NPASS Compound

Natural Product: NPC229784

Natural Product ID	NPC229784
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hebitol Ii
IUPAC Name	[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexoxy]oxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2436432
PubChem CID	53359965
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

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 65 66 0 0 0 0 0 0 0 0999 V2000 6.7266 0.7670 -1.9636 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0017 1.0153 -2.4725 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0917 0.5331 -1.7930 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8905 -0.1811 -0.6294 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6471 -0.4315 -0.1198 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5395 0.0554 -0.8053 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1956 -0.1762 -0.3195 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0784 0.2255 -0.8746 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7618 -0.0792 -0.2730 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7254 -0.7359 0.7908 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5986 0.3264 -0.8312 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2908 0.1781 -0.4405 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2042 0.9342 0.7125 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5673 1.0971 1.9554 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2664 -0.0242 2.8922 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4527 -1.1750 2.2359 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6036 -0.6960 1.4557 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0320 -1.4946 0.4445 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2344 -2.0411 0.3899 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3359 -1.0162 0.2036 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1874 -0.3046 -1.1202 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9889 0.9343 -1.2552 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3336 0.7635 -1.9138 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4250 0.2795 -1.0069 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6107 0.3128 -1.7813 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7186 2.0706 -2.3241 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0111 1.7533 -0.1506 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2066 -1.1519 -2.2189 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3369 -0.0899 1.2206 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 0.5848 1.0215 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8619 -1.9748 3.3453 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4100 -0.4587 3.5755 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0090 2.2606 2.6011 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0385 -0.6486 0.0211 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3852 0.7706 -2.2865 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9260 1.1803 -2.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1189 1.5812 -3.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4909 -0.9989 0.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0739 -0.7474 0.6133 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1396 0.7904 -1.7910 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9181 -0.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3384 0.5519 -1.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3569 2.0503 0.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6346 1.2761 1.8868 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4197 0.3349 3.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3299 -1.7381 1.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4767 -0.6831 2.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5025 -2.7525 1.2070 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2948 -2.7003 -0.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3306 -1.5446 0.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0850 0.0443 -1.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4194 1.5896 -2.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2177 0.0889 -2.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5500 0.9408 -0.1328 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3329 -0.7916 -0.7261 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3389 -0.1506 -1.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0975 2.4914 -1.4969 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7392 1.6181 0.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8001 -0.7753 -3.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9210 -0.3377 1.9824 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3686 -1.4433 3.9835 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6156 0.1088 4.3594 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6458 2.9814 2.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3305 -1.6138 0.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1246 0.7309 -1.6019 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 9 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 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 22 27 1 0 21 28 1 0 20 29 1 0 17 30 1 0 16 31 1 0 15 32 1 0 14 33 1 0 4 34 1 0 3 35 1 0 6 1 1 0 30 13 1 0 1 36 1 0 2 37 1 0 5 38 1 0 7 39 1 0 8 40 1 0 12 41 1 0 12 42 1 0 13 43 1 6 14 44 1 6 15 45 1 1 16 46 1 6 17 47 1 1 19 48 1 0 19 49 1 0 20 50 1 6 21 51 1 1 22 52 1 6 23 53 1 6 24 54 1 0 24 55 1 0 25 56 1 0 26 57 1 0 27 58 1 0 28 59 1 0 29 60 1 0 31 61 1 0 32 62 1 0 33 63 1 0 34 64 1 0 35 65 1 0 M END

Standard InCHIKey	NKNIPRJKUBSJDO-BCCHJPKLSA-N
Standard InCHI	InChI=1S/C21H30O14/c22-6-12(25)16(28)17(29)13(26)7-34-21-20(32)19(31)18(30)14(35-21)8-33-15(27)4-2-9-1-3-10(23)11(24)5-9/h1-5,12-14,16-26,28-32H,6-8H2/b4-2+/t12-,13-,14-,16-,17-,18-,19+,20-,21-/m1/s1
SMILES	c1cc(c(cc1/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](OC[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	506.16	Volume:	464.54 ? Van der Waals volume.
Dense:	1.09	LogP:	-0.825 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.215 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.359 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	14.0
TPSA:	247.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	10.0	Rings:	2.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.078	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.497	Fsp³:	0.571
MCE-18:	62.758 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.663	Fluc inhibitor:	0.616 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.221 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.264 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.258	Promiscuous compounds:	0.396

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.456	MDCK Permeability:	-5.107
Pgp-inhibitor:	0.0	Pgp-substrate:	0.086
PAMPA:	1.0 ? 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):	0.827
20% Bioavailability (F20%):	0.987	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.001
Plasma Protein Binding (PPB):	56.603%	Volume Distribution (VD):	-0.434
Fu:	44.137% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.0

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:	0.036
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.015 ? 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):

1.325

Half-life (T1/2):

2.39

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.154
Human Hepatotoxicity (H-HT):	0.302	Drug-induced Liver Injury (DILI):	0.091
AMES Toxicity:	0.795	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.026	Skin Sensitization:	0.999
Carcinogencity:	0.049	Eye Corrosion:	0.0
Eye Irritation:	0.209	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.994
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.522
Genotoxicity:	0.079	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.331	Hek293 Cytotoxicity:	0.064
BCF:	0.406 ? 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:	2.895 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.615 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.984 ? 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]
NPO30110	Veronica lavaudiana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21568305]
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	PMID[24035096]

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 NPC229784 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	15426
0.1-0.2	29616
0.2-0.3	3922
0.3-0.4	654
0.4-0.5	181
0.5-0.6	36
0.6-0.7	11
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
0.7778	Intermediate Similarity	NPC184633
0.7273	Intermediate Similarity	NPC470572
0.7206	Intermediate Similarity	NPC287597
0.6806	Remote Similarity	NPC219677
0.6579	Remote Similarity	NPC220942
0.6528	Remote Similarity	NPC34293
0.6479	Remote Similarity	NPC473924
0.6338	Remote Similarity	NPC477293
0.6234	Remote Similarity	NPC476867
0.6197	Remote Similarity	NPC288416
0.6154	Remote Similarity	NPC476864
0.6081	Remote Similarity	NPC157898
0.6	Remote Similarity	NPC232880
0.6	Remote Similarity	NPC476868
0.5972	Remote Similarity	NPC479473
0.5972	Remote Similarity	NPC275721
0.5972	Remote Similarity	NPC479468
0.5972	Remote Similarity	NPC479474
0.597	Remote Similarity	NPC476873
0.593	Remote Similarity	NPC69367
0.5802	Remote Similarity	NPC205195
0.575	Remote Similarity	NPC157816
0.5747	Remote Similarity	NPC476397
0.5714	Remote Similarity	NPC252114
0.5696	Remote Similarity	NPC291296
0.5696	Remote Similarity	NPC281798
0.5676	Remote Similarity	NPC477294
0.5667	Remote Similarity	NPC217472
0.561	Remote Similarity	NPC64141
0.5493	Remote Similarity	NPC52097
0.5488	Remote Similarity	NPC476866
0.5395	Remote Similarity	NPC78363
0.5366	Remote Similarity	NPC260425
0.5357	Remote Similarity	NPC476870
0.5349	Remote Similarity	NPC488081
0.5301	Remote Similarity	NPC226005
0.5294	Remote Similarity	NPC476865
0.527	Remote Similarity	NPC473867
0.5238	Remote Similarity	NPC321638
0.5233	Remote Similarity	NPC83743
0.5233	Remote Similarity	NPC265648
0.5222	Remote Similarity	NPC611523
0.5185	Remote Similarity	NPC225307
0.5128	Remote Similarity	NPC474641
0.5128	Remote Similarity	NPC291153
0.5119	Remote Similarity	NPC476869
0.5114	Remote Similarity	NPC300262
0.506	Remote Similarity	NPC28637
0.5056	Remote Similarity	NPC133984
0.5054	Remote Similarity	NPC171706

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC229784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5169
0.1-0.2	3889
0.2-0.3	86
0.3-0.4	2
0.4-0.5	4
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