NPASS Compound

Natural Product: NPC584501

Natural Product ID	NPC584501
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	hexadeca-5-enoic acid
IUPAC Name	hexadec-5-enoic acid
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 48 47 0 0 0 0 0 0 0 0999 V2000 5.0123 -1.0884 1.0943 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5467 0.0352 1.9274 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4642 0.9124 1.4497 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6533 1.6764 0.1954 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7994 0.9416 -1.0738 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7608 0.0372 -1.5685 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4012 0.4947 -1.9180 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5509 1.0576 -0.8396 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8148 1.4290 -1.3731 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6157 0.3212 -1.9469 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9054 -0.7799 -1.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1659 -1.0912 -0.7472 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5751 -2.1596 0.1428 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3239 -1.8788 1.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5984 -1.1470 1.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4477 0.2493 0.8211 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3371 0.8194 0.8582 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5381 0.9765 0.3583 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2642 -1.6855 0.5832 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4917 -1.8373 1.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8857 -0.7735 0.4812 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1971 -0.3964 2.9169 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4404 0.6460 2.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4646 0.3740 1.3942 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2690 1.6578 2.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9514 2.5165 0.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6761 2.2649 0.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8804 1.7793 -1.8816 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8303 0.4752 -1.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6830 -0.8883 -0.8748 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1540 -0.4783 -2.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8295 -0.3080 -2.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5124 1.3120 -2.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9816 2.0120 -0.4825 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4819 0.4120 0.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6954 2.2639 -2.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3888 1.8494 -0.4969 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6115 0.7029 -2.3478 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0865 -0.0870 -2.8375 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1435 -1.3841 -0.5532 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9476 -0.5216 -1.2580 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2057 -2.8863 -0.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6549 -2.7655 0.3907 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6943 -1.4080 2.1822 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5682 -2.8915 1.8371 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2427 -1.6399 0.4822 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1491 -1.0999 2.2352 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4716 1.9795 0.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 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 0 11 12 2 3 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 1 19 1 0 1 20 1 0 1 21 1 0 2 22 1 0 2 23 1 0 3 24 1 0 3 25 1 0 4 26 1 0 4 27 1 0 5 28 1 0 5 29 1 0 6 30 1 0 6 31 1 0 7 32 1 0 7 33 1 0 8 34 1 0 8 35 1 0 9 36 1 0 9 37 1 0 10 38 1 0 10 39 1 0 11 40 1 0 12 41 1 0 13 42 1 0 13 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 15 47 1 0 18 48 1 0 M END

Standard InCHIKey	KVXIRQZWCOAYRD-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h11-12H,2-10,13-15H2,1H3,(H,17,18)
SMILES	CCCCCCCCCCC=CCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	254.22	Volume:	297.6 ? Van der Waals volume.
Dense:	0.854	LogP:	6.164 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.449 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.089 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	2.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.356	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.017	Fsp³:	0.812
MCE-18:	0.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.035	Fluc inhibitor:	0.106 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.024 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.997	Promiscuous compounds:	0.894

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.123	MDCK Permeability:	-4.696
Pgp-inhibitor:	0.0	Pgp-substrate:	0.013
PAMPA:	0.412 ? 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):	0.605
20% Bioavailability (F20%):	0.294	30% Bioavailability (F30%):	0.692
50% Bioavailability (F50%):	0.241

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.981
Plasma Protein Binding (PPB):	97.58%	Volume Distribution (VD):	-0.299
Fu:	1.371% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.467
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.049
BSEP inhibitor:	0.143

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.827
CYP2C19-inhibitor:	0.126	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.291
CYP2D6-inhibitor:	0.994	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	1.0	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):

5.047

Half-life (T1/2):

0.471

ADMET: Toxicity

hERG Blockers:	0.108	hERG Blockers (10um):	0.301
Human Hepatotoxicity (H-HT):	0.254	Drug-induced Liver Injury (DILI):	0.012
AMES Toxicity:	0.114	Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.158	Skin Sensitization:	0.997
Carcinogencity:	0.205	Eye Corrosion:	0.997
Eye Irritation:	0.998	Respiratory Toxicity:	0.745
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.216
Hematotoxicity:	0.072	Drug-induced Nephrotoxicity:	0.34
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.136	Hek293 Cytotoxicity:	0.058
BCF:	1.004 ? 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:	3.952 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.431 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.187 ? 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
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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 NPC584501 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	37827
0.1-0.2	10113
0.2-0.3	1463
0.3-0.4	246
0.4-0.5	91
0.5-0.6	52
0.6-0.7	35
0.7-0.8	2
0.8-0.85	1
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC59051
0.8621	High Similarity	NPC91495
0.8571	High Similarity	NPC424
0.8571	High Similarity	NPC36061
0.8571	High Similarity	NPC69510
0.8571	High Similarity	NPC77272
0.8571	High Similarity	NPC290563
0.8571	High Similarity	NPC139029
0.8571	High Similarity	NPC281972
0.8571	High Similarity	NPC92114
0.8571	High Similarity	NPC261831
0.8571	High Similarity	NPC87564
0.8214	Intermediate Similarity	NPC281245
0.7742	Intermediate Similarity	NPC154245
0.7742	Intermediate Similarity	NPC85813
0.7742	Intermediate Similarity	NPC223697
0.7742	Intermediate Similarity	NPC6095
0.7667	Intermediate Similarity	NPC95145
0.7667	Intermediate Similarity	NPC325642
0.7667	Intermediate Similarity	NPC65174
0.7419	Intermediate Similarity	NPC321062
0.7419	Intermediate Similarity	NPC5413
0.6875	Remote Similarity	NPC48162
0.6667	Remote Similarity	NPC52955
0.6667	Remote Similarity	NPC88966
0.6667	Remote Similarity	NPC25417
0.6667	Remote Similarity	NPC1813
0.6579	Remote Similarity	NPC323597
0.6579	Remote Similarity	NPC211752
0.6579	Remote Similarity	NPC323498
0.6486	Remote Similarity	NPC477201
0.6452	Remote Similarity	NPC117572
0.6429	Remote Similarity	NPC171736
0.6429	Remote Similarity	NPC301585
0.6429	Remote Similarity	NPC261080
0.6429	Remote Similarity	NPC132565
0.6429	Remote Similarity	NPC209970
0.6429	Remote Similarity	NPC216630
0.6429	Remote Similarity	NPC201844
0.6429	Remote Similarity	NPC301696
0.6429	Remote Similarity	NPC196924
0.6429	Remote Similarity	NPC307783
0.6429	Remote Similarity	NPC154186
0.6429	Remote Similarity	NPC149184
0.6429	Remote Similarity	NPC279026
0.6429	Remote Similarity	NPC113928
0.6429	Remote Similarity	NPC14227
0.6389	Remote Similarity	NPC487561
0.6364	Remote Similarity	NPC70387
0.6154	Remote Similarity	NPC243532
0.6071	Remote Similarity	NPC155263
0.6061	Remote Similarity	NPC149821
0.6053	Remote Similarity	NPC106851
0.6053	Remote Similarity	NPC282788
0.6053	Remote Similarity	NPC274927
0.6	Remote Similarity	NPC68343
0.6	Remote Similarity	NPC328089
0.5952	Remote Similarity	NPC322461
0.5946	Remote Similarity	NPC606120
0.5897	Remote Similarity	NPC179764
0.5814	Remote Similarity	NPC605544
0.5814	Remote Similarity	NPC607260
0.5806	Remote Similarity	NPC180534
0.5806	Remote Similarity	NPC611531
0.5769	Remote Similarity	NPC174368
0.575	Remote Similarity	NPC251042
0.575	Remote Similarity	NPC255863
0.575	Remote Similarity	NPC473863
0.575	Remote Similarity	NPC174447
0.575	Remote Similarity	NPC136164
0.575	Remote Similarity	NPC122521
0.575	Remote Similarity	NPC245947
0.5714	Remote Similarity	NPC175342
0.5682	Remote Similarity	NPC329249
0.561	Remote Similarity	NPC320305
0.561	Remote Similarity	NPC317583
0.561	Remote Similarity	NPC321838
0.561	Remote Similarity	NPC318420
0.561	Remote Similarity	NPC326268
0.5588	Remote Similarity	NPC207292
0.5526	Remote Similarity	NPC225929
0.5476	Remote Similarity	NPC325977
0.5476	Remote Similarity	NPC320642
0.5476	Remote Similarity	NPC327112
0.5476	Remote Similarity	NPC329550
0.5455	Remote Similarity	NPC34416
0.5455	Remote Similarity	NPC262968
0.5429	Remote Similarity	NPC87394
0.5366	Remote Similarity	NPC318814
0.5366	Remote Similarity	NPC320669
0.5357	Remote Similarity	NPC214610
0.5357	Remote Similarity	NPC118968
0.5357	Remote Similarity	NPC183424
0.5357	Remote Similarity	NPC294085
0.5349	Remote Similarity	NPC328311
0.5349	Remote Similarity	NPC323045
0.5349	Remote Similarity	NPC49863
0.5349	Remote Similarity	NPC317881
0.5319	Remote Similarity	NPC322457
0.5294	Remote Similarity	NPC129972
0.5294	Remote Similarity	NPC8219
0.5294	Remote Similarity	NPC301528
0.5294	Remote Similarity	NPC71317
0.5294	Remote Similarity	NPC163746
0.5294	Remote Similarity	NPC103286
0.5143	Remote Similarity	NPC18712
0.5143	Remote Similarity	NPC74845
0.5128	Remote Similarity	NPC323436
0.5128	Remote Similarity	NPC327388

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC584501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6729
0.1-0.2	2132
0.2-0.3	215
0.3-0.4	41
0.4-0.5	13
0.5-0.6	7
0.6-0.7	7
0.7-0.8	2
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD3195	Phase 2
0.8571	High Similarity	NPD3196	Approved
0.7742	Intermediate Similarity	NPD4266	Phase 2
0.7419	Intermediate Similarity	NPD3173	Phase 4
0.6857	Remote Similarity	NPD3194	Phase 4
0.6842	Remote Similarity	NPD39	Phase 4
0.6667	Remote Similarity	NPD3172	Approved
0.6452	Remote Similarity	NPD4222	Phase 3
0.6429	Remote Similarity	NPD2270	Pre-clinical
0.6429	Remote Similarity	NPD633	Phase 3
0.6429	Remote Similarity	NPD9448	Phase 2
0.5806	Remote Similarity	NPD622	Pre-clinical
0.5476	Remote Similarity	NPD4246	Phase 2
0.5455	Remote Similarity	NPD28	Approved
0.5455	Remote Similarity	NPD29	Phase 4
0.5429	Remote Similarity	NPD3197	Phase 1
0.5357	Remote Similarity	NPD9655	Phase 4
0.5349	Remote Similarity	NPD4247	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