Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:53:06 -0600 |
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Update Date | 2015-06-03 15:54:08 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Undecaprenyl diphosphate |
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Description | Undecaprenyl diphosphate belongs to the class of Polyprenyl Phosphates. These are prenol lipids in which the phosphate group is linked to one end of the polyprenol moiety. (inferred from compound structure)C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate) is an essential molecule involved in construction of the bacterial peptidoglycan cell wall. (WikiPedia) |
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Structure | |
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Synonyms: | - Bactoprenyl pyrophosphate
- Bactoprenyl pyrophosphoric acid
- Di-trans,octa-cis-undecaprenyl diphosphate
- Di-trans-poly-cis-undecaprenyl diphosphate
- Di-trans,octa-cis-undecaprenyl diphosphate
- Di-trans,octa-cis-undecaprenyl diphosphoric acid
- Di-trans-poly-cis-undecaprenyl diphosphate
- Di-trans-poly-cis-undecaprenyl diphosphoric acid
- Diphosphate mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester
- Diphosphorate mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester
- Diphosphoric acid mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester
- Undecaprenyl diphosphate
- Undecaprenyl diphosphoric acid
- Undecaprenyl pyrophosphate
- Undecaprenyl pyrophosphate (ambiguous)
- Undecaprenyl pyrophosphoric acid
- Undecaprenyl pyrophosphoric acid (ambiguous)
- Undecaprenyl-PP
- Undecaprenyl-PP (ambiguous)
- UndPP
- UPP
- UPP (ambiguous)
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Chemical Formula: | C55H92O7P2 |
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Weight: | Average: 927.2623 Monoisotopic: 926.631828322 |
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InChI Key: | NTXGVHCCXVHYCL-RDQGWRCRSA-N |
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InChI: | InChI=1S/C55H92O7P2/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-61-64(59,60)62-63(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H,59,60)(H2,56,57,58)/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+,55-43+ |
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CAS number: | 23-13-2 |
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IUPAC Name: | {[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid |
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Traditional IUPAC Name: | undecaprenyl pyrophosphate |
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SMILES: | CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\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 bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety. |
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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 | Polyprenols |
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Direct Parent | Bactoprenol diphosphates |
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Alternative Parents | |
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Substituents | - Polyterpenoid
- Bactoprenol diphosphate
- Polyprenyl diphosphate
- Polyprenyl monophosphate
- 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: | Not Available |
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Charge: | -2 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Membrane |
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Reactions: | Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > Hydrogen ion + Undecaprenyl diphosphate + three linked disacharide pentapeptide murein units (uncrosslinked, middle of chain)2 Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine >2 Hydrogen ion +2 Undecaprenyl diphosphate + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain)Water + Undecaprenyl diphosphate > Hydrogen ion + Phosphate + Undecaprenyl phosphate(O16 antigen)x2 undecaprenyl diphosphate + O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x3 undecaprenyl diphosphate + Undecaprenyl diphosphate(O16 antigen)x3 undecaprenyl diphosphate + O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x4 undecaprenyl diphosphate + Undecaprenyl diphosphate2 O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x2 undecaprenyl diphosphate + Undecaprenyl diphosphate(enterobacterial common antigen)x2 undecaprenyl-diphosphate + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x3 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphate(enterobacterial common antigen)x3 undecaprenyl-diphosphate + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x4 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphate2 Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x2 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphateFarnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphatecore oligosaccharide lipid A + Undecaprenyl diphosphate > core oligosaccharide lipid A diphosphate + Undecaprenyl phosphatecore oligosaccharide lipid A + (enterobacterial common antigen)x4 undecaprenyl-diphosphate > (enterobacterial common antigen)x4 core oligosaccharide lipid A + Hydrogen ion + Undecaprenyl diphosphatecore oligosaccharide lipid A + (O16 antigen)x4 undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x4 core oligosaccharide lipid A + Undecaprenyl diphosphatedi-trans,poly-cis-Undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + PhosphateFarnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphateHydrogen ion + Lipid A-core + Undecaprenyl diphosphate lipid A-core 1-diphosphate + Di-trans,poly-cis-undecaprenyl phosphatea peptidoglycan + <i>N</i>-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-<i>N</i>-acetylglucosamine > Undecaprenyl diphosphate + a peptidoglycana peptidoglycan dimer (<I>meso</I>-diaminopimelate containing) + Water > a peptidoglycan with D,D cross-links (<I>meso</I>-diaminopimelate containing) + Undecaprenyl diphosphate + D-AlanineFarnesyl pyrophosphate + Isopentenyl pyrophosphate > Undecaprenyl diphosphate + PyrophosphateN-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-N-acetylglucosamine > Hydrogen ion + a peptidoglycan dimer (<I>meso</I>-diaminopimelate containing) + Undecaprenyl diphosphateUndecaprenyl diphosphate + Water > Hydrogen ion + Di-trans,poly-cis-undecaprenyl phosphate + Phosphate(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + Undecaprenyl diphosphateUndecaprenyl diphosphate + Water > di-trans,octa-cis-undecaprenyl phosphate + Inorganic phosphate[GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-g-D-Glu-L-Lys-D-Ala-D-Ala)]n-diphosphoundecaprenol + Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine <> Undecaprenyl diphosphate2 lipid II(A) > Undecaprenyl diphosphate + Hydrogen ion + a peptidoglycan dimer (meso-diaminopimelate containing)
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SMPDB Pathways: | |
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KEGG Pathways: | - Peptidoglycan biosynthesis ec00550
- Terpenoid backbone biosynthesis ec00900
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EcoCyc Pathways: | - di-trans,poly-cis-undecaprenyl phosphate biosynthesis PWY-5785
- peptidoglycan biosynthesis I (meso-diaminopimelate containing) PEPTIDOGLYCANSYN-PWY
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0100000954-8fbcdf9ba65fb4f798a4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-1000000910-edce154fa23a4d389b0f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-0011021910-1849ab2f92b33143879c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0400000009-a76202c14854f25f3701 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9400000001-55e96da13b4d53a1bb17 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-04849c4e73cca6e0f405 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000000009-1645404a3665e531266c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-2300010029-2f3b24b17d959569ec17 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-9400000000-82cd8a9cc8986cab6260 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-1100000459-f0ed52e6afe5c429d475 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052b-0001001690-18b947d234bc42e4513a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gea-0119566130-b9b2aff1eccdac589923 | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - 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. Pubmed: 22080510
- 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. Pubmed: 21097882
- Ogura K, Koyama T, Sagami H: Polyprenyl diphosphate synthases. Subcell Biochem. 1997;28:57-87. Pubmed: 9090291
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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