2.02012-05-31 13:50:27 -06002015-06-03 15:53:57 -0600ECMDB01347M2MDB000348Isopentenyl pyrophosphateIsopentenyl 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-PPΔ3-isopentenyl-PPΔ<SUP>3</SUP>-isopentenyl-PP3-Methyl-3-butenyl pyrophosphate3-Methyl-3-butenyl pyrophosphoric acidDelta(3)-Isopentenyl-PPDelta-3-Isopentenyl pyrophosphatDelta3-isopentenyl diphosphatedelta3-Isopentenyl diphosphoric acidDelta3-isopentenyl-PPDelta3-methyl-3-butenyl diphosphatedelta3-Methyl-3-butenyl diphosphoric acidDiphosphate mono(3-methyl-3-butenyl) esterDiphosphorate mono(3-methyl-3-butenyl) esterDiphosphoric acid mono(3-methyl-3-butenyl) esterIPPIPRIsopentenyl diphosphateIsopentenyl diphosphoric acidIsopentenyl pyrophosphateIsopentenyl pyrophosphoric acidIsopentenyl-ppMono(3-methyl-3-butenyl) diphosphatemono(3-Methyl-3-butenyl) diphosphoric acidδ(3)-Isopentenyl-PPδ-3-Isopentenyl pyrophosphatδ3-Isopentenyl diphosphateδ3-Isopentenyl diphosphoric acidδ3-Isopentenyl-PPδ3-Methyl-3-butenyl diphosphateδ3-Methyl-3-butenyl diphosphoric acidC5H12O7P2246.0921246.005825762({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acidisopentenyl-diphosphate358-71-4CC(=C)CCO[P@](O)(=O)OP(O)(O)=OInChI=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-NSolidCytosollogp0.04logs-1.57solubility6.69e+00 g/llogp0.2pka_strongest_acidic1.78iupac({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acidaverage_mass246.0921mono_mass246.005825762smilesCC(=C)CCO[P@](O)(=O)OP(O)(O)=OformulaC5H12O7P2inchiInChI=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)inchikeyNUHSROFQTUXZQQ-UHFFFAOYSA-Npolar_surface_area113.29refractivity48.21polarizability19.01rotatable_bond_count6acceptor_count5donor_count3physiological_charge-2formal_charge0Terpenoid backbone biosynthesisec00900Metabolic pathwayseco01100Secondary Metabolites: Ubiquinol biosynthesisThe 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.
PW000981MetabolicSecondary 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 pathwayPW000975MetabolicSecondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesisThe 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 diphosphatePW000958MetabolicSecondary Metabolites: Ubiquinol biosynthesis 2The 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.PW002036Metabolicmethylerythritol phosphate pathwayNONMEVIPP-PWY<i>trans, trans</i>-farnesyl diphosphate biosynthesisPWY-5123octaprenyl diphosphate biosynthesisPWY-5783di-<i>trans</i>,poly-<i>cis</i>-undecaprenyl phosphate biosynthesisPWY-5785Specdb::CMs3259Specdb::CMs136294Specdb::CMs144028Specdb::NmrOneD87772Specdb::NmrOneD87773Specdb::NmrOneD87774Specdb::NmrOneD87775Specdb::NmrOneD87776Specdb::NmrOneD87777Specdb::NmrOneD87778Specdb::NmrOneD87779Specdb::NmrOneD87780Specdb::NmrOneD87781Specdb::NmrOneD87782Specdb::NmrOneD87783Specdb::NmrOneD87784Specdb::NmrOneD87785Specdb::NmrOneD87786Specdb::NmrOneD87787Specdb::NmrOneD87788Specdb::NmrOneD87789Specdb::NmrOneD87790Specdb::NmrOneD87791Specdb::MsMs23561Specdb::MsMs23562Specdb::MsMs23563Specdb::MsMs30359Specdb::MsMs30360Specdb::MsMs30361Specdb::MsMs1471857Specdb::MsMs1471858Specdb::MsMs1471859Specdb::MsMs1471860Specdb::MsMs1471861Specdb::MsMs1471862Specdb::MsMs1471863Specdb::MsMs1471864Specdb::MsMs1471865Specdb::MsMs1471866Specdb::MsMs1471867Specdb::MsMs1471868Specdb::MsMs1471869Specdb::MsMs1471870Specdb::MsMs1471871Specdb::MsMs1471872Specdb::MsMs1471873Specdb::MsMs1471874Specdb::MsMs1471875HMDB013471158C0012916584DELTA3-ISOPENTENYL-PPIPEIsopentenyl pyrophosphateKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Daubenberger 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):6421-30.11714808Kao, 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 LetGeranyltranstransferaseP22939ISPA_ECOLIispAhttp://ecmdb.ca/proteins/P22939.xmlUndecaprenyl pyrophosphate synthaseP60472UPPS_ECOLIuppShttp://ecmdb.ca/proteins/P60472.xml4-hydroxy-3-methylbut-2-enyl diphosphate reductaseP62623ISPH_ECOLIispHhttp://ecmdb.ca/proteins/P62623.xmlIsopentenyl-diphosphate Delta-isomeraseQ46822IDI_ECOLIidihttp://ecmdb.ca/proteins/Q46822.xmlOctaprenyl-diphosphate synthaseP0AD57ISPB_ECOLIispBhttp://ecmdb.ca/proteins/P0AD57.xmlHydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NADR08209Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphateRXN-8999Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + PyrophosphateR01658GPPSYN-RXNGeranyl-PP + Isopentenyl pyrophosphate + Geranyl diphosphate <> Farnesyl pyrophosphate + PyrophosphateR02003FPPSYN-RXNIsopentenyl pyrophosphate <> DimethylallylpyrophosphateR01123IPPISOM-RXNFarnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 PyrophosphateR09248Dimethylallylpyrophosphate + Isopentenyl pyrophosphate <> Pyrophosphate + Geranyl-PPR01658GPPSYN-RXNGeranyl-PP + Isopentenyl pyrophosphate <> Pyrophosphate + Farnesyl pyrophosphateR02003FPPSYN-RXN1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion <> Isopentenyl pyrophosphate + NADP + WaterR05884Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphateR06447Isopentenyl pyrophosphate + NAD + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + Hydrogen ionR08209Geranyl-PP + Isopentenyl pyrophosphate > Farnesyl pyrophosphate + PyrophosphateFPPSYN-RXNIsopentenyl pyrophosphate + NAD(P)<sup>+</sup> + Water < 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H + Hydrogen ionISPH2-RXNFarnesyl pyrophosphate + Isopentenyl pyrophosphate > all-<i>trans</i>-octaprenyl diphosphate + PyrophosphateRXN-8992Farnesyl pyrophosphate + Isopentenyl pyrophosphate > Undecaprenyl diphosphate + PyrophosphateRXN-8999Isopentenyl pyrophosphate > DimethylallylpyrophosphateFarnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphateIsopentenyl pyrophosphate + NAD(P)(+) + Water > 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)HFarnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphateIsopentenyl pyrophosphate + NAD + NADP + Water + Dimethylallylpyrophosphate <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + NADPH + Hydrogen ionR05884 R08209 1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + Hydrogen ion + NADPH + NADPH > Water + NADPH + Isopentenyl pyrophosphate + Isopentenyl pyrophosphatePW_R003693Isopentenyl pyrophosphate + Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate + DimethylallylpyrophosphatePW_R003695Dimethylallylpyrophosphate + Isopentenyl pyrophosphate + Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Pyrophosphate + Geranyl-PP + Geranyl-PPPW_R003696Geranyl-PP + Isopentenyl pyrophosphate + Geranyl-PP + Isopentenyl pyrophosphate > Pyrophosphate + Farnesyl pyrophosphate + Farnesyl pyrophosphatePW_R003697Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphatePW_R003698Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate + Octaprenyl diphosphatePW_R003699Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphateDimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + PyrophosphateHydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NADFarnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 PyrophosphateFarnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphateDimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate