NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.19
Volume:	309.857
LogP:	5.381
LogD:	4.286
LogS:	-4.388
# Rotatable Bonds:	9
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	2.31
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	2.013361154240556e-05
Pgp-inhibitor:	0.135
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	98.66270446777344%
Volume Distribution (VD):	5.752
Pgp-substrate:	1.742640733718872%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.496
CYP2C9-inhibitor:	0.559
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.603
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	8.789
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.498
Skin Sensitization:	0.97
Carcinogencity:	0.099
Eye Corrosion:	0.824
Eye Irritation:	0.971
Respiratory Toxicity:	0.859

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474400

Natural Product ID:	NPC474400
*Common Name:**	2-Methoxy-6-Decyl-1,4-Benzoquinone
IUPAC Name:	2-decyl-6-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	AXAINABARGDXOC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H26O3/c1-3-4-5-6-7-8-9-10-11-14-12-15(18)13-16(20-2)17(14)19/h12-13H,3-11H2,1-2H3
SMILES:	CCCCCCCCCCC1=CC(=O)C=C(C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466558
PubChem CID:	10084963
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25763	Miconia lepidota	Species	Melastomataceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[11170656]
NPO25763	Miconia lepidota	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170656]
NPO25763	Miconia lepidota	Species	Melastomataceae	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	NP ID	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
Others	4

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT726	Cell Line	M109	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[573242]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	380.0	ug ml-1	PMID[573242]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	3.0	ug ml-1	PMID[573242]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474400 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2233
0.2-0.3	10672
0.3-0.4	18096
0.4-0.5	7605
0.5-0.6	3299
0.6-0.7	556
0.7-0.8	38
0.8-0.85	12
0.85-0.9	7
0.9-0.95	9
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34622
0.9833	High Similarity	NPC98897
0.9831	High Similarity	NPC57463
0.9831	High Similarity	NPC151728
0.9672	High Similarity	NPC16119
0.9516	High Similarity	NPC474619
0.9322	High Similarity	NPC473494
0.9219	High Similarity	NPC262673
0.9206	High Similarity	NPC243272
0.9077	High Similarity	NPC291062
0.9077	High Similarity	NPC94743
0.9062	High Similarity	NPC263382
0.9062	High Similarity	NPC134385
0.9062	High Similarity	NPC146376
0.9062	High Similarity	NPC125578
0.8923	High Similarity	NPC94488
0.8871	High Similarity	NPC477830
0.8676	High Similarity	NPC264178
0.8571	High Similarity	NPC143168
0.8571	High Similarity	NPC53109
0.8438	Intermediate Similarity	NPC7029
0.8305	Intermediate Similarity	NPC474805
0.8226	Intermediate Similarity	NPC139056
0.8167	Intermediate Similarity	NPC317796
0.8065	Intermediate Similarity	NPC224103
0.8065	Intermediate Similarity	NPC200831
0.8065	Intermediate Similarity	NPC299369
0.8056	Intermediate Similarity	NPC473536
0.7937	Intermediate Similarity	NPC320421
0.7867	Intermediate Similarity	NPC474085
0.7808	Intermediate Similarity	NPC283087
0.7797	Intermediate Similarity	NPC220191
0.7727	Intermediate Similarity	NPC477707
0.7667	Intermediate Similarity	NPC22329
0.7606	Intermediate Similarity	NPC474539
0.7468	Intermediate Similarity	NPC132228
0.7468	Intermediate Similarity	NPC8518
0.7468	Intermediate Similarity	NPC133652
0.7468	Intermediate Similarity	NPC6185
0.7468	Intermediate Similarity	NPC263997
0.7468	Intermediate Similarity	NPC241512
0.7432	Intermediate Similarity	NPC477708
0.7424	Intermediate Similarity	NPC143857
0.7424	Intermediate Similarity	NPC229252
0.7397	Intermediate Similarity	NPC147438
0.7286	Intermediate Similarity	NPC251429
0.7286	Intermediate Similarity	NPC298249
0.7237	Intermediate Similarity	NPC23778
0.72	Intermediate Similarity	NPC26504
0.7179	Intermediate Similarity	NPC474353
0.7119	Intermediate Similarity	NPC191337
0.7083	Intermediate Similarity	NPC469914
0.7051	Intermediate Similarity	NPC108955
0.7051	Intermediate Similarity	NPC304795
0.7049	Intermediate Similarity	NPC145311
0.7031	Intermediate Similarity	NPC129710
0.7024	Intermediate Similarity	NPC223093
0.7015	Intermediate Similarity	NPC274927
0.7015	Intermediate Similarity	NPC106851
0.7013	Intermediate Similarity	NPC478246
0.7013	Intermediate Similarity	NPC231739
0.7013	Intermediate Similarity	NPC478247
0.6986	Remote Similarity	NPC477455
0.6984	Remote Similarity	NPC137396
0.6974	Remote Similarity	NPC110725
0.6974	Remote Similarity	NPC40353
0.697	Remote Similarity	NPC281230
0.697	Remote Similarity	NPC192843
0.6962	Remote Similarity	NPC286229
0.6962	Remote Similarity	NPC55869
0.6962	Remote Similarity	NPC99308
0.6951	Remote Similarity	NPC203795
0.6951	Remote Similarity	NPC472009
0.6949	Remote Similarity	NPC25771
0.6949	Remote Similarity	NPC477686
0.6944	Remote Similarity	NPC134593
0.6944	Remote Similarity	NPC218477
0.6941	Remote Similarity	NPC32944
0.6941	Remote Similarity	NPC193396
0.6935	Remote Similarity	NPC15325
0.6923	Remote Similarity	NPC476177
0.6923	Remote Similarity	NPC471740
0.6912	Remote Similarity	NPC235242
0.6912	Remote Similarity	NPC122521
0.6912	Remote Similarity	NPC174447
0.6912	Remote Similarity	NPC251042
0.6905	Remote Similarity	NPC142159
0.6905	Remote Similarity	NPC95364
0.6883	Remote Similarity	NPC180290
0.6883	Remote Similarity	NPC471061
0.6875	Remote Similarity	NPC39633
0.6875	Remote Similarity	NPC103486
0.6875	Remote Similarity	NPC309606
0.6875	Remote Similarity	NPC139545
0.6875	Remote Similarity	NPC47450
0.6875	Remote Similarity	NPC168521
0.6867	Remote Similarity	NPC472007
0.6849	Remote Similarity	NPC477449
0.6849	Remote Similarity	NPC474060
0.6849	Remote Similarity	NPC477448
0.6829	Remote Similarity	NPC77971
0.6829	Remote Similarity	NPC470177
0.6829	Remote Similarity	NPC32037
0.6829	Remote Similarity	NPC474680
0.6825	Remote Similarity	NPC477458
0.6825	Remote Similarity	NPC234829
0.6824	Remote Similarity	NPC475823
0.6824	Remote Similarity	NPC474209
0.6812	Remote Similarity	NPC40082
0.6795	Remote Similarity	NPC475994
0.679	Remote Similarity	NPC8091
0.679	Remote Similarity	NPC288281
0.6786	Remote Similarity	NPC472008
0.6786	Remote Similarity	NPC53454
0.678	Remote Similarity	NPC292463
0.6757	Remote Similarity	NPC173321
0.6753	Remote Similarity	NPC473223
0.6753	Remote Similarity	NPC470525
0.675	Remote Similarity	NPC475833
0.675	Remote Similarity	NPC149237
0.675	Remote Similarity	NPC225515
0.675	Remote Similarity	NPC478262
0.6744	Remote Similarity	NPC166110
0.6712	Remote Similarity	NPC477452
0.6709	Remote Similarity	NPC475681
0.6709	Remote Similarity	NPC27817
0.6707	Remote Similarity	NPC474359
0.6706	Remote Similarity	NPC280833
0.6667	Remote Similarity	NPC10316
0.6667	Remote Similarity	NPC200845
0.6667	Remote Similarity	NPC472300
0.6667	Remote Similarity	NPC221231
0.6667	Remote Similarity	NPC28779
0.6667	Remote Similarity	NPC474391
0.6667	Remote Similarity	NPC224227
0.6667	Remote Similarity	NPC211279
0.6667	Remote Similarity	NPC128061
0.6667	Remote Similarity	NPC106547
0.6667	Remote Similarity	NPC471225
0.6667	Remote Similarity	NPC228473
0.6667	Remote Similarity	NPC223677
0.6667	Remote Similarity	NPC248193
0.6667	Remote Similarity	NPC66365
0.6667	Remote Similarity	NPC471739
0.6667	Remote Similarity	NPC186531
0.6667	Remote Similarity	NPC84038
0.6667	Remote Similarity	NPC41780
0.6667	Remote Similarity	NPC197089
0.6667	Remote Similarity	NPC187568
0.6667	Remote Similarity	NPC32351
0.6667	Remote Similarity	NPC471326
0.6628	Remote Similarity	NPC471399
0.6627	Remote Similarity	NPC96621
0.6627	Remote Similarity	NPC90287
0.6625	Remote Similarity	NPC162741
0.6625	Remote Similarity	NPC91332
0.6623	Remote Similarity	NPC329826
0.6623	Remote Similarity	NPC469414
0.6623	Remote Similarity	NPC244166
0.6623	Remote Similarity	NPC175079
0.6622	Remote Similarity	NPC261398
0.6622	Remote Similarity	NPC250928
0.6622	Remote Similarity	NPC10758
0.662	Remote Similarity	NPC477457
0.662	Remote Similarity	NPC477456
0.662	Remote Similarity	NPC150162
0.6615	Remote Similarity	NPC71761
0.6588	Remote Similarity	NPC241507
0.6585	Remote Similarity	NPC474703
0.6585	Remote Similarity	NPC477785
0.6585	Remote Similarity	NPC477786
0.6585	Remote Similarity	NPC477784
0.6585	Remote Similarity	NPC105803
0.6582	Remote Similarity	NPC478122
0.6582	Remote Similarity	NPC469996
0.6582	Remote Similarity	NPC471220
0.6582	Remote Similarity	NPC189485
0.6579	Remote Similarity	NPC474705
0.6575	Remote Similarity	NPC203335
0.6575	Remote Similarity	NPC473213
0.6571	Remote Similarity	NPC201939
0.6567	Remote Similarity	NPC473733
0.6567	Remote Similarity	NPC477201
0.6562	Remote Similarity	NPC262968
0.6557	Remote Similarity	NPC110396
0.6552	Remote Similarity	NPC146852
0.6552	Remote Similarity	NPC476484
0.6548	Remote Similarity	NPC472161
0.6548	Remote Similarity	NPC472136
0.6543	Remote Similarity	NPC275766
0.6538	Remote Similarity	NPC92080
0.6538	Remote Similarity	NPC1254
0.6538	Remote Similarity	NPC474527
0.6538	Remote Similarity	NPC27205
0.6538	Remote Similarity	NPC266119
0.6538	Remote Similarity	NPC471726
0.6528	Remote Similarity	NPC61473
0.6528	Remote Similarity	NPC474304
0.6528	Remote Similarity	NPC251118
0.6528	Remote Similarity	NPC474329

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	2767
0.2-0.3	4218
0.3-0.4	1497
0.4-0.5	324
0.5-0.6	148
0.6-0.7	13
0.7-0.8	1
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9672	High Similarity	NPD6108	Clinical (unspecified phase)
0.8571	High Similarity	NPD2664	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3704	Approved
0.831	Intermediate Similarity	NPD4756	Discovery
0.8065	Intermediate Similarity	NPD8779	Phase 3
0.7143	Intermediate Similarity	NPD7331	Phase 2
0.7051	Intermediate Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD29	Approved
0.6562	Remote Similarity	NPD28	Approved
0.6528	Remote Similarity	NPD7341	Phase 2
0.6395	Remote Similarity	NPD5737	Approved
0.6395	Remote Similarity	NPD6672	Approved
0.6389	Remote Similarity	NPD3197	Phase 1
0.6364	Remote Similarity	NPD3172	Approved
0.6269	Remote Similarity	NPD3195	Phase 2
0.6269	Remote Similarity	NPD3194	Approved
0.6269	Remote Similarity	NPD3196	Approved
0.6269	Remote Similarity	NPD4266	Approved
0.6222	Remote Similarity	NPD5282	Discontinued
0.622	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6110	Phase 1
0.6173	Remote Similarity	NPD3617	Approved
0.6163	Remote Similarity	NPD5279	Phase 3
0.6163	Remote Similarity	NPD5690	Phase 2
0.6136	Remote Similarity	NPD6904	Approved
0.6136	Remote Similarity	NPD6673	Approved
0.6136	Remote Similarity	NPD6080	Approved
0.6118	Remote Similarity	NPD4197	Approved
0.6104	Remote Similarity	NPD4691	Approved
0.6067	Remote Similarity	NPD5692	Phase 3
0.6047	Remote Similarity	NPD5329	Approved
0.6032	Remote Similarity	NPD3174	Discontinued
0.6	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD8039	Approved
0.5978	Remote Similarity	NPD5695	Phase 3
0.5977	Remote Similarity	NPD4694	Approved
0.5977	Remote Similarity	NPD5330	Approved
0.5977	Remote Similarity	NPD6098	Approved
0.5977	Remote Similarity	NPD7334	Approved
0.5977	Remote Similarity	NPD7146	Approved
0.5977	Remote Similarity	NPD5280	Approved
0.5977	Remote Similarity	NPD7521	Approved
0.5977	Remote Similarity	NPD6409	Approved
0.5977	Remote Similarity	NPD6684	Approved
0.5974	Remote Similarity	NPD4137	Phase 3
0.5955	Remote Similarity	NPD4753	Phase 2
0.5955	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.593	Remote Similarity	NPD3665	Phase 1
0.593	Remote Similarity	NPD3133	Approved
0.593	Remote Similarity	NPD3666	Approved
0.5909	Remote Similarity	NPD3573	Approved
0.5897	Remote Similarity	NPD4747	Approved
0.5882	Remote Similarity	NPD4221	Approved
0.5882	Remote Similarity	NPD3667	Approved
0.5882	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4223	Phase 3
0.5875	Remote Similarity	NPD4058	Approved
0.5862	Remote Similarity	NPD1696	Phase 3
0.5862	Remote Similarity	NPD1694	Approved
0.5851	Remote Similarity	NPD6084	Phase 2
0.5851	Remote Similarity	NPD6083	Phase 2
0.5843	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6903	Approved
0.5833	Remote Similarity	NPD5783	Phase 3
0.5823	Remote Similarity	NPD5276	Approved
0.5814	Remote Similarity	NPD7154	Phase 3
0.5806	Remote Similarity	NPD9297	Discontinued
0.5806	Remote Similarity	NPD5210	Approved
0.5806	Remote Similarity	NPD9091	Suspended
0.5806	Remote Similarity	NPD4629	Approved
0.5795	Remote Similarity	NPD3618	Phase 1
0.5789	Remote Similarity	NPD5696	Approved
0.5758	Remote Similarity	NPD3173	Approved
0.5747	Remote Similarity	NPD3668	Phase 3
0.5747	Remote Similarity	NPD4786	Approved
0.5745	Remote Similarity	NPD5222	Approved
0.5745	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5221	Approved
0.5694	Remote Similarity	NPD287	Approved
0.5684	Remote Similarity	NPD5173	Approved
0.5682	Remote Similarity	NPD5363	Approved
0.5679	Remote Similarity	NPD5733	Approved
0.5679	Remote Similarity	NPD4687	Approved
0.5667	Remote Similarity	NPD5208	Approved
0.5667	Remote Similarity	NPD4518	Approved
0.5658	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6079	Approved
0.5638	Remote Similarity	NPD5654	Approved
0.5618	Remote Similarity	NPD4519	Discontinued
0.5618	Remote Similarity	NPD4693	Phase 3
0.5618	Remote Similarity	NPD4623	Approved
0.5618	Remote Similarity	NPD4690	Approved
0.5618	Remote Similarity	NPD5205	Approved
0.5618	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD4689	Approved
0.5618	Remote Similarity	NPD4138	Approved
0.5618	Remote Similarity	NPD4688	Approved
0.5606	Remote Similarity	NPD622	Approved
0.5606	Remote Similarity	NPD5343	Approved
0.5604	Remote Similarity	NPD5328	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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