2.0 2012-05-31 13:50:27 -0600 2015-06-03 15:53:57 -0600 ECMDB01347 M2MDB000348 Isopentenyl pyrophosphate Isopentenyl pyrophosphate, IPP or isopentenyl diphosphate, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from Mevalonate-5-pyrophosphate, in a reaction catalyzed by the enzyme mevalonate-5-pyrophosphate decarboxylase. (wikipedia) δ(3)-isopentenyl-PP Δ3-isopentenyl-PP Δ3-isopentenyl-PP 3-Methyl-3-butenyl pyrophosphate 3-Methyl-3-butenyl pyrophosphoric acid Delta(3)-Isopentenyl-PP Delta-3-Isopentenyl pyrophosphat Delta3-isopentenyl diphosphate delta3-Isopentenyl diphosphoric acid Delta3-isopentenyl-PP Delta3-methyl-3-butenyl diphosphate delta3-Methyl-3-butenyl diphosphoric acid Diphosphate mono(3-methyl-3-butenyl) ester Diphosphorate mono(3-methyl-3-butenyl) ester Diphosphoric acid mono(3-methyl-3-butenyl) ester IPP IPR Isopentenyl diphosphate Isopentenyl diphosphoric acid Isopentenyl pyrophosphate Isopentenyl pyrophosphoric acid Isopentenyl-pp Mono(3-methyl-3-butenyl) diphosphate mono(3-Methyl-3-butenyl) diphosphoric acid δ(3)-Isopentenyl-PP δ-3-Isopentenyl pyrophosphat δ3-Isopentenyl diphosphate δ3-Isopentenyl diphosphoric acid δ3-Isopentenyl-PP δ3-Methyl-3-butenyl diphosphate δ3-Methyl-3-butenyl diphosphoric acid C5H12O7P2 246.0921 246.005825762 ({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid isopentenyl-diphosphate 358-71-4 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/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8) NUHSROFQTUXZQQ-UHFFFAOYSA-N Solid Cytosol logp 0.04 ALOGPS logs -1.57 ALOGPS solubility 6.69e+00 g/l ALOGPS logp 0.2 ChemAxon pka_strongest_acidic 1.78 ChemAxon iupac ({hydroxy[(3-methylbut-3-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/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8) ChemAxon inchikey NUHSROFQTUXZQQ-UHFFFAOYSA-N ChemAxon polar_surface_area 113.29 ChemAxon refractivity 48.21 ChemAxon polarizability 19.01 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Terpenoid backbone biosynthesis ec00900 Metabolic pathways eco01100 Secondary Metabolites: Ubiquinol biosynthesis The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8. PW000981 Metabolic 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 Secondary Metabolites: Ubiquinol biosynthesis 2 The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8. PW002036 Metabolic methylerythritol phosphate pathway NONMEVIPP-PWY trans, trans-farnesyl diphosphate biosynthesis PWY-5123 octaprenyl diphosphate biosynthesis PWY-5783 di-trans,poly-cis-undecaprenyl phosphate biosynthesis PWY-5785 Specdb::CMs 3259 Specdb::CMs 136294 Specdb::CMs 144028 Specdb::NmrOneD 87772 Specdb::NmrOneD 87773 Specdb::NmrOneD 87774 Specdb::NmrOneD 87775 Specdb::NmrOneD 87776 Specdb::NmrOneD 87777 Specdb::NmrOneD 87778 Specdb::NmrOneD 87779 Specdb::NmrOneD 87780 Specdb::NmrOneD 87781 Specdb::NmrOneD 87782 Specdb::NmrOneD 87783 Specdb::NmrOneD 87784 Specdb::NmrOneD 87785 Specdb::NmrOneD 87786 Specdb::NmrOneD 87787 Specdb::NmrOneD 87788 Specdb::NmrOneD 87789 Specdb::NmrOneD 87790 Specdb::NmrOneD 87791 Specdb::MsMs 23561 Specdb::MsMs 23562 Specdb::MsMs 23563 Specdb::MsMs 30359 Specdb::MsMs 30360 Specdb::MsMs 30361 Specdb::MsMs 1471857 Specdb::MsMs 1471858 Specdb::MsMs 1471859 Specdb::MsMs 1471860 Specdb::MsMs 1471861 Specdb::MsMs 1471862 Specdb::MsMs 1471863 Specdb::MsMs 1471864 Specdb::MsMs 1471865 Specdb::MsMs 1471866 Specdb::MsMs 1471867 Specdb::MsMs 1471868 Specdb::MsMs 1471869 Specdb::MsMs 1471870 Specdb::MsMs 1471871 Specdb::MsMs 1471872 Specdb::MsMs 1471873 Specdb::MsMs 1471874 Specdb::MsMs 1471875 HMDB01347 1158 C00129 16584 DELTA3-ISOPENTENYL-PP IPE Isopentenyl pyrophosphate 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 Daubenberger CA, Salomon M, Vecino W, Hubner B, Troll H, Rodriques R, Patarroyo ME, Pluschke G: Functional and structural similarity of V gamma 9V delta 2 T cells in humans and Aotus monkeys, a primate infection model for Plasmodium falciparum malaria. J Immunol. 2001 Dec 1;167(11):6421-30. 11714808 Kao, Chai-Lin; Kittleman, William; Zhang, Hua; Seto, Haruo; Liu, Hung-Wen. Stereochemical Analysis of Isopentenyl Diphosphate Isomerase Type II from Staphylococcus aureus Using Chemically Synthesized (S)- and (R)-[2-2H]Isopentenyl Diphosphates.Organic Let Geranyltranstransferase P22939 ISPA_ECOLI ispA http://ecmdb.ca/proteins/P22939.xml Undecaprenyl pyrophosphate synthase P60472 UPPS_ECOLI uppS http://ecmdb.ca/proteins/P60472.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 Octaprenyl-diphosphate synthase P0AD57 ISPB_ECOLI ispB http://ecmdb.ca/proteins/P0AD57.xml Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NAD R08209 Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphate RXN-8999 Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate R01658 GPPSYN-RXN Geranyl-PP + Isopentenyl pyrophosphate + Geranyl diphosphate <> Farnesyl pyrophosphate + Pyrophosphate R02003 FPPSYN-RXN Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate R01123 IPPISOM-RXN Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate R09248 Dimethylallylpyrophosphate + Isopentenyl pyrophosphate <> Pyrophosphate + Geranyl-PP R01658 GPPSYN-RXN Geranyl-PP + Isopentenyl pyrophosphate <> Pyrophosphate + Farnesyl pyrophosphate R02003 FPPSYN-RXN 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion <> Isopentenyl pyrophosphate + NADP + Water R05884 Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate R06447 Isopentenyl pyrophosphate + NAD + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + Hydrogen ion R08209 Geranyl-PP + Isopentenyl pyrophosphate > Farnesyl pyrophosphate + Pyrophosphate FPPSYN-RXN Isopentenyl pyrophosphate + NAD(P)+ + Water < 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H + Hydrogen ion ISPH2-RXN Farnesyl pyrophosphate + Isopentenyl pyrophosphate > all-trans-octaprenyl diphosphate + Pyrophosphate RXN-8992 Farnesyl pyrophosphate + Isopentenyl pyrophosphate > Undecaprenyl diphosphate + Pyrophosphate RXN-8999 Isopentenyl pyrophosphate > Dimethylallylpyrophosphate Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate Isopentenyl pyrophosphate + NAD(P)(+) + Water > 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate 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 > Water + NADPH + Isopentenyl pyrophosphate + Isopentenyl pyrophosphate PW_R003693 Isopentenyl pyrophosphate + Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate + Dimethylallylpyrophosphate PW_R003695 Dimethylallylpyrophosphate + Isopentenyl pyrophosphate + Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Pyrophosphate + Geranyl-PP + Geranyl-PP PW_R003696 Geranyl-PP + Isopentenyl pyrophosphate + Geranyl-PP + Isopentenyl pyrophosphate > Pyrophosphate + Farnesyl pyrophosphate + Farnesyl pyrophosphate PW_R003697 Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate PW_R003698 Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate + Octaprenyl diphosphate PW_R003699 Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NAD Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate