NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	367.898
LogP:	1.433
LogD:	1.829
LogS:	-3.493
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	4.751
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.294
MDCK Permeability:	0.0001024406446958892
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	93.0489273071289%
Volume Distribution (VD):	0.922
Pgp-substrate:	2.4395182132720947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.224
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	2.911
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.395
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.906
Carcinogencity:	0.82
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.77

Download Data

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

Natural Product: NPC478099

Natural Product ID:	NPC478099
*Common Name:**	Topsentolide B3
IUPAC Name:	(2S,4Z)-2-[(1E,3R,4S,6Z,9Z)-3,4-dihydroxydodeca-1,6,9-trienyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
Synonyms:	Topsentolide B3
Standard InCHIKey:	OIBRTSVGCWTYLU-VYXNFCKLSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-2-3-4-5-6-10-13-18(21)19(22)16-15-17-12-9-7-8-11-14-20(23)24-17/h3-4,6-7,9-10,15-19,21-22H,2,5,8,11-14H2,1H3/b4-3-,9-7-,10-6-,16-15+/t17-,18-,19+/m0/s1
SMILES:	CC/C=C\C/C=C\C[C@@H]([C@@H](/C=C/[C@@H]1C/C=C\CCCC(=O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44575276
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	At the 20 m depth, the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17190456]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[19653640]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[2045823]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20806907]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.6	ug/ml	PMID[16643027]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	6.5	ug/ml	PMID[16643027]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	4.9	ug/ml	PMID[16643027]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	7.8	ug/ml	PMID[16643027]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	7.6	ug/ml	PMID[16643027]

☑ 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 NPC478099 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	207
0.1-0.2	2743
0.2-0.3	10752
0.3-0.4	17569
0.4-0.5	7685
0.5-0.6	2670
0.6-0.7	896
0.7-0.8	159
0.8-0.85	11
0.85-0.9	0
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478098
0.9677	High Similarity	NPC478097
0.9516	High Similarity	NPC478101
0.9365	High Similarity	NPC478100
0.8507	High Similarity	NPC475982
0.8387	Intermediate Similarity	NPC478096
0.8254	Intermediate Similarity	NPC322186
0.8254	Intermediate Similarity	NPC478095
0.8226	Intermediate Similarity	NPC323436
0.8209	Intermediate Similarity	NPC25298
0.8182	Intermediate Similarity	NPC19769
0.8125	Intermediate Similarity	NPC81896
0.8125	Intermediate Similarity	NPC321919
0.806	Intermediate Similarity	NPC201356
0.8	Intermediate Similarity	NPC26810
0.7971	Intermediate Similarity	NPC130618
0.7941	Intermediate Similarity	NPC99619
0.7941	Intermediate Similarity	NPC26500
0.791	Intermediate Similarity	NPC96414
0.7857	Intermediate Similarity	NPC202011
0.7794	Intermediate Similarity	NPC146811
0.7778	Intermediate Similarity	NPC327388
0.7727	Intermediate Similarity	NPC113293
0.7727	Intermediate Similarity	NPC321838
0.7727	Intermediate Similarity	NPC55376
0.7692	Intermediate Similarity	NPC329249
0.7692	Intermediate Similarity	NPC322002
0.7681	Intermediate Similarity	NPC122627
0.7671	Intermediate Similarity	NPC478196
0.7671	Intermediate Similarity	NPC478193
0.7671	Intermediate Similarity	NPC478194
0.7671	Intermediate Similarity	NPC260396
0.7671	Intermediate Similarity	NPC473948
0.7671	Intermediate Similarity	NPC478195
0.7671	Intermediate Similarity	NPC478191
0.7671	Intermediate Similarity	NPC473582
0.7671	Intermediate Similarity	NPC478192
0.7656	Intermediate Similarity	NPC211752
0.7656	Intermediate Similarity	NPC323597
0.7656	Intermediate Similarity	NPC323498
0.7647	Intermediate Similarity	NPC476655
0.7647	Intermediate Similarity	NPC476657
0.7647	Intermediate Similarity	NPC476654
0.7647	Intermediate Similarity	NPC282760
0.7647	Intermediate Similarity	NPC273600
0.7647	Intermediate Similarity	NPC470123
0.7639	Intermediate Similarity	NPC470435
0.7639	Intermediate Similarity	NPC284006
0.7612	Intermediate Similarity	NPC68110
0.7576	Intermediate Similarity	NPC327112
0.7571	Intermediate Similarity	NPC63873
0.7536	Intermediate Similarity	NPC476659
0.7536	Intermediate Similarity	NPC276299
0.7536	Intermediate Similarity	NPC476656
0.7534	Intermediate Similarity	NPC473489
0.7534	Intermediate Similarity	NPC326504
0.7534	Intermediate Similarity	NPC315843
0.75	Intermediate Similarity	NPC293114
0.75	Intermediate Similarity	NPC99651
0.75	Intermediate Similarity	NPC475221
0.7432	Intermediate Similarity	NPC161038
0.7429	Intermediate Similarity	NPC271921
0.7429	Intermediate Similarity	NPC148192
0.7429	Intermediate Similarity	NPC49863
0.7429	Intermediate Similarity	NPC330426
0.7429	Intermediate Similarity	NPC22101
0.7429	Intermediate Similarity	NPC127091
0.7429	Intermediate Similarity	NPC104537
0.7424	Intermediate Similarity	NPC97570
0.7424	Intermediate Similarity	NPC302564
0.7424	Intermediate Similarity	NPC318306
0.7424	Intermediate Similarity	NPC222852
0.7397	Intermediate Similarity	NPC325627
0.7391	Intermediate Similarity	NPC323477
0.7385	Intermediate Similarity	NPC135863
0.7385	Intermediate Similarity	NPC265551
0.7385	Intermediate Similarity	NPC212730
0.7385	Intermediate Similarity	NPC472445
0.7368	Intermediate Similarity	NPC318481
0.7361	Intermediate Similarity	NPC476037
0.7361	Intermediate Similarity	NPC329904
0.7361	Intermediate Similarity	NPC473361
0.7353	Intermediate Similarity	NPC29697
0.7333	Intermediate Similarity	NPC49392
0.7333	Intermediate Similarity	NPC203277
0.7333	Intermediate Similarity	NPC190400
0.7324	Intermediate Similarity	NPC141481
0.7324	Intermediate Similarity	NPC324981
0.7324	Intermediate Similarity	NPC473559
0.7324	Intermediate Similarity	NPC273508
0.7324	Intermediate Similarity	NPC48218
0.7324	Intermediate Similarity	NPC209327
0.7313	Intermediate Similarity	NPC26223
0.7313	Intermediate Similarity	NPC328311
0.7297	Intermediate Similarity	NPC476590
0.7297	Intermediate Similarity	NPC107654
0.7297	Intermediate Similarity	NPC114727
0.7286	Intermediate Similarity	NPC328653
0.7273	Intermediate Similarity	NPC475210
0.7273	Intermediate Similarity	NPC254095
0.7273	Intermediate Similarity	NPC223679
0.726	Intermediate Similarity	NPC316185
0.7246	Intermediate Similarity	NPC476658
0.7246	Intermediate Similarity	NPC470808
0.7246	Intermediate Similarity	NPC470320
0.7237	Intermediate Similarity	NPC474278
0.7237	Intermediate Similarity	NPC275530
0.7222	Intermediate Similarity	NPC470436
0.7215	Intermediate Similarity	NPC310450
0.7215	Intermediate Similarity	NPC11383
0.7215	Intermediate Similarity	NPC474252
0.7215	Intermediate Similarity	NPC475046
0.7215	Intermediate Similarity	NPC474959
0.7206	Intermediate Similarity	NPC325929
0.7206	Intermediate Similarity	NPC66460
0.7206	Intermediate Similarity	NPC151648
0.7206	Intermediate Similarity	NPC271282
0.7206	Intermediate Similarity	NPC201939
0.7206	Intermediate Similarity	NPC328776
0.7206	Intermediate Similarity	NPC320305
0.7188	Intermediate Similarity	NPC137538
0.7183	Intermediate Similarity	NPC473829
0.7183	Intermediate Similarity	NPC475443
0.7162	Intermediate Similarity	NPC329890
0.7143	Intermediate Similarity	NPC28049
0.7143	Intermediate Similarity	NPC248775
0.7143	Intermediate Similarity	NPC279532
0.7143	Intermediate Similarity	NPC255863
0.7143	Intermediate Similarity	NPC473471
0.7143	Intermediate Similarity	NPC323045
0.7143	Intermediate Similarity	NPC317881
0.7143	Intermediate Similarity	NPC182292
0.7143	Intermediate Similarity	NPC136164
0.7143	Intermediate Similarity	NPC127526
0.7143	Intermediate Similarity	NPC245947
0.7125	Intermediate Similarity	NPC229799
0.7125	Intermediate Similarity	NPC286770
0.7125	Intermediate Similarity	NPC284472
0.7123	Intermediate Similarity	NPC59558
0.7123	Intermediate Similarity	NPC476012
0.7123	Intermediate Similarity	NPC42526
0.7123	Intermediate Similarity	NPC476660
0.7123	Intermediate Similarity	NPC4299
0.7121	Intermediate Similarity	NPC129150
0.7121	Intermediate Similarity	NPC249850
0.7121	Intermediate Similarity	NPC44542
0.7121	Intermediate Similarity	NPC293437
0.7105	Intermediate Similarity	NPC209113
0.7105	Intermediate Similarity	NPC127118
0.7105	Intermediate Similarity	NPC68819
0.7105	Intermediate Similarity	NPC301207
0.7101	Intermediate Similarity	NPC474774
0.7101	Intermediate Similarity	NPC473737
0.7089	Intermediate Similarity	NPC297440
0.7089	Intermediate Similarity	NPC150502
0.7083	Intermediate Similarity	NPC474823
0.7077	Intermediate Similarity	NPC474913
0.7077	Intermediate Similarity	NPC52264
0.7067	Intermediate Similarity	NPC92558
0.7059	Intermediate Similarity	NPC471278
0.7059	Intermediate Similarity	NPC243532
0.7051	Intermediate Similarity	NPC1180
0.7051	Intermediate Similarity	NPC321728
0.7051	Intermediate Similarity	NPC470149
0.7051	Intermediate Similarity	NPC470148
0.7051	Intermediate Similarity	NPC180725
0.7042	Intermediate Similarity	NPC248125
0.7042	Intermediate Similarity	NPC475675
0.7042	Intermediate Similarity	NPC475555
0.7037	Intermediate Similarity	NPC474776
0.7031	Intermediate Similarity	NPC477781
0.7031	Intermediate Similarity	NPC477780
0.7027	Intermediate Similarity	NPC477087
0.7027	Intermediate Similarity	NPC477086
0.7013	Intermediate Similarity	NPC474026
0.7013	Intermediate Similarity	NPC7563
0.7013	Intermediate Similarity	NPC475711
0.7013	Intermediate Similarity	NPC176329
0.7013	Intermediate Similarity	NPC51809
0.7013	Intermediate Similarity	NPC125365
0.7013	Intermediate Similarity	NPC474818
0.7013	Intermediate Similarity	NPC320630
0.7013	Intermediate Similarity	NPC116177
0.7013	Intermediate Similarity	NPC49302
0.7	Intermediate Similarity	NPC328089
0.7	Intermediate Similarity	NPC148233
0.7	Intermediate Similarity	NPC68343
0.7	Intermediate Similarity	NPC25747
0.7	Intermediate Similarity	NPC226592
0.7	Intermediate Similarity	NPC308457
0.7	Intermediate Similarity	NPC117572
0.6988	Remote Similarity	NPC45409
0.6986	Remote Similarity	NPC475004
0.6986	Remote Similarity	NPC143396
0.6986	Remote Similarity	NPC151481
0.6986	Remote Similarity	NPC473772
0.6986	Remote Similarity	NPC236208
0.6986	Remote Similarity	NPC101622
0.697	Remote Similarity	NPC472808
0.697	Remote Similarity	NPC324224

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 NPC478099 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	3106
0.2-0.3	3825
0.3-0.4	1615
0.4-0.5	298
0.5-0.6	73
0.6-0.7	27
0.7-0.8	5
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
0.7576	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6109	Phase 1
0.7429	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD585	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5343	Approved
0.7	Intermediate Similarity	NPD4222	Approved
0.7	Intermediate Similarity	NPD3197	Phase 1
0.6984	Remote Similarity	NPD6927	Phase 3
0.675	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3173	Approved
0.6557	Remote Similarity	NPD6096	Approved
0.6557	Remote Similarity	NPD6097	Approved
0.6506	Remote Similarity	NPD7154	Phase 3
0.65	Remote Similarity	NPD4271	Approved
0.65	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD39	Approved
0.6393	Remote Similarity	NPD5326	Phase 3
0.6364	Remote Similarity	NPD6698	Approved
0.6364	Remote Similarity	NPD46	Approved
0.6341	Remote Similarity	NPD4822	Approved
0.6341	Remote Similarity	NPD4252	Approved
0.6341	Remote Similarity	NPD4820	Approved
0.6341	Remote Similarity	NPD4821	Approved
0.6341	Remote Similarity	NPD4819	Approved
0.631	Remote Similarity	NPD5362	Discontinued
0.6296	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7983	Approved
0.6286	Remote Similarity	NPD69	Approved
0.6286	Remote Similarity	NPD9119	Approved
0.6279	Remote Similarity	NPD4249	Approved
0.6269	Remote Similarity	NPD3172	Approved
0.6207	Remote Similarity	NPD4250	Approved
0.6207	Remote Similarity	NPD4251	Approved
0.619	Remote Similarity	NPD4265	Approved
0.619	Remote Similarity	NPD3174	Discontinued
0.619	Remote Similarity	NPD4269	Approved
0.619	Remote Similarity	NPD4270	Approved
0.618	Remote Similarity	NPD7838	Discovery
0.618	Remote Similarity	NPD5785	Approved
0.6176	Remote Similarity	NPD3196	Approved
0.6176	Remote Similarity	NPD4266	Approved
0.6176	Remote Similarity	NPD3195	Phase 2
0.6176	Remote Similarity	NPD3194	Approved
0.6143	Remote Similarity	NPD9118	Approved
0.6118	Remote Similarity	NPD5332	Approved
0.6118	Remote Similarity	NPD5331	Approved
0.6092	Remote Similarity	NPD5786	Approved
0.6071	Remote Similarity	NPD4790	Discontinued
0.6047	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD5363	Approved
0.5977	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4756	Discovery
0.5909	Remote Similarity	NPD4220	Pre-registration
0.5895	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4225	Approved
0.5889	Remote Similarity	NPD5370	Suspended
0.5882	Remote Similarity	NPD5369	Approved
0.587	Remote Similarity	NPD5778	Approved
0.587	Remote Similarity	NPD5779	Approved
0.5851	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6435	Approved
0.5814	Remote Similarity	NPD5209	Approved
0.5761	Remote Similarity	NPD7637	Suspended
0.5761	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6110	Phase 1
0.5735	Remote Similarity	NPD29	Approved
0.5735	Remote Similarity	NPD28	Approved
0.5732	Remote Similarity	NPD8039	Approved
0.5714	Remote Similarity	NPD3730	Approved
0.5714	Remote Similarity	NPD3728	Approved
0.5684	Remote Similarity	NPD4228	Discovery
0.5684	Remote Similarity	NPD7839	Suspended
0.5625	Remote Similarity	NPD9411	Phase 1
0.5612	Remote Similarity	NPD5344	Discontinued

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