Natural Product: NPC245919

Natural Product IDNPC245919
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 PKWLAZVOBOLTFU-ZQJMOEEOSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID n.a.
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0000507] Isoflavonoid O-glycosides

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 PKWLAZVOBOLTFU-ZQJMOEEOSA-N
Standard InCHI InChI=1S/C23H26O12/c1-31-21-10(3-4-12(25)22(21)32-2)11-8-33-14-6-9(5-13(26)16(14)17(11)27)34-23-20(30)19(29)18(28)15(7-24)35-23/h3-6,11,15,18-20,23-26,28-30H,7-8H2,1-2H3/t11-,15-,18-,19+,20-,23-/m1/s1
SMILES COc1c(ccc(c1OC)O)[C@H]1COc2cc(cc(c2C1=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   494.14 Volume:   459.166
?
Van der Waals volume.
Dense:   1.076 LogP:   0.508
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.064
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.837
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   6.0 Rigid Bonds:   24.0
TPSA:   184.6
?
Topological Polar Surface Area.
 H-Bond Acceptor:   12.0
H-Bond Donor:   6.0 Rings:   4.0
Heavy Atoms:   12.0

MedChem Properties

QED Drug-Likeness Score:   0.307 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.274 Fsp3:   0.435
MCE-18:   92.455
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Accepted
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   0
Colloidal aggregators:   0.434 Fluc inhibitor:   0.202
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.107
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.825
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.091 Promiscuous compounds:   0.359

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.061 MDCK Permeability:   -5.259
Pgp-inhibitor:   0.0 Pgp-substrate:   0.634
PAMPA:   0.99
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.028
20% Bioavailability (F20%):   0.039 30% Bioavailability (F30%):   0.418
50% Bioavailability (F50%):   0.697

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.052 MRP1:   0.561
Plasma Protein Binding (PPB):   82.581% Volume Distribution (VD):   -0.183
Fu: 17.985%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.998
OATP1B3 inhibitor:   0.998 BCRP inhibitor:   0.128
BSEP inhibitor:   0.001

ADMET: Metabolism

CYP1A2-inhibitor:   0.228 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.002
HLM stability:   0.003
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  3.015 Half-life (T1/2):  3.46

ADMET: Toxicity

hERG Blockers:  0.018 hERG Blockers (10um):  0.146
Human Hepatotoxicity (H-HT):  0.732 Drug-induced Liver Injury (DILI):  0.91
AMES Toxicity:  0.924 Rat Oral Acute Toxicity:  0.068
Maximum Recommended Daily Dose:  0.027 Skin Sensitization:  0.996
Carcinogencity:  0.451 Eye Corrosion:  0.0
Eye Irritation:  0.129 Respiratory Toxicity:  0.039
Drug-induced Neurotoxicity:  0.01 Ototoxicity:  0.929
Hematotoxicity:  0.411 Drug-induced Nephrotoxicity:  0.837
Genotoxicity:  0.726 RPMI-8226 Immunitoxicity:  0.241
A549 Cytotoxicity:  0.547 Hek293 Cytotoxicity:  0.443
BCF:   0.454
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   3.073
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.7
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.821
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[ 17014425]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/bab.1236]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.indcrop.2010.09.006]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. root n.a. PMID[11374966]
NPO2280 Streptomyces griseochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[12964155]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[16038550]
NPO11789 Swertia decussata Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[16286309]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17583950]
NPO733 Pseudoceratina arabica Species Pseudoceratinidae Eukaryota n.a. Red Sea n.a. PMID[18598078]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18855446]
NPO2280 Streptomyces griseochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191560]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20455578]
NPO12644 Lunularia cruciata Species Lunulariaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21775156]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23286284]
NPO2280 Streptomyces griseochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23377931]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[24108414]
NPO3292 Desmodium styracifolium Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25620156]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[27569393]
NPO4734 Syzygium nervosum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[27797185]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29185738]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30351923]
NPO12644 Lunularia cruciata Species Lunulariaceae Eukaryota n.a. n.a. n.a. PMID[30848895]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. root n.a. PMID[3655791]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota roots n.a. n.a. PMID[9834151]
NPO12644 Lunularia cruciata Species Lunulariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26606 Macadamia ternifolia Species Proteaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9640 Dinophysis fortii Species Dinophysiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8398 Cymodocea nodosa Species Cymodoceaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO733 Pseudoceratina arabica Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9452 Pulsatilla campanella Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11223 Pleurotus japonicus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2280 Streptomyces griseochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO11789 Swertia decussata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7319 Jamesoniella colorata Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8701 Bonamia spectabilis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3292 Desmodium styracifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11910 Peltogyne pubescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3292 Desmodium styracifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7001 Berberis floribunda Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24178 Citrus rugulosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26606 Macadamia ternifolia Species Proteaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3292 Desmodium styracifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7319 Jamesoniella colorata Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9452 Pulsatilla campanella Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8701 Bonamia spectabilis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7001 Berberis floribunda Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24178 Citrus rugulosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26606 Macadamia ternifolia Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3292 Desmodium styracifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3292 Desmodium styracifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11534 Astragalus spinosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15439 Iyengaria stellata Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8701 Bonamia spectabilis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6572 Dunalia solanacea Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12169 Ranunculus peltatus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO733 Pseudoceratina arabica Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12864 Trogoderma granarium Species Dermestidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11789 Swertia decussata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9009 Atuna racemosa Species Chrysobalanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4734 Syzygium nervosum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8006 Berlinia tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9640 Dinophysis fortii Species Dinophysiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7001 Berberis floribunda Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7319 Jamesoniella colorata Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3292 Desmodium styracifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23899 Rosulabryum capillare Species Bryaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2280 Streptomyces griseochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12644 Lunularia cruciata Species Lunulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11223 Pleurotus japonicus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10546 Allagopappus viscosissimus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9226 Astragalus pycnanthus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7627 Fumaria micrantha Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24178 Citrus rugulosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8398 Cymodocea nodosa Species Cymodoceaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2565 Aglaia australiensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4910 Lepidosperma ustulatum Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18447 Papaver tatricum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11910 Peltogyne pubescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3658 Achillea pseudopectinata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3311 Diplacus longiflorus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9452 Pulsatilla campanella Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26606 Macadamia ternifolia Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7949 Pterodon emarginatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12284 Hydrangea serrata Species Hydrangeaceae 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 NPC245919 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
0.7746 Intermediate Similarity NPC308265
0.6377 Remote Similarity NPC23084
0.6026 Remote Similarity NPC271479
0.575 Remote Similarity NPC163191
0.5714 Remote Similarity NPC236934
0.5634 Remote Similarity NPC311144
0.557 Remote Similarity NPC99233
0.5488 Remote Similarity NPC39351
0.5488 Remote Similarity NPC486379
0.5422 Remote Similarity NPC106625
0.5357 Remote Similarity NPC29830
0.5301 Remote Similarity NPC219163
0.5294 Remote Similarity NPC300537
0.5238 Remote Similarity NPC149244
0.5139 Remote Similarity NPC145900
0.5135 Remote Similarity NPC218685
0.5068 Remote Similarity NPC214454

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC245919 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
NPD

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