Page last updated: 2024-11-12
biapigenin
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
biapigenin: bis-apigenin coupled at 3' & 3' positions; inhibits various cytochrome P450 enzymes; isolated from St. John's Wort [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 10414856 |
| CHEMBL ID | 515252 |
| CHEBI ID | 192848 |
| SCHEMBL ID | 617814 |
| MeSH ID | M0414212 |
Synonyms (32)
| Synonym |
|---|
| 3,8''-biapigenin |
| 101140-06-1 |
| MEGXP0_000393 |
| ACON1_000118 |
| smr000440615 |
| MLS000877033 |
| BRD-K19704761-001-01-8 |
| 3,8''''-biapigenin |
| bdbm50259862 |
| cid_10414856 |
| CHEMBL515252 , |
| 3,8'-biapigenin |
| 13,ii8-biapigenin |
| CHEBI:192848 |
| 3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one |
| 4',4''',5,5'',7,7''-hexahydroxy-3,8''-biflavone |
| HMS2270H19 |
| SCHEMBL617814 |
| AKOS022184825 |
| 5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-4h,4'h-[3,8'-bichromene]-4,4'-dione |
| biapigenin; i3,ii8-biapigenin |
| i3,ii8-biapigenin, analytical standard |
| biapigenin |
| 5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[3,8'-bi-4h-1-benzopyran]-4,4'-dione, 9ci |
| FT-0775290 |
| B0005-189866 |
| DTXSID301318358 |
| CS-0017652 |
| HY-N1799 |
| PD151053 |
| [3,8'-bi-4h-1-benzopyran]-4,4'-dione, 5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)- |
| FS-10070 |
Research Excerpts
Bioavailability
| Excerpt | Reference | Relevance |
|---|---|---|
| " Co-effectors in the extract improve the bioavailability of active constituents such as hypericin (1) (pharmacokinetic synergy)." | ( Lessons learned from herbal medicinal products: the example of St. John's Wort (perpendicular). Butterweck, V; Nahrstedt, A, 2010) | 0.36 |
Dosage Studied
| Excerpt | Relevance | Reference |
|---|---|---|
| " Five SJW preparations were chosen to determine the amount of biapigenin in the dosage form and to investigate their release characteristics." | ( Development of a high-performance-liquid-chromatographic method for the determination of biapigenin in biorelevant media. Schubert-Zsilavecz, M; Schulte-Löbbert, S; Westerhoff, K; Wilke, A; Wurglics, M, 2003) | 0.78 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Drug Classes (1)
| Class | Description |
|---|---|
| flavonoid oligomer | A phenylpropanoid obtained by the coupling of two or more units of aryl-substituted benzopyran units and their substituted derivatives. |
| [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 Targets (39)
Potency Measurements
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 1.3948 | 0.0032 | 45.4673 | 12,589.2998 | AID2517; AID2572 |
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 19.9526 | 0.0447 | 17.8581 | 100.0000 | AID485341 |
| Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 50.1187 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
| Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 35.4813 | 0.1778 | 14.3909 | 39.8107 | AID2147 |
| Chain A, ATP-DEPENDENT DNA HELICASE Q1 | Homo sapiens (human) | Potency | 12.5893 | 0.1259 | 19.1169 | 125.8920 | AID2549 |
| Chain A, Ferritin light chain | Equus caballus (horse) | Potency | 28.1838 | 5.6234 | 17.2929 | 31.6228 | AID485281 |
| endonuclease IV | Escherichia coli | Potency | 7.9433 | 0.7079 | 12.4324 | 31.6228 | AID2565 |
| WRN | Homo sapiens (human) | Potency | 56.2341 | 0.1683 | 31.2583 | 100.0000 | AID651768 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 79.4328 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 11.4642 | 0.1800 | 13.5574 | 39.8107 | AID1460; AID1468 |
| nonstructural protein 1 | Influenza A virus (A/WSN/1933(H1N1)) | Potency | 19.9526 | 0.2818 | 9.7212 | 35.4813 | AID2326 |
| glucocerebrosidase | Homo sapiens (human) | Potency | 17.7828 | 0.0126 | 8.1569 | 44.6684 | AID2101 |
| bromodomain adjacent to zinc finger domain 2B | Homo sapiens (human) | Potency | 28.1838 | 0.7079 | 36.9043 | 89.1251 | AID504333 |
| Bloom syndrome protein isoform 1 | Homo sapiens (human) | Potency | 12.5893 | 0.5406 | 17.6392 | 96.1227 | AID2528 |
| parathyroid hormone/parathyroid hormone-related peptide receptor precursor | Homo sapiens (human) | Potency | 31.6228 | 3.5481 | 19.5427 | 44.6684 | AID743266 |
| importin subunit beta-1 isoform 1 | Homo sapiens (human) | Potency | 44.6684 | 5.8048 | 36.1306 | 65.1308 | AID540263 |
| pyruvate kinase PKM isoform a | Homo sapiens (human) | Potency | 7.9433 | 0.0401 | 7.4590 | 31.6228 | AID1631; AID1634 |
| DNA polymerase beta | Homo sapiens (human) | Potency | 3.1623 | 0.0224 | 21.0102 | 89.1251 | AID485314 |
| flap endonuclease 1 | Homo sapiens (human) | Potency | 50.1187 | 0.1337 | 25.4129 | 89.1251 | AID588795 |
| serine/threonine-protein kinase PLK1 | Homo sapiens (human) | Potency | 23.7781 | 0.1683 | 16.4040 | 67.0158 | AID720504 |
| snurportin-1 | Homo sapiens (human) | Potency | 44.6684 | 5.8048 | 36.1306 | 65.1308 | AID540263 |
| peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | Homo sapiens (human) | Potency | 44.6684 | 0.4256 | 12.0591 | 28.1838 | AID504891 |
| DNA polymerase eta isoform 1 | Homo sapiens (human) | Potency | 23.0548 | 0.1000 | 28.9256 | 213.3130 | AID588591; AID720502 |
| DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 25.1137 | 0.0501 | 27.0736 | 89.1251 | AID588590; AID720496 |
| geminin | Homo sapiens (human) | Potency | 9.3078 | 0.0046 | 11.3741 | 33.4983 | AID624296; AID624297 |
| DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 35.4813 | 0.0316 | 22.3146 | 100.0000 | AID588579 |
| Rap guanine nucleotide exchange factor 3 | Homo sapiens (human) | Potency | 56.2341 | 6.3096 | 60.2008 | 112.2020 | AID720709 |
| Glutamate receptor 1 | Rattus norvegicus (Norway rat) | Potency | 1.9953 | 0.0141 | 8.6024 | 39.8107 | AID2572 |
| Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 1.9953 | 0.0015 | 51.7393 | 15,848.9004 | AID2572 |
| Glutamate receptor 3 | Rattus norvegicus (Norway rat) | Potency | 1.9953 | 0.0141 | 8.6024 | 39.8107 | AID2572 |
| Glutamate receptor 4 | Rattus norvegicus (Norway rat) | Potency | 1.9953 | 0.0141 | 8.6024 | 39.8107 | AID2572 |
| TAR DNA-binding protein 43 | Homo sapiens (human) | Potency | 15.8489 | 1.7783 | 16.2081 | 35.4813 | AID652104 |
| phosphoglycerate kinase | Trypanosoma brucei brucei TREU927 | Potency | 14.1254 | 0.0757 | 8.4742 | 29.0628 | AID602233 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| SUMO-1 | Homo sapiens (human) | IC50 (µMol) | 37.9000 | 0.6470 | 7.4947 | 15.9000 | AID624382; AID624383 |
| integrase, partial | Human immunodeficiency virus 1 | IC50 (µMol) | 3.8760 | 0.0795 | 3.5203 | 9.9390 | AID1053171; AID1053172 |
| lens epithelium-derived growth factor p75 | Homo sapiens (human) | IC50 (µMol) | 3.8760 | 0.0795 | 3.5203 | 9.9390 | AID1053171; AID1053172 |
| Mcl-1 | Homo sapiens (human) | IC50 (µMol) | 2.7255 | 0.4000 | 7.1344 | 54.0000 | AID1417 |
| Cytochrome P450 3A4 | Homo sapiens (human) | IC50 (µMol) | 0.0800 | 0.0001 | 1.7536 | 10.0000 | AID478702 |
| Tyrosine-protein phosphatase non-receptor type 1 | Homo sapiens (human) | IC50 (µMol) | 4.5000 | 0.0005 | 3.4984 | 9.7600 | AID1231481 |
| Tyrosine-protein phosphatase non-receptor type 1 | Homo sapiens (human) | Ki | 4.6000 | 0.1900 | 4.8327 | 9.6000 | AID1231482 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (84)
Molecular Functions (44)
Ceullar Components (29)
Bioassays (27)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID333523 | Cytotoxicity against human A549 cells after 3 days by SRB assay | 2004 | Journal of natural products, Nov, Volume: 67, Issue:11 | Prenylated benzophenones and xanthones from Hypericum scabrum. |
| AID1231481 | Inhibition of human recombinant PTP1B using p-NPP as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by microplate reader analysis | 2015 | Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13 | Selaginellin and biflavonoids as protein tyrosine phosphatase 1B inhibitors from Selaginella tamariscina and their glucose uptake stimulatory effects. |
| AID1231479 | Inhibition of PTP1B in mouse 3T3L1 cells assessed as stimulation of 2-NBDG uptake at 10 uM preincubated for 24 hrs followed by 2-NBDG addition measured after 30 mins by fluorescence reader analysis relative to control | 2015 | Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13 | Selaginellin and biflavonoids as protein tyrosine phosphatase 1B inhibitors from Selaginella tamariscina and their glucose uptake stimulatory effects. |
| AID478702 | Inhibition of CYP3A4 | 2010 | Journal of natural products, May-28, Volume: 73, Issue:5 | Lessons learned from herbal medicinal products: the example of St. John's Wort (perpendicular). |
| AID1231478 | Inhibition of PTP1B in mouse 3T3L1 cells assessed as stimulation of 2-NBDG uptake preincubated for 24 hrs followed by 2-NBDG addition measured after 30 mins by fluorescence reader analysis | 2015 | Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13 | Selaginellin and biflavonoids as protein tyrosine phosphatase 1B inhibitors from Selaginella tamariscina and their glucose uptake stimulatory effects. |
| AID333524 | Cytotoxicity against human MCF7 cells after 3 days by SRB assay | 2004 | Journal of natural products, Nov, Volume: 67, Issue:11 | Prenylated benzophenones and xanthones from Hypericum scabrum. |
| AID333526 | Cytotoxicity against human MCF7 cells at 20 mcg/mL after 3 days by SRB assay | 2004 | Journal of natural products, Nov, Volume: 67, Issue:11 | Prenylated benzophenones and xanthones from Hypericum scabrum. |
| AID1231480 | Cytotoxicity against mouse 3T3L1 cells assessed as inhibition of cell viability at 5 to 10 uM after 48 hrs by MTT assay | 2015 | Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13 | Selaginellin and biflavonoids as protein tyrosine phosphatase 1B inhibitors from Selaginella tamariscina and their glucose uptake stimulatory effects. |
| AID1231482 | Mixed-competitive inhibition of human recombinant PTP1B using p-NPP as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by Lineweaver-Burk/Dixon plot analysis | 2015 | Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13 | Selaginellin and biflavonoids as protein tyrosine phosphatase 1B inhibitors from Selaginella tamariscina and their glucose uptake stimulatory effects. |
| AID377447 | Antioxidant activity assessed as DPPH radical scavenging activity | 2005 | Journal of natural products, Mar, Volume: 68, Issue:3 | Bioactive benzophenones from Garcinia xanthochymus fruits. |
| AID377448 | Cytotoxicity against human SW480 cells after 72 hrs by MTT assay | 2005 | Journal of natural products, Mar, Volume: 68, Issue:3 | Bioactive benzophenones from Garcinia xanthochymus fruits. |
| AID333525 | Cytotoxicity against human A549 cells at 20 mcg/mL after 3 days by SRB assay | 2004 | Journal of natural products, Nov, Volume: 67, Issue:11 | Prenylated benzophenones and xanthones from Hypericum scabrum. |
| AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | 2014 | Journal of biomolecular screening, Jul, Volume: 19, Issue:6 | A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum. |
| AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | |||
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (20)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 9 (45.00) | 29.6817 |
| 2010's | 8 (40.00) | 24.3611 |
| 2020's | 3 (15.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 22.92
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 (22.92) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (4.55%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 21 (95.45%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||