Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:38:23 UTC |
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Updated at | 2021-08-12 19:51:54 UTC |
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NP-MRD ID | NP0002705 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Barbituric acid |
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Provided By | BMRB |
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Description | Barbituric acid, also known as barbitursaeure or malonylurea, 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. Barbituric acid exists in all living organisms, ranging from bacteria to humans. Barbituric acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 1987 (PMID: 3654008). Based on a literature review a significant number of articles have been published on Barbituric acid (PMID: 17984079) (PMID: 22139480) (PMID: 23038042) (PMID: 23915243). |
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Structure | InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9) |
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Synonyms | Value | Source |
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2,4,6(1H,3H,5H)-Pyrimidinetrione | ChEBI | Barbitursaeure | ChEBI | Malonylharnstoff | ChEBI | Malonylurea | ChEBI | Barbitate | Generator | Barbitic acid | Generator | 2,4,6(1H,3H,5H)-Pyrimidinetrione (acd/name 4.0) | HMDB | 2,4,6-(1H,3H,5H)-Pyrimidinetrione | HMDB | 2,4,6-Pyrimidinetriol | HMDB | 2,4,6-Pyrimidinetrione(1H,3H,5H) | HMDB | 2,4,6-Trihydroxypyrimidine | HMDB | 2,4,6-Trioxohexahydropyrimidine | HMDB | 6-Hydroxyuracil | HMDB | Barbiturate | HMDB | Barbitursaure | HMDB | N,N'-(1,3-dioxo-1,3-propanediyl)-urea | HMDB | NN'-(1,3-Dioxo-1,3-propanediyl)-urea | HMDB | Pyrimidine-2,4,6(1H,3H,5H)-trione | HMDB | Pyrimidinetrione | HMDB | Barbituric acid, monosodium salt | HMDB | Sodium barbiturate | HMDB |
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Chemical Formula | C4H4N2O3 |
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Average Mass | 128.0862 Da |
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Monoisotopic Mass | 128.02219 Da |
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IUPAC Name | 4,6-dihydroxy-2,5-dihydropyrimidin-2-one |
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Traditional Name | barbituric acid |
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CAS Registry Number | Not Available |
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SMILES | OC1=NC(=O)N=C(O)C1 |
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InChI Identifier | InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9) |
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InChI Key | HNYOPLTXPVRDBG-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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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 | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Azizian H, Nabati F, Sharifi A, Siavoshi F, Mahdavi M, Amanlou M: Large-scale virtual screening for the identification of new Helicobacter pylori urease inhibitor scaffolds. J Mol Model. 2012 Jul;18(7):2917-27. doi: 10.1007/s00894-011-1310-2. Epub 2011 Dec 3. [PubMed:22139480 ]
- Sen A, Ganguly B: Is dual morphology of rock-salt crystals possible with a single additive? The answer is yes, with barbituric acid. Angew Chem Int Ed Engl. 2012 Nov 5;51(45):11279-83. doi: 10.1002/anie.201206170. Epub 2012 Oct 4. [PubMed:23038042 ]
- Dong A, Sun Y, Lan S, Wang Q, Cai Q, Qi X, Zhang Y, Gao G, Liu F, Harnoode C: Barbituric acid-based magnetic N-halamine nanoparticles as recyclable antibacterial agents. ACS Appl Mater Interfaces. 2013 Aug 28;5(16):8125-33. doi: 10.1021/am402191j. Epub 2013 Aug 16. [PubMed:23915243 ]
- Harle DG, Baldo BA, Smal MA, Fisher MM: Drugs as allergens: the molecular basis of IgE binding to thiopentone. Int Arch Allergy Appl Immunol. 1987;84(3):277-83. doi: 10.1159/000234435. [PubMed:3654008 ]
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