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 02:52:01 UTC |
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HMDB ID | HMDB0015541 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Meticillin |
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Description | Meticillin is only found in individuals that have used or taken this drug. It is one of the penicillins which is resistant to penicillinase but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection. [PubChem]Like other beta-lactam antibiotics, meticillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. It does this by binding to and competitively inhibiting the transpeptidase enzyme used by bacteria to cross-link the peptide (D-alanyl-alanine) used in peptidogylcan synthesis. |
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Structure | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1 |
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Synonyms | Value | Source |
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(2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | ChEBI | 6beta-(2,6-Dimethoxybenzamido)penicillanic acid | ChEBI | Meticilina | ChEBI | Meticilline | ChEBI | Meticillinum | ChEBI | (2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | 6b-(2,6-Dimethoxybenzamido)penicillanate | Generator | 6b-(2,6-Dimethoxybenzamido)penicillanic acid | Generator | 6beta-(2,6-Dimethoxybenzamido)penicillanate | Generator | 6Β-(2,6-dimethoxybenzamido)penicillanate | Generator | 6Β-(2,6-dimethoxybenzamido)penicillanic acid | Generator | (2,6-Dimethoxyphenyl)penicillin | HMDB | 6-(2,6-Dimethoxybenzamido)penicillanic acid | HMDB | Methicillinum | HMDB | Methycillin | HMDB | Staphcillin | HMDB | CSL Brand OF methicillin sodium | HMDB | Dimethoxyphenyl penicillin | HMDB | Penicillin, dimethoxyphenyl | HMDB | Methicillin hydrate, monosodium salt | HMDB | Methicillin monohydrate, monosodium salt | HMDB | Methicillin sodium | HMDB | Metin | HMDB | Meticillin | ChEBI |
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Chemical Formula | C17H20N2O6S |
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Average Molecular Weight | 380.415 |
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Monoisotopic Molecular Weight | 380.104207072 |
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IUPAC Name | (2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
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Traditional Name | methicillin |
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CAS Registry Number | 61-32-5 |
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SMILES | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O |
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InChI Identifier | InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1 |
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InChI Key | RJQXTJLFIWVMTO-TYNCELHUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acid esters |
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Alternative Parents | |
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Substituents | - Alpha-amino acid ester
- Penam
- Azepane
- Acylal
- Dicarboxylic acid or derivatives
- Beta-lactam
- Tertiary carboxylic acid amide
- Thiazolidine
- Azetidine
- Carboxamide group
- Carboxylic acid ester
- Lactam
- Acetal
- Amidine
- Formamidine
- Carboxylic acid amidine
- Azacycle
- Organoheterocyclic compound
- Dialkylthioether
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Hemithioaminal
- Thioether
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Organic nitrogen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.31 g/L | Not Available | LogP | 1.22 | HANSCH,C ET AL. (1995) |
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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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Meticillin,1TMS,isomer #1 | COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12 | 2947.4 | Semi standard non polar | 33892256 | Meticillin,1TMS,isomer #2 | COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12)[Si](C)(C)C | 2905.3 | Semi standard non polar | 33892256 | Meticillin,2TMS,isomer #1 | COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C | 2888.4 | Semi standard non polar | 33892256 | Meticillin,2TMS,isomer #1 | COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C | 2863.6 | Standard non polar | 33892256 | Meticillin,2TMS,isomer #1 | COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C | 3633.4 | Standard polar | 33892256 | Meticillin,1TBDMS,isomer #1 | COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12 | 3202.2 | Semi standard non polar | 33892256 | Meticillin,1TBDMS,isomer #2 | COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C | 3136.0 | Semi standard non polar | 33892256 | Meticillin,2TBDMS,isomer #1 | COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C | 3304.6 | Semi standard non polar | 33892256 | Meticillin,2TBDMS,isomer #1 | COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C | 3324.3 | Standard non polar | 33892256 | Meticillin,2TBDMS,isomer #1 | COC1=CC=CC(OC)=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C | 3779.1 | 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 - Meticillin GC-MS (Non-derivatized) - 70eV, Positive | splash10-00xu-9756000000-82b89a7719dfc1d955bc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meticillin GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9210200000-1eab4718d201402b682f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meticillin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meticillin 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 - Meticillin 10V, Positive-QTOF | splash10-03k9-0975000000-99eb60da9aa2b5de1442 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 20V, Positive-QTOF | splash10-044i-1930000000-a4b4f247a46fae18026b | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 40V, Positive-QTOF | splash10-0cei-5910000000-e7efdc9557d573640952 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 10V, Negative-QTOF | splash10-000i-0091000000-26a50b80740c915f0f14 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 20V, Negative-QTOF | splash10-000i-0392000000-c1ee20b1a433f17a6ead | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 40V, Negative-QTOF | splash10-0079-8970000000-ce17545fc8fc88701a3f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 10V, Positive-QTOF | splash10-001i-0419000000-d58fb75de5a467abe798 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 20V, Positive-QTOF | splash10-014i-0933000000-26dda514ee65613e1362 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 40V, Positive-QTOF | splash10-014i-2910000000-27d1d63f349d91f14d7a | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 10V, Negative-QTOF | splash10-003r-0908000000-956a7dbf20ae4631b6e1 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 20V, Negative-QTOF | splash10-0a6u-9735000000-0b07aadf554b6ef2480a | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meticillin 40V, Negative-QTOF | splash10-000y-9434000000-9284224377162a990dca | 2021-10-11 | Wishart Lab | View Spectrum |
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