NPASS Compound

Natural Product: NPC486546

Natural Product ID	NPC486546
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GJUUUEMPCBRUSX-INYQHVAZSA-N
IUPAC Name	n.a.
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 73 0 0 0 0 0 0 0 0999 V2000 4.5137 3.0165 0.9990 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4228 2.2073 1.6832 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8102 0.9981 1.1177 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3222 0.5637 -0.1113 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7148 -0.6388 -0.6619 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6184 -1.3948 0.0660 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1057 -0.9655 1.2889 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7099 0.2348 1.8319 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1930 0.6828 3.0663 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1910 -1.0864 -1.9622 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9406 -1.9000 -1.8731 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7873 -1.1912 -1.2365 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2918 -0.3047 -2.3862 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5915 -1.0193 -3.5470 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4382 -2.0864 -3.2792 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7077 -3.0049 -4.0747 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7217 -2.2487 -0.9371 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5318 -1.6385 -0.3008 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5179 -1.2870 1.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5829 -0.7228 1.6204 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7686 -0.4669 0.8974 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7533 -0.8170 -0.4296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6313 -1.3838 -0.9959 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8541 -0.6188 -1.2526 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8920 -0.9552 -2.6031 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8339 0.0976 1.5364 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0769 0.4531 1.1145 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1989 -0.1622 1.9531 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4946 0.1137 1.2207 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6477 1.6161 1.0876 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3769 2.2036 0.5769 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4345 3.7088 0.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2703 4.1714 -0.0845 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2483 1.8543 1.3115 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6516 1.8776 0.1669 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5871 -0.4251 1.8768 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9942 -1.5155 2.1518 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2884 -3.2538 -0.1674 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5745 4.0351 1.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7064 3.1260 -0.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4942 2.5958 1.1246 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6167 1.1734 -0.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9637 -2.3511 -0.3175 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8172 -1.5509 1.8719 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1303 0.4141 3.3926 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9336 -1.6841 -2.5410 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9615 -0.2054 -2.6187 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0863 -2.8773 -1.3779 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0285 -0.5993 -0.3560 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2097 -0.1112 -2.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8395 0.6572 -2.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3734 -2.7179 -1.8798 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4421 -1.4885 1.5897 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5767 -0.4496 2.6820 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6653 -1.6496 -2.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7948 -0.4529 -3.0440 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0219 -0.5888 -3.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0737 -2.0463 -2.7355 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3690 0.2915 0.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2270 0.4051 2.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4472 -0.2953 0.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9608 2.0534 2.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2261 1.8057 -0.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4249 4.0816 1.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3481 4.0720 -0.0010 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5455 4.7312 -0.8709 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7206 1.1848 -0.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8578 -1.3143 1.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0415 -1.6871 3.1345 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0018 -3.2691 0.7607 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 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 2 0 12 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 29 36 1 0 28 37 1 0 17 38 1 0 8 3 1 0 15 11 1 0 23 18 1 0 34 27 1 0 1 39 1 0 1 40 1 0 1 41 1 0 4 42 1 0 6 43 1 0 7 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 1 12 49 1 1 13 50 1 0 13 51 1 0 17 52 1 6 19 53 1 0 20 54 1 0 23 55 1 0 25 56 1 0 25 57 1 0 25 58 1 0 27 59 1 6 28 60 1 1 29 61 1 6 30 62 1 1 31 63 1 6 32 64 1 0 32 65 1 0 33 66 1 0 35 67 1 0 36 68 1 0 37 69 1 0 38 70 1 0 M END

Standard InCHIKey	GJUUUEMPCBRUSX-INYQHVAZSA-N
Standard InCHI	InChI=1S/C26H32O12/c1-34-18-8-12(3-5-16(18)28)7-14-15(11-36-25(14)33)21(29)13-4-6-17(19(9-13)35-2)37-26-24(32)23(31)22(30)20(10-27)38-26/h3-6,8-9,14-15,20-24,26-32H,7,10-11H2,1-2H3/t14-,15+,20+,21-,22+,23-,24+,26+/m0/s1
SMILES	COc1cc(ccc1O)C[C@H]1[C@@H](COC1=O)[C@H](c1ccc(c(c1)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.19	Volume:	511.054 ? Van der Waals volume.
Dense:	1.049	LogP:	-0.957 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.149 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.556 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	24.0
TPSA:	184.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.229	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.361	Fsp³:	0.5
MCE-18:	92.077 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.587	Fluc inhibitor:	0.114 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.049 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.398 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.074	Promiscuous compounds:	0.197

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.69	MDCK Permeability:	-5.123
Pgp-inhibitor:	0.004	Pgp-substrate:	0.679
PAMPA:	0.528 ? 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):	0.348
20% Bioavailability (F20%):	0.595	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.086
Plasma Protein Binding (PPB):	62.136%	Volume Distribution (VD):	-0.287
Fu:	39.506% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.068
BSEP inhibitor:	0.083

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.575	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.606	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.97
HLM stability:	0.059 ? 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):

2.591

Half-life (T1/2):

4.419

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.199
Human Hepatotoxicity (H-HT):	0.833	Drug-induced Liver Injury (DILI):	0.932
AMES Toxicity:	0.823	Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.09	Skin Sensitization:	0.997
Carcinogencity:	0.211	Eye Corrosion:	0.0
Eye Irritation:	0.053	Respiratory Toxicity:	0.025
Drug-induced Neurotoxicity:	0.081	Ototoxicity:	0.99
Hematotoxicity:	0.54	Drug-induced Nephrotoxicity:	0.983
Genotoxicity:	0.958	RPMI-8226 Immunitoxicity:	0.219
A549 Cytotoxicity:	0.341	Hek293 Cytotoxicity:	0.282
BCF:	0.328 ? 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:	2.913 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.496 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.571 ? 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
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10571166]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700070]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30232882]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6409	Eutrema japonicum	Species	Brassicaceae	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
Activity	2
IC50	5

Activity Type	# Activity
Cell line	7

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
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	103.3	%	PMID[27700070]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	98.2	%	PMID[27700070]
NPT34	Cell line	BV-2	Mus musculus	IC50	>	50000.0	nM	PMID[27700070]
NPT457	Cell line	BT-549	Homo sapiens	IC50	>	10000.0	nM	PMID[27700070]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[27700070]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[27700070]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[27700070]

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 NPC486546 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	12947
0.1-0.2	31649
0.2-0.3	4179
0.3-0.4	905
0.4-0.5	138
0.5-0.6	24
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9067	High Similarity	NPC486548
0.8571	High Similarity	NPC486547
0.7722	Intermediate Similarity	NPC299706
0.7722	Intermediate Similarity	NPC115466
0.7722	Intermediate Similarity	NPC61604
0.7654	Intermediate Similarity	NPC486549
0.6712	Remote Similarity	NPC100675
0.6712	Remote Similarity	NPC601691
0.6667	Remote Similarity	NPC245615
0.6512	Remote Similarity	NPC163635
0.65	Remote Similarity	NPC158635
0.65	Remote Similarity	NPC229882
0.6136	Remote Similarity	NPC185307
0.5909	Remote Similarity	NPC486545
0.5778	Remote Similarity	NPC470950
0.5714	Remote Similarity	NPC470235
0.5714	Remote Similarity	NPC283995
0.5625	Remote Similarity	NPC278961
0.5625	Remote Similarity	NPC113680
0.5581	Remote Similarity	NPC38041
0.5581	Remote Similarity	NPC22150
0.5435	Remote Similarity	NPC478055
0.5376	Remote Similarity	NPC129417
0.5281	Remote Similarity	NPC38699
0.5227	Remote Similarity	NPC18979
0.5217	Remote Similarity	NPC39657
0.519	Remote Similarity	NPC210015
0.5125	Remote Similarity	NPC300776
0.5125	Remote Similarity	NPC176814
0.5125	Remote Similarity	NPC4982
0.5125	Remote Similarity	NPC606629
0.5106	Remote Similarity	NPC46092
0.5063	Remote Similarity	NPC472024
0.5063	Remote Similarity	NPC270849
0.5056	Remote Similarity	NPC279298
0.5056	Remote Similarity	NPC147596
0.5053	Remote Similarity	NPC112861

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4092
0.1-0.2	4898
0.2-0.3	151
0.3-0.4	9
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