NPASS Compound

Natural Product: NPC157898

Natural Product ID	NPC157898
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VOQFGNABAAEXTC-PZPWNCOQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3402768
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

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 57 59 0 0 0 0 0 0 0 0999 V2000 6.7791 0.7808 3.1407 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0947 -0.5349 3.0656 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4118 -1.4122 3.8818 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0861 -0.7218 2.0334 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3877 -1.9191 1.8728 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4469 -2.0934 0.9092 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1295 -1.0812 0.0274 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7880 0.1167 0.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7478 0.2634 1.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1740 -1.2685 -0.9485 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6814 -0.3896 -1.9032 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0854 -0.7296 -3.3071 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1624 -1.6919 -3.9927 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3459 -2.3882 -2.9217 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4561 -1.2653 -2.2612 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3615 -1.9292 -1.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2209 -1.0226 -0.6631 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1400 -0.2996 -1.3657 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2690 -0.4143 -2.6068 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0051 0.6425 -0.6537 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8883 0.7757 0.6342 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6882 1.6744 1.4369 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6497 2.4765 0.8946 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3750 3.3062 1.7227 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1673 3.3577 3.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1937 2.5405 3.5977 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4655 1.7144 2.8042 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9415 2.5517 4.9590 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8968 4.1915 3.9031 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3236 -0.2822 -1.7115 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6117 -3.2026 -3.5604 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8068 -2.5797 -4.8349 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1852 0.4129 -4.1000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2404 1.0336 2.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6180 0.7714 3.8721 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0320 1.5733 3.3354 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6407 -2.7262 2.5773 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9289 -3.0390 0.8213 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5975 0.9794 -0.5244 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2671 1.2194 1.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1106 0.6097 -1.7119 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0920 -1.1881 -3.2751 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4475 -1.1094 -4.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9550 -2.9489 -2.2042 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0670 -0.8261 -3.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7972 -2.5493 -0.5266 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9870 -2.6818 -1.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7357 1.2207 -1.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1270 0.1567 1.1266 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8576 2.4802 -0.1508 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1322 3.9338 1.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6968 1.0728 3.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5799 2.1658 5.6208 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2893 5.0586 3.5593 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1812 -3.7004 -4.3231 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7120 -2.2234 -5.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5033 1.1379 -3.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 7 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 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 25 29 1 0 15 30 1 0 14 31 1 0 13 32 1 0 12 33 1 0 9 4 1 0 30 11 1 0 27 22 1 0 1 34 1 0 1 35 1 0 1 36 1 0 5 37 1 0 6 38 1 0 8 39 1 0 9 40 1 0 11 41 1 1 12 42 1 1 13 43 1 6 14 44 1 1 15 45 1 6 16 46 1 0 16 47 1 0 20 48 1 0 21 49 1 0 23 50 1 0 24 51 1 0 27 52 1 0 28 53 1 0 29 54 1 0 31 55 1 0 32 56 1 0 33 57 1 0 M END

Standard InCHIKey	VOQFGNABAAEXTC-PZPWNCOQSA-N
Standard InCHI	InChI=1S/C23H24O10/c1-12(24)14-4-6-15(7-5-14)32-23-22(30)21(29)20(28)18(33-23)11-31-19(27)9-3-13-2-8-16(25)17(26)10-13/h2-10,18,20-23,25-26,28-30H,11H2,1H3/b9-3+/t18-,20-,21+,22-,23-/m1/s1
SMILES	CC(=O)c1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	460.14	Volume:	444.869 ? Van der Waals volume.
Dense:	1.034	LogP:	1.439 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.772 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.009 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	21.0
TPSA:	162.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.172	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.701	Fsp³:	0.304
MCE-18:	70.0 ? 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:	1
Colloidal aggregators:	0.749	Fluc inhibitor:	0.995 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.166 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.806 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.194	Promiscuous compounds:	0.38

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.003	MDCK Permeability:	-5.23
Pgp-inhibitor:	0.002	Pgp-substrate:	0.007
PAMPA:	0.905 ? 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):	0.615
20% Bioavailability (F20%):	0.951	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.003
Plasma Protein Binding (PPB):	82.362%	Volume Distribution (VD):	-0.388
Fu:	15.187% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.158

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.479
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.968 ? 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):

4.556

Half-life (T1/2):

3.073

ADMET: Toxicity

hERG Blockers:	0.083	hERG Blockers (10um):	0.445
Human Hepatotoxicity (H-HT):	0.561	Drug-induced Liver Injury (DILI):	0.911
AMES Toxicity:	0.942	Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.09	Skin Sensitization:	0.999
Carcinogencity:	0.236	Eye Corrosion:	0.0
Eye Irritation:	0.423	Respiratory Toxicity:	0.014
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.942
Hematotoxicity:	0.151	Drug-induced Nephrotoxicity:	0.449
Genotoxicity:	0.772	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.615	Hek293 Cytotoxicity:	0.317
BCF:	0.584 ? 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:	3.287 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.844 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.27 ? 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
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	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	3

Activity Type	# Activity
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
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	290800.0	nM	PMID[1517742]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	1277100.0	nM	PMID[18973387]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	8000.0	nM	PMID[23701598]

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 NPC157898 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	10795
0.1-0.2	33045
0.2-0.3	4690
0.3-0.4	1023
0.4-0.5	235
0.5-0.6	47
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8615	High Similarity	NPC291153
0.7534	Intermediate Similarity	NPC476867
0.7162	Intermediate Similarity	NPC291296
0.7143	Intermediate Similarity	NPC476870
0.6933	Remote Similarity	NPC10205
0.6842	Remote Similarity	NPC471405
0.6753	Remote Similarity	NPC157816
0.6753	Remote Similarity	NPC476864
0.6627	Remote Similarity	NPC476871
0.6582	Remote Similarity	NPC476868
0.6463	Remote Similarity	NPC488081
0.6316	Remote Similarity	NPC137813
0.625	Remote Similarity	NPC470572
0.6125	Remote Similarity	NPC204937
0.6118	Remote Similarity	NPC133984
0.6081	Remote Similarity	NPC229784
0.6049	Remote Similarity	NPC476866
0.6	Remote Similarity	NPC186406
0.6	Remote Similarity	NPC287597
0.5976	Remote Similarity	NPC488082
0.5942	Remote Similarity	NPC476873
0.5882	Remote Similarity	NPC479769
0.587	Remote Similarity	NPC214621
0.587	Remote Similarity	NPC34267
0.587	Remote Similarity	NPC81042
0.5833	Remote Similarity	NPC476865
0.573	Remote Similarity	NPC67134
0.5699	Remote Similarity	NPC603856
0.5696	Remote Similarity	NPC219677
0.5663	Remote Similarity	NPC476869
0.5638	Remote Similarity	NPC599948
0.5634	Remote Similarity	NPC79908
0.5581	Remote Similarity	NPC472876
0.5543	Remote Similarity	NPC477629
0.5542	Remote Similarity	NPC220942
0.5522	Remote Similarity	NPC192229
0.551	Remote Similarity	NPC139571
0.5455	Remote Similarity	NPC11411
0.5443	Remote Similarity	NPC34293
0.5435	Remote Similarity	NPC270675
0.5435	Remote Similarity	NPC195685
0.5402	Remote Similarity	NPC479767
0.5376	Remote Similarity	NPC80068
0.5326	Remote Similarity	NPC476620
0.5316	Remote Similarity	NPC199977
0.5263	Remote Similarity	NPC223426
0.5213	Remote Similarity	NPC85751
0.5213	Remote Similarity	NPC19240
0.52	Remote Similarity	NPC479768
0.519	Remote Similarity	NPC473924
0.519	Remote Similarity	NPC78363
0.5128	Remote Similarity	NPC479473
0.5128	Remote Similarity	NPC275721
0.5128	Remote Similarity	NPC288416
0.5128	Remote Similarity	NPC479468
0.5128	Remote Similarity	NPC479474
0.5104	Remote Similarity	NPC472994
0.507	Remote Similarity	NPC232880
0.5063	Remote Similarity	NPC477293
0.5063	Remote Similarity	NPC606353
0.506	Remote Similarity	NPC292443
0.5057	Remote Similarity	NPC64141
0.5056	Remote Similarity	NPC83743
0.5055	Remote Similarity	NPC175230
0.5051	Remote Similarity	NPC480796
0.5051	Remote Similarity	NPC472993

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC157898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3164
0.1-0.2	5811
0.2-0.3	158
0.3-0.4	15
0.4-0.5	2
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