NPASS Compound

Natural Product: NPC208912

Natural Product ID	NPC208912
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1R,3S,3As,4S,5As,5Br,7As,11As,11Br,13S,13As,13Bs)-1,4-Dihydroxy-3,5B,8,8,11A,13A-Hexamethylicosahydrochryseno[2,1-C]Furan-13-Yl Acetate
IUPAC Name	[(1R,3S,3aS,4S,5aS,5bR,7aS,11aS,11bR,13S,13aS,13bS)-1,4-dihydroxy-3,5b,8,8,11a,13a-hexamethyl-1,3,3a,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-hexadecahydrophenanthro[2,1-e][2]benzofuran-13-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL464295
PubChem CID	11005073
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

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 79 83 0 0 0 0 0 0 0 0999 V2000 2.4346 2.3502 3.9564 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0448 1.0370 3.3834 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2553 0.0160 4.0375 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4646 0.8284 2.1823 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1185 -0.4006 1.6797 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3710 -0.6689 1.6196 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0081 0.0019 0.4187 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4446 -0.5686 -0.8176 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0212 -0.1848 -0.8100 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7988 -0.7134 0.3780 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0649 -2.1997 0.2832 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1321 -0.0392 0.2869 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1730 -0.3799 1.2683 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7898 0.7830 1.8096 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2754 -0.9509 0.5612 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2009 -0.2995 -0.7050 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7785 -0.5666 -1.0069 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1156 0.1555 -2.1028 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6759 -0.3879 -2.1198 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6640 -0.0238 -3.3566 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0625 -1.1213 -1.6346 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7254 -1.9850 -1.1196 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0472 0.2321 -1.9867 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5545 0.2182 -1.9514 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0484 0.7692 -0.6423 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4845 0.1032 0.5703 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1497 -1.1577 0.9960 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7330 1.1002 1.7212 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7743 2.1035 1.3985 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9644 1.6055 0.6540 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5443 0.9429 -0.6320 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3126 -0.2881 -0.9650 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8354 1.9605 -1.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1320 3.1968 3.3051 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4919 2.3921 4.2605 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8387 2.4615 4.8996 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4754 -1.1434 2.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8216 -0.4324 2.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5038 -1.7534 1.4514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6460 1.0814 0.4307 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0041 0.9391 -0.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9385 -2.6533 -0.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0802 -2.4658 0.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3500 -2.7043 0.9860 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0244 1.0735 0.1145 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9003 -1.0033 2.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4175 1.6021 1.3800 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4916 0.7449 -0.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6653 -1.6667 -1.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0538 1.2263 -1.8654 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6334 -1.3814 -2.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1572 0.2967 -2.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8575 0.8285 -3.8229 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8489 -2.1929 -1.3896 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7615 -0.9999 -2.6996 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1401 -0.9698 -1.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6575 -2.7145 -0.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7338 -2.1399 -1.6104 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0470 -2.3077 -1.9559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6821 1.2562 -2.0045 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7668 -0.3598 -2.9072 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0201 -0.7115 -2.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8623 0.9812 -2.7297 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6405 1.8297 -0.6144 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0375 -2.0322 0.3786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2114 -0.9763 1.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6951 -1.4225 1.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7908 1.6703 1.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0056 0.5878 2.6552 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3906 3.0126 0.8677 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1552 2.5092 2.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6351 0.9464 1.2776 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6152 2.5120 0.4655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9324 -0.1868 -1.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7071 -1.1916 -1.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0956 -0.4276 -0.1617 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7509 2.5349 -1.5419 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9858 2.6516 -1.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9451 1.3999 -2.7149 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 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 16 21 1 0 8 22 1 6 8 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 10 5 1 0 17 12 1 0 31 25 1 0 26 7 1 0 19 9 1 0 1 34 1 0 1 35 1 0 1 36 1 0 5 37 1 1 6 38 1 0 6 39 1 0 7 40 1 1 9 41 1 1 11 42 1 0 11 43 1 0 11 44 1 0 12 45 1 6 13 46 1 1 14 47 1 0 16 48 1 1 17 49 1 6 18 50 1 1 19 51 1 0 19 52 1 0 20 53 1 0 21 54 1 0 21 55 1 0 21 56 1 0 22 57 1 0 22 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 24 62 1 0 24 63 1 0 25 64 1 1 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 M END

Standard InCHIKey	YXMVZNUXPZBMJR-KCEWOJSZSA-N
Standard InCHI	InChI=1S/C28H46O5/c1-15-22-17(30)13-20-27(6)12-9-18-25(3,4)10-8-11-26(18,5)19(27)14-21(33-16(2)29)28(20,7)23(22)24(31)32-15/h15,17-24,30-31H,8-14H2,1-7H3/t15-,17-,18-,19+,20-,21-,22+,23+,24+,26-,27+,28+/m0/s1
SMILES	CC(=O)O[C@H]1C[C@H]2[C@@]([C@H]3[C@@]1(C)[C@H]1[C@H](O)O[C@H]([C@@H]1[C@H](C3)O)C)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.33	Volume:	491.376 ? Van der Waals volume.
Dense:	0.941	LogP:	3.61 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.633 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.388 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	75.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.541	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.159	Fsp³:	0.964
MCE-18:	100.909 ? 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:	0.638	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.142	Promiscuous compounds:	0.342

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.574	MDCK Permeability:	-5.288
Pgp-inhibitor:	0.408	Pgp-substrate:	0.011
PAMPA:	0.971 ? 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%):	0.068	30% Bioavailability (F30%):	0.053
50% Bioavailability (F50%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279	MRP1:	0.792
Plasma Protein Binding (PPB):	90.26%	Volume Distribution (VD):	-0.39
Fu:	7.441% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.985	BCRP inhibitor:	0.278
BSEP inhibitor:	0.971

ADMET: Metabolism

CYP1A2-inhibitor:	0.107	CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.393
CYP2C9-inhibitor:	0.055	CYP2C9-substrate:	0.508
CYP2D6-inhibitor:	0.089	CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.477	CYP3A4-substrate:	0.981
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.864
HLM stability:	0.919 ? 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):

5.602

Half-life (T1/2):

1.184

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.093
Human Hepatotoxicity (H-HT):	0.414	Drug-induced Liver Injury (DILI):	0.788
AMES Toxicity:	0.857	Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.455	Skin Sensitization:	0.998
Carcinogencity:	0.892	Eye Corrosion:	0.506
Eye Irritation:	0.824	Respiratory Toxicity:	0.913
Drug-induced Neurotoxicity:	0.073	Ototoxicity:	0.55
Hematotoxicity:	0.914	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.388	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.851	Hek293 Cytotoxicity:	0.363
BCF:	1.617 ? 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:	3.986 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.537 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.903 ? 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
NPO33404	phyllospongia sp.	Species	Thorectidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[12502324]

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
Inhibition	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
NPT91	Cell line	KB	Homo sapiens	Inhibition	=	30.0	%	PubChem BioAssay data set

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 NPC208912 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	19239
0.1-0.2	25819
0.2-0.3	4459
0.3-0.4	273
0.4-0.5	40
0.5-0.6	21
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8393	Intermediate Similarity	NPC2096
0.6935	Remote Similarity	NPC474253
0.6935	Remote Similarity	NPC474346
0.6667	Remote Similarity	NPC131104
0.6061	Remote Similarity	NPC213737
0.5902	Remote Similarity	NPC83242
0.5821	Remote Similarity	NPC474284
0.5806	Remote Similarity	NPC219535
0.5692	Remote Similarity	NPC194951
0.5692	Remote Similarity	NPC608115
0.5692	Remote Similarity	NPC611248
0.5538	Remote Similarity	NPC3032
0.5441	Remote Similarity	NPC228251
0.5441	Remote Similarity	NPC477972
0.5312	Remote Similarity	NPC181871
0.5303	Remote Similarity	NPC95899
0.5217	Remote Similarity	NPC94905
0.5217	Remote Similarity	NPC163902
0.5217	Remote Similarity	NPC112457
0.5217	Remote Similarity	NPC8954
0.5147	Remote Similarity	NPC325229
0.5147	Remote Similarity	NPC475456
0.5077	Remote Similarity	NPC473299
0.5072	Remote Similarity	NPC325054
0.5072	Remote Similarity	NPC31522
0.5072	Remote Similarity	NPC607359

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC208912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6823
0.1-0.2	2245
0.2-0.3	82
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