NPASS Compound

Natural Product: NPC291153

Natural Product ID	NPC291153
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Scrophenoside B
IUPAC Name	[(2R,3S,4S,5R,6S)-6-(4-acetylphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2436434
PubChem CID	73357070
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 56 58 0 0 0 0 0 0 0 0999 V2000 2.4578 1.0025 1.1196 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9318 1.2357 -0.0221 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3529 1.1046 -0.3228 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1843 0.7309 0.6181 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6168 0.5684 0.4291 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3792 0.1630 1.5291 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7226 0.0104 1.3524 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3430 0.2389 0.1449 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5910 0.6383 -0.9382 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2291 0.7984 -0.7793 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7041 0.0752 -0.0001 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0641 1.6266 -1.0076 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6954 1.7985 -0.8895 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0282 0.5092 -0.4683 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3400 0.8137 -0.3924 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2427 -0.2095 -0.3747 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.2938 -0.8503 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6558 0.3866 -0.2105 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8806 -0.0173 1.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1626 0.1364 1.6157 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2040 0.6782 0.9002 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9842 1.0876 -0.3977 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7189 0.9352 -0.9282 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5222 0.8147 1.5128 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4708 1.3124 0.8520 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7375 0.3674 2.9078 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8884 -1.3946 -1.2198 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4400 -1.7993 -1.0808 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3585 -0.5422 -1.4527 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6942 -0.8659 -1.3199 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1592 -2.8524 -1.9115 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 -2.4906 -0.8442 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7041 1.3130 -1.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7388 0.5369 1.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8988 -0.0139 2.4635 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3200 -0.3024 2.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0289 0.8252 -1.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6698 1.1068 -1.6273 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2333 0.7789 -0.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3846 2.5918 -0.1877 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2739 2.0587 -1.8809 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3333 0.1877 0.5312 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3566 -0.5490 0.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0823 -0.4482 1.6674 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3377 -0.1836 2.6328 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7903 1.5259 -1.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5187 1.2467 -1.9407 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1748 1.0743 3.5667 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8146 0.3696 3.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2993 -0.6499 2.9990 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0781 -1.2242 -2.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2153 -2.0880 -0.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0728 -0.3020 -2.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8616 -1.8004 -1.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9960 -3.2614 -2.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6161 -2.2684 -1.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 9 10 2 0 8 11 1 0 2 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 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 21 24 1 0 24 25 2 0 24 26 1 0 16 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 10 5 1 0 29 14 1 0 23 18 1 0 3 33 1 0 4 34 1 0 6 35 1 0 7 36 1 0 9 37 1 0 10 38 1 0 11 39 1 0 13 40 1 0 13 41 1 0 14 42 1 1 16 43 1 1 19 44 1 0 20 45 1 0 22 46 1 0 23 47 1 0 26 48 1 0 26 49 1 0 26 50 1 0 27 51 1 6 28 52 1 1 29 53 1 6 30 54 1 0 31 55 1 0 32 56 1 0 M END

Standard InCHIKey	MEEFNALTIANJSU-WLFPCALSSA-N
Standard InCHI	InChI=1S/C23H24O9/c1-13(24)15-5-9-17(10-6-15)31-23-22(29)21(28)20(27)18(32-23)12-30-19(26)11-4-14-2-7-16(25)8-3-14/h2-11,18,20-23,25,27-29H,12H2,1H3/b11-4+/t18-,20-,21+,22-,23-/m1/s1
SMILES	O=C(/C=C/c1ccc(cc1)O)OC[C@H]1O[C@@H](Oc2ccc(cc2)C(=O)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	444.14	Volume:	436.079 ? Van der Waals volume.
Dense:	1.018	LogP:	1.561 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.844 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.205 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	21.0
TPSA:	142.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.28	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.585	Fsp³:	0.304
MCE-18:	66.667 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.728	Fluc inhibitor:	0.998 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.143 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.673 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.206	Promiscuous compounds:	0.265

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.894	MDCK Permeability:	-5.078
Pgp-inhibitor:	0.026	Pgp-substrate:	0.017
PAMPA:	0.922 ? 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):	0.234
20% Bioavailability (F20%):	0.745	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.002
Plasma Protein Binding (PPB):	88.794%	Volume Distribution (VD):	-0.315
Fu:	10.852% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.788

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.404
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.934 ? 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):

3.398

Half-life (T1/2):

2.728

ADMET: Toxicity

hERG Blockers:	0.115	hERG Blockers (10um):	0.341
Human Hepatotoxicity (H-HT):	0.647	Drug-induced Liver Injury (DILI):	0.898
AMES Toxicity:	0.932	Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.105	Skin Sensitization:	0.989
Carcinogencity:	0.292	Eye Corrosion:	0.0
Eye Irritation:	0.339	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.079	Ototoxicity:	0.833
Hematotoxicity:	0.237	Drug-induced Nephrotoxicity:	0.746
Genotoxicity:	0.748	RPMI-8226 Immunitoxicity:	0.149
A549 Cytotoxicity:	0.19	Hek293 Cytotoxicity:	0.559
BCF:	0.557 ? 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:	3.237 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.76 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.144 ? 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
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	root	n.a.	PMID[15133218]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	root	n.a.	PMID[15706916]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24035096]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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
Organism	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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	25000.0	nM	DailyMed

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 NPC291153 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	8873
0.1-0.2	33935
0.2-0.3	5549
0.3-0.4	1190
0.4-0.5	224
0.5-0.6	59
0.6-0.7	19
0.7-0.8	0
0.8-0.85	1
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	NPC157898
0.8	Intermediate Similarity	NPC10205
0.6933	Remote Similarity	NPC471405
0.6842	Remote Similarity	NPC204937
0.6711	Remote Similarity	NPC476867
0.6622	Remote Similarity	NPC137813
0.6538	Remote Similarity	NPC476869
0.6538	Remote Similarity	NPC476866
0.642	Remote Similarity	NPC472876
0.6322	Remote Similarity	NPC477629
0.6207	Remote Similarity	NPC270675
0.6207	Remote Similarity	NPC195685
0.6173	Remote Similarity	NPC476870
0.6154	Remote Similarity	NPC291296
0.6136	Remote Similarity	NPC80068
0.6094	Remote Similarity	NPC192229
0.6027	Remote Similarity	NPC479473
0.6027	Remote Similarity	NPC275721
0.6027	Remote Similarity	NPC288416
0.6027	Remote Similarity	NPC479468
0.6027	Remote Similarity	NPC479474
0.5955	Remote Similarity	NPC85751
0.5955	Remote Similarity	NPC19240
0.5942	Remote Similarity	NPC79908
0.5909	Remote Similarity	NPC476620
0.5882	Remote Similarity	NPC476872
0.5824	Remote Similarity	NPC223426
0.5824	Remote Similarity	NPC472994
0.5802	Remote Similarity	NPC157816
0.5802	Remote Similarity	NPC476864
0.5789	Remote Similarity	NPC199977
0.5747	Remote Similarity	NPC476871
0.5735	Remote Similarity	NPC479769
0.5714	Remote Similarity	NPC36138
0.5714	Remote Similarity	NPC34293
0.5663	Remote Similarity	NPC476868
0.5581	Remote Similarity	NPC488081
0.5579	Remote Similarity	NPC472993
0.5579	Remote Similarity	NPC477895
0.557	Remote Similarity	NPC252114
0.5556	Remote Similarity	NPC281798
0.5529	Remote Similarity	NPC476865
0.5521	Remote Similarity	NPC217520
0.5517	Remote Similarity	NPC300262
0.5493	Remote Similarity	NPC198487
0.5476	Remote Similarity	NPC488082
0.5467	Remote Similarity	NPC470572
0.5467	Remote Similarity	NPC140750
0.5465	Remote Similarity	NPC479767
0.5455	Remote Similarity	NPC133984
0.5444	Remote Similarity	NPC67134
0.5426	Remote Similarity	NPC214621
0.5426	Remote Similarity	NPC34267
0.5417	Remote Similarity	NPC480796
0.5342	Remote Similarity	NPC233559
0.5341	Remote Similarity	NPC11411
0.5286	Remote Similarity	NPC604356
0.527	Remote Similarity	NPC479768
0.5263	Remote Similarity	NPC81042
0.5244	Remote Similarity	NPC225307
0.5238	Remote Similarity	NPC134905
0.5222	Remote Similarity	NPC125823
0.5222	Remote Similarity	NPC7145
0.5222	Remote Similarity	NPC143480
0.5217	Remote Similarity	NPC201148
0.5208	Remote Similarity	NPC599948
0.519	Remote Similarity	NPC320259
0.5185	Remote Similarity	NPC43638
0.5155	Remote Similarity	NPC470416
0.5135	Remote Similarity	NPC52097
0.5128	Remote Similarity	NPC229784
0.5063	Remote Similarity	NPC478884
0.5063	Remote Similarity	NPC186406
0.5063	Remote Similarity	NPC287597
0.5062	Remote Similarity	NPC40664
0.5062	Remote Similarity	NPC3293
0.5062	Remote Similarity	NPC197723
0.5059	Remote Similarity	NPC235294
0.5056	Remote Similarity	NPC172033
0.505	Remote Similarity	NPC484988

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC291153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3083
0.1-0.2	5833
0.2-0.3	216
0.3-0.4	17
0.4-0.5	1
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