Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:51:58 UTC |
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HMDB ID | HMDB0015412 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Sulfacytine |
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Description | Sulfacytine is a short-acting sulfonamide. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Sulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid. |
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Structure | CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17) |
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Synonyms | Value | Source |
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Renoquid | Kegg | Sulphacytine | Generator | 1-Ethyl N4-sulfanilylcytosin | HMDB | 1-Ethyl-N-sulfanilylcytosine | HMDB | N-Sulfanilyl-L-ethylcytosine | HMDB | N(1)-(1-Ethyl-1,2-dihydro-2-oxo-4-pyrimidinyl)sulfanilamide | HMDB |
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Chemical Formula | C12H14N4O3S |
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Average Molecular Weight | 294.33 |
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Monoisotopic Molecular Weight | 294.078661024 |
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IUPAC Name | 4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide |
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Traditional Name | sulfacytine |
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CAS Registry Number | 17784-12-2 |
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SMILES | CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O |
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InChI Identifier | InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17) |
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InChI Key | SIBQAECNSSQUOD-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzenesulfonamides |
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Direct Parent | Aminobenzenesulfonamides |
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Alternative Parents | |
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Substituents | - Aminobenzenesulfonamide
- Benzenesulfonyl group
- Aniline or substituted anilines
- Pyrimidone
- Hydropyrimidine
- Pyrimidine
- Organosulfonic acid amide
- Imidolactam
- Organic sulfonic acid or derivatives
- Organosulfonic acid or derivatives
- Sulfonyl
- Aminosulfonyl compound
- Heteroaromatic compound
- Organoheterocyclic compound
- Azacycle
- Hydrocarbon derivative
- Organic nitrogen compound
- Amine
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organic oxygen compound
- Organonitrogen 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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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 | Not Available |
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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 | 166.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.47 g/L | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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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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Sulfacytine,1TMS,isomer #1 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O | 3095.0 | Semi standard non polar | 33892256 | Sulfacytine,1TMS,isomer #1 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O | 2839.4 | Standard non polar | 33892256 | Sulfacytine,1TMS,isomer #1 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O | 4028.7 | Standard polar | 33892256 | Sulfacytine,1TMS,isomer #2 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O | 2793.4 | Semi standard non polar | 33892256 | Sulfacytine,1TMS,isomer #2 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O | 2740.2 | Standard non polar | 33892256 | Sulfacytine,1TMS,isomer #2 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O | 4189.5 | Standard polar | 33892256 | Sulfacytine,2TMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O | 2851.7 | Semi standard non polar | 33892256 | Sulfacytine,2TMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O | 2872.8 | Standard non polar | 33892256 | Sulfacytine,2TMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O | 3672.0 | Standard polar | 33892256 | Sulfacytine,2TMS,isomer #2 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O | 2865.2 | Semi standard non polar | 33892256 | Sulfacytine,2TMS,isomer #2 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O | 2898.6 | Standard non polar | 33892256 | Sulfacytine,2TMS,isomer #2 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O | 3775.2 | Standard polar | 33892256 | Sulfacytine,3TMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O | 2735.0 | Semi standard non polar | 33892256 | Sulfacytine,3TMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O | 2957.1 | Standard non polar | 33892256 | Sulfacytine,3TMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O | 3475.2 | Standard polar | 33892256 | Sulfacytine,1TBDMS,isomer #1 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3341.2 | Semi standard non polar | 33892256 | Sulfacytine,1TBDMS,isomer #1 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3047.6 | Standard non polar | 33892256 | Sulfacytine,1TBDMS,isomer #1 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 4033.0 | Standard polar | 33892256 | Sulfacytine,1TBDMS,isomer #2 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O | 3094.6 | Semi standard non polar | 33892256 | Sulfacytine,1TBDMS,isomer #2 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O | 2971.0 | Standard non polar | 33892256 | Sulfacytine,1TBDMS,isomer #2 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O | 4175.3 | Standard polar | 33892256 | Sulfacytine,2TBDMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3319.1 | Semi standard non polar | 33892256 | Sulfacytine,2TBDMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3318.1 | Standard non polar | 33892256 | Sulfacytine,2TBDMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3723.9 | Standard polar | 33892256 | Sulfacytine,2TBDMS,isomer #2 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3392.4 | Semi standard non polar | 33892256 | Sulfacytine,2TBDMS,isomer #2 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3330.4 | Standard non polar | 33892256 | Sulfacytine,2TBDMS,isomer #2 | CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3770.4 | Standard polar | 33892256 | Sulfacytine,3TBDMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3468.3 | Semi standard non polar | 33892256 | Sulfacytine,3TBDMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3615.8 | Standard non polar | 33892256 | Sulfacytine,3TBDMS,isomer #1 | CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O | 3610.4 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Sulfacytine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0699-5970000000-fcf781e9c8d92fac41fe | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sulfacytine 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 10V, Positive-QTOF | splash10-002b-0490000000-f5ef4a3fc969278d52f3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 20V, Positive-QTOF | splash10-0ab9-1930000000-cca50de9df755740762c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 40V, Positive-QTOF | splash10-0gb9-9100000000-0e0f88d63239781bb3dd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 10V, Negative-QTOF | splash10-0006-0190000000-5678559deb4df7cd70e5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 20V, Negative-QTOF | splash10-0zml-1590000000-f8b5e6818df98f145ac8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 40V, Negative-QTOF | splash10-05bf-9710000000-fe4bdffade8dc1239d0f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 10V, Positive-QTOF | splash10-052b-0790000000-858e661c23fea2a281ef | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 20V, Positive-QTOF | splash10-0005-1950000000-8efb821459dc738d0bc6 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 40V, Positive-QTOF | splash10-0006-9310000000-af522fa67546c379ca39 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 10V, Negative-QTOF | splash10-0006-0290000000-14fefa164bb613784c58 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 20V, Negative-QTOF | splash10-00dm-0920000000-252f3b6dbf3bb165dace | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sulfacytine 40V, Negative-QTOF | splash10-052f-6900000000-bc74a22245fbb377bce2 | 2021-10-11 | Wishart Lab | View Spectrum |
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