Identification |
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YMDB ID | YMDB00396 |
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Name | L-Dihydroorotic acid |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | L-Dihydroorotic acid, also known as (S)-4,5-dihydroorotate or dihydro-L-orotate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L-Dihydroorotic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Dihydroorotic acid exists in all living species, ranging from bacteria to humans. |
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Structure | |
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Synonyms | - (S)-2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid
- (S)-4,5-Dihydroorotate
- (S)-Dihydroorotate
- 2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid
- 4,5-dihydro-L-orotate
- 5-dihydroorotate
- Dihydro-L-orotate
- Dihydro-L-orotic acid
- L-Dihydroorotate
- L-Dihydroorotic acid
- (S)-4,5-Dihydroorotic acid
- 4,5-Dihydroorotic acid, (L)-isomer
- 5,6-Dihydroorotate
- 4,5-Dihydroorotic acid
- 4,5-Dihydroorotic acid, (DL)-isomer
- Dihydroorotate
- Hydroorotic acid
- 4,5-Dihydroorotic acid, (D)-isomer
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CAS number | 5988-19-2 |
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Weight | Average: 158.1121 Monoisotopic: 158.03275669 |
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InChI Key | UFIVEPVSAGBUSI-REOHCLBHSA-N |
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InChI | InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)/t2-/m0/s1 |
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IUPAC Name | (4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid |
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Traditional IUPAC Name | L-dihydroorotic acid |
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Chemical Formula | C5H6N2O4 |
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SMILES | [H]OC(=O)[C@@]1([H])N([H])C(=O)N([H])C(=O)C1([H])[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acids and derivatives |
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Alternative Parents | |
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Substituents | - Alpha-amino acid or derivatives
- N-acyl urea
- Pyrimidone
- Ureide
- 1,3-diazinane
- Pyrimidine
- Dicarboximide
- Urea
- Carbonic acid derivative
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | |
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SMPDB Reactions | Not Available |
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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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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0zfs-1920000000-6e853bcb65fafce1f25e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-000j-1900000000-4c364adc386eb5db027b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0zfs-0930000000-373786ac89c19f0cbc6b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-0pb9-2951000000-9975cf569acb6854865d | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-005a-5938000000-6f622577780cd53385eb | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0zfs-1920000000-6e853bcb65fafce1f25e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0pb9-2951000000-9975cf569acb6854865d | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-005a-5938000000-6f622577780cd53385eb | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000f-9400000000-248b8d6d703ba73c2058 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-03di-3900000000-b0776f22820e6e570a09 | 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) | splash10-059i-9700000000-681989bb70419ccf0e26 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-c08746cfe4c476aff942 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-006x-9000000000-c59db6f9b23380c30e8c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-2920000000-1c8b06ed77517a0e8606 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-03k9-4900000000-5b6e94f06ce0c97ad751 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03dl-9800000000-933d1487bcb4d23e2a5a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0006-9000000000-34d46a3aa973f0412a45 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00di-9100000000-0004fe5f5bbd6b1f1a41 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-9000000000-9accaaec3ae3b41f55a9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00di-9000000000-41686c36ddb271856b65 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-074u-9500000000-c4e4ed6470c8ad78afec | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-8214c2f0d9df1ac7c79c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-022i-9400000000-257f9838bad9d558822c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-2e8bea71938b0c3ee548 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9100000000-8cda59dcc275524136f4 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-2ddb498acc970a567f6b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dl-5900000000-4b73ae512e57466dd4e6 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9100000000-d6c31a36d6fe5c68d9e1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-1900000000-c84801951eaa1da750f7 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-4ae1d11ab20f903606c3 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-aec3a40befb20e60f21b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-b0c5e687f246809cdae9 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ox-6900000000-cb60b796898e6ca4336d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-fccf5d7216b23cffed7a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-06r6-0900000000-86736ae769db7bc83c23 | 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 | 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 | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C 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
- Guyonvarch, A., Nguyen-Juilleret, M., Hubert, J. C., Lacroute, F. (1988). "Structure of the Saccharomyces cerevisiae URA4 gene encoding dihydroorotase." Mol Gen Genet 212:134-141.2897615
- Nagy, M., Lacroute, F., Thomas, D. (1992). "Divergent evolution of pyrimidine biosynthesis between anaerobic and aerobic yeasts." Proc Natl Acad Sci U S A 89:8966-8970.1409592
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Synthesis Reference: | Not Available |
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External Links: | |
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