Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-22 06:57:14 UTC |
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Update Date | 2016-11-09 01:16:09 UTC |
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Accession Number | CHEM020248 |
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Identification |
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Common Name | 2,4-Diamino-6-hydroxypyrimidine |
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Class | Small Molecule |
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Description | 2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective inhibitor of GTP cyclohydrolase I (GTPCH) that restricts the de novo synthesis of tetrahydrobiopterin (BH4) or the BH4 precursor in vascular smooth muscle cells (VSMC). (PMID 12883322). 2,4-Diamino-6-hydroxypyrimidine also inhibits nitric oxide (NO) in both Interferon-gamma (IFN-gamma) and antigen (Ag)/IgE (Ag/IgE) systems, increasing Mast cells (MC) degranulation. (PMID 14514683). Sepiapterin, a precursor to tetrahydrobiopterin in the salvage pathway, completely reverses the effect of 2,4-diamino-6-hydroxypyrimidine on neuronal NO-synthase (nNOS) ubiquitylation. (PMID 16216381). |
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Contaminant Sources | - FooDB Chemicals
- ToxCast & Tox21 Chemicals
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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2,4-diamino-6-Pyrimidinone | HMDB | 2,6-diamino-4(1H)-Pyrimidinone | HMDB | 2,6-diamino-4(3H)-Pyrimidinone | HMDB | 2,6-diamino-4-Hydroxypyrimidine | HMDB | 2,6-diamino-4-Pyrimidinol | HMDB | 2,6-Diaminopyrimidin-4-one | HMDB | 6-Aminoisocytosine | HMDB | 6-Hydroxy-2,4-pyrimidinediamine | HMDB | 2,4-DAHP | MeSH, HMDB | 2,4-Diaminohypoxanthine sulfate | MeSH, HMDB | DHAP-2,4 | MeSH, HMDB | 2,4-Diaminohypoxanthine | MeSH, HMDB | 2,4-Diamino-6-hydroxypyrimidine | MeSH |
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Chemical Formula | C4H6N4O |
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Average Molecular Mass | 126.117 g/mol |
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Monoisotopic Mass | 126.054 g/mol |
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CAS Registry Number | 56-06-4 |
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IUPAC Name | 2,6-diamino-1,4-dihydropyrimidin-4-one |
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Traditional Name | 6-aminoisocytosine |
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SMILES | NC1=CC(=O)N=C(N)N1 |
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InChI Identifier | InChI=1S/C4H6N4O/c5-2-1-3(9)8-4(6)7-2/h1H,(H5,5,6,7,8,9) |
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InChI Key | SWELIMKTDYHAOY-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. 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 | Pyrimidones |
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Alternative Parents | |
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Substituents | - Aminopyrimidine
- Pyrimidone
- Hydropyrimidine
- Vinylogous amide
- Heteroaromatic compound
- Azacycle
- Amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-4900000000-1e063b05226e8896a663 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0900000000-00f9b9f5ce4b5cad43b0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014i-9000000000-40b3a1d8e972f237c69e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-9000000000-bedf37ced21617434775 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-5e3c38e0a0a648095bbd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-2900000000-b08fbf010a25872f527e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000f-9000000000-37474e4ea02c53c6dbbf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-2900000000-33f401e4d08da16fa38f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-3900000000-d44c471a63adfa036032 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000x-9000000000-515cef0906e879cd3b67 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-17e49b273de10b22c70b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002f-9200000000-f64008e5d2bac657c5a4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9000000000-8fe725f865981c7d648f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-7900000000-8ac5ea6d8dbacebc0edf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-76ada99b8a779fab63d8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9000000000-9c42190a2a1ee0031cf7 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0002128 |
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FooDB ID | FDB022857 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | 6500 |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 2840 |
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ChEBI ID | 804916 |
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PubChem Compound ID | 2944 |
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Kegg Compound ID | Not Available |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp. | 2. Yoshida M, Nakanishi N, Wang X, Hattori Y: Exogenous biopterins requirement for iNOS function in vascular smooth muscle cells. J Cardiovasc Pharmacol. 2003 Aug;42(2):197-203. | 3. Gilchrist M, Hesslinger C, Befus AD: Tetrahydrobiopterin, a critical factor in the production and role of nitric oxide in mast cells. J Biol Chem. 2003 Dec 12;278(50):50607-14. Epub 2003 Sep 26. | 4. Kamada Y, Jenkins GJ, Lau M, Dunbar AY, Lowe ER, Osawa Y: Tetrahydrobiopterin depletion and ubiquitylation of neuronal nitric oxide synthase. Brain Res Mol Brain Res. 2005 Dec 7;142(1):19-27. Epub 2005 Oct 10. |
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