glabranin : A dihydroxyflavanone that is pinocembrin substituted by a prenyl group at position 8. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 124049 |
| CHEMBL ID | 253998 |
| CHEBI ID | 5368 |
| SCHEMBL ID | 320136 |
| Synonym |
|---|
| (2s)-5,7-dihydroxy-8-(3-methylbut-2-enyl)-2-phenyl-chroman-4-one |
| 4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-, (2s)- |
| glabranine |
| (s)-2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-4h-1-benzopyran-4-one |
| 4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-, (s)- |
| TIMTEC1_002029 |
| NCGC00017206-01 |
| tnp00074 , |
| glabranin |
| 41983-91-9 |
| C09752 |
| NCGC00142379-01 |
| (2s)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-phenyl-3,4-dihydro-2h-1-benzopyran-4-one |
| bdbm26663 |
| LMPK12140164 |
| HMS1539M05 |
| chebi:5368 , |
| CHEMBL253998 |
| BRD-K83252656-001-01-7 |
| (2s)-5,7-dihydroxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one |
| (2s)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-phenyl-2,3-dihydro-4h-chromen-4-one |
| AKOS001737904 |
| NCGC00017206-02 |
| SCHEMBL320136 |
| (2s)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-phenyl-2,3-dihydro-4h-1-benzopyran-4-one |
| 8-dimethylallylpinocembrin |
| sr-01000530493 |
| DTXSID00194796 |
| 8-prenylpinocembrin |
| SR-01000530493-1 |
| Q27106734 |
| HY-N3942 |
| CS-0024491 |
| STL564423 |
| MS-24833 |
| XP161632 |
| Role | Description |
|---|---|
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| dihydroxyflavanone | Any hydroxyflavanone carrying two hydroxy substituents. |
| (2S)-flavan-4-one | Any flavanone in which the chiral centre at position 2 has S-configuration. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| cytochrome P450 2D6 isoform 1 | Homo sapiens (human) | Potency | 31.6228 | 0.0020 | 7.5337 | 39.8107 | AID891 |
| cytochrome P450 2C19 precursor | Homo sapiens (human) | Potency | 1.0000 | 0.0025 | 5.8400 | 31.6228 | AID899 |
| cytochrome P450 2C9 precursor | Homo sapiens (human) | Potency | 3.1623 | 0.0063 | 6.9043 | 39.8107 | AID883 |
| cytochrome P450 3A4 isoform 1 | Homo sapiens (human) | Potency | 12.5893 | 0.0316 | 10.2792 | 39.8107 | AID884; AID885 |
| lethal factor (plasmid) | Bacillus anthracis str. A2012 | Potency | 31.6228 | 0.0200 | 10.7869 | 31.6228 | AID912 |
| Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Histamine H2 receptor | Cavia porcellus (domestic guinea pig) | Potency | 3.1623 | 0.0063 | 8.2350 | 39.8107 | AID883 |
| Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| GABA theta subunit | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Acetylcholinesterase | Electrophorus electricus (electric eel) | IC50 (µMol) | 23.0000 | 0.0000 | 0.9453 | 9.9400 | AID696908 |
| Serine/threonine-protein kinase pim-1 | Homo sapiens (human) | IC50 (µMol) | 12.5000 | 0.0004 | 0.8871 | 10.0000 | AID1798717 |
| Acetylcholinesterase | Homo sapiens (human) | IC50 (µMol) | 0.0064 | 0.0000 | 0.9332 | 10.0000 | AID1742993 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1798717 | Solid-Phase ELISA Kinase Assay from Article 10.1158/1535-7163.MCT-06-0397: \\Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase.\\ | 2007 | Molecular cancer therapeutics, Jan, Volume: 6, Issue:1 | Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase. |
| AID1742984 | Cytotoxicity against Sprague-Dawley rat primary cerebellar granule neurons assessed as reduction in cell viability measured after 48 hrs by MTT assay | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID1742987 | Neuroprotective activity against H2O2-induced neuronal death in Sprague-Dawley rat primary cerebellar granule neurons assessed as increase in cell viability at 0.5 to 10 uM preincubated for 24 hrs followed by H2O2 addition and measured after 24 hrs by MTT | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID1742985 | Neuroprotective activity against H2O2-induced neuronal death in Sprague-Dawley rat primary cerebellar granule neurons assessed as increase in cell viability preincubated for 24 hrs followed by H2O2 addition and measured after 24 hrs by MTT assay | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID696908 | Inhibition of Electrophorus electricus C2888 AChE using acetylthiocholine iodide as substrate by Ellman's spectroscopic method | 2012 | Journal of natural products, Nov-26, Volume: 75, Issue:11 | Acetylcholinesterase inhibitors from the leaves of Macaranga kurzii. |
| AID1713999 | Inhibition of monophenolase activity of mushroom tyrosinase using L-Tyrosine substrate incubated for 10 mins followed by substrate addition and measured for 20 mins | |||
| AID1742989 | Neuroprotective activity against H2O2-induced neuronal death in Sprague-Dawley rat primary cerebellar granule neurons assessed as reduction in nuclear condensation at 0.5 to 300 uM preincubated for 24 hrs followed by H2O2 addition and measured after 24 hr | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID1742994 | Potency index, ratio of physostigmine IC50 to test compound IC50 for human erythrocytes AChE | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID311148 | Inhibition of PIM1 kinase | 2007 | Bioorganic & medicinal chemistry, Oct-01, Volume: 15, Issue:19 | Comparative molecular field analysis of flavonoid inhibitors of the PIM-1 kinase. |
| AID1742990 | Neuroprotective activity against H2O2-induced neuronal death in Sprague-Dawley rat primary cerebellar granule neurons assessed as reduction in neurite fragmentation at 0.5 to 300 uM preincubated for 24 hrs followed by H2O2 addition and measured after 24 h | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID696905 | Cytotoxicity against human KB cells at 20 uM after 72 hrs by neutral red staining | 2012 | Journal of natural products, Nov-26, Volume: 75, Issue:11 | Acetylcholinesterase inhibitors from the leaves of Macaranga kurzii. |
| AID1742991 | Cytotoxicity against human PC12D cells assessed as reduction in cell viability measured after 24 hrs by neutral red staining based spectrophotometric method | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID1742993 | Inhibition of human erythrocytes AChE using acetylthiocholine iodide as substrate measured after 30 mins by Ellman's method | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID1742992 | Neuroprotective activity against H2O2-induced cell death in human PC12D cells at 0.5 uM preincubated for 24 hrs followed by H2O2 addition and measured after 24 hrs by neutral red staining based spectrophotometric method relative to control | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID1742986 | Neuroprotective activity against H2O2-induced neuronal death in Sprague-Dawley rat primary cerebellar granule neurons assessed as increase in cell viability preincubated for 24 hrs followed by H2O2 addition and measured after 24 hrs by MTT assay relative | 2020 | European journal of medicinal chemistry, Nov-15, Volume: 206 | Neuroprotective effects of prenylated flavanones isolated from Dalea species, in vitro and in silico studies. |
| AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
| AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 2 (28.57) | 29.6817 |
| 2010's | 4 (57.14) | 24.3611 |
| 2020's | 1 (14.29) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (20.06) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 7 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||