Natural Product: NPC307113

Natural Product IDNPC307113
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 KAWBLROQFPLJEU-UHFFFAOYSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 588705
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002497] Indoles
          • [CHEMONTID:0004196] 3-alkylindoles

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey KAWBLROQFPLJEU-UHFFFAOYSA-N
Standard InCHI InChI=1S/C12H13NO2/c1-9(14)15-7-6-10-8-13-12-5-3-2-4-11(10)12/h2-5,8,13H,6-7H2,1H3
SMILES CC(=O)OCCc1c[nH]c2ccccc12

  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
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO15684 Cochliobolus heterostrophus Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[10395513]
NPO7093 Oncorhynchus keta Species Salmonidae Eukaryota eggs Pacific n.a. PMID[10654418]
NPO7093 Oncorhynchus keta Species Salmonidae Eukaryota Eggs n.a. n.a. PMID[10654418]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO958 Tambja ceutae Species Polyceridae Eukaryota n.a. Azorean n.a. PMID[20227875]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[36838931]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[37480748]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. leaf n.a. PMID[9433811]
NPO4350 Chlorella pyrenoidosa Species Chlorellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6107 Acacia lemmoni Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3023 Achillea pratensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3913 Alcea nudiflora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6722 Anaphalis margaritacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1977 Arum montanum Species Araceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4050 Boronia lanceolata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16714 Campanula pendula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7161 Capparis angulata Species Capparaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9099 Carissa spinarum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO798 Chloranthus holostegius Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3528 Cinnamomum pedunculatum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10450 Clerodendrum infortunatum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15684 Cochliobolus heterostrophus Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4125 Corydalis crystallina Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6951 Dictyota spinulosa Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3456 Eucalyptus campanulata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1814 Euphorbia cattimandoo Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7377 Hemiphragma heterophyllum Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7640 Klaseopsis chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4847 Lasianthus wallichii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO586 Lomandra hastilis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO518 Mercurialis leiocarpa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6421 Neolitsea sericea Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4204 Ochradenus baccatus Species Resedaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7093 Oncorhynchus keta Species Salmonidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4411 Plantago ovata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6345 Podocarpus sellowii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1659 Primula denticulata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4773 Pteromys volans Species Sciuridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5739 Rubus foliolosus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6523 Streptococcus pneumoniae Species Streptococcaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO958 Tambja ceutae Species Polyceridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO241 Teucrium cossonii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5518 Thuja dolabrata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1244 Trimusculus conica Species Trimusculidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2339 Turnera ulmifolia Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5809 Xanthoparmelia tinctina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO7093 Oncorhynchus keta Species Salmonidae Eukaryota n.a. n.a. Database[FooDB]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota Leaves n.a. Database[FooDB]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7377 Hemiphragma heterophyllum Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6421 Neolitsea sericea Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6722 Anaphalis margaritacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4847 Lasianthus wallichii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4773 Pteromys volans Species Sciuridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7377 Hemiphragma heterophyllum Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4847 Lasianthus wallichii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6421 Neolitsea sericea Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6722 Anaphalis margaritacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4773 Pteromys volans Species Sciuridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6722 Anaphalis margaritacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9099 Carissa spinarum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6523 Streptococcus pneumoniae Species Streptococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2339 Turnera ulmifolia Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6722 Anaphalis margaritacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4847 Lasianthus wallichii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1244 Trimusculus conica Species Trimusculidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4050 Boronia lanceolata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15684 Cochliobolus heterostrophus Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1659 Primula denticulata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4411 Plantago ovata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO798 Chloranthus holostegius Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7093 Oncorhynchus keta Species Salmonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16714 Campanula pendula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4350 Chlorella pyrenoidosa Species Chlorellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6107 Acacia lemmoni Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5739 Rubus foliolosus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10450 Clerodendrum infortunatum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO241 Teucrium cossonii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5809 Xanthoparmelia tinctina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3528 Cinnamomum pedunculatum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6951 Dictyota spinulosa Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6421 Neolitsea sericea Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1814 Euphorbia cattimandoo Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3456 Eucalyptus campanulata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7640 Klaseopsis chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4773 Pteromys volans Species Sciuridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3913 Alcea nudiflora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7377 Hemiphragma heterophyllum Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO586 Lomandra hastilis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5518 Thuja dolabrata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1977 Arum montanum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO518 Mercurialis leiocarpa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3023 Achillea pratensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4125 Corydalis crystallina Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4204 Ochradenus baccatus Species Resedaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7161 Capparis angulata Species Capparaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6345 Podocarpus sellowii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO958 Tambja ceutae Species Polyceridae 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
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 NPC307113 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8043 Intermediate Similarity NPC469358
0.8 Intermediate Similarity NPC489200
0.6792 Remote Similarity NPC71037
0.6522 Remote Similarity NPC310665
0.6327 Remote Similarity NPC190296
0.619 Remote Similarity NPC601214
0.6154 Remote Similarity NPC480549
0.6122 Remote Similarity NPC600736
0.6111 Remote Similarity NPC480548
0.6 Remote Similarity NPC279081
0.5962 Remote Similarity NPC200214
0.5962 Remote Similarity NPC471957
0.587 Remote Similarity NPC29886
0.5778 Remote Similarity NPC96102
0.5652 Remote Similarity NPC230869
0.5577 Remote Similarity NPC480551
0.5556 Remote Similarity NPC480550
0.551 Remote Similarity NPC605863
0.549 Remote Similarity NPC55772
0.5472 Remote Similarity NPC609424
0.5417 Remote Similarity NPC84911
0.537 Remote Similarity NPC608269
0.5345 Remote Similarity NPC259644
0.5345 Remote Similarity NPC70922
0.5345 Remote Similarity NPC211572
0.5345 Remote Similarity NPC75540
0.5345 Remote Similarity NPC212376
0.5345 Remote Similarity NPC469765
0.5345 Remote Similarity NPC80597
0.5345 Remote Similarity NPC25008
0.5345 Remote Similarity NPC73952
0.5333 Remote Similarity NPC300149
0.5333 Remote Similarity NPC42372
0.5333 Remote Similarity NPC230002
0.5319 Remote Similarity NPC138370
0.5306 Remote Similarity NPC73767
0.5294 Remote Similarity NPC78020
0.5283 Remote Similarity NPC480318
0.5246 Remote Similarity NPC105818
0.5208 Remote Similarity NPC72435
0.52 Remote Similarity NPC67288
0.5192 Remote Similarity NPC315555
0.5192 Remote Similarity NPC59269
0.5179 Remote Similarity NPC602670
0.5094 Remote Similarity NPC149155
0.5094 Remote Similarity NPC203468
0.5094 Remote Similarity NPC110500
0.5094 Remote Similarity NPC605329
0.5085 Remote Similarity NPC605381
0.5079 Remote Similarity NPC75907

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC307113 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.5778 Remote Similarity NPD198 Clinical (unspecified phase)
0.551 Remote Similarity NPD786 Pre-clinical
0.5283 Remote Similarity NPD749 Clinical (unspecified phase)
0.5094 Remote Similarity NPD482 Phase 4

Bioactivity similarity

  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