NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.11
Volume:	208.405
LogP:	-1.059
LogD:	-1.442
LogS:	-0.056
# Rotatable Bonds:	3
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	3.627
Fsp3:	1.0
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:	-5.308
MDCK Permeability:	0.00032206365722231567
Pgp-inhibitor:	0.001
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.15

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	16.056110382080078%
Volume Distribution (VD):	0.654
Pgp-substrate:	72.56212615966797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.681
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	2.212
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.443
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.078
Carcinogencity:	0.046
Eye Corrosion:	0.009
Eye Irritation:	0.76
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC23134

Natural Product ID:	NPC23134
*Common Name:**	Isopropyl O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-propan-2-yloxyoxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	UOEFDXYUEPHESS-SYHAXYEDSA-N
Standard InCHI:	InChI=1S/C9H18O6/c1-4(2)14-9-8(13)7(12)6(11)5(3-10)15-9/h4-13H,3H2,1-2H3/t5-,6-,7+,8-,9-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3326714
PubChem CID:	21572943
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO30686	Citrus hystrix	Species	Rutaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[20964319]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24813739]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6648	Piper retrofractum	Species	Piperaceae	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
Others	6

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Inhibition	=	7.31	%	PMID[552021]
NPT35	Others	n.a.		Activity	=	0.22	uM	PMID[552021]
NPT35	Others	n.a.		Activity	=	1.79	uM	PMID[552021]
NPT35	Others	n.a.		Activity	=	0.29	uM	PMID[552021]
NPT35	Others	n.a.		Activity	=	0.54	uM	PMID[552021]
NPT35	Others	n.a.		Activity	=	20.97	%	PMID[552021]

☑ 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 NPC23134 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	1129
0.1-0.2	9242
0.2-0.3	18040
0.3-0.4	10017
0.4-0.5	3486
0.5-0.6	565
0.6-0.7	108
0.7-0.8	48
0.8-0.85	18
0.85-0.9	20
0.9-0.95	14
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233726
1.0	High Similarity	NPC124963
0.9583	High Similarity	NPC326533
0.9574	High Similarity	NPC157193
0.9574	High Similarity	NPC282143
0.9574	High Similarity	NPC299781
0.9574	High Similarity	NPC42503
0.94	High Similarity	NPC303727
0.9362	High Similarity	NPC14144
0.92	High Similarity	NPC157514
0.92	High Similarity	NPC89145
0.92	High Similarity	NPC242073
0.92	High Similarity	NPC323361
0.92	High Similarity	NPC58629
0.92	High Similarity	NPC145112
0.92	High Similarity	NPC246558
0.92	High Similarity	NPC269166
0.92	High Similarity	NPC165198
0.92	High Similarity	NPC107914
0.92	High Similarity	NPC130683
0.92	High Similarity	NPC67660
0.9149	High Similarity	NPC277475
0.9149	High Similarity	NPC321087
0.9038	High Similarity	NPC148424
0.898	High Similarity	NPC323574
0.8936	High Similarity	NPC165846
0.8936	High Similarity	NPC255377
0.8936	High Similarity	NPC69445
0.8936	High Similarity	NPC199857
0.8936	High Similarity	NPC21209
0.8936	High Similarity	NPC73906
0.8936	High Similarity	NPC92246
0.8936	High Similarity	NPC285364
0.8936	High Similarity	NPC176017
0.8936	High Similarity	NPC289758
0.8868	High Similarity	NPC219040
0.8868	High Similarity	NPC472025
0.8776	High Similarity	NPC82512
0.8704	High Similarity	NPC320032
0.8704	High Similarity	NPC322855
0.8545	High Similarity	NPC143326
0.8511	High Similarity	NPC70756
0.8511	High Similarity	NPC320240
0.8393	Intermediate Similarity	NPC477757
0.8393	Intermediate Similarity	NPC155457
0.8393	Intermediate Similarity	NPC477762
0.8393	Intermediate Similarity	NPC472026
0.8393	Intermediate Similarity	NPC477763
0.8393	Intermediate Similarity	NPC477750
0.8393	Intermediate Similarity	NPC477755
0.8393	Intermediate Similarity	NPC477753
0.8367	Intermediate Similarity	NPC230789
0.8367	Intermediate Similarity	NPC252918
0.8364	Intermediate Similarity	NPC290179
0.8364	Intermediate Similarity	NPC34877
0.8364	Intermediate Similarity	NPC317023
0.8298	Intermediate Similarity	NPC298699
0.8298	Intermediate Similarity	NPC291502
0.8298	Intermediate Similarity	NPC86191
0.8298	Intermediate Similarity	NPC134252
0.8298	Intermediate Similarity	NPC213159
0.8298	Intermediate Similarity	NPC317182
0.8103	Intermediate Similarity	NPC277570
0.8103	Intermediate Similarity	NPC325773
0.7966	Intermediate Similarity	NPC294813
0.7966	Intermediate Similarity	NPC31496
0.7966	Intermediate Similarity	NPC13143
0.7872	Intermediate Similarity	NPC266553
0.7833	Intermediate Similarity	NPC190418
0.7833	Intermediate Similarity	NPC471761
0.7833	Intermediate Similarity	NPC76881
0.7833	Intermediate Similarity	NPC471760
0.7833	Intermediate Similarity	NPC12040
0.7833	Intermediate Similarity	NPC147292
0.7797	Intermediate Similarity	NPC268243
0.7778	Intermediate Similarity	NPC317626
0.7778	Intermediate Similarity	NPC314821
0.7778	Intermediate Similarity	NPC317501
0.7755	Intermediate Similarity	NPC29721
0.7705	Intermediate Similarity	NPC477764
0.7705	Intermediate Similarity	NPC477756
0.7705	Intermediate Similarity	NPC477751
0.7705	Intermediate Similarity	NPC477752
0.7667	Intermediate Similarity	NPC6848
0.7581	Intermediate Similarity	NPC477760
0.7581	Intermediate Similarity	NPC477759
0.7581	Intermediate Similarity	NPC477754
0.7581	Intermediate Similarity	NPC477758
0.7581	Intermediate Similarity	NPC206601
0.7581	Intermediate Similarity	NPC477761
0.7551	Intermediate Similarity	NPC320189
0.746	Intermediate Similarity	NPC50228
0.746	Intermediate Similarity	NPC97736
0.746	Intermediate Similarity	NPC250619
0.746	Intermediate Similarity	NPC67099
0.7344	Intermediate Similarity	NPC211428
0.7344	Intermediate Similarity	NPC285003
0.7344	Intermediate Similarity	NPC241265
0.7302	Intermediate Similarity	NPC32148
0.7255	Intermediate Similarity	NPC107091
0.7255	Intermediate Similarity	NPC207656
0.7231	Intermediate Similarity	NPC53760
0.7231	Intermediate Similarity	NPC52268
0.7231	Intermediate Similarity	NPC474078
0.7121	Intermediate Similarity	NPC185419
0.7121	Intermediate Similarity	NPC184550
0.7015	Intermediate Similarity	NPC291228
0.7015	Intermediate Similarity	NPC163812
0.7015	Intermediate Similarity	NPC169085
0.7015	Intermediate Similarity	NPC206823
0.7015	Intermediate Similarity	NPC225748
0.7015	Intermediate Similarity	NPC308096
0.7015	Intermediate Similarity	NPC9763
0.7015	Intermediate Similarity	NPC39266
0.6981	Remote Similarity	NPC88638
0.697	Remote Similarity	NPC471879
0.6912	Remote Similarity	NPC166250
0.6912	Remote Similarity	NPC472173
0.6912	Remote Similarity	NPC308489
0.6912	Remote Similarity	NPC472174
0.6897	Remote Similarity	NPC326557
0.6809	Remote Similarity	NPC293908
0.6809	Remote Similarity	NPC86412
0.6809	Remote Similarity	NPC325034
0.6809	Remote Similarity	NPC66052
0.6809	Remote Similarity	NPC192065
0.6786	Remote Similarity	NPC329095
0.6769	Remote Similarity	NPC179823
0.6765	Remote Similarity	NPC470659
0.6765	Remote Similarity	NPC55652
0.6765	Remote Similarity	NPC132938
0.6765	Remote Similarity	NPC470660
0.6714	Remote Similarity	NPC326661
0.6714	Remote Similarity	NPC477350
0.6714	Remote Similarity	NPC229655
0.6714	Remote Similarity	NPC279575
0.6667	Remote Similarity	NPC258690
0.6667	Remote Similarity	NPC320043
0.6667	Remote Similarity	NPC103672
0.6667	Remote Similarity	NPC317651
0.662	Remote Similarity	NPC476783
0.662	Remote Similarity	NPC110813
0.662	Remote Similarity	NPC476782
0.662	Remote Similarity	NPC188793
0.662	Remote Similarity	NPC216883
0.662	Remote Similarity	NPC476781
0.6607	Remote Similarity	NPC322158
0.6607	Remote Similarity	NPC329128
0.6567	Remote Similarity	NPC327753
0.6567	Remote Similarity	NPC223174
0.6567	Remote Similarity	NPC327486
0.6528	Remote Similarity	NPC477325
0.6528	Remote Similarity	NPC475425
0.6528	Remote Similarity	NPC113745
0.6528	Remote Similarity	NPC477330
0.6528	Remote Similarity	NPC177343
0.6528	Remote Similarity	NPC477328
0.6528	Remote Similarity	NPC133377
0.6528	Remote Similarity	NPC477329
0.6528	Remote Similarity	NPC109887
0.6528	Remote Similarity	NPC477326
0.6528	Remote Similarity	NPC150557
0.6528	Remote Similarity	NPC477323
0.6528	Remote Similarity	NPC316807
0.6528	Remote Similarity	NPC281563
0.6528	Remote Similarity	NPC146380
0.6528	Remote Similarity	NPC477320
0.6528	Remote Similarity	NPC272841
0.6522	Remote Similarity	NPC248427
0.6471	Remote Similarity	NPC111882
0.6471	Remote Similarity	NPC88278
0.6471	Remote Similarity	NPC227707
0.6471	Remote Similarity	NPC99573
0.6471	Remote Similarity	NPC102981
0.6438	Remote Similarity	NPC158302
0.6438	Remote Similarity	NPC477346
0.6438	Remote Similarity	NPC146992
0.6438	Remote Similarity	NPC477344
0.6438	Remote Similarity	NPC22742
0.6438	Remote Similarity	NPC85759
0.6438	Remote Similarity	NPC294748
0.6438	Remote Similarity	NPC170595
0.6429	Remote Similarity	NPC138273
0.64	Remote Similarity	NPC473991
0.6364	Remote Similarity	NPC129100
0.6364	Remote Similarity	NPC291650
0.6364	Remote Similarity	NPC322801
0.6351	Remote Similarity	NPC471420
0.6351	Remote Similarity	NPC267592
0.6351	Remote Similarity	NPC163362
0.6351	Remote Similarity	NPC127295
0.6351	Remote Similarity	NPC100697
0.6327	Remote Similarity	NPC313405
0.6301	Remote Similarity	NPC98750
0.6296	Remote Similarity	NPC62014
0.6267	Remote Similarity	NPC16090
0.6267	Remote Similarity	NPC472201
0.6267	Remote Similarity	NPC123204
0.6267	Remote Similarity	NPC259294
0.6267	Remote Similarity	NPC477347

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 NPC23134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1304
0.1-0.2	5236
0.2-0.3	1871
0.3-0.4	445
0.4-0.5	178
0.5-0.6	56
0.6-0.7	29
0.7-0.8	11
0.8-0.85	2
0.85-0.9	10
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD904	Phase 3
0.9583	High Similarity	NPD905	Approved
0.92	High Similarity	NPD893	Approved
0.92	High Similarity	NPD889	Approved
0.92	High Similarity	NPD895	Approved
0.92	High Similarity	NPD890	Clinical (unspecified phase)
0.92	High Similarity	NPD887	Approved
0.92	High Similarity	NPD894	Approved
0.92	High Similarity	NPD891	Phase 3
0.92	High Similarity	NPD888	Phase 3
0.92	High Similarity	NPD892	Phase 3
0.9	High Similarity	NPD2269	Approved
0.8936	High Similarity	NPD8998	Phase 2
0.8936	High Similarity	NPD8999	Phase 3
0.8936	High Similarity	NPD9000	Phase 3
0.8936	High Similarity	NPD8997	Approved
0.8936	High Similarity	NPD8993	Phase 1
0.8571	High Similarity	NPD8965	Approved
0.8571	High Similarity	NPD8966	Approved
0.8333	Intermediate Similarity	NPD2267	Suspended
0.8298	Intermediate Similarity	NPD8788	Approved
0.807	Intermediate Similarity	NPD6123	Approved
0.7797	Intermediate Similarity	NPD847	Phase 1
0.7778	Intermediate Similarity	NPD9036	Phase 3
0.7778	Intermediate Similarity	NPD9035	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD9006	Approved
0.7636	Intermediate Similarity	NPD7346	Approved
0.7544	Intermediate Similarity	NPD369	Approved
0.7377	Intermediate Similarity	NPD1457	Discontinued
0.7302	Intermediate Similarity	NPD896	Approved
0.7302	Intermediate Similarity	NPD898	Approved
0.7302	Intermediate Similarity	NPD897	Approved
0.7255	Intermediate Similarity	NPD9219	Approved
0.7255	Intermediate Similarity	NPD9218	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8994	Approved
0.6897	Remote Similarity	NPD885	Approved
0.6897	Remote Similarity	NPD884	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8958	Phase 2
0.6863	Remote Similarity	NPD8957	Approved
0.6809	Remote Similarity	NPD9052	Approved
0.6809	Remote Similarity	NPD9053	Approved
0.6809	Remote Similarity	NPD9051	Approved
0.6765	Remote Similarity	NPD3181	Approved
0.6667	Remote Similarity	NPD9050	Approved
0.6667	Remote Similarity	NPD9049	Discontinued
0.6667	Remote Similarity	NPD8961	Approved
0.6567	Remote Similarity	NPD9445	Approved
0.6491	Remote Similarity	NPD1399	Approved
0.6491	Remote Similarity	NPD1400	Approved
0.6471	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8995	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8996	Phase 3
0.6438	Remote Similarity	NPD7329	Approved
0.6364	Remote Similarity	NPD9033	Approved
0.6364	Remote Similarity	NPD9032	Approved
0.6364	Remote Similarity	NPD9031	Approved
0.6364	Remote Similarity	NPD9030	Approved
0.6346	Remote Similarity	NPD8967	Approved
0.6286	Remote Similarity	NPD389	Phase 3
0.625	Remote Similarity	NPD9139	Approved
0.6197	Remote Similarity	NPD1810	Approved
0.6197	Remote Similarity	NPD1811	Approved
0.617	Remote Similarity	NPD8814	Phase 3
0.6129	Remote Similarity	NPD8959	Approved
0.6027	Remote Similarity	NPD372	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD361	Discontinued
0.6	Remote Similarity	NPD370	Phase 3
0.5946	Remote Similarity	NPD9435	Approved
0.5946	Remote Similarity	NPD9434	Approved
0.5902	Remote Similarity	NPD3728	Approved
0.5902	Remote Similarity	NPD3730	Approved
0.5849	Remote Similarity	NPD7536	Approved
0.5833	Remote Similarity	NPD9034	Approved
0.5833	Remote Similarity	NPD67	Phase 2
0.5821	Remote Similarity	NPD371	Approved
0.5679	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.561	Remote Similarity	NPD3207	Approved
0.561	Remote Similarity	NPD3202	Approved
0.561	Remote Similarity	NPD2698	Approved
0.561	Remote Similarity	NPD3209	Approved
0.561	Remote Similarity	NPD3208	Approved
0.561	Remote Similarity	NPD3203	Approved
0.561	Remote Similarity	NPD3201	Approved
0.5606	Remote Similarity	NPD393	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