Compounds > (e)-4-hydroxy-3-methylbut-2-enyl diphosphate
Page last updated: 2024-12-10

(e)-4-hydroxy-3-methylbut-2-enyl diphosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

**(E)-4-Hydroxy-3-methylbut-2-enyl diphosphate**, often abbreviated as **HMBPP**, is a key intermediate in the biosynthesis of isoprenoids, a diverse class of organic molecules found in all living organisms.

**Importance in Research:**

* **Understanding Isoprenoid Biosynthesis:** HMBPP is a crucial intermediate in the mevalonate pathway, which is the major route for isoprenoid biosynthesis in animals and fungi. Studying HMBPP provides insights into the mechanisms of this pathway, including the enzymes involved and their regulation.

* **Developing New Drugs:** Isoprenoids have a wide range of biological functions, including roles in hormones, vitamins, and cell signaling. Dysregulation of isoprenoid biosynthesis is implicated in various diseases, such as cancer and cardiovascular disease. Research into HMBPP and its metabolic pathway is essential for developing new drugs that target these diseases.

* **Biotechnology Applications:** Isoprenoids have potential applications in biotechnology, such as the production of biofuels and pharmaceuticals. Understanding the biosynthesis of HMBPP and related compounds could lead to improved production methods for these valuable products.

**Specific Research Areas:**

* **Enzyme Studies:** Research focuses on the enzymes involved in the synthesis and metabolism of HMBPP, including the elucidation of their catalytic mechanisms and structure-function relationships.
* **Metabolic Engineering:** Efforts are underway to manipulate the mevalonate pathway, including HMBPP production, to enhance the biosynthesis of desired isoprenoids.
* **Drug Discovery:** Researchers are investigating the potential of HMBPP analogs and inhibitors as therapeutic agents for various diseases.

**Conclusion:**

(E)-4-Hydroxy-3-methylbut-2-enyl diphosphate (HMBPP) is a crucial intermediate in isoprenoid biosynthesis, a pathway of significant biological and biotechnological importance. Research into HMBPP plays a key role in understanding isoprenoid metabolism, developing new drugs, and advancing biotechnology applications.

(E)-4-hydroxy-3-methylbut-2-enyl diphosphate: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(2E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate : A prenol phosphate comprising (2E)-4-hydroxy-3-methylbut-2-en-1-ol having an O-diphosphate substituent. [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]

Cross-References

ID SourceID
PubMed CID5281976
CHEMBL ID145233
CHEBI ID15664
MeSH IDM0544188

Synonyms (20)

Synonym
(2e)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate
(e)-4-hydroxy-3-methyl-2-buten-1-yl pyrophosphate
(e)-4-hydroxy-3-methylbut-2-enyl pyrophosphate
(2e)-4-hydroxy-3-methylbut-2-en-1-yl trihydrogen diphosphate
(2e)-4-hydroxy-3-methylbut-2-en-1-yl pyrophosphate
(e)-4-hydroxy-3-methyl-2-buten-1-yl diphosphate
CHEBI:15664 ,
1-hydroxy-2-methylbut-2(e)-en-4-yl pyrophosphate
1-hydroxy-2-methylbut-2(e)-en-4-yl diphosphate
(e)-4-hydroxy-3-methyl-but-2-enyl diphosphate
1-hydroxy-2-methyl-2-butenyl 4-diphosphate
(e)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate
1PPW
CHEMBL145233 ,
(e)-4-hydroxy-3-methylbut-2-enyl diphosphate
LMPR01010009
[(e)-4-hydroxy-3-methylbut-2-enyl] phosphono hydrogen phosphate
EPITOPE ID:194672
DTXSID60649459
bdbm50236893
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
epitopeThe biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
phosphoantigenAny antigen that is a phosphorylated microbial metabolite which activates an immune response in humans.
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
[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]

Drug Classes (1)

ClassDescription
prenol phosphate
[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]

Pathways (2)

PathwayProteinsCompounds
Methylerythritol phosphate pathway07
DXP pathway520

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Isopentenyl-diphosphate delta-isomeraseEscherichia coliIC50 (µMol)50.000050.000050.000050.0000AID977608
Butyrophilin subfamily 3 member A1Homo sapiens (human)IC50 (µMol)46.70004.56007.10009.6400AID1569592; AID1569593; AID1569594; AID1569595; AID1569596; AID1569597; AID1569600; AID1569602; AID1569603; AID1569604
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Butyrophilin subfamily 3 member A1Homo sapiens (human)EC50 (µMol)0.00090.00010.47193.0600AID1386821; AID1441713; AID1441734; AID1494447; AID1569584; AID1569591; AID1676481; AID1676487
Butyrophilin subfamily 3 member A1Homo sapiens (human)Kd2.90501.54002.90504.2700AID1569598; AID1569599
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
positive regulation of cytokine productionButyrophilin subfamily 3 member A1Homo sapiens (human)
adaptive immune responseButyrophilin subfamily 3 member A1Homo sapiens (human)
positive regulation of type II interferon productionButyrophilin subfamily 3 member A1Homo sapiens (human)
activated T cell proliferationButyrophilin subfamily 3 member A1Homo sapiens (human)
T cell receptor signaling pathwayButyrophilin subfamily 3 member A1Homo sapiens (human)
regulation of cytokine productionButyrophilin subfamily 3 member A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
protein bindingButyrophilin subfamily 3 member A1Homo sapiens (human)
signaling receptor bindingButyrophilin subfamily 3 member A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneButyrophilin subfamily 3 member A1Homo sapiens (human)
external side of plasma membraneButyrophilin subfamily 3 member A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (58)

Assay IDTitleYearJournalArticle
AID317319Effect on proliferation of human T cell expressing Vgamma9Vdelta2 receptor in cynomolgus monkey co-treated with IL2 assessed as circulating T cells in blood at 5 mg/kg, iv2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1724595Induction of IL2-stimulated IFNgamma production in human PBMC-derived Vgamma9Vdelta2 T cells co-cultured with compound treated human K562 cells measured after 60 mins by ELISA2020Bioorganic & medicinal chemistry, 10-01, Volume: 28, Issue:19
Potent double prodrug forms of synthetic phosphoantigens.
AID1569603Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 R448A mutant (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1569593Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 full interaction domain (unknown origin) expressed in Escherichia coli BL21 (DE) at pH 6 to 9 measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID317317Agonist activity at human Vgamma9Vdelta2 receptor expressed in T cells assessed as stimulation of TNFalpha release by ELISA2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1808210Displacement of GDP-BODIPY probe from BTN3A1 full intracellular domain (unknown origin) at 0.1 mM measured after 60 mins by fluorescence polarization assay2022ACS medicinal chemistry letters, Feb-10, Volume: 13, Issue:2
Synthesis and Metabolism of BTN3A1 Ligands: Studies on Diene Modifications to the Phosphoantigen Scaffold.
AID317323Drug level in iv dosed rat assessed as excreted compound in urine2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1569592Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 full interaction domain (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1676481Binding affinity to BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assessed as increase in CD69/CD25 level incubated for overnight by flow cytometric analysis
AID317327Chemical stability in 0.1 N HCl at 60 degC after 2 hrs2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID216548Activity against isopentenyl pyrophosphate (IPP) in Vgamma9 / Vdelta2 T cell2003Bioorganic & medicinal chemistry letters, Apr-07, Volume: 13, Issue:7
Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates Its potential to activate human gammadelta T cells but does not lead to competitive antagonism.
AID317324Chemical stability at 4 degC after 7 days2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1676478Binding affinity to BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assessed as induction of Vgamma9/Vdelta2 T cell mediated T-24 cell lysis co-expressing GFP at 10 pM preincubated 4 hrs followed by compound washout and subsequent Vgamma9Vdelta2 T ce
AID1569584Activation of BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assessed as induction of IL2-stimulated cell proliferation by measuring increase in CD3+ cells preincubated for 3 days followed by 11 days incubation post compound washout and subsequent I2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1494451Binding affinity to butyrophilin 3A1 in human Vgamma9/Vdelta2 T-cells assessed as activation of Vgamma9/Vdelta2 T-cells by measuring levels of CD69 and CD25 at 0.01 uM after 18 hrs relative to control2018Journal of medicinal chemistry, 03-08, Volume: 61, Issue:5
Synthesis and Biological Evaluation of ( E)-4-Hydroxy-3-methylbut-2-enyl Phosphate (HMBP) Aryloxy Triester Phosphoramidate Prodrugs as Activators of Vγ9/Vδ2 T-Cell Immune Responses.
AID317328Chemical stability assessed as degradation in 3% H2O2 at 60 degC after 2 hrs2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1569599Binding affinity to C-terminal 6His-tagged BTN3A1 B30.2 domain (unknown origin) expressed in Escherichia coli BL21 (DE) by isothermal calorimetric titration method2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1441716Toxicity in human Vgamma9/Vdelta2 T cells treated for 72 hrs measured on day 11 post last treatment by flow cytometry2017Journal of medicinal chemistry, 03-23, Volume: 60, Issue:6
Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.
AID216550Mean effective concentration of compound was determined in stimulating Vgamma9 / Vdelta2 T cell2003Bioorganic & medicinal chemistry letters, Apr-07, Volume: 13, Issue:7
Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates Its potential to activate human gammadelta T cells but does not lead to competitive antagonism.
AID1676486Half life in human serum at 5 mg and measured up to 12 hrs by 31PNMR analysis
AID1569596Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 B30.2 domain (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1676479Cytotoxicity against human T-24 cells co-expressing GFP assessed as reduction in cell viability at 10 pM after 4 hrs by eFluor 780 fixable viability dye based fluorescence assay
AID1441736Antiproliferative activity against human K562 cells after 72 hrs by fluorescence spectroscopy2017Journal of medicinal chemistry, 03-23, Volume: 60, Issue:6
Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.
AID1441733Selectivity index, ratio of IC50 for human Vgamma9Vdelta2 T cells to EC50 for BTN3A1 in human Vgamma9Vdelta2 T cells2017Journal of medicinal chemistry, 03-23, Volume: 60, Issue:6
Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.
AID1724597Induction of IL2-stimulated IFNgamma production in human PBMC-derived Vgamma9Vdelta2 T cells co-cultured with compound treated human K562 cells measured after 15 mins by ELISA2020Bioorganic & medicinal chemistry, 10-01, Volume: 28, Issue:19
Potent double prodrug forms of synthetic phosphoantigens.
AID1569597Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 H381R mutant (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1569598Binding affinity to C-terminal 6His-tagged BTN3A1 full interaction domain (unknown origin) expressed in Escherichia coli BL21 (DE) by isothermal calorimetric titration method2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1569591Activation of BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assessed as induction of IL2-stimulated IFNgamma production measured after 48 hrs by ELISA2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1494447Binding affinity to butyrophilin 3A1 in human Vgamma9/Vdelta2 T-cells assessed as activation of Vgamma9/Vdelta2 T-cells by upregulation of CD69 and CD25 after 18 hrs2018Journal of medicinal chemistry, 03-08, Volume: 61, Issue:5
Synthesis and Biological Evaluation of ( E)-4-Hydroxy-3-methylbut-2-enyl Phosphate (HMBP) Aryloxy Triester Phosphoramidate Prodrugs as Activators of Vγ9/Vδ2 T-Cell Immune Responses.
AID317318Effect on proliferation of human T cell expressing Vgamma9Vdelta2 receptor in cynomolgus monkey co-treated with IL2 assessed as circulating T cells in blood at 0.02 mg/kg, iv2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1441712Activation of BTN3A1 in human Vgamma9Vdelta2 T cells assessed as induction of interleukin 2 stimulated cell proliferation by measuring increase in gammadelta T cell receptor positive cells at 0.1 uM treated for 72 hrs measured on day 11 post last treatmen2017Journal of medicinal chemistry, 03-23, Volume: 60, Issue:6
Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.
AID1724596Induction of IL2-stimulated IFNgamma production in human PBMC-derived Vgamma9Vdelta2 T cells co-cultured with compound treated human K562 cells measured after 240 mins by ELISA2020Bioorganic & medicinal chemistry, 10-01, Volume: 28, Issue:19
Potent double prodrug forms of synthetic phosphoantigens.
AID1724594Induction of IL2-stimulated IFNgamma production in human PBMC-derived Vgamma9Vdelta2 T cells co-cultured with compound treated human K562 cells measured after 4 mins by ELISA2020Bioorganic & medicinal chemistry, 10-01, Volume: 28, Issue:19
Potent double prodrug forms of synthetic phosphoantigens.
AID216549Effective concentration range of compound was determined in stimulating Vgamma9 / Vdelta2 T cell2003Bioorganic & medicinal chemistry letters, Apr-07, Volume: 13, Issue:7
Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates Its potential to activate human gammadelta T cells but does not lead to competitive antagonism.
AID1569595Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 full interaction domain (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins in presence of magnesium by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1569604Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 R499A mutant (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1676477Binding affinity to BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assessed as induction of Vgamma9/Vdelta2 T cell mediated T-24 cell lysis co-expressing GFP at 10 pM preincubated 4 hrs followed by compound washout and subsequent Vgamma9Vdelta2 T ce
AID1569585Activation of BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells assessed as induction of IL2-stimulated cell proliferation by measuring increase in CD3+ cells at 0.1 uM preincubated for 3 days followed by 11 days incubation post compound washout and su2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID317321Effect on proliferation of human T cell expressing Vgamma9Vdelta2 receptor in cynomolgus monkey co-treated with IL2 assessed as circulating T cells in blood at 2.5 mg/kg, iv2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1676487Binding affinity to BTN3A1 in human PBMC-derived Vgamma9/Vdelta2 T cells
AID1494449Binding affinity to butyrophilin 3A1 in human Vgamma9/Vdelta2 T-cells assessed as activation of Vgamma9/Vdelta2 T-cell-mediated lysis of human T24 cells preincubated for 4 hrs followed by compound washout measured after 18 hrs2018Journal of medicinal chemistry, 03-08, Volume: 61, Issue:5
Synthesis and Biological Evaluation of ( E)-4-Hydroxy-3-methylbut-2-enyl Phosphate (HMBP) Aryloxy Triester Phosphoramidate Prodrugs as Activators of Vγ9/Vδ2 T-Cell Immune Responses.
AID317322Drug level in iv dosed rat assessed as recovered compound after 7 days2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID317325Chemical stability assessed as degradation at 25 degC after 7 days2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1569602Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 R442A mutant (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1569600Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 W421A mutant (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID317326Chemical stability assessed as degradation at 60 degC after 24 hrs2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1441713Activation of BTN3A1 in human Vgamma9Vdelta2 T cells assessed as induction of interleukin 2 stimulated cell proliferation treated for 72 hrs measured on day 11 post last treatment by flow cytometry2017Journal of medicinal chemistry, 03-23, Volume: 60, Issue:6
Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.
AID1441711Activation of BTN3A1 in human Vgamma9Vdelta2 T cells assessed as induction of interleukin 2 stimulated cell proliferation by measuring increase in CD3 positive cells at 0.1 uM treated for 72 hrs measured on day 11 post last treatment by flow cytometry2017Journal of medicinal chemistry, 03-23, Volume: 60, Issue:6
Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.
AID1569594Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 full interaction domain (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins in presence of calcium by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID1494455Upregulation of CD69/CD25 levels in human CD8-positive T cells expressing alpha-beta TCR2018Journal of medicinal chemistry, 03-08, Volume: 61, Issue:5
Synthesis and Biological Evaluation of ( E)-4-Hydroxy-3-methylbut-2-enyl Phosphate (HMBP) Aryloxy Triester Phosphoramidate Prodrugs as Activators of Vγ9/Vδ2 T-Cell Immune Responses.
AID317320Effect on proliferation of human T cell expressing Vgamma9Vdelta2 receptor in cynomolgus monkey co-treated with IL2 assessed as circulating T cells in blood at 10 mg/kg, iv2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.
AID1569601Displacement of GDP-BODIPY from C-terminal 6His-tagged BTN3A1 M424A mutant (unknown origin) expressed in Escherichia coli BL21 (DE) measured after 60 mins by fluorescence polarization assay2019Journal of medicinal chemistry, 07-25, Volume: 62, Issue:14
Probing the Ligand-Binding Pocket of BTN3A1.
AID221770Effective concentration to activate gammadelta T cells2002Journal of medicinal chemistry, Oct-24, Volume: 45, Issue:22
Quantitative structure--activity relations for gammadelta T cell activation by phosphoantigens.
AID1441734Activation of BTN3A1 in human Vgamma9Vdelta2 T cells assessed as induction of T effector cells mediated K562 cell lysis preincubated with K562 cells for 2 hrs followed by T effector cell addition measured after 4 hrs2017Journal of medicinal chemistry, 03-23, Volume: 60, Issue:6
Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.
AID1386826Binding affinity to BTN3A1 in human PBMC assessed as stimulation of Vgamma9 Vdelta2 T cells at 100 nM incubated for 3 days and measured after 11 days post compound removal by flow cytometry2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Phosphonamidate Prodrugs of a Butyrophilin Ligand Display Plasma Stability and Potent Vγ9 Vδ2 T Cell Stimulation.
AID1386821Binding affinity to BTN3A1 in human PBMC assessed as stimulation of Vgamma9 Vdelta2 T cells incubated for 3 days and measured after 11 days post compound removal by flow cytometry2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Phosphonamidate Prodrugs of a Butyrophilin Ligand Display Plasma Stability and Potent Vγ9 Vδ2 T Cell Stimulation.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2005Journal of the American Chemical Society, Jan-19, Volume: 127, Issue:2
A crystallographic investigation of phosphoantigen binding to isopentenyl pyrophosphate/dimethylallyl pyrophosphate isomerase.
AID1811Experimentally measured binding affinity data derived from PDB2005Journal of the American Chemical Society, Jan-19, Volume: 127, Issue:2
A crystallographic investigation of phosphoantigen binding to isopentenyl pyrophosphate/dimethylallyl pyrophosphate isomerase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (29.41)29.6817
2010's8 (47.06)24.3611
2020's4 (23.53)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.86

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.86 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.75 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
2,3-diphosphoglycerate
2,3-Diphosphoglycerate: A highly anionic organic phosphate which is present in human red blood cells at about the same molar ratio as hemoglobin. It binds to deoxyhemoglobin but not the oxygenated form, therefore diminishing the oxygen affinity of hemoglobin. This is essential in enabling hemoglobin to unload oxygen in tissue capillaries. It is also an intermediate in the conversion of 3-phosphoglycerate to 2-phosphoglycerate by phosphoglycerate mutase (EC 5.4.2.1). (From Stryer Biochemistry, 4th ed, p160; Enzyme Nomenclature, 1992, p508). 2,3-bisphosphoglyceric acid : A bisphosphoglyceric acid that is glyceric acid carrying two phospho substituents at positions 2 and 3.		2.0110bisphosphoglyceric acid;
tetronic acid derivative		human metabolite
phosphoglycolate
phosphoglycolate: RN given refers to parent acid. 2-phosphoglycolic acid : The O-phospho derivative of glycolic acid.		2.0110carboxyalkyl phosphateEscherichia coli metabolite;
mouse metabolite
3,3-dimethylallyl pyrophosphate
3,3-dimethylallyl pyrophosphate: isomeric with isopentenyl pyrophosphate. prenyl diphosphate : A prenol phosphate that is a phosphoantigen comprising the O-pyrophosphate of prenol.		2.4620prenol phosphateepitope;
Escherichia coli metabolite;
mouse metabolite;
phosphoantigen
alpha-glycerophosphoric acid
[no description available]		2.0110glycerol monophosphatealgal metabolite;
human metabolite
phenol
[no description available]		2.1710phenolsantiseptic drug;
disinfectant;
human xenobiotic metabolite;
mouse metabolite
isopentenyl pyrophosphate
isopentenyl pyrophosphate: substrate for isopentenyl pyrophosphate isomerase; RN given refers to unlabeled cpd; a nonpeptide mycobacterial antigen that stimulates gamma delta T cells. isopentenyl diphosphate : A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.		3.1550prenol phosphateantigen;
antioxidant;
epitope;
Escherichia coli metabolite;
mouse metabolite;
phosphoantigen
alendronate
alendronic acid : A 1,1-bis(phosphonic acid) that is methanebis(phosphonic acid) in which the two methylene hydrogens are replaced by hydroxy and 3-aminopropyl groups.		2.01101,1-bis(phosphonic acid);
primary amino compound		bone density conservation agent;
EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor
pamidronate
[no description available]		2.0110phosphonoacetic acid
1-naphthol
1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.		2.1710naphtholgenotoxin;
human xenobiotic metabolite
tetraethyl pyrophosphate
tetraethyl pyrophosphate: topical agent for glaucoma; structure		2.0110organic diphosphate
2-naphthol
2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.		2.1710naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
thiazoles
[no description available]		2.41101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
methylphosphate
methylphosphate: specifically and irreversibly inactivates inorganic pyrophosphatase; RN given refers to parent cpd. methyl dihydrogen phosphate : A monoalkyl phosphate having methyl as the alkyl group.		2.0110monoalkyl phosphate;
one-carbon compound		algal metabolite;
epitope;
phosphoantigen
sodium pyrophosphate
sodium pyrophosphate: RN refers to diphosphoric acid, tetra-Na salt; structure. sodium diphosphate : An inorganic sodium salt comprised of a diphosphate(4-) anion and four sodium(1+) cations. More commonly known as tetrasodium pyrophosphate, it finds much use in the food industry as an emulsifier and in dental hygiene as a calcium-chelating salt.		2.2110inorganic sodium saltchelator;
food emulsifier;
food thickening agent
ibandronic acid
Ibandronic Acid: Aminobisphosphonate that is a potent inhibitor of BONE RESORPTION. It is used in the treatment of HYPERCALCEMIA associated with malignancy, for the prevention of fracture and bone complications in patients with breast cancer and bone metastases, and for the treatment and prevention of POSTMENOPAUSAL OSTEOPOROSIS.		2.0110
zoledronic acid
Zoledronic Acid: An imidobisphosphonate inhibitor of BONE RESORPTION that is used for the treatment of malignancy-related HYPERCALCEMIA; OSTEITIS DEFORMANS; and OSTEOPOROSIS.. zoledronic acid : An imidazole compound having a 2,2-bis(phosphono)-2-hydroxyethane-1-yl substituent at the 1-position.		2.17101,1-bis(phosphonic acid);
imidazoles		bone density conservation agent
biotin
vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.		7.1510biotins;
vitamin B7		coenzyme;
cofactor;
Escherichia coli metabolite;
fundamental metabolite;
human metabolite;
mouse metabolite;
nutraceutical;
prosthetic group;
Saccharomyces cerevisiae metabolite
ribose 1-phosphate
ribose 1-phosphate: RN given refers to (D)-isomer. alpha-D-ribose 1-phosphate : The 1-phospho derivative of alpha-D-ribose.		2.0110D-ribose 1-phosphateEscherichia coli metabolite
2-phospholactic acid
2-phospholactic acid: RN given refers to cpd without isomeric designation. 2-phospholactic acid : The phosphoric acid monoester resulting from formal condensation of the alcohol group of lactic acid with phosphoric acid.		2.0110carboxyalkyl phosphate
bromohydrin pyrophosphate
bromohydrin pyrophosphate: stimulates human gammadelta T cells; structure in first osurce. bromohydrin pyrophosphate : An alkyl diphosphate having bromohydrin as the alkyl group.		2.7130alkyl diphosphate;
organobromine compound		phosphoantigen
sulfur
Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.		2.0710chalcogen;
nonmetal atom		macronutrient
alendronate sodium
[no description available]		2.0110
ConditionIndicatedRelationship StrengthStudiesTrials
Bladder Cancer
[description not available]		02.1710
Urinary Bladder Neoplasms
Tumors or cancer of the URINARY BLADDER.		02.1710