NPASS Compound

Natural Product: NPC561341

Natural Product ID	NPC561341
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-dihydroxy-2-(4-methoxyphenyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,7-dihydroxy-2-(4-methoxyphenyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
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 54 57 0 0 0 0 0 0 0 0999 V2000 -3.2008 5.8041 1.2252 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3165 4.8865 1.7992 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1524 3.5778 1.3959 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2357 2.7988 2.0679 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0955 1.4742 1.6310 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8243 0.9674 0.5899 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6007 -0.4038 0.1283 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5218 -1.1581 0.4033 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5545 -0.7775 1.1462 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7318 -0.2023 0.5390 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5898 -1.3015 0.3729 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8152 -0.9543 -0.1281 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1554 -1.5963 -1.4422 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9644 0.5641 -0.2841 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2439 0.8729 -0.7538 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7291 1.1365 1.0910 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0042 2.4900 1.1683 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2818 0.8233 1.4451 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1900 0.4807 2.7972 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5263 -2.4536 -0.1487 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4540 -3.1922 0.0821 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5533 -2.9249 -0.9187 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5720 -4.1891 -1.4670 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5136 -5.0443 -1.2423 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6219 -4.6325 -2.2395 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6786 -3.7713 -2.4607 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7425 -4.2409 -3.2522 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6811 -2.5161 -1.9280 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6220 -2.0728 -1.1503 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6051 -0.8777 -0.6321 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7359 1.7852 -0.0578 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8929 3.0797 0.3482 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2333 5.5168 1.5594 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9338 6.8217 1.5894 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1938 5.8078 0.1191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6415 3.1796 2.9001 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4144 0.8656 2.1764 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4006 0.1248 -0.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5951 -1.2512 0.6038 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7385 -0.9898 -2.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8372 -2.6464 -1.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2759 -1.6031 -1.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1791 0.8953 -0.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7038 1.3754 -0.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3473 0.5371 1.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6478 2.6957 1.8853 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7430 1.7993 1.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7336 1.2207 3.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1750 -5.7070 -1.9107 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6542 -5.6229 -2.6788 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5568 -4.6463 -2.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5163 -1.8619 -2.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2945 1.3494 -0.8769 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6095 3.7069 -0.1679 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 8 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 2 0 26 27 1 0 26 28 1 0 28 29 2 0 29 30 1 0 6 31 1 0 31 32 2 0 32 3 1 0 30 7 1 0 18 10 1 0 29 22 1 0 1 33 1 0 1 34 1 0 1 35 1 0 4 36 1 0 5 37 1 0 10 38 1 6 12 39 1 1 13 40 1 0 13 41 1 0 13 42 1 0 14 43 1 6 15 44 1 0 16 45 1 1 17 46 1 0 18 47 1 1 19 48 1 0 24 49 1 0 25 50 1 0 27 51 1 0 28 52 1 0 31 53 1 0 32 54 1 0 M END

Standard InCHIKey	NUFNGCDVYZKSKE-NXYBHTNZSA-N
Standard InCHI	InChI=1S/C22H22O10/c1-9-16(25)18(27)19(28)22(30-9)32-21-17(26)15-13(24)7-11(23)8-14(15)31-20(21)10-3-5-12(29-2)6-4-10/h3-9,16,18-19,22-25,27-28H,1-2H3/t9-,16-,18+,19-,22-/m0/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]3O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11762	Agrimonia eupatoria	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11762	Agrimonia eupatoria	Species	Rosaceae	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 NPC561341 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	14777
0.1-0.2	30878
0.2-0.3	3017
0.3-0.4	639
0.4-0.5	234
0.5-0.6	80
0.6-0.7	92
0.7-0.8	0
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC219904
0.8472	Intermediate Similarity	NPC472459
0.8429	Intermediate Similarity	NPC111929
0.8429	Intermediate Similarity	NPC320283
0.8429	Intermediate Similarity	NPC41121
0.8194	Intermediate Similarity	NPC265530
0.8056	Intermediate Similarity	NPC127546
0.8056	Intermediate Similarity	NPC57625
0.8056	Intermediate Similarity	NPC173637
0.8056	Intermediate Similarity	NPC317489
0.8056	Intermediate Similarity	NPC223424
0.8056	Intermediate Similarity	NPC600591
0.7945	Intermediate Similarity	NPC64305
0.7917	Intermediate Similarity	NPC135599
0.7917	Intermediate Similarity	NPC73855
0.7917	Intermediate Similarity	NPC113968
0.7917	Intermediate Similarity	NPC328940
0.7917	Intermediate Similarity	NPC277174
0.7917	Intermediate Similarity	NPC606877
0.7895	Intermediate Similarity	NPC223747
0.7308	Intermediate Similarity	NPC120099
0.7176	Intermediate Similarity	NPC473327
0.7143	Intermediate Similarity	NPC46420
0.7105	Intermediate Similarity	NPC77672
0.7105	Intermediate Similarity	NPC133671
0.7105	Intermediate Similarity	NPC135391
0.7105	Intermediate Similarity	NPC78263
0.7105	Intermediate Similarity	NPC250069
0.6988	Remote Similarity	NPC173582
0.6988	Remote Similarity	NPC265885
0.6988	Remote Similarity	NPC181465
0.6988	Remote Similarity	NPC215710
0.6988	Remote Similarity	NPC473438
0.6988	Remote Similarity	NPC253788
0.6962	Remote Similarity	NPC60735
0.6962	Remote Similarity	NPC175107
0.6962	Remote Similarity	NPC26230
0.6962	Remote Similarity	NPC611303
0.6951	Remote Similarity	NPC278419
0.6951	Remote Similarity	NPC179198
0.6883	Remote Similarity	NPC249281
0.6875	Remote Similarity	NPC609478
0.6835	Remote Similarity	NPC325555
0.6835	Remote Similarity	NPC226304
0.6795	Remote Similarity	NPC145038
0.6795	Remote Similarity	NPC56077
0.6795	Remote Similarity	NPC281131
0.6795	Remote Similarity	NPC253662
0.6795	Remote Similarity	NPC179950
0.6795	Remote Similarity	NPC88789
0.6795	Remote Similarity	NPC491374
0.6716	Remote Similarity	NPC59951
0.6711	Remote Similarity	NPC288084
0.6709	Remote Similarity	NPC305811
0.6709	Remote Similarity	NPC271692
0.6707	Remote Similarity	NPC203050
0.6707	Remote Similarity	NPC225434
0.6707	Remote Similarity	NPC476215
0.6706	Remote Similarity	NPC203259
0.6706	Remote Similarity	NPC33054
0.6706	Remote Similarity	NPC176740
0.6706	Remote Similarity	NPC471725
0.6706	Remote Similarity	NPC134532
0.6706	Remote Similarity	NPC602582
0.6667	Remote Similarity	NPC19388
0.6667	Remote Similarity	NPC240431
0.6667	Remote Similarity	NPC55786
0.6667	Remote Similarity	NPC609888
0.6629	Remote Similarity	NPC476472
0.6629	Remote Similarity	NPC294815
0.6629	Remote Similarity	NPC16194
0.6627	Remote Similarity	NPC116864
0.6627	Remote Similarity	NPC244776
0.6588	Remote Similarity	NPC39834
0.6582	Remote Similarity	NPC158674
0.6552	Remote Similarity	NPC153755
0.6543	Remote Similarity	NPC159579
0.6512	Remote Similarity	NPC605592
0.6429	Remote Similarity	NPC95866
0.642	Remote Similarity	NPC216496
0.641	Remote Similarity	NPC67037
0.641	Remote Similarity	NPC255615
0.6395	Remote Similarity	NPC163242
0.6395	Remote Similarity	NPC272068
0.6386	Remote Similarity	NPC209023
0.6386	Remote Similarity	NPC116458
0.6386	Remote Similarity	NPC246943
0.6364	Remote Similarity	NPC54802
0.6364	Remote Similarity	NPC197304
0.6341	Remote Similarity	NPC129217
0.631	Remote Similarity	NPC276377
0.6296	Remote Similarity	NPC52550
0.6296	Remote Similarity	NPC27640
0.6282	Remote Similarity	NPC34531
0.6279	Remote Similarity	NPC471079
0.6279	Remote Similarity	NPC139320
0.6264	Remote Similarity	NPC76831
0.625	Remote Similarity	NPC289667
0.625	Remote Similarity	NPC129264
0.6163	Remote Similarity	NPC251417
0.6145	Remote Similarity	NPC182121
0.6136	Remote Similarity	NPC155877
0.6111	Remote Similarity	NPC12013
0.6111	Remote Similarity	NPC11432
0.6111	Remote Similarity	NPC477613
0.6092	Remote Similarity	NPC187379
0.6087	Remote Similarity	NPC220173
0.6076	Remote Similarity	NPC276222
0.6076	Remote Similarity	NPC274618
0.6076	Remote Similarity	NPC118284
0.6076	Remote Similarity	NPC608147
0.6053	Remote Similarity	NPC268668
0.6049	Remote Similarity	NPC143851
0.6044	Remote Similarity	NPC270448
0.6044	Remote Similarity	NPC606657
0.6024	Remote Similarity	NPC59534
0.6023	Remote Similarity	NPC471748
0.6023	Remote Similarity	NPC67326
0.6	Remote Similarity	NPC470125
0.6	Remote Similarity	NPC605784
0.5978	Remote Similarity	NPC5319
0.5955	Remote Similarity	NPC150164
0.5955	Remote Similarity	NPC156869
0.593	Remote Similarity	NPC170052
0.593	Remote Similarity	NPC66087
0.593	Remote Similarity	NPC135846
0.5926	Remote Similarity	NPC476771
0.5914	Remote Similarity	NPC85751
0.5914	Remote Similarity	NPC19240
0.5914	Remote Similarity	NPC89127
0.5909	Remote Similarity	NPC29958
0.5904	Remote Similarity	NPC488080
0.5904	Remote Similarity	NPC349108
0.5904	Remote Similarity	NPC169977
0.5889	Remote Similarity	NPC473571
0.5889	Remote Similarity	NPC110941
0.5889	Remote Similarity	NPC186816
0.5882	Remote Similarity	NPC85707
0.5882	Remote Similarity	NPC224530
0.5876	Remote Similarity	NPC173837
0.5876	Remote Similarity	NPC477895
0.587	Remote Similarity	NPC122467
0.587	Remote Similarity	NPC37668
0.587	Remote Similarity	NPC72016
0.5862	Remote Similarity	NPC265115
0.5854	Remote Similarity	NPC476772
0.5851	Remote Similarity	NPC221342
0.5851	Remote Similarity	NPC476470
0.5842	Remote Similarity	NPC470713
0.5833	Remote Similarity	NPC89052
0.5833	Remote Similarity	NPC203145
0.5816	Remote Similarity	NPC470712
0.5789	Remote Similarity	NPC602448
0.5783	Remote Similarity	NPC297987
0.5773	Remote Similarity	NPC189564
0.5765	Remote Similarity	NPC48093
0.5761	Remote Similarity	NPC483414
0.5747	Remote Similarity	NPC355481
0.5745	Remote Similarity	NPC470447
0.5745	Remote Similarity	NPC471669
0.5729	Remote Similarity	NPC214621
0.5729	Remote Similarity	NPC34267
0.5714	Remote Similarity	NPC48984
0.5699	Remote Similarity	NPC32641
0.5699	Remote Similarity	NPC256188
0.5699	Remote Similarity	NPC104883
0.5699	Remote Similarity	NPC35119
0.5699	Remote Similarity	NPC488679
0.5698	Remote Similarity	NPC259957
0.5682	Remote Similarity	NPC254855
0.5682	Remote Similarity	NPC94610
0.5667	Remote Similarity	NPC470405
0.5657	Remote Similarity	NPC217520
0.5652	Remote Similarity	NPC296018
0.5652	Remote Similarity	NPC126784
0.5652	Remote Similarity	NPC241423
0.5647	Remote Similarity	NPC42773
0.5647	Remote Similarity	NPC21100
0.5647	Remote Similarity	NPC45522
0.5647	Remote Similarity	NPC599850
0.5634	Remote Similarity	NPC184536
0.5634	Remote Similarity	NPC103342
0.5632	Remote Similarity	NPC88023
0.5632	Remote Similarity	NPC309025
0.5631	Remote Similarity	NPC474522
0.5625	Remote Similarity	NPC483767
0.5625	Remote Similarity	NPC223426
0.5625	Remote Similarity	NPC483769
0.5625	Remote Similarity	NPC483768
0.5625	Remote Similarity	NPC483766
0.5616	Remote Similarity	NPC82325
0.5604	Remote Similarity	NPC65563
0.5604	Remote Similarity	NPC470949
0.5591	Remote Similarity	NPC483415
0.5581	Remote Similarity	NPC235260
0.5581	Remote Similarity	NPC191306
0.5581	Remote Similarity	NPC155763
0.5567	Remote Similarity	NPC81042
0.5556	Remote Similarity	NPC258044
0.5556	Remote Similarity	NPC292019

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC561341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4282
0.1-0.2	4766
0.2-0.3	85
0.3-0.4	11
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
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
0.6706	Remote Similarity	NPD6797	Phase 2
0.5978	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.52	Remote Similarity	NPD7808	Phase 3
0.5102	Remote Similarity	NPD7251	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