Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2020-02-26 21:39:52 UTC |
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HMDB ID | HMDB0014554 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Mupirocin |
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Description | Mupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations. Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance. |
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Structure | |
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Synonyms | Value | Source |
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Bactroban | ChEBI | Centany | ChEBI | Mupirocina | ChEBI | Mupirocine | ChEBI | Mupirocinum | ChEBI | Pseudomonic acid a | ChEBI | MUP | Kegg | Pseudomonate a | Generator | MRC | HMDB | Pseudomonic acid | HMDB | BRL 4910a | HMDB | Mupirocin, 14C-labeled | HMDB | Mupirocin, calcium salt (2:1), dihydrate | HMDB | 14C-Labeled mupirocin | HMDB | BRL-4910a | HMDB | Mupirocin, 14C labeled | HMDB | Mupirocin, lithium salt | HMDB | Acid, pseudomonic | HMDB | Mupirocin, calcium salt (2:1) | HMDB | Mupirocin, sodium salt | HMDB | Mupirocin calcium | MeSH |
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Chemical Formula | C26H44O9 |
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Average Molecular Weight | 500.6222 |
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Monoisotopic Molecular Weight | 500.298533006 |
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IUPAC Name | 9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid |
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Traditional Name | mupirocin |
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CAS Registry Number | 12650-69-0 |
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SMILES | C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1 |
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InChI Key | MINDHVHHQZYEEK-HBBNESRFSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-chain fatty acid
- Branched fatty acid
- Epoxy fatty acid
- Fatty acid ester
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Dicarboxylic acid or derivatives
- Oxane
- Monosaccharide
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Carboxylic acid ester
- Secondary alcohol
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Carbonyl group
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 77 - 78 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.026 g/L | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fc1-2972400000-21f057ea2a2e95898b9d | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00di-4966726000-06f4a51b9c0619130ac4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-056r-1976100000-dfa28e3b7efa7b734a99 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0bwa-3920000000-b910c0ca6dcc91904891 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-056r-1976100000-dfa28e3b7efa7b734a99 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0bwa-3920000000-b910c0ca6dcc91904891 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-1342920000-677def34a6e414632f7e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0670-6981300000-69aa4a4ddd0866e13409 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zgi-7920100000-472a053832ce780dd335 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0227900000-2b3bd45c30c76c00ada4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0kka-9776600000-a91ac251679e309216a5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0kml-9840000000-4c1976a6372a21fd11fd | Spectrum |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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