2.0 2012-05-31 13:02:37 -0600 2015-09-13 12:56:09 -0600 ECMDB00961 M2MDB000210 Farnesyl pyrophosphate Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia ω,E,E-farnesyl diphosphate ω,e,e-farnesyl diphosphate ω,e,e-farnesyl diphosphoric acid (2E,6E)-Farnesyl diphosphate (2E,6E)-Farnesyl diphosphoric acid (2E,6E)-Farnesyl pyrophosphate (2E,6E)-Farnesyl pyrophosphoric acid (E,E)-farnesyl diphosphate (all-E)-Farnesyl diphosphate (all-e)-Farnesyl diphosphoric acid (E,E)-Farnesyl diphosphate (e,e)-Farnesyl diphosphoric acid (E,E)-Farnesyl pyrophosphate (e,e)-Farnesyl pyrophosphoric acid 2-trans,6-trans-farnesyl diphosphate 2-trans,6-trans-Farnesyl diphosphate 2-trans,6-trans-Farnesyl diphosphoric acid 2-trans,6-trans-Farnesyl pyrophosphate 2-trans,6-trans-Farnesyl pyrophosphoric acid all-trans-farnesyl diphosphate trans, trans-farnesyl diphosphate All-trans-farnesyl diphosphate all-trans-Farnesyl diphosphoric acid All-trans-Farnesyl pyrophosphate all-trans-Farnesyl pyrophosphoric acid Farnesyl diphosphate Farnesyl diphosphoric acid Farnesyl pyrophosphate Farnesyl pyrophosphoric acid Farnesyl-PP FPP Omega,E,E-farnesyl diphosphate Omega,e,e-farnesyl diphosphoric acid Trans, trans-Farnesyl diphosphate trans, trans-Farnesyl diphosphoric acid Trans-Farnesyl pyrophosphate trans-Farnesyl pyrophosphoric acid Trans-trans-Farnesyl diphosphate trans-trans-Farnesyl diphosphoric acid Trans-trans-Farnesyl pyrophosphate trans-trans-Farnesyl pyrophosphoric acid C15H28O7P2 382.3261 382.131026274 {[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid farnesyl diphosphate 13058-04-3 CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+ VWFJDQUYCIWHTN-YFVJMOTDSA-N Solid Membrane logp 2.40 ALOGPS logs -3.68 ALOGPS solubility 8.07e-02 g/l ALOGPS logp 3.62 ChemAxon pka_strongest_acidic 1.77 ChemAxon iupac {[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid ChemAxon average_mass 382.3261 ChemAxon mono_mass 382.131026274 ChemAxon smiles CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O ChemAxon formula C15H28O7P2 ChemAxon inchi InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+ ChemAxon inchikey VWFJDQUYCIWHTN-YFVJMOTDSA-N ChemAxon polar_surface_area 113.29 ChemAxon refractivity 96.73 ChemAxon polarizability 37.94 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Terpenoid backbone biosynthesis ec00900 Metabolic pathways eco01100 Porphyrin metabolism The metabolism of porphyrin begins with with glutamic acid being processed by an ATP-driven glutamyl-tRNA synthetase by interacting with hydrogen ion and tRNA(Glu), resulting in amo, pyrophosphate and L-glutamyl-tRNA(Glu) Glutamic acid. Glutamic acid can be obtained as a result of L-glutamate metabolism pathway, glutamate / aspartate : H+ symporter GltP, glutamate:sodium symporter or a glutamate / aspartate ABC transporter . L-glutamyl-tRNA(Glu) Glutamic acid interacts with a NADPH glutamyl-tRNA reductase resulting in a NADP, a tRNA(Glu) and a (S)-4-amino-5-oxopentanoate. This compound interacts with a glutamate-1-semialdehyde aminotransferase resulting a 5-aminolevulinic acid. This compound interacts with a porphobilinogen synthase resulting in a hydrogen ion, water and porphobilinogen. The latter compound interacts with water resulting in hydroxymethylbilane synthase resulting in ammonium, and hydroxymethylbilane. Hydroxymethylbilane can either be dehydrated to produce uroporphyrinogen I or interact with a uroporphyrinogen III synthase resulting in a water molecule and a uroporphyrinogen III. Uroporphyrinogen I interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a coproporphyrinogen I Uroporphyrinogen III can be metabolized into precorrin by interacting with a S-adenosylmethionine through a siroheme synthase resulting in hydrogen ion, an s-adenosylhomocysteine and a precorrin-1. On the other hand, Uroporphyrinogen III interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a Coproporphyrinogen III. Precorrin-1 reacts with a S-adenosylmethionine through a siroheme synthase resulting in a S-adenosylhomocysteine and a Precorrin-2. The latter compound is processed by a NAD dependent uroporphyrin III C-methyltransferase [multifunctional] resulting in a NADH and a sirohydrochlorin. This compound then interacts with Fe 2+ uroporphyrin III C-methyltransferase [multifunctional] resulting in a hydrogen ion and a siroheme. The siroheme is then processed in sulfur metabolism pathway. Uroporphyrinogen III can be processed in anaerobic or aerobic condition. Anaerobic: Uroporphyrinogen III interacts with an oxygen molecule, a hydrogen ion through a coproporphyrinogen III oxidase resulting in water, carbon dioxide and protoporphyrinogen IX. The latter compound then interacts with an 3 oxygen molecule through a protoporphyrinogen oxidase resulting in 3 hydrogen peroxide and a Protoporphyrin IX Aerobic: Uroporphyrinogen III reacts with S-adenosylmethionine through a coproporphyrinogen III dehydrogenase resulting in carbon dioxide, 5-deoxyadenosine, L-methionine and protoporphyrinogen IX. The latter compound interacts with a meanquinone through a protoporphyrinogen oxidase resulting in protoporphyrin IX. The protoporphyrin IX interacts with Fe 2+ through a ferrochelatase resulting in a hydrogen ion and a ferroheme b. The ferroheme b can either be incorporated into the oxidative phosphorylation as a cofactor of the enzymes involved in that pathway or it can interact with hydrogen peroxide through a catalase HPII resulting in a heme D. Heme D can then be incorporated into the oxidative phosphyrlation pathway as a cofactor of the enzymes involved in that pathway. Ferroheme b can also interact with water and a farnesyl pyrophosphate through a heme O synthase resulting in a release of pyrophosphate and heme O. Heme O is then incorporated into the Oxidative phosphorylation pathway. PW000936 Metabolic 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: 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 trans, trans-farnesyl diphosphate biosynthesis PWY-5123 octaprenyl diphosphate biosynthesis PWY-5783 di-trans,poly-cis-undecaprenyl phosphate biosynthesis PWY-5785 Specdb::CMs 2694 Specdb::CMs 173893 Specdb::NmrOneD 308731 Specdb::NmrOneD 308732 Specdb::NmrOneD 308733 Specdb::NmrOneD 308734 Specdb::NmrOneD 308735 Specdb::NmrOneD 308736 Specdb::NmrOneD 308737 Specdb::NmrOneD 308738 Specdb::NmrOneD 308739 Specdb::NmrOneD 308740 Specdb::NmrOneD 308741 Specdb::NmrOneD 308742 Specdb::NmrOneD 308743 Specdb::NmrOneD 308744 Specdb::NmrOneD 308745 Specdb::NmrOneD 308746 Specdb::NmrOneD 308747 Specdb::NmrOneD 308748 Specdb::NmrOneD 308749 Specdb::NmrOneD 308750 Specdb::MsMs 24932 Specdb::MsMs 24933 Specdb::MsMs 24934 Specdb::MsMs 31490 Specdb::MsMs 31491 Specdb::MsMs 31492 Specdb::MsMs 1471330 Specdb::MsMs 1473174 Specdb::MsMs 1473175 Specdb::MsMs 1473176 Specdb::MsMs 1473177 Specdb::MsMs 1473178 Specdb::MsMs 1473179 Specdb::MsMs 1473180 Specdb::MsMs 1473404 Specdb::MsMs 2739028 Specdb::MsMs 2739029 Specdb::MsMs 2739030 Specdb::MsMs 2969821 Specdb::MsMs 2969822 Specdb::MsMs 2969823 HMDB00961 445713 393270 C00448 17407 FARNESYL-PP FPP Farnesyl pyrophosphate Keseler, I. 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(1977), 193 pp. http://hmdb.ca/system/metabolites/msds/000/000/865/original/HMDB00961.pdf?1358462186 Geranyltranstransferase P22939 ISPA_ECOLI ispA http://ecmdb.ca/proteins/P22939.xml Undecaprenyl pyrophosphate synthase P60472 UPPS_ECOLI uppS http://ecmdb.ca/proteins/P60472.xml Octaprenyl-diphosphate synthase P0AD57 ISPB_ECOLI ispB http://ecmdb.ca/proteins/P0AD57.xml Protoheme IX farnesyltransferase P0AEA5 CYOE_ECOLI cyoE http://ecmdb.ca/proteins/P0AEA5.xml Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphate RXN-8999 Geranyl-PP + Isopentenyl pyrophosphate + Geranyl diphosphate <> Farnesyl pyrophosphate + Pyrophosphate R02003 FPPSYN-RXN Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate R07411 HEMEOSYN-RXN Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate R09248 Geranyl-PP + Isopentenyl pyrophosphate <> Pyrophosphate + Farnesyl pyrophosphate R02003 FPPSYN-RXN Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate R06447 Heme + Water + Farnesyl pyrophosphate <> Heme O + Pyrophosphate R07411 HEMEOSYN-RXN Geranyl-PP + Isopentenyl pyrophosphate > Farnesyl pyrophosphate + Pyrophosphate FPPSYN-RXN Farnesyl pyrophosphate + Isopentenyl pyrophosphate > all-trans-octaprenyl diphosphate + Pyrophosphate RXN-8992 Farnesyl pyrophosphate + Isopentenyl pyrophosphate > Undecaprenyl diphosphate + Pyrophosphate RXN-8999 Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate ferroheme b + Water + Farnesyl pyrophosphate + Farnesyl pyrophosphate > Heme O + Pyrophosphate PW_R003487 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 + Water + Heme > Heme O + Pyrophosphate Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate