Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 01:38:21 UTC |
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Update date | 2015-07-21 06:59:23 UTC |
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Primary ID | FDB028348 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine |
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Description | 2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine is a methylated derivative of 2,6-Diamino-4-hydroxy-5-N-formamidopyrimidine or FapyGua. It is produced by DNA-formamidopyrimidine glycosylase (EC 3.2.2.23). This enzyme catalyzes the hydrolysis of DNA containing ring-opened 7-methylguanine residues, releasing 2,6-diamino-4-hydroxy-5-(N-methyl)formamidopyrimidine. More specifically, this enzyme catalyzes the removal of oxidized purine bases by cleaving the N-C1' glycosidic bond between the oxidized purine and the deoxyribose sugar. The reaction involves the formation of a covalent enzyme substrate intermediate. Release of the enzyme and free base by a beta-elimination or a beta, gamma-elimination mechanism results in the cleavage of the DNA backbone 3' of the apurinic (AP) site. The presence of this compound in urine is indicative of oxidative damage to DNA (oxidized purine base lesions) [HMDB] |
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CAS Number | 77440-13-2 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C6H9N5O2 |
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IUPAC name | N-(2,4-diamino-6-hydroxypyrimidin-5-yl)-N-methylformamide |
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InChI Identifier | InChI=1S/C6H9N5O2/c1-11(2-12)3-4(7)9-6(8)10-5(3)13/h2H,1H3,(H5,7,8,9,10,13) |
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InChI Key | CGWDNAFNQOBSCK-UHFFFAOYSA-N |
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Isomeric SMILES | CN(C=O)C1=C(N)N=C(N)N=C1O |
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Average Molecular Weight | 183.168 |
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Monoisotopic Molecular Weight | 183.075624557 |
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Classification |
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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 | - Aminopyrimidine
- Hydroxypyrimidine
- Hydropyrimidine
- Tertiary carboxylic acid amide
- Heteroaromatic compound
- Amino acid or derivatives
- Carboxamide group
- Azacycle
- Carboxylic acid derivative
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Amine
- Carbonyl group
- Organic nitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | 2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0kai-2900000000-a67d7f80d254667fa8ae | Spectrum | Predicted GC-MS | 2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0itd-1390000000-7af95ca919277dda70d8 | Spectrum | Predicted GC-MS | 2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-053r-0900000000-161782a982bd9e0f746b | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a59-0900000000-8aabbbca1867aa5ee470 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-9200000000-79543490b30fc623afa9 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-1a59e57626ce37c5638e | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0w29-2900000000-e8832d2c064b26923301 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9300000000-78862d713f4e4a809290 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-053r-0900000000-7cddc5f02d68b5f58fe5 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0540-0900000000-1299b98119aa35f053c7 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-007d-9200000000-3b5b503fd38c06191869 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-c5ca8ed84c0281e2cfb3 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0gw0-3900000000-4ce1f6206fd7400e51ec | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-afeccf534860ddaa88be | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 113157 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C04744 |
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Pubchem Compound ID | 127546 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB11657 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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