NPASS Compound

Natural Product: NPC118266

Natural Product ID	NPC118266
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Mooloolabene E
IUPAC Name	[(1S,5aR,7aS,11aS,11bR,13aS,13bR)-8,8,11a,13a-tetramethyl-3,5,5a,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[1,2-g][2]benzofuran-1-yl] acetate
Synonyms	Mooloolabene E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL469399
PubChem CID	11994181
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 67 71 0 0 0 0 0 0 0 0999 V2000 7.1056 -0.9502 2.0204 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0520 -1.0720 0.9903 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6509 -2.1635 0.5404 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4727 0.0765 0.4913 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4409 0.0172 -0.5141 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8825 0.7353 -1.6117 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7231 2.0898 -1.2295 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3297 2.0723 -0.7079 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2614 2.8218 -0.7283 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9755 2.4738 -0.0658 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9896 1.1053 0.5100 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9140 0.2034 -0.2865 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2861 0.7500 0.0295 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6532 0.2996 -1.7890 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7063 -1.2111 0.1270 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3181 -1.6444 -0.2947 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6933 -0.8949 0.5061 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3306 0.5162 0.7931 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2318 1.2996 1.3459 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5962 0.8142 1.6783 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0292 -0.3825 0.9109 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0695 -0.8525 -0.1432 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9932 -0.0118 -1.3522 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5286 -2.2438 -0.5346 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8590 -2.0700 -1.2228 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8927 -1.3839 -0.4300 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4505 -0.2393 0.4061 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7254 1.0822 -0.2514 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3200 -0.2741 1.6789 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9170 -0.0636 2.6557 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1136 -0.7780 1.5571 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1336 -1.8276 2.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 -1.0454 -0.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8668 2.7515 -2.0826 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4517 2.3452 -0.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3040 3.7636 -1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1885 2.5974 -0.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 3.2038 0.7668 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4880 1.1891 1.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3301 0.9364 1.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7844 -0.7143 -2.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6979 0.7696 -2.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4360 0.9194 -2.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4118 -1.8840 -0.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7833 -1.3724 1.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2073 -2.7290 -0.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1736 -1.6041 -1.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 -1.4034 1.4900 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9789 2.3453 1.5726 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3291 1.6734 1.6229 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5573 0.6188 2.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0790 -1.2414 1.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9596 0.1686 -1.8625 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5198 0.9887 -1.1814 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3607 -0.5183 -2.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6662 -2.8525 0.3850 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8237 -2.6915 -1.2471 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6935 -1.6685 -2.2569 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2283 -3.1227 -1.4279 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6720 -0.9882 -1.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4627 -2.1521 0.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1615 0.9257 -1.2832 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5315 1.6757 0.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8721 1.7603 -0.3302 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8960 0.3609 2.4644 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3367 0.0413 1.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4132 -1.3406 1.9821 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 6 12 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 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 13 5 1 0 22 17 1 0 13 8 1 0 27 21 1 0 18 11 1 0 1 30 1 0 1 31 1 0 1 32 1 0 5 33 1 6 7 34 1 0 7 35 1 0 9 36 1 0 10 37 1 0 10 38 1 0 11 39 1 1 13 40 1 1 14 41 1 0 14 42 1 0 14 43 1 0 15 44 1 0 15 45 1 0 16 46 1 0 16 47 1 0 17 48 1 1 19 49 1 0 20 50 1 0 20 51 1 0 21 52 1 1 23 53 1 0 23 54 1 0 23 55 1 0 24 56 1 0 24 57 1 0 25 58 1 0 25 59 1 0 26 60 1 0 26 61 1 0 28 62 1 0 28 63 1 0 28 64 1 0 29 65 1 0 29 66 1 0 29 67 1 0 M END

Standard InCHIKey	FUWJINVJERRROR-LMZXXRHXSA-N
Standard InCHI	InChI=1S/C26H38O3/c1-16(27)29-23-22-17(15-28-23)7-9-19-18-8-10-21-24(2,3)12-6-13-25(21,4)20(18)11-14-26(19,22)5/h7-8,19-23H,6,9-15H2,1-5H3/t19-,20-,21-,22+,23-,25+,26-/m0/s1
SMILES	CC(=O)O[C@@H]1OCC2=CC[C@@H]3[C@]([C@@H]12)(C)CC[C@H]1C3=CC[C@@H]2[C@]1(C)CCCC2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	398.28	Volume:	433.931 ? Van der Waals volume.
Dense:	0.918	LogP:	5.42 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.255 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.731 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	35.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.398	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.841	Fsp³:	0.808
MCE-18:	85.787 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.624	Fluc inhibitor:	0.236 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.447	Promiscuous compounds:	0.453

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.623	MDCK Permeability:	-4.688
Pgp-inhibitor:	0.753	Pgp-substrate:	0.0
PAMPA:	0.061 ? 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):	0.001
20% Bioavailability (F20%):	0.063	30% Bioavailability (F30%):	0.316
50% Bioavailability (F50%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.765	MRP1:	0.382
Plasma Protein Binding (PPB):	97.409%	Volume Distribution (VD):	0.434
Fu:	3.345% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.868
BSEP inhibitor:	0.91

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.325
CYP2C19-inhibitor:	0.933	CYP2C19-substrate:	0.587
CYP2C9-inhibitor:	0.465	CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.591	CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.957	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.958
HLM stability:	0.997 ? 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):

9.591

Half-life (T1/2):

0.45

ADMET: Toxicity

hERG Blockers:	0.079	hERG Blockers (10um):	0.311
Human Hepatotoxicity (H-HT):	0.696	Drug-induced Liver Injury (DILI):	0.905
AMES Toxicity:	0.595	Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.799	Skin Sensitization:	0.985
Carcinogencity:	0.875	Eye Corrosion:	0.029
Eye Irritation:	0.662	Respiratory Toxicity:	0.758
Drug-induced Neurotoxicity:	0.29	Ototoxicity:	0.327
Hematotoxicity:	0.709	Drug-induced Nephrotoxicity:	0.766
Genotoxicity:	0.534	RPMI-8226 Immunitoxicity:	0.059
A549 Cytotoxicity:	0.375	Hek293 Cytotoxicity:	0.537
BCF:	3.09 ? 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:	5.24 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.79 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.861 ? 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
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	Inner Gneerings, a group of shoals off Mooloolaba (Australia)	2005-JUL	PMID[17125226]
NPO21592	Urtica circularis	Species	Urticaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21608987]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7153777]
NPO18198	Selaginella willdenowii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19595	Lathyrus chloranthus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21265	Teucrium webbianum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19439	Calea zacatechichi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21265	Teucrium webbianum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19439	Calea zacatechichi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21592	Urtica circularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18198	Selaginella willdenowii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17690	Sideritis sventenii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19735	Euonymus pellucidifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16397	Didymocarpus oblonga	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19595	Lathyrus chloranthus	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

Activity Type	# Activity
IC50	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
NPT168	Cell line	P388	Mus musculus	IC50	=	3.0	ug.mL-1	PMID[17125226]

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 NPC118266 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	22831
0.1-0.2	24310
0.2-0.3	2513
0.3-0.4	172
0.4-0.5	25
0.5-0.6	5
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	Natural Product ID
0.6984	Remote Similarity	NPC293044
0.5909	Remote Similarity	NPC94905
0.55	Remote Similarity	NPC219232
0.55	Remote Similarity	NPC128346
0.5217	Remote Similarity	NPC8954
0.5075	Remote Similarity	NPC173917

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC118266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7137
0.1-0.2	1976
0.2-0.3	37
0.3-0.4	0
0.4-0.5	0
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