Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2009-01-29 12:14:58 UTC |
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Update Date | 2023-02-21 17:17:28 UTC |
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HMDB ID | HMDB0011600 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Methyladenine |
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Description | 3-Methyladenine, also known as 3-ma nucleobase, belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 3-Methyladenine exists in all living species, ranging from bacteria to humans. 3-Methyladenine has been detected, but not quantified, in several different foods, such as soft-necked garlics, chinese bayberries, burbots, amaranths, and tea. This could make 3-methyladenine a potential biomarker for the consumption of these foods. 3-Methyladenine is one of the purines damaged by alkylation and oxidation which can be recognized and excised by the human 3-methyladenine DNA glycosylase (AAG) (EC: EC3.2.2.21). |
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Structure | InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3 |
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Synonyms | Value | Source |
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3-Methyl-3H-adenine | ChEBI | 3-METHYL-3H-purin-6-ylamine | ChEBI | 6-Amino-3-methylpurine | ChEBI | 3-Methyl-3H-purin-6-amine | HMDB | 3-Methyl-3H-purin-6-amine (acd/name 4.0) | HMDB | 3-Methyl-3H-purin-6-ylamine (acd/name 4.0) | HMDB | 3-Methyl-adenine | HMDB | 3-MA nucleobase | HMDB | N(3)-Methyladenine | HMDB |
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Chemical Formula | C6H7N5 |
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Average Molecular Weight | 149.1533 |
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Monoisotopic Molecular Weight | 149.070145249 |
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IUPAC Name | 3-methyl-3H-purin-6-amine |
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Traditional Name | 3-methyladenine |
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CAS Registry Number | 5142-23-4 |
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SMILES | CN1C=NC(N)=C2N=CN=C12 |
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InChI Identifier | InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3 |
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InChI Key | FSASIHFSFGAIJM-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Imidazopyrimidines |
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Sub Class | Purines and purine derivatives |
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Direct Parent | 6-aminopurines |
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Alternative Parents | |
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Substituents | - 6-aminopurine
- Aminopyrimidine
- Imidolactam
- Pyrimidine
- Heteroaromatic compound
- Imidazole
- Azole
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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3-Methyladenine,1TMS,isomer #1 | CN1C=NC(N[Si](C)(C)C)=C2N=CN=C21 | 2037.9 | Semi standard non polar | 33892256 | 3-Methyladenine,1TMS,isomer #1 | CN1C=NC(N[Si](C)(C)C)=C2N=CN=C21 | 1854.8 | Standard non polar | 33892256 | 3-Methyladenine,1TMS,isomer #1 | CN1C=NC(N[Si](C)(C)C)=C2N=CN=C21 | 2882.3 | Standard polar | 33892256 | 3-Methyladenine,2TMS,isomer #1 | CN1C=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N=CN=C21 | 1913.9 | Semi standard non polar | 33892256 | 3-Methyladenine,2TMS,isomer #1 | CN1C=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N=CN=C21 | 1946.2 | Standard non polar | 33892256 | 3-Methyladenine,2TMS,isomer #1 | CN1C=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N=CN=C21 | 2461.0 | Standard polar | 33892256 | 3-Methyladenine,1TBDMS,isomer #1 | CN1C=NC(N[Si](C)(C)C(C)(C)C)=C2N=CN=C21 | 2258.9 | Semi standard non polar | 33892256 | 3-Methyladenine,1TBDMS,isomer #1 | CN1C=NC(N[Si](C)(C)C(C)(C)C)=C2N=CN=C21 | 2015.2 | Standard non polar | 33892256 | 3-Methyladenine,1TBDMS,isomer #1 | CN1C=NC(N[Si](C)(C)C(C)(C)C)=C2N=CN=C21 | 2927.9 | Standard polar | 33892256 | 3-Methyladenine,2TBDMS,isomer #1 | CN1C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CN=C21 | 2352.0 | Semi standard non polar | 33892256 | 3-Methyladenine,2TBDMS,isomer #1 | CN1C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CN=C21 | 2350.6 | Standard non polar | 33892256 | 3-Methyladenine,2TBDMS,isomer #1 | CN1C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CN=C21 | 2542.5 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 3-Methyladenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-0a4i-4980000000-d3e94e4150e2b870d9b2 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Methyladenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-0a4i-3890000000-235f39119df7c967e9ba | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Methyladenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0a4i-2980000000-251ceed13f156eff1fc4 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Methyladenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-0ab9-9760000000-e3d1a7f774e6bfb718ae | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Methyladenine GC-EI-TOF (Non-derivatized) | splash10-0a4i-4980000000-d3e94e4150e2b870d9b2 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Methyladenine GC-EI-TOF (Non-derivatized) | splash10-0a4i-3890000000-235f39119df7c967e9ba | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Methyladenine GC-EI-TOF (Non-derivatized) | splash10-0a4i-2980000000-251ceed13f156eff1fc4 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Methyladenine GC-EI-TOF (Non-derivatized) | splash10-0ab9-9760000000-e3d1a7f774e6bfb718ae | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Methyladenine GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dj-6900000000-26ef3d4c1c9edc2697ef | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Methyladenine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF | splash10-0udi-0900000000-b32577a48ebafc94ae9a | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF | splash10-0udi-1900000000-485f684fffa023d0050e | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF | splash10-0udi-4900000000-6b3b3dd2f2f2d875bf14 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF | splash10-0a59-9800000000-fe6c9700b9c081b8697a | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF | splash10-0udi-1900000000-b4a28f0f1bd551992615 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF | splash10-0udi-0900000000-8db506e73a05ea922d94 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOF | splash10-0udi-0900000000-f67b128eb2b6ac7139b4 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ , positive-QTOF | splash10-0udi-0900000000-b32577a48ebafc94ae9a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ , positive-QTOF | splash10-0udi-1900000000-485f684fffa023d0050e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ , positive-QTOF | splash10-0udi-4900000000-49dc94a0b10083c8230f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ , positive-QTOF | splash10-0a59-9800000000-fe6c9700b9c081b8697a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QQ , positive-QTOF | splash10-0udi-1900000000-b4a28f0f1bd551992615 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QTOF , positive-QTOF | splash10-0udi-0900000000-8db506e73a05ea922d94 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine LC-ESI-QTOF , positive-QTOF | splash10-0udi-0900000000-f67b128eb2b6ac7139b4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine , positive-QTOF | splash10-0udi-0900000000-e564522269418ab462fb | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methyladenine 30V, Positive-QTOF | splash10-0udi-0900000000-f67b128eb2b6ac7139b4 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 10V, Positive-QTOF | splash10-0udi-0900000000-53161ff2cee1a6ff34d7 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 20V, Positive-QTOF | splash10-0udi-0900000000-1ab536fe3bbb9bdfde76 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 40V, Positive-QTOF | splash10-0giv-9600000000-a22dc2c9e956ce0b2b86 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 10V, Negative-QTOF | splash10-0002-0900000000-31965d8430668c1cef72 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 20V, Negative-QTOF | splash10-006t-2900000000-1c6ebd899170870682a9 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 40V, Negative-QTOF | splash10-0pc0-5900000000-23b69a04a094c620fe7f | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 10V, Negative-QTOF | splash10-0002-0900000000-0fdae69660ea9759916e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 20V, Negative-QTOF | splash10-0002-1900000000-ca190dc061692e2ec221 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methyladenine 40V, Negative-QTOF | splash10-0006-9100000000-b683819a0ea24a91254f | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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General References | - Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
- Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
- Li M, Yang X, Wang H, Xu E, Xi Z: Inhibition of androgen induces autophagy in benign prostate epithelial cells. Int J Urol. 2014 Feb;21(2):195-9. doi: 10.1111/iju.12210. Epub 2013 Jul 2. [PubMed:23819759 ]
- Huang YT, Cheng CC, Lin TC, Chiu TH, Lai PC: Therapeutic potential of sepantronium bromide YM155 in gemcitabine-resistant human urothelial carcinoma cells. Oncol Rep. 2014 Feb;31(2):771-80. doi: 10.3892/or.2013.2882. Epub 2013 Nov 28. [PubMed:24297644 ]
- Pickard RD, Spencer BH, McFarland AJ, Bernaitis N, Davey AK, Perkins AV, Chess-Williams R, McDermott CM, Forbes A, Christie D, Anoopkumar-Dukie S: Paradoxical effects of the autophagy inhibitor 3-methyladenine on docetaxel-induced toxicity in PC-3 and LNCaP prostate cancer cells. Naunyn Schmiedebergs Arch Pharmacol. 2015 Jul;388(7):793-9. doi: 10.1007/s00210-015-1104-7. Epub 2015 Feb 24. [PubMed:25708950 ]
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