Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:57:18 -0600 |
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Update Date | 2015-09-13 12:56:12 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | 5-Methylcytosine |
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Description | 5-Methylcytosine is a methylated form of cytosine in which a methyl group is attached to carbon 5, altering its structure without altering its base-pairing properties. 5-Methylcytosine is an epigenetic modification formed by the action of DNA methyltransferases. Its function varies significantly among species. In bacteria, 5-methylcytosine can be found at a variety of sites, and is often used as a marker to protect DNA from being cut by native methylation-sensitive restriction enzymes. (Wikipedia) |
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Structure | |
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Synonyms: | - 2(1H)-Pyrimidinone, 4-amino-5-methyl-
- 4-Amino-5-methyl-2(1H)-Pyrimidinone
- 4-Amino-5-methyl-2-(1H)-Pyrimidinone
- 4-Amino-5-methyl-2-pyrimidinol
- 5-Methyl-Cytosine
- 5-Methylcytosine
- 5-Methylcytosine>96
- Cytosine, 5-methyl-
- Cytosine, 5-methyl- (VAN)
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Chemical Formula: | C5H7N3O |
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Weight: | Average: 125.1286 Monoisotopic: 125.058911861 |
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InChI Key: | LRSASMSXMSNRBT-UHFFFAOYSA-N |
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InChI: | InChI=1S/C5H7N3O/c1-3-2-7-5(9)8-4(3)6/h2H,1H3,(H3,6,7,8,9) |
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CAS number: | 554-01-8 |
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IUPAC Name: | 6-amino-5-methyl-1,2-dihydropyrimidin-2-one |
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Traditional IUPAC Name: | 5-methylcytosine |
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SMILES: | CC1=C(N)NC(=O)N=C1 |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazines |
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Sub Class | Pyrimidines and pyrimidine derivatives |
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Direct Parent | Hydroxypyrimidines |
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Alternative Parents | |
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Substituents | - Hydroxypyrimidine
- Imidolactam
- Hydropyrimidine
- Heteroaromatic compound
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic 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: | 270 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 34.5 mg/mL [MERCK INDEX (1996)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | |
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KEGG Pathways: | |
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EcoCyc Pathways: | Not Available |
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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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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-001i-4900000000-73c143c463607343e59d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0udi-3950000000-332af504e32034e6ea67 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-0059-3934000000-6eb3288b70641721809a | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-2970000000-9bae58e66a60384a4b47 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-1890000000-547f8dd8c93c7e653e8c | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-1960000000-eb731b2f4381755effcf | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fk9-8970000000-8e71ebdb5a55e2426344 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001i-4900000000-73c143c463607343e59d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-3950000000-332af504e32034e6ea67 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0059-3934000000-6eb3288b70641721809a | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-6900000000-cb2ceeb7f5bd935faa19 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0089-9600000000-aa86d3c38a48514c2a4d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-0900000000-045ecf28f36874a7b146 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-0900000000-17d0aa6deb42e4974069 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0a59-6900000000-2ba4efb5ece00114fe13 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0a59-9300000000-1a71fa46d7b0fd6269f3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0zgi-9000000000-61088abf446eafee8dd2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-0900000000-a1c6199ce762a7fb6855 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-1900000000-e85c44ed5cd560d17d60 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-004i-0900000000-7ce4adb73357e05cc8b5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-004i-3900000000-b2832b699d97e3d2bfaa | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-008c-9300000000-7427dfe8792596330411 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-004i-0900000000-bb76593a12a5655ad756 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-011e24f4e333703cb5cb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-004i-0900000000-a84f7e26153cb2255dc5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-004i-0900000000-7e7dde0bdedd7250d617 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-bb789d0a4d3bce440b9a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-004i-1900000000-e85c44ed5cd560d17d60 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-efc3476af90e31d453f8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0a7i-5900000000-e991fa239913a7dfb67d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-63ea0e71e72b5a60804b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-5900000000-8b8c84afdb6f620a4706 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pb9-9300000000-a069a5c69d4eb3143d95 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-1900000000-04225473bccf83af00d8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00e9-9500000000-e5c525a63af7fcf81390 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-8eb88ca79a619c9357ae | 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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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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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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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
- Pfeifer GP, You YH, Besaratinia A: Mutations induced by ultraviolet light. Mutat Res. 2005 Apr 1;571(1-2):19-31. Epub 2005 Jan 20. Pubmed: 15748635
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Synthesis Reference: | Umetani, Hideki. Method for preparing 5-methylcytosine. Jpn. Kokai Tokkyo Koho (2006), 8 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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