NPASS Compound

Natural Product: NPC186847

Natural Product ID	NPC186847
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,2'r,3R,3'r)-2'-(3,4-Dihydroxyphenyl)-3',5,5',7,7'-Pentahydroxy-2-(4-Hydroxyphenyl)-3,8'-Bichroman-4,4'-Dione
IUPAC Name	(2R,3R)-8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508885
PubChem CID	161259
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 64 69 0 0 0 0 0 0 0 0999 V2000 -2.0547 -0.7283 2.5080 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6738 -0.1456 3.5841 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9353 1.2015 3.5989 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 1.9544 2.5144 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9338 1.3402 1.4253 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6559 0.0034 1.3725 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0055 -0.7105 0.2542 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8410 0.1646 -0.9280 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0492 -0.4149 -1.9692 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4512 -1.0150 -3.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4275 -1.5600 -4.0470 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7925 -1.5034 -3.8740 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2897 -0.8967 -2.7381 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7141 -0.7991 -2.4841 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5336 -1.4784 -3.1368 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1450 0.1575 -1.4004 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2359 -0.0168 -0.2467 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5810 0.6888 0.9883 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7910 0.5989 2.1216 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0932 1.2678 3.2864 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2225 2.0633 3.3465 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0265 2.1715 2.2343 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6955 1.4784 1.0576 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1565 2.9736 2.3099 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5454 2.7539 4.5309 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8990 0.2545 -0.6512 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4297 -0.3575 -1.7945 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4811 -0.1465 -1.1001 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6976 -2.0204 -4.7746 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7857 -1.1266 -3.3700 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1956 0.4428 -1.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4233 1.4598 -2.2053 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3433 -0.4274 -1.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6190 -0.1606 -1.6424 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6795 -1.0019 -1.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4205 -2.1597 -0.6731 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1423 -2.4792 -0.2227 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1267 -1.5907 -0.5150 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8057 -1.8342 -0.0998 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4229 -3.0788 -0.3607 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8639 1.0038 -2.3566 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5729 1.7959 4.7098 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8371 -1.7986 2.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9669 -0.7372 4.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7603 3.0178 2.5030 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6646 1.9824 0.5802 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0278 -1.1445 0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4269 1.1621 -0.5963 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0344 -2.0313 -4.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0867 1.1970 -1.7768 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2138 -1.1413 -0.0385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8909 -0.0121 2.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4576 1.1879 4.1792 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3945 1.6453 0.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0684 2.6338 2.5847 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3955 2.4167 4.9864 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0752 0.3782 -1.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9683 -1.4402 -5.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2096 -0.9685 -4.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6815 -0.7881 -1.7186 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9278 -3.3718 0.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7439 -3.7851 -1.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3845 0.9138 -3.2174 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2439 2.5614 4.5761 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 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 14 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 22 24 1 0 21 25 1 0 17 26 1 0 26 27 1 0 16 28 1 0 12 29 1 0 10 30 1 0 8 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 36 40 1 0 34 41 1 0 3 42 1 0 6 1 1 0 39 7 1 0 27 9 1 0 38 33 1 0 27 13 2 0 23 18 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 7 47 1 1 8 48 1 1 11 49 1 0 16 50 1 6 17 51 1 1 19 52 1 0 20 53 1 0 23 54 1 0 24 55 1 0 25 56 1 0 28 57 1 0 29 58 1 0 30 59 1 0 35 60 1 0 37 61 1 0 40 62 1 0 41 63 1 0 42 64 1 0 M END

Standard InCHIKey	SNFOQVRNAHJPMU-BENTYHEHSA-N
Standard InCHI	InChI=1S/C30H22O12/c31-13-4-1-11(2-5-13)28-24(25(38)21-17(35)8-14(32)9-20(21)41-28)22-18(36)10-19(37)23-26(39)27(40)29(42-30(22)23)12-3-6-15(33)16(34)7-12/h1-10,24,27-29,31-37,40H/t24-,27-,28+,29+/m0/s1
SMILES	c1cc(ccc1[C@@H]1[C@@H](c2c(cc(c3C(=O)[C@@H]([C@@H](c4ccc(c(c4)O)O)Oc23)O)O)O)C(=O)c2c(cc(cc2O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	574.11	Volume:	544.67 ? Van der Waals volume.
Dense:	1.054	LogP:	2.259 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.926 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.226 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	36.0
TPSA:	214.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.165	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.331	Fsp³:	0.133
MCE-18:	122.941 ? 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:	0.925	Fluc inhibitor:	0.347 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.177 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.671 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.623	Promiscuous compounds:	0.29

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.644	MDCK Permeability:	-4.98
Pgp-inhibitor:	0.028	Pgp-substrate:	0.193
PAMPA:	0.397 ? 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):	0.0
20% Bioavailability (F20%):	0.684	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.943
Plasma Protein Binding (PPB):	96.252%	Volume Distribution (VD):	-0.245
Fu:	5.323% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.972
BSEP inhibitor:	0.264

ADMET: Metabolism

CYP1A2-inhibitor:	0.996	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.425
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.003 ? 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):

6.485

Half-life (T1/2):

2.881

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.627
Human Hepatotoxicity (H-HT):	0.699	Drug-induced Liver Injury (DILI):	0.464
AMES Toxicity:	0.641	Rat Oral Acute Toxicity:	0.512
Maximum Recommended Daily Dose:	0.85	Skin Sensitization:	0.997
Carcinogencity:	0.084	Eye Corrosion:	0.0
Eye Irritation:	0.858	Respiratory Toxicity:	0.758
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.827
Hematotoxicity:	0.049	Drug-induced Nephrotoxicity:	0.153
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.127
A549 Cytotoxicity:	0.982	Hek293 Cytotoxicity:	0.963
BCF:	1.163 ? 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:	4.04 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.903 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.432 ? 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
NPO32446	calophyllum panciflorum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654415]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[32644811]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19087	Garcinia kola	Species	Clusiaceae	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
Activity	8
MIC	2
MBC	2

Activity Type	# Activity
Cell line	4
Organism	4
Non-molecular	4

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[11356111]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	DOI[10.6019/CHEMBL1201861]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	28.7	%	PMID[10654415]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	63.9	%	PMID[10654415]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	90.3	%	PMID[10654415]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[10654415]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	>	1000000.0	nM	PMID[32644811]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MBC	>	1000.0	uM	PMID[32644811]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MIC	=	250000.0	nM	PMID[32644811]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MBC	=	1000.0	uM	PMID[32644811]

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 NPC186847 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	22499
0.1-0.2	23478
0.2-0.3	3339
0.3-0.4	397
0.4-0.5	116
0.5-0.6	14
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC63438
0.8429	Intermediate Similarity	NPC75827
0.7083	Intermediate Similarity	NPC224851
0.6719	Remote Similarity	NPC36835
0.6719	Remote Similarity	NPC246162
0.6719	Remote Similarity	NPC9743
0.6719	Remote Similarity	NPC260491
0.6719	Remote Similarity	NPC61506
0.6719	Remote Similarity	NPC240476
0.6528	Remote Similarity	NPC69531
0.6	Remote Similarity	NPC62290
0.6	Remote Similarity	NPC142731
0.6	Remote Similarity	NPC326506
0.6	Remote Similarity	NPC479054
0.5441	Remote Similarity	NPC246328
0.5441	Remote Similarity	NPC27532
0.5441	Remote Similarity	NPC19721
0.527	Remote Similarity	NPC262038
0.527	Remote Similarity	NPC319910
0.5211	Remote Similarity	NPC611035
0.5205	Remote Similarity	NPC326037
0.5205	Remote Similarity	NPC13858
0.5147	Remote Similarity	NPC21835
0.5139	Remote Similarity	NPC320825
0.5139	Remote Similarity	NPC244250
0.5072	Remote Similarity	NPC279417
0.5072	Remote Similarity	NPC4152
0.5072	Remote Similarity	NPC49130

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC186847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4731
0.1-0.2	4352
0.2-0.3	57
0.3-0.4	4
0.4-0.5	6
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