NPASS Compound

Natural Product: NPC190360

Natural Product ID	NPC190360
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NXFZOPWISUHFDD-VRVFRTJPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 82 86 0 0 0 0 0 0 0 0999 V2000 -6.1803 1.9037 0.1999 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9420 1.0755 0.5492 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4429 1.6046 1.8769 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4058 -0.3590 0.6499 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1980 -1.2649 0.6522 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5861 -1.1928 -0.7501 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7578 -1.4046 -1.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6420 -2.3148 -0.9134 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2309 -1.9612 -1.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7194 -0.8685 -0.4279 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6327 -1.3630 1.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6383 0.3141 -0.4271 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1891 1.4428 0.0585 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1776 1.6390 0.6128 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1160 0.5486 0.2689 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5701 0.9721 0.1360 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8370 1.9745 -0.9187 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9845 1.5796 1.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6608 0.5992 2.3721 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9761 0.2074 1.7263 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7871 -0.2471 0.2987 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3047 -1.6963 0.2549 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6264 0.5194 -0.6635 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9745 0.3104 -0.2779 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3406 -0.3206 0.0047 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9964 -1.0298 -1.2881 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5467 -1.4754 -1.1432 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6319 -0.3156 -0.8636 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4866 0.4388 -2.1641 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8249 1.3258 1.7964 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0131 0.1918 -0.9744 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9246 1.2495 -0.5275 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8742 2.3421 -1.0446 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4969 -2.5755 0.9659 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2854 1.8122 -0.9162 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9737 2.9740 0.4361 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0515 1.4990 0.7323 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3488 1.4985 1.9912 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6868 2.6896 2.0014 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9669 1.0895 2.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8852 -0.4684 1.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1194 -0.5655 -0.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4563 -0.7987 1.3390 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2304 -0.4327 -1.9775 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3571 -1.8057 -2.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4597 -2.1564 -1.3420 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7002 -2.9915 -0.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9906 -2.9941 -1.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1574 -1.8412 -2.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6159 -2.8814 -1.0407 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4429 -2.0806 1.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3019 -1.9745 1.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7444 -0.5438 1.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8495 2.3020 0.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5086 2.6495 0.2926 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0538 1.7185 1.7176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1575 -0.1453 1.1649 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4199 1.6089 -1.7881 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4449 2.8472 -0.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9308 2.4710 -1.3400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6894 2.4188 1.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1157 2.0074 2.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0562 -0.2459 2.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9439 1.1688 3.2982 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4379 -0.5593 2.3808 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5954 -1.9690 -0.7833 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5315 -2.3878 0.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2194 -1.7544 0.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4998 1.6188 -0.6016 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5270 0.1021 -1.6642 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5354 1.0974 -0.5042 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8993 -0.9941 0.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6081 -1.9602 -1.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1908 -0.4494 -2.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 -1.8612 -2.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4567 -2.3189 -0.4634 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1035 -0.1968 -2.8797 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 0.5367 -2.6869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0516 1.3793 -2.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0362 1.4443 2.7589 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9188 0.2964 -2.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4716 -2.7025 0.7378 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 20 30 1 0 12 31 1 0 31 32 1 0 32 33 2 0 5 34 1 0 32 2 1 0 31 6 1 0 28 10 1 0 28 15 1 0 25 16 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 1 7 44 1 0 7 45 1 0 7 46 1 0 8 47 1 0 8 48 1 0 9 49 1 0 9 50 1 0 11 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 1 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 20 65 1 1 22 66 1 0 22 67 1 0 22 68 1 0 23 69 1 0 23 70 1 0 24 71 1 0 25 72 1 1 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 31 81 1 6 34 82 1 0 M END

Standard InCHIKey	NXFZOPWISUHFDD-VRVFRTJPSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-25(2)16-22(33)27(4)14-15-29(6)18(23(27)24(25)34)8-9-20-26(3)12-11-21(32)28(5,17-31)19(26)10-13-30(20,29)7/h8,19-23,31-33H,9-17H2,1-7H3/t19-,20-,21+,22-,23-,26+,27+,28-,29-,30-/m1/s1
SMILES	CC1(C)C[C@H]([C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H]([C@](C)(CO)[C@@H]5CC[C@@]34C)O)[C@@H]2C1=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.734 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.596 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.242 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.453	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.068	Fsp³:	0.9
MCE-18:	106.667 ? 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:	0.691	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.065 ? 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:	0.339	Promiscuous compounds:	0.199

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.358	MDCK Permeability:	-5.037
Pgp-inhibitor:	0.598	Pgp-substrate:	0.073
PAMPA:	0.966 ? 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%):	0.978	30% Bioavailability (F30%):	0.405
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988	MRP1:	0.994
Plasma Protein Binding (PPB):	85.164%	Volume Distribution (VD):	-0.101
Fu:	13.588% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.847	BCRP inhibitor:	0.286
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.127	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.852	CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.508	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.426	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.468
HLM stability:	0.392 ? 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):

11.216

Half-life (T1/2):

0.914

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.128
Human Hepatotoxicity (H-HT):	0.559	Drug-induced Liver Injury (DILI):	0.16
AMES Toxicity:	0.363	Rat Oral Acute Toxicity:	0.612
Maximum Recommended Daily Dose:	0.559	Skin Sensitization:	0.994
Carcinogencity:	0.981	Eye Corrosion:	0.006
Eye Irritation:	0.563	Respiratory Toxicity:	0.705
Drug-induced Neurotoxicity:	0.105	Ototoxicity:	0.583
Hematotoxicity:	0.546	Drug-induced Nephrotoxicity:	0.893
Genotoxicity:	0.962	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.599	Hek293 Cytotoxicity:	0.578
BCF:	1.045 ? 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:	3.538 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.231 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.476 ? 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
NPO28164	Knema laurina	Species	Myristicaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[21641207]
NPO28164	Knema laurina	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28484	Dalbergia ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28484	Dalbergia ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28164	Knema laurina	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28484	Dalbergia ferruginea	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 NPC190360 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	21407
0.1-0.2	23901
0.2-0.3	3859
0.3-0.4	528
0.4-0.5	142
0.5-0.6	18
0.6-0.7	3
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
0.6667	Remote Similarity	NPC230295
0.6667	Remote Similarity	NPC98386
0.6029	Remote Similarity	NPC213412
0.5846	Remote Similarity	NPC196753
0.5441	Remote Similarity	NPC253402
0.5333	Remote Similarity	NPC116457
0.5278	Remote Similarity	NPC270768
0.5278	Remote Similarity	NPC59263
0.5278	Remote Similarity	NPC210106
0.5278	Remote Similarity	NPC229281
0.5278	Remote Similarity	NPC121798
0.5278	Remote Similarity	NPC234346
0.527	Remote Similarity	NPC263393
0.527	Remote Similarity	NPC191412
0.527	Remote Similarity	NPC114159
0.527	Remote Similarity	NPC6818
0.5205	Remote Similarity	NPC61543
0.5205	Remote Similarity	NPC293048
0.5205	Remote Similarity	NPC225585
0.52	Remote Similarity	NPC127689
0.52	Remote Similarity	NPC130520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7419
0.1-0.2	1671
0.2-0.3	57
0.3-0.4	1
0.4-0.5	1
0.5-0.6	1
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
0.5493	Remote Similarity	NPD7645	Phase 2

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