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Identification |
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YMDB ID | YMDB00257 |
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Name | Guanosine diphosphate |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Guanosine diphosphate, also known as 5'-GDP or 5'-diphosphate, guanosine, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. Guanosine diphosphate is a moderately basic compound (based on its pKa). Guanosine diphosphate exists in all living species, ranging from bacteria to humans. In yeast, guanosine diphosphate is involved in the metabolic pathway called n-glycan biosynthesis pathway. |
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Structure | |
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Synonyms | - 5'-GDP
- GDP
- Guanosine 5'-(trihydrogen pyrophosphate)
- Guanosine 5'-diphosphate
- Guanosine 5'-pyrophosphate
- Guanosine mono(trihydrogen diphosphate)
- Guanosine pyrophosphate
- guanosine-5'-diphosphate
- guanosine-diphosphate
- ppG
- Guanosine 5'-diphosphoric acid
- Guanosine diphosphoric acid
- 5'-Diphosphate, guanosine
- Diphosphate, guanosine 5'-trihydrogen
- Guanosine 5' diphosphate
- Guanosine 5' trihydrogen diphosphate
- 5'-Trihydrogen diphosphate, guanosine
- Diphosphate, guanosine
- Guanosine 5'-trihydrogen diphosphate
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CAS number | 146-91-8 |
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Weight | Average: 443.2005 Monoisotopic: 443.024329371 |
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InChI Key | QGWNDRXFNXRZMB-UUOKFMHZSA-N |
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InChI | InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1 |
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IUPAC Name | [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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Traditional IUPAC Name | {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid |
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Chemical Formula | C10H15N5O11P2 |
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SMILES | [H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N1C([H])=NC2=C1N=C(N([H])[H])N([H])C2=O)C([H])([H])OP(=O)(O[H])OP(=O)(O[H])O[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Purine ribonucleotides |
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Direct Parent | Purine ribonucleoside diphosphates |
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Alternative Parents | |
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Substituents | - Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-oxopurine
- Hypoxanthine
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- Pyrimidone
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Pyrimidine
- Vinylogous amide
- Tetrahydrofuran
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- 1,2-diol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Organooxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Alcohol
- Amine
- Organic oxygen compound
- Primary amine
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | - Golgi
- mitochondrion
- nucleus
- cytoplasm
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Organoleptic Properties | Not Available |
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SMPDB Pathways |
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KEGG Pathways | |
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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 | splash10-004i-5930200000-bdc0893316c12636a495 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0229-6393250000-a57b7f18975223fa888c | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udl-0900600000-5c7173a5771dfefadc5e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-0900000000-d38af29994fa5108c331 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0udi-0900000000-3072d857dcc8a1b2cbaa | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0kdi-5901100000-24a5c807e53370f01d0c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0udi-0900000000-6399eaf97235815c4cb7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0udi-0900000000-80f8e0b42526cc03fef4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0pdl-2902100000-027fb059218f84756c35 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0pdl-2902200000-876f01fe6b2be177ac75 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0pdl-3902100000-054557b6d17ed830f7e5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9600000000-2f85040f9b280383ec8a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-054o-5904800000-e39f64dcf91afa144498 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0001900000-cdce5e7d8986462632b2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0kdi-5901100000-ba4bded631640c110a56 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0911300000-fcd49d8a5e9d3dc3f933 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-ded96f0f499982ac1ab0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0900000000-ac93e95f54842f42e273 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f6x-0900800000-1ed1199fdace4d1b4d80 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zir-3900000000-b9aeef613c34fe99a48c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-f630c9237e72a76d3d63 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900200000-fa2d42f6050d9ab60119 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-ed3d09503a04c850d595 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0900000000-19a5699334c495daa4e5 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0001900000-7b9b9276c5e39c703f8c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9202300000-fa0fbdc8c265ee49a371 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9100000000-278ab542160fff840256 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C 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 | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D 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
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- 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
- Romero, P. A., Lussier, M., Sdicu, A. M., Bussey, H., Herscovics, A. (1997). "Ktr1p is an alpha-1,2-mannosyltransferase of Saccharomyces cerevisiae. Comparison of the enzymic properties of soluble recombinant Ktr1p and Kre2p/Mnt1p produced in Pichia pastoris." Biochem J 321 ( Pt 2):289-295.9020857
- Vozza, A., Blanco, E., Palmieri, L., Palmieri, F. (2004). "Identification of the mitochondrial GTP/GDP transporter in Saccharomyces cerevisiae." J Biol Chem 279:20850-20857.14998997
- Lobsanov, Y. D., Romero, P. A., Sleno, B., Yu, B., Yip, P., Herscovics, A., Howell, P. L. (2004). "Structure of Kre2p/Mnt1p: a yeast alpha1,2-mannosyltransferase involved in mannoprotein biosynthesis." J Biol Chem 279:17921-17931.14752117
- Gao, X. D., Kaigorodov, V., Jigami, Y. (1999). "YND1, a homologue of GDA1, encodes membrane-bound apyrase required for Golgi N- and O-glycosylation in Saccharomyces cerevisiae." J Biol Chem 274:21450-21456.10409709
- Lussier, M., Sdicu, A. M., Camirand, A., Bussey, H. (1996). "Functional characterization of the YUR1, KTR1, and KTR2 genes as members of the yeast KRE2/MNT1 mannosyltransferase gene family." J Biol Chem 271:11001-11008.8631921
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Synthesis Reference: | Edlin, Gordon; Donini, P. Synthesis of guanosine 5'-diphosphate, 2'-(or 3'-) diphosphate, and related nucleotides in a variety of physiological conditions. Journal of Biological Chemistry (1971), 246(13), 4371-3. |
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