Identification |
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YMDB ID | YMDB00359 |
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Name | 2-trans,6-trans,10-trans-geranylgeranyl diphosphate |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | 2-trans,6-trans,10-trans-Geranylgeranyl diphosphate (GPP) is a crucial compound involved in the biosynthesis of a variety of terpenoids including chlorophylls, carotenoids, tocopherols, plastoquinones, and the plant hormones gibberellin and abscisic acid. GPP is also used in posttranslational modifications of proteins (geranylgeranylation) which is important for membrane adhesion as well as the function of some proteins. [Biocyc PWY-5120] |
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Structure | |
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Synonyms | - all-trans-geranylgeranyl diphosphate
- all-trans-geranylgeranyl pyrophosphate
- Geranylgeranyl diphosphate
- geranylgeranyl pyrophosphate
- GGDP
- ggpp
- (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphate
- all-trans-Geranylgeranyl diphosphoric acid
- all-trans-Geranylgeranyl pyrophosphoric acid
- Geranylgeranyl diphosphoric acid
- Geranylgeranyl pyrophosphoric acid
- (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphoric acid
- 2-trans,6-trans,10-trans-Geranylgeranyl diphosphate
- 3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl diphosphate
- all-trans-Geranyl-geranyl-PP
- Geranylgeranyl-diphosphate
- Geranylgeraniol diphosphate
- Geranylgeranyl pyrophosphate, (Z,e,e)-isomer
- Nerylneryl diphosphate
- GGPP Diphosphate
- Geranylgeranyl pyrophosphate, 14C-labeled, (e,e,e)-isomer
- GGPP CPD
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CAS number | 6699-20-3 |
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Weight | Average: 450.4432 Monoisotopic: 450.19362653 |
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InChI Key | OINNEUNVOZHBOX-QIRCYJPOSA-N |
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InChI | InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+ |
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IUPAC Name | {[hydroxy({[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid |
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Traditional IUPAC Name | geranylgeranyl diphosphate |
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Chemical Formula | C20H36O7P2 |
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SMILES | CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Acyclic diterpenoids |
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Alternative Parents | |
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Substituents | - Acyclic diterpenoid
- Organic pyrophosphate
- Isoprenoid phosphate
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | Terpenoid backbone biosynthesis | ec00900 |  |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00p1-8966200000-998d239f267a150b43ed | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 11V, negative | splash10-0002-0000900000-e7c9a733fcef12117c3d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 15V, negative | splash10-0002-1000900000-51a8d5ce498d65e79691 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 19V, negative | splash10-004j-9000800000-4beea4fd2eb20ffa4ad9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 26V, negative | splash10-004i-9000000000-4db0a53ff36e5e4b9935 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 31V, negative | splash10-004i-9000000000-cf199ce4e78be9534fb7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 37V, negative | splash10-004i-9000000000-7867ab9db012f87e43c8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 44V, negative | splash10-004i-9000000000-be17e3662a7647d871aa | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 52V, negative | splash10-004i-9000000000-1f4ff46767d08f6c4824 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 60V, negative | splash10-004i-9000000000-d99bb72e9136380d8698 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 72V, negative | splash10-004i-9000000000-d99bb72e9136380d8698 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 31V, negative | splash10-001i-0300900000-fecb2380f7e0ec863abc | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 31V, negative | splash10-004i-9000000000-5ef060d5ec4b80c35c1a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 31V, negative | splash10-0a4i-0900000000-dc954ce23ecf1a263189 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 31V, negative | splash10-0a4i-0900000000-8ab5606bd668c2535e4d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 31V, negative | splash10-004i-9000000000-5ef060d5ec4b80c35c1a | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0fk9-1394600000-c6d91e9bfb5eeb46563e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-3592000000-c8aa1820057f6139aad8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00xs-5690000000-5fa48d769648b6310c2d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0400900000-86700e111b6b2b0215c0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-7900100000-c5c0d2a89df8d138cebb | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-0ec0eed3d4d479d9c002 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-1214900000-f698165f4dfead7c9d55 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-1189100000-6a265357a808fdf96bf8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05s1-3910000000-59003e6f3766239ee38a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0000900000-582b037b919c4a7e747f | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
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Synthesis Reference: | Not Available |
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External Links: | |
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