Detailed information for compound 571312

Basic information

Technical information
  • TDR Targets ID: 571312
  • Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S ,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrah ydropyran-2-yl]oxy-chromen-4-one
  • MW: 432.378 | Formula: C21H20O10
  • H donors: 6 H acceptors: 7 LogP: 0.86 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 2
  • SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
  • InChi: 1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1
  • InChiKey: KMOUJOKENFFTPU-QNDFHXLGSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-hydroxy-2-(4-hydroxyphenyl)-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-1-benzopyran-4-one
  • 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-chromen-4-one
  • 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-chromone
  • 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
  • apigetrin
  • 5-hydroxy-2-(4-hydroxyphenyl)-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-4-chromenone
  • 578-74-5
  • KBioSS_000656
  • Spectrum_000176
  • SPECTRUM211950
  • 44692_FLUKA
  • Apigenin 7-glucoside
  • DivK1c_007023
  • Spectrum3_001249
  • KBio2_000656
  • 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
  • 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
  • CHEBI:16778
  • KBio2_005792
  • Spectrum5_000562
  • 7-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  • 7-O-beta-D-Glucosyl-5,7,4'-trihydroxyflavone
  • Apigenin 7-O-beta-D-glucoside
  • Apigenin 7-O-glucoside
  • C04608
  • Cosmetin
  • Cosmosiin
  • Spectrum2_001752
  • SpecPlus_000927
  • KBio2_003224
  • BSPBio_002758
  • Thalictiin
  • SPBio_001884
  • KBio3_002258
  • Apigenin-7-O-glucoside
  • KBio1_001967
  • AIDS-026340
  • AIDS026340
  • Apigenin-7-O-.beta.-D-glucopyranoside
  • KBioGR_002182
  • MEGxp0_001431
  • Spectrum4_001741

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens tumor necrosis factor Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus sex peptide receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis cAMP specific 3',5' cyclic phosphodiesterase 0.0082 0.7642 0.8379
Echinococcus multilocularis peptide (allatostatin:somatostatin) 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus multilocularis allatostatin A receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis neuropeptide receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis g-protein coupled receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis alpha 1A adrenergic receptor 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus neuropeptide receptor A26 0.0024 0.0076 0.0083
Echinococcus granulosus glutamate receptor NMDA 0.0077 0.6972 0.7644
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus tm gpcr rhodopsin 0.0024 0.0076 0.0083
Echinococcus granulosus 7TM GPCR rhodopsin 0.0024 0.0076 0.0083
Echinococcus granulosus serotonin receptor 0.0024 0.0076 0.0083
Echinococcus granulosus rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus granulosus rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus g protein coupled receptor 0.0024 0.0076 0.0083
Echinococcus granulosus neuropeptides capa receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis neuropeptides capa receptor 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus multilocularis rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus granulosus g protein coupled receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis g protein coupled receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis 7TM GPCR, rhodopsin 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus thyrotropin releasing hormone receptor 0.0024 0.0076 0.0083
Echinococcus granulosus peptide allatostatin:somatostatin 0.0024 0.0076 0.0083
Echinococcus granulosus rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis G protein coupled receptor 139 0.0024 0.0076 0.0083
Echinococcus granulosus growth hormone secretagogue receptor type 1 0.0024 0.0076 0.0083
Echinococcus granulosus hypothetical protein 0.0024 0.0076 0.0083
Echinococcus multilocularis fmrfamide receptor 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus biogenic amine 5HT receptor 0.0024 0.0076 0.0083
Echinococcus granulosus fmrfamide receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis pyroglutamylated rfamide peptide receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis neuropeptide s receptor 0.0024 0.0076 0.0083
Onchocerca volvulus Dopamine\/Ecdysteroid receptor homolog 0.0024 0.0076 0.5
Echinococcus granulosus neuropeptide s receptor 0.0024 0.0076 0.0083
Echinococcus granulosus rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis G protein coupled 5 hydroxytryptamine receptor 0.0024 0.0076 0.0083
Echinococcus granulosus g-protein coupled receptor 0.0024 0.0076 0.0083
Echinococcus granulosus g protein coupled receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis dro:myosuppressin receptor 0.0024 0.0076 0.0083
Giardia lamblia CAMP-specific 3,5-cyclic phosphodiesterase 4B 0.0093 0.9121 0.5
Echinococcus granulosus cAMP specific 3'5' cyclic phosphodiesterase 0.0093 0.9121 1
Echinococcus granulosus neuropeptide FF receptor 2 0.0024 0.0076 0.0083
Echinococcus multilocularis growth hormone secretagogue receptor type 1 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus multilocularis neuropeptide receptor 0.0024 0.0076 0.0083
Echinococcus granulosus rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis tm gpcr rhodopsin gpcr rhodopsin superfamily 0.0024 0.0076 0.0083
Echinococcus multilocularis g protein coupled receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis nmda type glutamate receptor 0.008 0.7455 0.8174
Echinococcus granulosus rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis cAMP specific 3',5' cyclic phosphodiesterase 0.0093 0.9121 1
Echinococcus granulosus biogenic amine 5HT receptor 0.0024 0.0076 0.0083
Echinococcus granulosus rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Loa Loa (eye worm) hypothetical protein 0.0093 0.9121 1
Echinococcus multilocularis neuropeptides capa receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis g protein coupled receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis nmda type glutamate receptor 0.0084 0.7914 0.8677
Echinococcus granulosus neuropeptide receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis tachykinin peptides receptor 99D 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus neuropeptide Y receptor 0.0024 0.0076 0.0083
Echinococcus granulosus pyroglutamylated rfamide peptide receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis fmrfamide receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis neuropeptide receptor A26 0.0024 0.0076 0.0083
Echinococcus granulosus G protein coupled receptor 139 0.0024 0.0076 0.0083
Echinococcus multilocularis neuropeptide Y receptor 0.0024 0.0076 0.0083
Echinococcus granulosus neuropeptide Y receptor 0.0024 0.0076 0.0083
Loa Loa (eye worm) cyclic AMP specific phosphodiesterase PDE4D5A 0.0082 0.7642 0.8365
Echinococcus granulosus g protein linked acetylcholine receptor gar 2a 0.0024 0.0076 0.0083
Echinococcus multilocularis tm gpcr rhodopsin gpcr rhodopsin superfamily 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus multilocularis rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis somatostatin receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis orexin receptor type 2 0.0024 0.0076 0.0083
Echinococcus granulosus nmda type glutamate receptor 0.008 0.7455 0.8174
Echinococcus multilocularis rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus multilocularis g protein linked acetylcholine receptor gar 2a 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus cAMP specific 3'5' cyclic phosphodiesterase 0.0082 0.7642 0.8379
Echinococcus multilocularis serotonin receptor 0.0024 0.0076 0.0083
Echinococcus granulosus tm gpcr rhodopsin 0.0024 0.0076 0.0083
Echinococcus granulosus tm gpcr rhodopsin 0.0024 0.0076 0.0083
Echinococcus granulosus alpha 1A adrenergic receptor 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus neuropeptides capa receptor 0.0024 0.0076 0.0083
Echinococcus granulosus 7tm_1 domain containing protein 0.0024 0.0076 0.0083
Brugia malayi Probable 3',5'-cyclic phosphodiesterase R153.1, putative 0.0082 0.7642 1
Echinococcus multilocularis tm gpcr rhodopsin gpcr rhodopsin superfamily 0.0024 0.0076 0.0083
Echinococcus granulosus dro:myosuppressin receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis G-protein coupled receptor, putative 0.0024 0.0076 0.0083
Echinococcus granulosus g protein linked acetylcholine receptor gar 2a 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus multilocularis rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus granulosus G protein coupled 5 hydroxytryptamine receptor 0.0024 0.0076 0.0083
Echinococcus granulosus cAMP specific 3'5' cyclic phosphodiesterase 0.0093 0.9121 1
Echinococcus multilocularis neuropeptide FF receptor 2 0.0024 0.0076 0.0083
Echinococcus multilocularis thyrotropin releasing hormone receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis g protein linked acetylcholine receptor gar 2a 0.0024 0.0076 0.0083
Onchocerca volvulus Neuropeptide F receptor homolog 0.0024 0.0076 0.5
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus multilocularis glutamate receptor NMDA 0.0077 0.6972 0.7644
Onchocerca volvulus 0.0024 0.0076 0.5
Echinococcus granulosus tachykinin peptides receptor 99D 0.0024 0.0076 0.0083
Echinococcus granulosus orexin receptor type 2 0.0024 0.0076 0.0083
Onchocerca volvulus 0.0024 0.0076 0.5
Toxoplasma gondii 3'5'-cyclic nucleotide phosphodiesterase domain-containing protein 0.0093 0.9121 0.5
Echinococcus granulosus allatostatin A receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis cAMP specific 3',5' cyclic phosphodiesterase 0.0093 0.9121 1
Echinococcus multilocularis rhodopsin orphan GPCR 0.0024 0.0076 0.0083
Echinococcus granulosus somatostatin receptor 0.0024 0.0076 0.0083
Echinococcus granulosus nmda type glutamate receptor 0.0084 0.7914 0.8677
Echinococcus granulosus neuropeptide receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis biogenic amine (5HT) receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis serotonin receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis neuropeptide Y receptor 0.0024 0.0076 0.0083
Echinococcus multilocularis sex peptide receptor 0.0024 0.0076 0.0083
Schistosoma mansoni camp-specific 35-cyclic phosphodiesterase 0.0093 0.9121 0.9114

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) < 0.1 uM Antiestrogenic activity in human MCF7 cells assessed as drug level causing inhibition of 100 pM E2-enhanced cell proliferation to level equivalent to 50 pM E2 after 96 hrs by alamar blue assay ChEMBL. 19943620
Activity (functional) < 0.1 uM Antiestrogenic activity in human MCF7 cells assessed as drug level causing inhibition of 100 pM E2-enhanced cell proliferation to level equivalent to 10 pM E2 after 96 hrs by alamar blue assay ChEMBL. 19943620
Activity (functional) < 0.1 uM Antiestrogenic activity in human T47D cells assessed as drug level causing inhibition of 100 pM E2-enhanced cell proliferation to level equivalent to 50 pM E2 after 96 hrs by alamar blue assay ChEMBL. 19943620
Activity (functional) < 0.1 uM Antiestrogenic activity in human T47D cells assessed as drug level causing inhibition of 100 pM E2-enhanced cell proliferation to level equivalent to 10 pM E2 after 96 hrs by alamar blue assay ChEMBL. 19943620
Activity (functional) = 2 uM Antiestrogenic activity in human T47D cells assessed as drug level causing inhibition of 100 pM E2-enhanced cell proliferation to level equivalent to 1 pM E2 after 96 hrs by alamar blue assay ChEMBL. 19943620
Activity (functional) > 100 uM Antiestrogenic activity in human MCF7 cells assessed as drug level causing inhibition of 100 pM E2-enhanced cell proliferation to level equivalent to 1 pM E2 after 96 hrs by alamar blue assay ChEMBL. 19943620
EC50 (functional) = 1.8 ug ml-1 Inhibitory activity of the compound against HIV-1 IIIB replication in H9 cell line ChEMBL. No reference
ED50 (functional) > 100 ug ml-1 Cytotoxicity against human KB cells ChEMBL. 469554
GI50 (functional) -4.582 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the ACHN Renal cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.365 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the UO-31 Renal cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.337 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the MDA-N Breast cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.337 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SK-MEL-5 Melanoma cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.314 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SF-539 Central Nervous System cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.294 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the NCI-H23 Non-Small Cell Lung cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.234 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the DU-145 Prostate cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.094 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HL-60(TB) Leukemia cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.076 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HOP-92 Non-Small Cell Lung cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SN12C Renal cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) = 76 nM Growth inhibitory activity against human cancer cell line in the NCI ChEMBL. 15743190
IC50 (binding) Inhibition of BCRP expressed in MDCK cells using Hoechst 33342 staining ChEMBL. 21354800
IC50 (binding) Inhibition of BCRP expressed in MCF-7 MX cells using Hoechst 33342 staining ChEMBL. 21354800
IC50 (functional) > 100 ug ml-1 Inhibitory activity of the compound against H9 cells uninfected with HIV-1 ChEMBL. No reference
IC50 (functional) > 20 uM Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced nitrite accumulation after 24 hrs by Griess reagent method ChEMBL. 19778086
IC50 (binding) = 39.3 uM Inhibition of Clostridium perfringens neuraminidase ChEMBL. 19729316
IC50 (binding) = 46.9 uM Noncompetitive inhibition of recombinant influenza A virus rvH1N1 A/Bervig_Mission/1/18 neuraminidase ChEMBL. 19729316
IC50 (functional) = 90.6 uM Anticancer activity against human HepG2 cells assessed as cell viability after 24 hrs by MTT assay ChEMBL. 24974349
IC50 (ADMET) = 115 uM Cytotoxicity against human H9 cells after 3 days ChEMBL. 8158164
Inhibition (binding) = 13.9 % Inhibition of cow milk xanthine oxidase at 50 ug/mL ChEMBL. 3379415
Inhibition (functional) = 22.27 % Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated TNFalpha production at 0.4 to 10 uM by ELISA ChEMBL. 25497988
Inhibition (functional) > 90 % Antiestrogenic activity in human MCF7 cells assessed as inhibition of E2-enhanced cell proliferation at 0.1 to 100 uM after 96 hrs by alamar blue assay ChEMBL. 19943620
Inhibition (ADMET) = 134.6386815 % Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM ChEMBL. 23571415
Inhibition (ADMET) = 204.4391191 % Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM ChEMBL. 23571415
Kd (binding) = 0.2 uM Binding affinity to TNF-alpha (unknown origin) ChEMBL. 24974349
Ki (binding) = 53.8 uM Noncompetitive inhibition of recombinant influenza A virus rvH1N1 A/Bervig_Mission/1/18 neuraminidase ChEMBL. 19729316

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.

Annotated phenotypes:

We have no manually annotated phenotypes for this drug. What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by drugs, or by genetic manipulation of cells (e.g. gene knockouts or knockdowns) is manually curated from the literature. These descriptions help to describe the potential of the target for drug development. If no information is available for this gene or if the information is incomplete, this may mean that i) the papers containing this information either appeared after the curation effort for this organism was carried out or they were inadvertently missed by curators; or that ii) the curation effort for this organism has not yet started.
 
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.

External resources for this compound

Bibliographic References

4 literature references were collected for this gene.

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