2.0 2012-05-31 13:45:34 -0600 2015-09-13 12:56:10 -0600 ECMDB01120 M2MDB000260 Dimethylallylpyrophosphate Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. &delta;-prenyl diphosphate &delta;-prenyl diphosphoric acid &delta;2-isopentenyl-diphosphate &delta;2-isopentenyl-diphosphoric acid 1,1-Dimethyl-4-phenylpiperazinium iodide 2-Isopentenyl diphosphate 2-Isopentenyl diphosphoric acid 3,3-Dimethylallyl pyrophosphate 3,3-Dimethylallyl pyrophosphoric acid 3-Methyl-2-Buten-1-ol pyrophosphate 3-Methyl-2-buten-1-ol pyrophosphoric acid 3-Methyl-2-Buten-1-ol trihydrogen pyrophosphate 3-Methyl-2-buten-1-ol trihydrogen pyrophosphoric acid 3-Methyl-2-butenyl pyrophosphate 3-Methyl-2-butenyl pyrophosphoric acid 3-Methylbut-2-enyl pyrophosphate 3-Methylbut-2-enyl pyrophosphoric acid Delta-Prenyl diphosphate delta-Prenyl diphosphoric acid Delta2-Isopentenyl diphosphate delta2-Isopentenyl diphosphoric acid Delta2-isopentenyl-diphosphate delta2-Isopentenyl-diphosphoric acid Di-CH3-allyl-PPi Dimethylallyl diphosphate Dimethylallyl diphosphoric acid Dimethylallyl pyrophosphate Dimethylallyl pyrophosphoric acid Dimethylallyl-diphosphate Dimethylallyl-diphosphoric acid Dimethylallyl-PP Dimethylallyl-PPi Dimethylallyl-pyrophosphate Dimethylallyl-pyrophosphoric acid Dimethylallylpyrophosphate Dimethylallylpyrophosphoric acid Diphosphate mono(3-methyl-2-butenyl) ester Diphosphorate mono(3-methyl-2-butenyl) ester Diphosphoric acid mono(3-methyl-2-butenyl) ester DMAPP DMAProP DMPP DPP IPE Prenyl diphosphate Prenyl diphosphoric acid Prenyl-diphosphate Prenyl-diphosphoric acid δ-Prenyl diphosphate δ-Prenyl diphosphoric acid δ2-Isopentenyl diphosphate δ2-Isopentenyl diphosphoric acid δ2-Isopentenyl-diphosphate δ2-Isopentenyl-diphosphoric acid C5H12O7P2 246.0921 246.005825762 ({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid dimethylallyl diphosphate 358-72-5 CC(C)=CCO[P@](O)(=O)OP(O)(O)=O 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 Solid Cytosol logp 0.30 ALOGPS logs -1.58 ALOGPS solubility 6.54e+00 g/l ALOGPS melting_point 234 - 238 oC logp 0.3 ChemAxon pka_strongest_acidic 1.77 ChemAxon iupac ({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid ChemAxon average_mass 246.0921 ChemAxon mono_mass 246.005825762 ChemAxon smiles CC(C)=CCO[P@](O)(=O)OP(O)(O)=O ChemAxon formula C5H12O7P2 ChemAxon inchi 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) ChemAxon inchikey CBIDRCWHNCKSTO-UHFFFAOYSA-N ChemAxon polar_surface_area 113.29 ChemAxon refractivity 49.13 ChemAxon polarizability 19.19 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Zeatin biosynthesis ec00908 Terpenoid backbone biosynthesis ec00900 Metabolic pathways eco01100 Secondary metabolites: isoprenoid biosynthesis (nonmevalonate pathway) The biosynthesis of isoprenoids starts with a D-glyceraldehyde 3-phosphate interacting with a hydrogen ion through a 1-deoxyxylulose-5-phosphate synthase resulting in a carbon dioxide and 1-Deoxy-D-xylulose. The latter compound then interacts with a hydrogen ion through a NADPH driven 1-deoxy-D-xylulose 5-phosphate reductoisomerase resulting in a NADP and a 2-C-methyl-D-erythritol 4-phosphate. The latter compound then interacts with a cytidine triphosphate and a hydrogen ion through a 4-diphosphocytidyl-2C-methyl-D-erythritol synthase resulting in a pyrophosphate and a 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol. The latter compound is then phosphorylated through an ATP driven 4-diphosphocytidyl-2-C-methylerythritol kinase resulting in a release of an ADP, a hydrogen ion and a 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol. The latter compound then interacts with a 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase resulting in the release of a 2-C-methyl-D-erythritol-2,4-cyclodiphosphate resulting in the release of a cytidine monophosphate and 2-C-methyl-D-erythritol-2,4-cyclodiphosphate. The latter compound then interacts with a reduced flavodoxin through a 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate synthase resulting in the release of a water molecule, a hydrogen ion, an oxidized flavodoxin and a 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate. The compound 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate can interact with an NADPH,a hydrogen ion through a 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase resulting in a NADP, a water molecule and either a Dimethylallylpyrophosphate or a Isopentenyl pyrophosphate. These two last compounds can be are isomers that can be produced through a isopentenyl diphosphate isomerase.and then get incorporated into the methylerythritol phosphate and polyisoprenoid biosynthesis pathway PW000975 Metabolic Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesis The biosynthesis of isoprenoids starts with a D-glyceraldehyde 3-phosphate interacting with a hydrogen ion through a 1-deoxyxylulose-5-phosphate synthase resulting in a carbon dioxide and 1-Deoxy-D-xylulose. The latter compound then interacts with a hydrogen ion through a NADPH driven 1-deoxy-D-xylulose 5-phosphate reductoisomerase resulting in a NADP and a 2-C-methyl-D-erythritol 4-phosphate. The latter compound then interacts with a cytidine triphosphate and a hydrogen ion through a 4-diphosphocytidyl-2C-methyl-D-erythritol synthase resulting in a pyrophosphate and a 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol. The latter compound is then phosphorylated through an ATP driven 4-diphosphocytidyl-2-C-methylerythritol kinase resulting in a release of an ADP, a hydrogen ion and a 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol. The latter compound then interacts with a 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase resulting in the release of a 2-C-methyl-D-erythritol-2,4-cyclodiphosphate resulting in the release of a cytidine monophosphate and 2-C-methyl-D-erythritol-2,4-cyclodiphosphate. The latter compound then interacts with a reduced flavodoxin through a 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate synthase resulting in the release of a water molecule, a hydrogen ion, an oxidized flavodoxin and a 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate. The compound 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate can interact with an NADPH,a hydrogen ion through a 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase resulting in a NADP, a water molecule and either a Dimethylallylpyrophosphate or a Isopentenyl pyrophosphate. These two last compounds can be are isomers that can be produced through a isopentenyl diphosphate isomerase. Dimethylallylpyrophosphate interacts with the isopentenyl pyrophosphate through a geranyl diphosphate synthase / farnesyl diphosphate synthase resulting in a pyrophosphate and a geranyl--PP. The latter compound interacts with a Isopentenyl pyrophosphate through a geranyl diphosphate synthase / farnesyl diphosphate synthase resulting in the release of a pyrophosphate and a farnesyl pyrophosphate. The latter compound interacts with isopentenyl pyrophosphate either through a undecaprenyl diphosphate synthase resulting in a release of a pyrophosphate and a di-trans,octa-cis-undecaprenyl diphosphate or through a octaprenyl diphosphate synthase resulting in a pyrophosphate and an octaprenyl diphosphate PW000958 Metabolic methylerythritol phosphate pathway NONMEVIPP-PWY <i>trans, trans</i>-farnesyl diphosphate biosynthesis PWY-5123 Specdb::CMs 3360 Specdb::CMs 167782 Specdb::NmrOneD 1645 Specdb::NmrOneD 146450 Specdb::NmrOneD 146451 Specdb::NmrOneD 146452 Specdb::NmrOneD 146453 Specdb::NmrOneD 146454 Specdb::NmrOneD 146455 Specdb::NmrOneD 146456 Specdb::NmrOneD 146457 Specdb::NmrOneD 146458 Specdb::NmrOneD 146459 Specdb::NmrOneD 146460 Specdb::NmrOneD 146461 Specdb::NmrOneD 146462 Specdb::NmrOneD 146463 Specdb::NmrOneD 146464 Specdb::NmrOneD 146465 Specdb::NmrOneD 146466 Specdb::NmrOneD 146467 Specdb::NmrOneD 146468 Specdb::NmrOneD 146469 Specdb::MsMs 20858 Specdb::MsMs 20859 Specdb::MsMs 20860 Specdb::MsMs 22409 Specdb::MsMs 22410 Specdb::MsMs 22411 Specdb::MsMs 1471326 Specdb::MsMs 2841489 Specdb::MsMs 2841490 Specdb::MsMs 2841491 Specdb::MsMs 2863941 Specdb::MsMs 2863942 Specdb::MsMs 2863943 Specdb::NmrTwoD 1586 HMDB01120 647 627 C00235 16057 CPD-4211 DMA Dimethylallylpyrophosphate Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Smith AS, Smid SD: Impaired capsaicin and neurokinin-evoked colonic motility in inflammatory bowel disease. J Gastroenterol Hepatol. 2005 May;20(5):697-704. 15853981 http://hmdb.ca/system/metabolites/msds/000/001/007/original/HMDB01120.pdf?1358463394 tRNA dimethylallyltransferase P16384 MIAA_ECOLI miaA http://ecmdb.ca/proteins/P16384.xml Geranyltranstransferase P22939 ISPA_ECOLI ispA http://ecmdb.ca/proteins/P22939.xml 4-hydroxy-3-methylbut-2-enyl diphosphate reductase P62623 ISPH_ECOLI ispH http://ecmdb.ca/proteins/P62623.xml Isopentenyl-diphosphate Delta-isomerase Q46822 IDI_ECOLI idi http://ecmdb.ca/proteins/Q46822.xml Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Dimethylallylpyrophosphate + Water + NAD R08210 Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate R01658 GPPSYN-RXN Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate R01123 IPPISOM-RXN Dimethylallylpyrophosphate + tRNA <> Pyrophosphate + tRNA containing 6-isopentenyladenosine R01122 Dimethylallylpyrophosphate + Isopentenyl pyrophosphate <> Pyrophosphate + Geranyl-PP R01658 GPPSYN-RXN Dimethylallylpyrophosphate + NADP + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion R07219 Dimethylallylpyrophosphate + NAD + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + Hydrogen ion R08210 NAD(P)⁺ + Dimethylallylpyrophosphate + Water < NAD(P)H + Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate RXN0-884 Isopentenyl pyrophosphate > Dimethylallylpyrophosphate Dimethylallylpyrophosphate + NAD(P)(+) + Water > 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H Dimethylallylpyrophosphate + tRNA > Pyrophosphate + tRNA containing 6-dimethylallyladenosine Isopentenyl pyrophosphate + NAD + NADP + Water + Dimethylallylpyrophosphate <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + NADPH + Hydrogen ion R05884 R08209 1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + Hydrogen ion + NADPH + NADPH > NADP + Water + Dimethylallylpyrophosphate + Dimethylallylpyrophosphate PW_R003694 Isopentenyl pyrophosphate + Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate + Dimethylallylpyrophosphate PW_R003695 Dimethylallylpyrophosphate + Isopentenyl pyrophosphate + Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Pyrophosphate + Geranyl-PP + Geranyl-PP PW_R003696 Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate Dimethylallylpyrophosphate + tRNA <> Pyrophosphate + tRNA containing 6-isopentenyladenosine Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate Dimethylallylpyrophosphate + tRNA <> Pyrophosphate + tRNA containing 6-isopentenyladenosine