NPASS Compound

Natural Product: NPC493812

Natural Product ID	NPC493812
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-3-[4-hydroxy-3-[(2~{S},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-methoxy-chromen-4-one
IUPAC Name	5-hydroxy-3-[4-hydroxy-3-[(2~{S},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-methoxy-chromen-4-one
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 55 58 0 0 0 0 0 0 0 0999 V2000 7.2440 -3.4203 -0.7081 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9968 -2.1721 -1.2903 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8219 -1.4864 -0.9200 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9458 -2.0273 -0.0151 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7940 -1.3617 0.3517 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8836 -1.8843 1.2681 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4857 -0.1184 -0.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3404 0.5642 0.1661 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5266 0.0850 0.9927 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0753 1.8028 -0.3976 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8728 2.5472 -0.0426 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8646 3.8914 0.2424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2806 4.5789 0.5789 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4718 3.9041 0.6353 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6466 4.5534 0.9684 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5240 2.5272 0.3532 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7653 1.9490 0.4382 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0127 0.6084 0.1893 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0581 0.5177 -0.7235 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6786 -0.6790 -0.8244 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9062 -0.9987 -2.2945 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7136 -1.0581 -3.0082 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0078 -1.8667 -0.2077 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0930 -2.4318 -1.0968 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4028 -1.5657 1.1452 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9103 -2.3771 2.1576 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5303 -0.0891 1.4677 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8281 0.2511 1.7528 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3508 1.8753 0.0197 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0096 2.2732 -1.2993 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0887 1.5835 -1.6043 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3766 0.4127 -1.0958 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5303 -0.2533 -1.4636 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3503 -4.1064 -0.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1362 -3.8929 -1.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3716 -3.2646 0.3969 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1536 -2.9925 0.4227 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2656 -2.2396 2.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8365 4.3989 0.1868 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2620 5.6398 0.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1712 5.1424 0.3448 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1238 0.0679 -0.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7122 -0.5961 -0.3870 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4928 -1.9510 -2.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5214 -0.1892 -2.7188 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5799 -1.9260 -3.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7996 -2.6363 -0.0397 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8637 -3.3380 -0.7119 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3175 -1.7877 1.0704 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7273 -2.0435 2.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8735 0.1498 2.3001 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0336 1.2007 1.6275 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3452 0.8238 -0.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8062 3.2420 -1.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2278 0.1635 -2.1760 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 1 0 5 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 14 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 20 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 16 29 2 0 10 30 2 0 30 31 1 0 31 32 1 0 32 33 2 0 33 3 1 0 32 7 1 0 29 11 1 0 27 18 1 0 1 34 1 0 1 35 1 0 1 36 1 0 4 37 1 0 6 38 1 0 12 39 1 0 13 40 1 0 15 41 1 0 18 42 1 6 20 43 1 1 21 44 1 0 21 45 1 0 22 46 1 0 23 47 1 1 24 48 1 0 25 49 1 6 26 50 1 0 27 51 1 1 28 52 1 0 29 53 1 0 30 54 1 0 33 55 1 0 M END

Standard InCHIKey	RICTWLNXKRIFKF-WWOGRVQXSA-N
Standard InCHI	InChI=1S/C22H22O11/c1-30-10-5-13(25)17-15(6-10)31-8-11(18(17)26)9-2-3-12(24)14(4-9)32-22-21(29)20(28)19(27)16(7-23)33-22/h2-6,8,16,19-25,27-29H,7H2,1H3/t16-,19+,20-,21-,22+/m0/s1
SMILES	COC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O[C@@H]4O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)=C3)=COC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.12	Volume:	430.443 ? Van der Waals volume.
Dense:	1.074	LogP:	0.734 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.409 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.823 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	179.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.302	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.914	Fsp³:	0.318
MCE-18:	86.966 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.592	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.952 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.866 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.104	Promiscuous compounds:	0.404

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.368	MDCK Permeability:	-5.38
Pgp-inhibitor:	0.0	Pgp-substrate:	0.543
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):	0.971
20% Bioavailability (F20%):	0.966	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.639
Plasma Protein Binding (PPB):	84.833%	Volume Distribution (VD):	0.041
Fu:	16.27% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.804
OATP1B3 inhibitor:	0.963	BCRP inhibitor:	0.329
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.552	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.851	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.05
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.774
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):

3.295

Half-life (T1/2):

2.437

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.169
Human Hepatotoxicity (H-HT):	0.635	Drug-induced Liver Injury (DILI):	0.966
AMES Toxicity:	0.916	Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.107	Skin Sensitization:	0.98
Carcinogencity:	0.394	Eye Corrosion:	0.0
Eye Irritation:	0.487	Respiratory Toxicity:	0.147
Drug-induced Neurotoxicity:	0.031	Ototoxicity:	0.846
Hematotoxicity:	0.493	Drug-induced Nephrotoxicity:	0.782
Genotoxicity:	0.808	RPMI-8226 Immunitoxicity:	0.184
A549 Cytotoxicity:	0.634	Hek293 Cytotoxicity:	0.319
BCF:	0.511 ? 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:	3.159 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.563 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.732 ? 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
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	Heartwood	India	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[21784631]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	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

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

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 NPC493812 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	23342
0.1-0.2	22351
0.2-0.3	2912
0.3-0.4	935
0.4-0.5	237
0.5-0.6	54
0.6-0.7	21
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
0.7922	Intermediate Similarity	NPC73511
0.7792	Intermediate Similarity	NPC197896
0.7792	Intermediate Similarity	NPC313163
0.7654	Intermediate Similarity	NPC48773
0.7439	Intermediate Similarity	NPC479407
0.6914	Remote Similarity	NPC234739
0.6867	Remote Similarity	NPC80140
0.6849	Remote Similarity	NPC114192
0.6818	Remote Similarity	NPC479405
0.6742	Remote Similarity	NPC479404
0.6628	Remote Similarity	NPC601586
0.6585	Remote Similarity	NPC348541
0.6548	Remote Similarity	NPC205076
0.6353	Remote Similarity	NPC100720
0.6322	Remote Similarity	NPC307518
0.6279	Remote Similarity	NPC224462
0.6265	Remote Similarity	NPC160515
0.6207	Remote Similarity	NPC229729
0.6207	Remote Similarity	NPC601144
0.6136	Remote Similarity	NPC311830
0.6118	Remote Similarity	NPC105511
0.6118	Remote Similarity	NPC161749
0.6118	Remote Similarity	NPC156457
0.6092	Remote Similarity	NPC481043
0.6064	Remote Similarity	NPC479403
0.6023	Remote Similarity	NPC486578
0.5914	Remote Similarity	NPC303913
0.5882	Remote Similarity	NPC45165
0.5795	Remote Similarity	NPC138540
0.5769	Remote Similarity	NPC473045
0.5761	Remote Similarity	NPC487212
0.573	Remote Similarity	NPC479402
0.573	Remote Similarity	NPC285197
0.5714	Remote Similarity	NPC231194
0.5698	Remote Similarity	NPC135345
0.5667	Remote Similarity	NPC22832
0.5658	Remote Similarity	NPC303644
0.5604	Remote Similarity	NPC479406
0.5604	Remote Similarity	NPC607707
0.5568	Remote Similarity	NPC95090
0.5568	Remote Similarity	NPC258035
0.5568	Remote Similarity	NPC27408
0.5543	Remote Similarity	NPC469931
0.5506	Remote Similarity	NPC22195
0.5506	Remote Similarity	NPC84362
0.5506	Remote Similarity	NPC21190
0.5495	Remote Similarity	NPC243930
0.5495	Remote Similarity	NPC601607
0.5495	Remote Similarity	NPC610187
0.5435	Remote Similarity	NPC607201
0.5393	Remote Similarity	NPC277205
0.5393	Remote Similarity	NPC37919
0.5393	Remote Similarity	NPC323593
0.5393	Remote Similarity	NPC203500
0.5385	Remote Similarity	NPC307938
0.5385	Remote Similarity	NPC479401
0.5357	Remote Similarity	NPC191154
0.5326	Remote Similarity	NPC197285
0.5325	Remote Similarity	NPC116632
0.5281	Remote Similarity	NPC289667
0.5281	Remote Similarity	NPC39360
0.5281	Remote Similarity	NPC29763
0.5281	Remote Similarity	NPC210003
0.5263	Remote Similarity	NPC251417
0.5222	Remote Similarity	NPC297987
0.5222	Remote Similarity	NPC487213
0.5222	Remote Similarity	NPC136042
0.5222	Remote Similarity	NPC189142
0.5222	Remote Similarity	NPC77660
0.5185	Remote Similarity	NPC254702
0.5161	Remote Similarity	NPC601710
0.5116	Remote Similarity	NPC134819
0.5111	Remote Similarity	NPC259070
0.5111	Remote Similarity	NPC211014
0.5109	Remote Similarity	NPC60966
0.5106	Remote Similarity	NPC602805
0.5055	Remote Similarity	NPC603782
0.5053	Remote Similarity	NPC203050
0.5053	Remote Similarity	NPC488072
0.5053	Remote Similarity	NPC225434

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC493812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5364
0.1-0.2	3697
0.2-0.3	72
0.3-0.4	12
0.4-0.5	4
0.5-0.6	0
0.6-0.7	1
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
0.6118	Remote Similarity	NPD4381	Clinical (unspecified phase)

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