Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-22 19:51:22 UTC |
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Update Date | 2021-09-14 15:39:07 UTC |
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HMDB ID | HMDB0061154 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Monic acid |
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Description | Monic acid is a metabolite of mupirocin. Mupirocin (Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens NCIMB 10586, developed by Beecham. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations. It is used topically and is effective against Gram-positive bacteria, including MRSA. Mupirocin is a mixture of several pseudomonic acids, with pseudomonic acid A (PA-A) constituting greater than 90% of the mixture. (Wikipedia ) No systemic absorption of mupirocin or its major metabolite, monic acid, has been detected in short courses of topical administration to healthy volunteers or to patients with epidermolysis bullosa after prolonged courses of therapy with Bactroban ointment. (PMID: 2112164 ) |
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Structure | [H][C@]1(O[C@H]1CC1CC[C@@H](C\C(C)=C\C(O)=O)[C@H](O)[C@@H]1O)[C@@H](C)C(C)O InChI=1S/C18H30O6/c1-9(7-15(20)21)6-12-4-5-13(17(23)16(12)22)8-14-18(24-14)10(2)11(3)19/h7,10-14,16-19,22-23H,4-6,8H2,1-3H3,(H,20,21)/b9-7+/t10-,11?,12-,13?,14-,16-,17+,18-/m0/s1 |
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Synonyms | Value | Source |
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Monate | Generator |
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Chemical Formula | C18H30O6 |
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Average Molecular Weight | 342.4272 |
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Monoisotopic Molecular Weight | 342.204238692 |
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IUPAC Name | (2E)-4-[(1S,2S,3R)-2,3-dihydroxy-4-{[(2S,3S)-3-[(2S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}cyclohexyl]-3-methylbut-2-enoic acid |
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Traditional Name | (2E)-4-[(1S,2S,3R)-2,3-dihydroxy-4-{[(2S,3S)-3-[(2S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}cyclohexyl]-3-methylbut-2-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@]1(O[C@H]1CC1CC[C@@H](C\C(C)=C\C(O)=O)[C@H](O)[C@@H]1O)[C@@H](C)C(C)O |
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InChI Identifier | InChI=1S/C18H30O6/c1-9(7-15(20)21)6-12-4-5-13(17(23)16(12)22)8-14-18(24-14)10(2)11(3)19/h7,10-14,16-19,22-23H,4-6,8H2,1-3H3,(H,20,21)/b9-7+/t10-,11?,12-,13?,14-,16-,17+,18-/m0/s1 |
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InChI Key | MUWNEQMGMLXEFO-CXSJRMNRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain. |
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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 | Epoxy fatty acids |
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Alternative Parents | |
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Substituents | - Branched fatty acid
- Cyclohexanol
- Epoxy fatty acid
- Hydroxy fatty acid
- Short-chain hydroxy acid
- Methyl-branched fatty acid
- Unsaturated fatty acid
- Cyclic alcohol
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid
- Carboxylic acid derivative
- Dialkyl ether
- Oxirane
- Ether
- Monocarboxylic acid or derivatives
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic 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 | Not Available |
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Experimental Molecular 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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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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Monic acid,1TMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O | 2671.5 | Semi standard non polar | 33892256 | Monic acid,1TMS,isomer #2 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O[Si](C)(C)C | 2639.8 | Semi standard non polar | 33892256 | Monic acid,1TMS,isomer #3 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C)[C@H]1O | 2638.6 | Semi standard non polar | 33892256 | Monic acid,1TMS,isomer #4 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O)[C@H]1O | 2688.4 | Semi standard non polar | 33892256 | Monic acid,2TMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O)[C@H]1O | 2663.7 | Semi standard non polar | 33892256 | Monic acid,2TMS,isomer #2 | C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C)[C@H]1O | 2620.9 | Semi standard non polar | 33892256 | Monic acid,2TMS,isomer #3 | C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O[Si](C)(C)C | 2606.5 | Semi standard non polar | 33892256 | Monic acid,2TMS,isomer #4 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C | 2670.2 | Semi standard non polar | 33892256 | Monic acid,2TMS,isomer #5 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C | 2651.5 | Semi standard non polar | 33892256 | Monic acid,2TMS,isomer #6 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O | 2685.4 | Semi standard non polar | 33892256 | Monic acid,3TMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O | 2639.7 | Semi standard non polar | 33892256 | Monic acid,3TMS,isomer #2 | C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C | 2611.8 | Semi standard non polar | 33892256 | Monic acid,3TMS,isomer #3 | C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C | 2596.7 | Semi standard non polar | 33892256 | Monic acid,3TMS,isomer #4 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C | 2659.9 | Semi standard non polar | 33892256 | Monic acid,4TMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C | 2619.3 | Semi standard non polar | 33892256 | Monic acid,1TBDMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O | 2896.1 | Semi standard non polar | 33892256 | Monic acid,1TBDMS,isomer #2 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C | 2887.9 | Semi standard non polar | 33892256 | Monic acid,1TBDMS,isomer #3 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O | 2876.3 | Semi standard non polar | 33892256 | Monic acid,1TBDMS,isomer #4 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O | 2955.2 | Semi standard non polar | 33892256 | Monic acid,2TBDMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O | 3149.1 | Semi standard non polar | 33892256 | Monic acid,2TBDMS,isomer #2 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O | 3075.6 | Semi standard non polar | 33892256 | Monic acid,2TBDMS,isomer #3 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C | 3063.6 | Semi standard non polar | 33892256 | Monic acid,2TBDMS,isomer #4 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C | 3138.4 | Semi standard non polar | 33892256 | Monic acid,2TBDMS,isomer #5 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C | 3087.2 | Semi standard non polar | 33892256 | Monic acid,2TBDMS,isomer #6 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O | 3134.6 | Semi standard non polar | 33892256 | Monic acid,3TBDMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O | 3313.5 | Semi standard non polar | 33892256 | Monic acid,3TBDMS,isomer #2 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C | 3309.5 | Semi standard non polar | 33892256 | Monic acid,3TBDMS,isomer #3 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C | 3263.6 | Semi standard non polar | 33892256 | Monic acid,3TBDMS,isomer #4 | C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C | 3340.0 | Semi standard non polar | 33892256 | Monic acid,4TBDMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C | 3499.0 | Semi standard non 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 - Monic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0095-9467000000-2afd4130843c2ad8e89d | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Monic acid GC-MS (4 TMS) - 70eV, Positive | splash10-014i-1800449000-d401b70ceced92a825fd | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Monic acid 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 - Monic acid 10V, Positive-QTOF | splash10-056r-1049000000-a7226eb85976b545db06 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 20V, Positive-QTOF | splash10-07gi-6393000000-302582cb8b9200ef1065 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 40V, Positive-QTOF | splash10-0gc9-9420000000-c62e53171bac899c3e3a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 10V, Negative-QTOF | splash10-006x-0198000000-a4fc56197eef205118f8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 20V, Negative-QTOF | splash10-00fr-6093000000-7f949004e886a4facc5f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 40V, Negative-QTOF | splash10-05fr-9020000000-22d33ac086c5bf86df30 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 10V, Negative-QTOF | splash10-002f-0079000000-113116320d521335dad3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 20V, Negative-QTOF | splash10-056u-0093000000-0943e4dce172d49d585b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 40V, Negative-QTOF | splash10-0a4r-1193000000-b5245ab73d3d7b48be27 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 10V, Positive-QTOF | splash10-004l-0397000000-cf697b3c5b7124b66b48 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 20V, Positive-QTOF | splash10-0a4i-2495000000-8c5069063d568c3317d6 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Monic acid 40V, Positive-QTOF | splash10-000x-9000000000-cc67e9d53157aa0d5107 | 2021-09-25 | Wishart Lab | View Spectrum |
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