NPASS Compound

Natural Product: NPC479766

Natural Product ID	NPC479766
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YWPAPDQONXTGIY-ZJQFWPFFSA-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 67 70 0 0 0 0 0 0 0 0999 V2000 2.0125 -5.1438 0.5163 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0670 -3.9681 -0.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5941 -3.9617 -1.5543 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6721 -2.8274 0.0627 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7901 -1.6334 -0.7117 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2729 -1.3865 -0.9006 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9001 -0.8099 0.3441 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1652 0.4336 0.7364 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0599 1.6597 0.7096 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5107 1.8336 -0.6147 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3413 2.8368 -1.0461 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7357 3.6742 -0.1901 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7481 2.9139 -2.4761 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1295 2.4062 -2.6339 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7695 2.0027 -1.6402 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7001 2.3854 -3.8956 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0883 0.6353 -0.1224 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2145 -0.4504 0.0597 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9144 -0.1634 -0.2935 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2165 -0.2632 0.4915 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2373 -0.6870 1.7985 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4044 -0.7723 2.5529 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6005 -0.4275 2.0026 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7960 -0.4905 2.6997 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7717 -0.8808 3.8836 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9468 -0.1162 2.0399 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9048 0.3084 0.7227 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0767 0.7191 -0.0388 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3281 0.7122 0.5043 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4142 1.1073 -0.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3096 1.5233 -1.5532 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0191 1.5171 -2.0728 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9222 1.1268 -1.3435 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3980 1.9257 -2.3229 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6736 1.8991 -1.7110 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7479 0.3468 0.1168 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6104 0.0020 0.6920 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4567 0.0873 -0.0568 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3618 -1.2087 3.8707 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8585 -1.7870 1.3525 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5309 -0.6371 -2.0344 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2710 -5.8875 0.1492 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7222 -4.8376 1.5614 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9833 -5.6461 0.5968 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3398 -1.7425 -1.7118 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7327 -2.4083 -1.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9717 -0.5956 0.0876 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7771 0.2746 1.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8736 1.5126 1.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4048 2.5326 0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0942 2.2206 -3.0442 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6611 3.9568 -2.8530 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3751 1.6473 -4.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2912 -0.7382 1.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6989 -0.9698 2.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8812 -0.1573 2.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4680 0.3959 1.5253 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4011 1.0950 0.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9170 1.8469 -3.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9511 1.1544 -1.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7121 2.7295 -0.9485 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8713 0.9385 -1.1987 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4884 2.0231 -2.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4587 0.4273 -1.0975 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7742 -2.0306 4.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3267 -1.5115 2.1290 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5208 -0.6717 -2.1818 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 8 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 31 34 1 0 34 35 1 0 27 36 1 0 36 37 1 0 37 38 2 0 22 39 1 0 7 40 1 0 6 41 1 0 18 5 1 0 38 20 1 0 37 23 1 0 33 28 1 0 1 42 1 0 1 43 1 0 1 44 1 0 5 45 1 6 6 46 1 6 7 47 1 6 8 48 1 1 9 49 1 0 9 50 1 0 13 51 1 0 13 52 1 0 16 53 1 0 18 54 1 1 21 55 1 0 26 56 1 0 29 57 1 0 30 58 1 0 32 59 1 0 33 60 1 0 35 61 1 0 35 62 1 0 35 63 1 0 38 64 1 0 39 65 1 0 40 66 1 0 41 67 1 0 M END

Standard InCHIKey	YWPAPDQONXTGIY-ZJQFWPFFSA-N
Standard InCHI	InChI=1S/C27H26O14/c1-12(28)38-26-25(35)24(34)20(11-37-22(33)10-21(31)32)41-27(26)39-15-7-16(29)23-17(30)9-18(40-19(23)8-15)13-3-5-14(36-2)6-4-13/h3-9,20,24-27,29,34-35H,10-11H2,1-2H3,(H,31,32)/t20-,24-,25+,26-,27-/m1/s1
SMILES	CC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](COC(=O)CC(=O)O)O[C@H]1Oc1cc(c2c(=O)cc(c3ccc(cc3)OC)oc2c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	574.13	Volume:	535.384 ? Van der Waals volume.
Dense:	1.072	LogP:	1.598 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.794 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.111 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	27.0
TPSA:	208.49 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.207	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.084	Fsp³:	0.333
MCE-18:	91.778 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.493	Fluc inhibitor:	0.458 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.931 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.639 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.031	Promiscuous compounds:	0.348

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.934	MDCK Permeability:	-5.188
Pgp-inhibitor:	0.0	Pgp-substrate:	0.025
PAMPA:	0.994 ? 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):	0.629
20% Bioavailability (F20%):	0.171	30% Bioavailability (F30%):	0.951
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.475
Plasma Protein Binding (PPB):	80.847%	Volume Distribution (VD):	-0.327
Fu:	18.19% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.021
BSEP inhibitor:	0.041

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.03 ? 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):

0.705

Half-life (T1/2):

2.089

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.016
Human Hepatotoxicity (H-HT):	0.565	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.874	Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.045	Skin Sensitization:	0.989
Carcinogencity:	0.551	Eye Corrosion:	0.0
Eye Irritation:	0.3	Respiratory Toxicity:	0.016
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.781
Hematotoxicity:	0.507	Drug-induced Nephrotoxicity:	0.927
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.093
A549 Cytotoxicity:	0.014	Hek293 Cytotoxicity:	0.066
BCF:	0.293 ? 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:	2.963 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.399 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.708 ? 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
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38791403]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26351	Agastache rugosa	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell line	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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	28800.0	nM	PMID[31747281]

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 NPC479766 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	11199
0.1-0.2	35440
0.2-0.3	2459
0.3-0.4	582
0.4-0.5	122
0.5-0.6	34
0.6-0.7	14
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
0.7865	Intermediate Similarity	NPC46202
0.7717	Intermediate Similarity	NPC479765
0.7241	Intermediate Similarity	NPC80188
0.6915	Remote Similarity	NPC64051
0.6869	Remote Similarity	NPC11468
0.6771	Remote Similarity	NPC229409
0.6699	Remote Similarity	NPC488087
0.6635	Remote Similarity	NPC488088
0.6571	Remote Similarity	NPC488086
0.6415	Remote Similarity	NPC68592
0.6381	Remote Similarity	NPC488083
0.619	Remote Similarity	NPC473644
0.6132	Remote Similarity	NPC311850
0.604	Remote Similarity	NPC488089
0.602	Remote Similarity	NPC22062
0.602	Remote Similarity	NPC473634
0.602	Remote Similarity	NPC138811
0.5957	Remote Similarity	NPC608742
0.5929	Remote Similarity	NPC262222
0.5895	Remote Similarity	NPC220169
0.5806	Remote Similarity	NPC181712
0.5784	Remote Similarity	NPC473623
0.5766	Remote Similarity	NPC298666
0.5752	Remote Similarity	NPC120952
0.5699	Remote Similarity	NPC95090
0.5699	Remote Similarity	NPC27408
0.5612	Remote Similarity	NPC211594
0.5556	Remote Similarity	NPC29353
0.5487	Remote Similarity	NPC198199
0.5472	Remote Similarity	NPC260504
0.5472	Remote Similarity	NPC89809
0.5345	Remote Similarity	NPC209550
0.5333	Remote Similarity	NPC209296
0.5306	Remote Similarity	NPC43761
0.5278	Remote Similarity	NPC253685
0.5234	Remote Similarity	NPC475382
0.5192	Remote Similarity	NPC122809
0.5185	Remote Similarity	NPC101636
0.5185	Remote Similarity	NPC298171
0.5146	Remote Similarity	NPC44931
0.514	Remote Similarity	NPC270675
0.514	Remote Similarity	NPC195685
0.5133	Remote Similarity	NPC277532
0.5102	Remote Similarity	NPC27942
0.5098	Remote Similarity	NPC606546
0.5096	Remote Similarity	NPC65003
0.5093	Remote Similarity	NPC195257
0.5089	Remote Similarity	NPC472993
0.5051	Remote Similarity	NPC282169
0.505	Remote Similarity	NPC190003
0.5045	Remote Similarity	NPC121703

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3101
0.1-0.2	5911
0.2-0.3	128
0.3-0.4	8
0.4-0.5	1
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
0.5333	Remote Similarity	NPD7054	Phase 4

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