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| prenyl diphosphate |
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| CHEBI:16057 |
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| A prenol phosphate that is a phosphoantigen comprising the O-pyrophosphate of prenol. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:12280, CHEBI:26245, CHEBI:23803, CHEBI:42074, CHEBI:8394, CHEBI:4616, CHEBI:18108, CHEBI:14883, CHEBI:14169, CHEBI:341937
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| No supplier information found for this compound. |
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Molfile
XML
SDF
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more structures >>
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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js
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| InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8) |
| CBIDRCWHNCKSTO-UHFFFAOYSA-N |
| CC(C)=CCOP(O)(=O)OP(O)(O)=O |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
epitope
The 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.
phosphoantigen
Any antigen that is a phosphorylated microbial metabolite which activates an immune response in humans.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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View more via ChEBI Ontology
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3-methylbut-2-en-1-yl trihydrogen diphosphate
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2-Isopentenyl diphosphate
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KEGG COMPOUND
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3,3-dimethylallyl pyrophosphate
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ChemIDplus
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3-methylbut-2-enyl phosphono hydrogen phosphate
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DrugBank
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delta-Prenyl diphosphate
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KEGG COMPOUND
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delta2-Isopentenyl diphosphate
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KEGG COMPOUND
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Dimethylallyl diphosphate
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KEGG COMPOUND
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DIMETHYLALLYL DIPHOSPHATE
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PDBeChem
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Dimethylallyl pyrophosphate
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ChEMBL
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Dimethylallyl pyrophosphate
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KEGG COMPOUND
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DMAPP
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KEGG COMPOUND
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DMAPP
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ChEBI
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Monoprenyl diphosphate
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KEGG COMPOUND
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Prenol pyrophosphate
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KEGG COMPOUND
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Prenyl diphosphate
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KEGG COMPOUND
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C00007294
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KNApSAcK
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C00235
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KEGG COMPOUND
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C17627
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KEGG COMPOUND
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DB01785
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DrugBank
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DMA
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PDBeChem
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LMPR01010001
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LIPID MAPS
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| View more database links |
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1713791
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Beilstein Registry Number
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Beilstein
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1713791
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Reaxys Registry Number
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Reaxys
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358-72-5
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CAS Registry Number
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KEGG COMPOUND
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358-72-5
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CAS Registry Number
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ChemIDplus
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Yang T, Fang L, Rimando AM, Sobolev V, Mockaitis K, Medina-Bolivar F (2016)
A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway.
Plant physiology 171, 2483-2498 [PubMed:27356974]
[show Abstract]
Prenylated stilbenoids synthesized in some legumes exhibit plant pathogen defense properties and pharmacological activities with potential benefits to human health. Despite their importance, the biosynthetic pathways of these compounds remain to be elucidated. Peanut (Arachis hypogaea) hairy root cultures produce a diverse array of prenylated stilbenoids upon treatment with elicitors. Using metabolic inhibitors of the plastidic and cytosolic isoprenoid biosynthetic pathways, we demonstrated that the prenyl moiety on the prenylated stilbenoids derives from a plastidic pathway. We further characterized, to our knowledge for the first time, a membrane-bound stilbenoid-specific prenyltransferase activity from the microsomal fraction of peanut hairy roots. This microsomal fraction-derived resveratrol 4-dimethylallyl transferase utilizes 3,3-dimethylallyl pyrophosphate as a prenyl donor and prenylates resveratrol to form arachidin-2. It also prenylates pinosylvin to chiricanine A and piceatannol to arachidin-5, a prenylated stilbenoid identified, to our knowledge, for the first time in this study. This prenyltransferase exhibits strict substrate specificity for stilbenoids and does not prenylate flavanone, flavone, or isoflavone backbones, even though it shares several common features with flavonoid-specific prenyltransferases. | Weise SE, Li Z, Sutter AE, Corrion A, Banerjee A, Sharkey TD (2013)
Measuring dimethylallyl diphosphate available for isoprene synthesis.
Analytical biochemistry 435, 27-34 [PubMed:23262281]
[show Abstract]
Dimethylallyl diphosphate (DMADP) is a central metabolite in isoprenoid metabolism, but it is difficult to measure. Three different methods for measuring DMADP are compared, and a new method based on the conversion of DMADP to isoprene using recombinant isoprene synthase is introduced. Mass spectrometry is reliable but does not distinguish between DMADP and isopentenyl diphosphate. Acid hydrolysis is reliable for measuring DMADP in bacterial extracts but overestimates DMADP in plant samples. To measure the DMADP in chloroplasts, light minus dark measurements are normally used. Chloroplast DMADP amounts measured using acid hydrolysis and a mass spectrometric method were comparable in this assay. Post-illumination isoprene emission tended to slightly overestimate chloroplast DMADP concentration. The DMADP pool size in bacteria is highly regulated, consistent with previous observations made with plants. DMADP is a very labile metabolite, but four methods described here allow measurements of samples from plants and bacteria. The use of recombinant isoprene synthase can greatly simplify the analysis. The various techniques tested here have advantages and disadvantages, and it is useful to have more than one method available when studying biological isoprene production. | Bang S, Yoo S, Yang TJ, Cho H, Hwang SW (2012)
Nociceptive and pro-inflammatory effects of dimethylallyl pyrophosphate via TRPV4 activation.
British journal of pharmacology 166, 1433-1443 [PubMed:22300296]
[show Abstract]
Background and purposeSensory neuronal and epidermal transient receptor potential ion channels (TRPs) serve an important role as pain sensor molecules. While many natural and synthetic ligands for sensory TRPs have been identified, little is known about the endogenous activator for TRPV4. Recently, we reported that endogenous metabolites produced by the mevalonate pathway regulate the activities of sensory neuronal TRPs. Here, we show that dimethylallyl pyrophosphate (DMAPP), a substance produced by the same pathway is an activator of TRPV4.Experimental approachWe examined the effects of DMAPP on sensory TRPs using Ca²⁺ imaging and whole-cell electrophysiology experiments with a heterologous expression system (HEK293T cells transfected with individual TRP channels), cultured sensory neurons and keratinocytes. We then evaluated nociceptive behavioural and inflammatory changes upon DMAPP administration in mice in vivo.Key resultsIn the HEK cell heterologous expression system, cultured sensory neurons and keratinocytes, µM concentrations of DMAPP activated TRPV4. Agonistic and antagonistic potencies of DMAPP for other sensory TRP channels were examined and activation of TRPV3 by camphor was found to be inhibited by DMAPP. In vivo assays, intraplantar injection of DMAPP acutely elicited nociceptive flinches that were prevented by pretreatment with TRPV4 blockers, indicating that DMAPP is a novel pain-producing molecule through TRPV4 activation. Further, DMAPP induced acute inflammation and noxious mechanical hypersensitivities in a TRPV4-dependent manner.Conclusions and implicationsOverall, we found a novel sensory TRP acting metabolite and suggest that its use may help to elucidate the physiological role of TRPV4 in nociception and associated inflammation. | Fisher AJ, Rosenstiel TN, Shirk MC, Fall R (2001)
Nonradioactive assay for cellular dimethylallyl diphosphate.
Analytical biochemistry 292, 272-279 [PubMed:11355861]
[show Abstract]
A sensitive, nonradioactive method was developed to measure cellular levels of dimethylallyl diphosphate (DMAPP), a central intermediate of isoprenoid metabolism in nature. The assay is based on the hydrolysis of DMAPP in acid to the volatile hydrocarbon isoprene (2-methyl-1,3-butadiene), with subsequent analysis of isoprene by headspace gas chromatography with reduction gas detection. In the assay, cell samples are directly acidified with 4 M H(2)SO(4) in sealed reaction vials. Therefore, there is no need to extract metabolites, purify them, and keep them stable prior to analysis, and degradative enzymatic activities are destroyed. DMAPP levels of 23 +/- 4 nmol (g fresh weight)(-1) [ca. 85 nmol (g dry weight)(-1)] and 80 +/- 14 nmol (g fresh weight)(-1) [ca. 296 nmol (g dry weight)(-1)] were measured in dark- and light-adapted leaves of Populus deltoides (Eastern cottonwood), respectively. Evidence is presented to show that DMAPP is the major leaf metabolite giving rise to isoprene following acid hydrolysis. DMAPP levels in Bacillus subtilis and Saccharomyces cerevisiae were determined to be 40.8 +/- 16.7 pmol (OD(600))(-1) [ca. 638 pmol (mg dry weight)(-1)] and 6.3 +/- 3.7 pmol (OD(600))(-1) [ca. 139 pmol (mg dry weight)(-1)], respectively. The method should be suitable for any cell or tissue type and isolated cellular organelles. | Dieli F, Sireci G, Di Sano C, Romano A, Titone L, Di Carlo P, Ivanyi J, Fourniè JJ, Salerno A (2000)
Ligand-specific alphabeta and gammadelta T cell responses in childhood tuberculosis.
The Journal of infectious diseases 181, 294-301 [PubMed:10608778]
[show Abstract]
The alphabeta and gammadelta T cell responses were analyzed in the peripheral blood of children affected by active tuberculosis (TB) and in healthy children who tested positive (PPD+) or negative (PPD-) for purified protein derivative. PPD+ healthy and diseased children responded equally well to PPD in vitro. In contrast, only 18% of PPD+ TB patients responded to peptide p38G derived from the 38-kDa protein of Mycobacterium tuberculosis. Analysis of the whole gammadelta T cell population and of its Vgamma9/Vdelta2 subset showed similar frequencies in PPD+ children with TB and in healthy PPD+ and PPD- children. Vgamma9/Vdelta2 cells from children with TB responded to 5 different phosphoantigens similarly to those from healthy PPD+ children, but healthy PPD- children responded very poorly. Chemotherapy had contrasting effects on the tested lymphocyte population, represented by increase of alphabeta and decline of Vgamma9/Vdelta2 T cell responses. T cell responses in childhood TB may be similar to those in adult TB. |
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