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 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:46 UTC |
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HMDB ID | HMDB0014877 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hetacillin |
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Description | Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name 'penicillin' can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs). |
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Structure | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1 |
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Synonyms | Value | Source |
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(2S,5R,6R)-6-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | ChEBI | 6beta-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid | ChEBI | Hetacilina | ChEBI | Hetacilline | ChEBI | Hetacillinum | ChEBI | Versapen | Kegg | (2S,5R,6R)-6-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | 6b-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanate | Generator | 6b-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid | Generator | 6beta-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanate | Generator | 6Β-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanate | Generator | 6Β-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid | Generator | Hetacillin, monosodium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomer | HMDB | Hetacillin, monosodium salt, (2S-(2alpha,5alpha,6beta))-isomer | HMDB | Phenazacillin | HMDB | Hetacillin, (2S-(2alpha,5alpha,6alpha))-isomer | HMDB | Hetacillin, aluminum salt (3:1), (2S-(2alpha,5alpha,6beta(s*)))-isomer | HMDB | Hetacillin, monopotassium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomer | HMDB |
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Chemical Formula | C19H23N3O4S |
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Average Molecular Weight | 389.469 |
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Monoisotopic Molecular Weight | 389.140926929 |
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IUPAC Name | (2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
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Traditional Name | hetacillin |
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CAS Registry Number | 3511-16-8 |
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SMILES | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O |
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InChI Identifier | InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1 |
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InChI Key | DXVUYOAEDJXBPY-NFFDBFGFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1]. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactams |
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Sub Class | Beta lactams |
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Direct Parent | Penicillins |
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Alternative Parents | |
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Substituents | - Penicillin
- Phenylimidazolidine
- Alpha-amino acid or derivatives
- Monocyclic benzene moiety
- Imidazolidinone
- Benzenoid
- Imidazolidine
- Thiazolidine
- Tertiary carboxylic acid amide
- Amino acid or derivatives
- Azetidine
- Amino acid
- Carboxamide group
- Carboxylic acid derivative
- Carboxylic acid
- Secondary aliphatic amine
- Azacycle
- Dialkylthioether
- Monocarboxylic acid or derivatives
- Hemithioaminal
- Thioether
- Secondary amine
- Amine
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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 | 190 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.51 g/L | Not Available | LogP | 1.3 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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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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Hetacillin,1TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)NC3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2798.6 | Semi standard non polar | 33892256 | Hetacillin,1TMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O | 2746.6 | Semi standard non polar | 33892256 | Hetacillin,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2726.3 | Semi standard non polar | 33892256 | Hetacillin,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2948.7 | Standard non polar | 33892256 | Hetacillin,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 3460.3 | Standard polar | 33892256 | Hetacillin,1TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)NC3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 3016.6 | Semi standard non polar | 33892256 | Hetacillin,1TBDMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O | 2975.3 | Semi standard non polar | 33892256 | Hetacillin,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 3149.2 | Semi standard non polar | 33892256 | Hetacillin,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 3389.5 | Standard non polar | 33892256 | Hetacillin,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 3623.7 | 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 - Hetacillin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0597-7943000000-e629ee26cef364aec2d7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hetacillin GC-MS (1 TMS) - 70eV, Positive | splash10-00xu-9143300000-6fa9d2cea0ccf74ae209 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hetacillin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hetacillin 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 - Hetacillin 10V, Positive-QTOF | splash10-03di-0902000000-912bca5479e6d278d37f | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 20V, Positive-QTOF | splash10-03di-0910000000-9531e0f64a1e00ef3488 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 40V, Positive-QTOF | splash10-0btc-3900000000-a2875c749c7af28b9466 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 10V, Negative-QTOF | splash10-0002-0092000000-1d1ea0d542ee0060a90d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 20V, Negative-QTOF | splash10-0002-0093000000-fea6a48a167d8b663fb0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 40V, Negative-QTOF | splash10-00c1-9521000000-936ddaa0d3690efedc74 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 10V, Positive-QTOF | splash10-0006-0009000000-3ec18c91e5d64861d13d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 20V, Positive-QTOF | splash10-0006-0239000000-4f0de60022c322c73392 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 40V, Positive-QTOF | splash10-0006-5911000000-2d78f162743e488a050d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 10V, Negative-QTOF | splash10-000i-0009000000-e24e100bd150f5e8fbba | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 20V, Negative-QTOF | splash10-052r-0094000000-0aaabd2b493b44418bbe | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hetacillin 40V, Negative-QTOF | splash10-0zg3-3791000000-daeb0fa6db82a3343e56 | 2021-10-11 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum |
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