7628 -0.2339 -3.1457 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9278 1.5623 -3.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1184 2.3169 -1.8305 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5794 1.9679 -3.4852 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5720 -0.5521 -2.6068 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6254 -2.6037 -2.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3506 -2.3044 -0.8272 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3948 -2.8677 0.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -3.3634 -1.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9579 -1.0681 -1.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6270 -1.6584 1.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0850 -3.0356 0.0704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5023 -2.6126 -1.5353 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1465 -0.9930 -1.8893 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9295 -2.2597 -0.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6649 -0.7898 -0.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7528 2.6720 1.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4036 1.9352 2.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2647 1.9199 2.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7113 2.2244 0.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4075 -0.4983 2.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6382 -1.7043 2.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1961 -0.2393 2.9867 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6527 0.4496 -0.8841 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6928 2.1159 0.6467 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8035 0.8291 1.5276 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4674 1.9275 -0.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7651 1.2917 -1.4430 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4246 0.3536 1.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1941 -0.9006 1.4956 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7322 -1.4043 0.8279 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 2 0 6 7 1 0 5 8 1 0 8 9 1 0 8 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 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 7 2 1 0 28 10 1 0 28 13 1 0 25 14 1 0 23 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 1 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 7 38 1 0 7 39 1 0 8 40 1 6 9 41 1 0 9 42 1 0 9 43 1 0 10 44 1 6 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 6 14 50 1 1 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 18 55 1 0 21 56 1 0 21 57 1 0 22 58 1 0 22 59 1 0 24 60 1 0 24 61 1 0 24 62 1 0 25 63 1 6 26 64 1 0 26 65 1 0 27 66 1 0 27 67 1 0 29 68 1 0 29 69 1 0 29 70 1 0 M END

Standard InCHIKey	LGMIOFBBNYCMNF-FWCABEFESA-N
Standard InCHI	InChI=1S/C27H41NO/c1-17-5-10-25(28-16-17)18(2)22-8-9-23-21-7-6-19-15-20(29)11-13-26(19,3)24(21)12-14-27(22,23)4/h15,17-18,21-24H,5-14,16H2,1-4H3/t17-,18+,21-,22+,23-,24-,26-,27+/m0/s1
SMILES	C[C@H]1CCC(=NC1)[C@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	395.32	Volume:	444.643 ? Van der Waals volume.
Dense:	0.889	LogP:	4.748 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.947 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.183 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	29.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.515	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.719	Fsp³:	0.852
MCE-18:	81.6 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.648	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.073	Promiscuous compounds:	0.673

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.587	MDCK Permeability:	-4.783
Pgp-inhibitor:	0.945	Pgp-substrate:	0.009
PAMPA:	0.001 ? 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%):	0.005	30% Bioavailability (F30%):	0.026
50% Bioavailability (F50%):	0.252

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.633	MRP1:	0.312
Plasma Protein Binding (PPB):	94.986%	Volume Distribution (VD):	0.007
Fu:	5.734% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.843
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.107	CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.192	CYP2D6-substrate:	0.26
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.972 ? 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):

12.517

Half-life (T1/2):

0.538

ADMET: Toxicity

hERG Blockers:	0.206	hERG Blockers (10um):	0.436
Human Hepatotoxicity (H-HT):	0.822	Drug-induced Liver Injury (DILI):	0.542
AMES Toxicity:	0.458	Rat Oral Acute Toxicity:	0.253
Maximum Recommended Daily Dose:	0.829	Skin Sensitization:	0.987
Carcinogencity:	0.984	Eye Corrosion:	0.072
Eye Irritation:	0.948	Respiratory Toxicity:	0.933
Drug-induced Neurotoxicity:	0.293	Ototoxicity:	0.411
Hematotoxicity:	0.736	Drug-induced Nephrotoxicity:	0.642
Genotoxicity:	0.441	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.143	Hek293 Cytotoxicity:	0.714
BCF:	2.552 ? 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:	4.317 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.136 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.02 ? 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
NPO33146	eclipta alba	Species	n.a.	Eukaryota	n.a.	suriname rainforest1	n.a.	PMID[9784152]

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
IC12	3
IC50	1

Activity Type	# Activity
Cell line	1
Organism	3

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
NPT726	Cell line	M109	Mus musculus	IC50	=	16.8	ug.mL-1	PMID[8778240]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	14.0	ug ml-1	Open TG-GATES in vivo data: Biochemistry
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	45.0	ug ml-1	PMID[16792413]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	50.0	ug ml-1	DOI[10.6019/CHEMBL1201861]

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 NPC249312 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	21270
0.1-0.2	25906
0.2-0.3	2495
0.3-0.4	120
0.4-0.5	35
0.5-0.6	19
0.6-0.7	10
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
0.7308	Intermediate Similarity	NPC35734
0.6863	Remote Similarity	NPC307176
0.6863	Remote Similarity	NPC321874
0.6792	Remote Similarity	NPC282593
0.6667	Remote Similarity	NPC159577
0.6667	Remote Similarity	NPC115023
0.6667	Remote Similarity	NPC602429
0.6545	Remote Similarity	NPC149203
0.6481	Remote Similarity	NPC214043
0.6481	Remote Similarity	NPC85774
0.625	Remote Similarity	NPC237712
0.5902	Remote Similarity	NPC320514
0.5741	Remote Similarity	NPC139397
0.5645	Remote Similarity	NPC243985
0.5645	Remote Similarity	NPC280710
0.5536	Remote Similarity	NPC2634
0.5536	Remote Similarity	NPC265782
0.5536	Remote Similarity	NPC251929
0.541	Remote Similarity	NPC469948
0.5345	Remote Similarity	NPC227064
0.5345	Remote Similarity	NPC329043
0.5345	Remote Similarity	NPC58841
0.5345	Remote Similarity	NPC161423
0.5333	Remote Similarity	NPC323765
0.5254	Remote Similarity	NPC144258
0.5254	Remote Similarity	NPC327115
0.5224	Remote Similarity	NPC187159
0.5156	Remote Similarity	NPC45365
0.5156	Remote Similarity	NPC293299
0.5082	Remote Similarity	NPC303613

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC249312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6487
0.1-0.2	2427
0.2-0.3	159
0.3-0.4	50
0.4-0.5	14
0.5-0.6	8
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	Drug ID	Developmental Stage
0.6863	Remote Similarity	NPD4747	Phase 4
0.6207	Remote Similarity	NPD5737	Phase 4
0.6	Remote Similarity	NPD6672	Phase 4
0.5536	Remote Similarity	NPD4691	Approved
0.55	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.55	Remote Similarity	NPD6939	Phase 3
0.5345	Remote Similarity	NPD3666	Phase 4
0.5345	Remote Similarity	NPD4221	Phase 4
0.5323	Remote Similarity	NPD6409	Approved
0.5246	Remote Similarity	NPD5330	Phase 4
0.5082	Remote Similarity	NPD4693	Phase 3

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