NPASS Compound

Natural Product: NPC291296

Natural Product ID	NPC291296
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FEXQIFZINKFUAH-WNTHUPNMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44203442
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 62 64 0 0 0 0 0 0 0 0999 V2000 9.8124 0.0524 -2.6229 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0055 -0.3501 -1.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1206 -0.6283 -0.7282 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8313 -0.4184 -0.2859 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6410 -0.1271 -0.7555 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4333 -0.1742 0.0827 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5016 -0.5304 1.4083 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3378 -0.5554 2.1452 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1236 -0.2325 1.5789 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9944 0.1302 0.2624 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2093 0.1422 -0.4536 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8424 0.4653 -0.3846 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5723 0.5267 0.0806 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9489 1.9363 -0.1217 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3422 1.9207 0.6294 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9738 0.5609 0.7199 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5284 -0.3971 -0.3252 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4132 -0.3341 -1.5644 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7889 -0.4456 -1.1730 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7863 -0.4147 -2.1307 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4835 -0.2907 -3.3282 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2030 -0.5273 -1.7432 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5131 -0.6576 -0.4817 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8732 -0.7753 -0.0014 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1290 -0.9127 1.3675 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3966 -1.0253 1.8530 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4871 -1.0098 1.0268 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2604 -0.8765 -0.3129 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9749 -0.7607 -0.8246 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3630 -0.8586 -1.1718 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7846 -1.1229 1.5006 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7637 -0.2868 -0.7321 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8552 -0.0134 1.9851 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2504 2.9008 0.1835 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8268 2.9108 0.3796 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9788 -0.2802 2.3927 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2010 -0.7021 -3.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2384 1.0118 -2.6020 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7693 0.2515 -3.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0073 -0.7089 0.7329 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5721 0.1567 -1.8085 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4600 -0.7933 1.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3779 -0.8323 3.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1501 0.4231 -1.4958 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3360 0.2866 1.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7414 2.1073 -1.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1035 2.2284 1.6905 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0829 0.7212 0.5735 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6663 -1.4357 0.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2420 0.6120 -2.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2178 -1.1609 -2.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9705 -0.5020 -2.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6973 -0.6791 0.2551 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2500 -0.9247 2.0258 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5292 -1.1289 2.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8605 -0.6577 -1.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1616 -0.2741 -1.0287 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2489 -0.3533 1.9871 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7056 -0.4224 2.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7742 3.2651 0.9562 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5310 3.1363 -0.2702 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5890 -1.1656 2.6695 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 9 10 1 0 10 11 2 0 10 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 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 17 32 1 0 16 33 1 0 15 34 1 0 14 35 1 0 9 36 1 0 11 6 1 0 32 13 1 0 29 24 1 0 1 37 1 0 1 38 1 0 1 39 1 0 4 40 1 0 5 41 1 0 7 42 1 0 8 43 1 0 11 44 1 0 13 45 1 1 14 46 1 6 15 47 1 1 16 48 1 6 17 49 1 1 18 50 1 0 18 51 1 0 22 52 1 0 23 53 1 0 25 54 1 0 26 55 1 0 29 56 1 0 30 57 1 0 31 58 1 0 33 59 1 0 34 60 1 0 35 61 1 0 36 62 1 0 M END

Standard InCHIKey	FEXQIFZINKFUAH-WNTHUPNMSA-N
Standard InCHI	InChI=1S/C25H26O11/c1-13(26)2-3-15-5-8-17(28)19(11-15)35-25-24(33)23(32)22(31)20(36-25)12-34-21(30)9-6-14-4-7-16(27)18(29)10-14/h2-11,20,22-25,27-29,31-33H,12H2,1H3/b3-2+,9-6+/t20-,22-,23+,24-,25-/m1/s1
SMILES	CC(=O)/C=C/c1ccc(c(c1)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)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.15	Volume:	485.615 ? Van der Waals volume.
Dense:	1.034	LogP:	1.383 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.707 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.937 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	22.0
TPSA:	183.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	3.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.171	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.011	Fsp³:	0.28
MCE-18:	72.875 ? 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:	1
Colloidal aggregators:	0.766	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.218 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.861 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.23	Promiscuous compounds:	0.325

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.19	MDCK Permeability:	-5.348
Pgp-inhibitor:	0.003	Pgp-substrate:	0.017
PAMPA:	0.935 ? 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):	0.445
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.009
Plasma Protein Binding (PPB):	80.452%	Volume Distribution (VD):	-0.46
Fu:	16.54% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.009
BSEP inhibitor:	0.169

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.043 ? 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):

4.782

Half-life (T1/2):

2.785

ADMET: Toxicity

hERG Blockers:	0.089	hERG Blockers (10um):	0.449
Human Hepatotoxicity (H-HT):	0.693	Drug-induced Liver Injury (DILI):	0.787
AMES Toxicity:	0.886	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.142	Skin Sensitization:	1.0
Carcinogencity:	0.082	Eye Corrosion:	0.0
Eye Irritation:	0.353	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.923
Hematotoxicity:	0.053	Drug-induced Nephrotoxicity:	0.306
Genotoxicity:	0.727	RPMI-8226 Immunitoxicity:	0.056
A549 Cytotoxicity:	0.653	Hek293 Cytotoxicity:	0.289
BCF:	0.842 ? 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:	3.599 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.086 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.697 ? 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
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	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
EC50	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
NPT804	Cell line	HT-22	Mus musculus	EC50	=	62200.0	nM	PMID[32991171]

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 NPC291296 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	11153
0.1-0.2	33477
0.2-0.3	4055
0.3-0.4	871
0.4-0.5	233
0.5-0.6	47
0.6-0.7	13
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
0.7895	Intermediate Similarity	NPC488082
0.7895	Intermediate Similarity	NPC476868
0.75	Intermediate Similarity	NPC488081
0.7162	Intermediate Similarity	NPC157898
0.6905	Remote Similarity	NPC133984
0.6875	Remote Similarity	NPC476869
0.6835	Remote Similarity	NPC471405
0.6829	Remote Similarity	NPC476865
0.675	Remote Similarity	NPC157816
0.675	Remote Similarity	NPC476864
0.642	Remote Similarity	NPC476867
0.6207	Remote Similarity	NPC11411
0.6163	Remote Similarity	NPC479767
0.6154	Remote Similarity	NPC291153
0.6118	Remote Similarity	NPC476870
0.6071	Remote Similarity	NPC476866
0.6067	Remote Similarity	NPC476871
0.596	Remote Similarity	NPC484988
0.5952	Remote Similarity	NPC204937
0.5904	Remote Similarity	NPC10205
0.5844	Remote Similarity	NPC470572
0.5795	Remote Similarity	NPC83743
0.5729	Remote Similarity	NPC603856
0.5698	Remote Similarity	NPC226005
0.5696	Remote Similarity	NPC229784
0.5673	Remote Similarity	NPC484984
0.567	Remote Similarity	NPC599948
0.5667	Remote Similarity	NPC300262
0.5625	Remote Similarity	NPC287597
0.5543	Remote Similarity	NPC125823
0.5543	Remote Similarity	NPC7145
0.5543	Remote Similarity	NPC143480
0.5541	Remote Similarity	NPC476873
0.5532	Remote Similarity	NPC201148
0.5506	Remote Similarity	NPC262182
0.5455	Remote Similarity	NPC470416
0.5408	Remote Similarity	NPC214621
0.5408	Remote Similarity	NPC34267
0.5408	Remote Similarity	NPC81042
0.54	Remote Similarity	NPC480796
0.5392	Remote Similarity	NPC139571
0.5357	Remote Similarity	NPC137813
0.5357	Remote Similarity	NPC219677
0.5349	Remote Similarity	NPC194095
0.5288	Remote Similarity	NPC484982
0.5283	Remote Similarity	NPC484983
0.5253	Remote Similarity	NPC484980
0.5248	Remote Similarity	NPC472993
0.5244	Remote Similarity	NPC186406
0.5227	Remote Similarity	NPC220942
0.5158	Remote Similarity	NPC3460
0.5128	Remote Similarity	NPC157554
0.5119	Remote Similarity	NPC34293
0.5109	Remote Similarity	NPC472876
0.5104	Remote Similarity	NPC472611
0.5104	Remote Similarity	NPC67134
0.5104	Remote Similarity	NPC600370
0.5093	Remote Similarity	NPC484981
0.5068	Remote Similarity	NPC110313
0.5054	Remote Similarity	NPC216819
0.5054	Remote Similarity	NPC80732
0.5053	Remote Similarity	NPC287615
0.5053	Remote Similarity	NPC199311
0.5052	Remote Similarity	NPC476620

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC291296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3853
0.1-0.2	5183
0.2-0.3	105
0.3-0.4	7
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