Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-06-15 18:06:03 UTC |
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Update Date | 2021-09-14 15:46:00 UTC |
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HMDB ID | HMDB0060618 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 6-Aminopenicillanic acid |
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Description | 6-Aminopenicillanic acid, also known as 6-APA or penicin, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 6-Aminopenicillanic acid is a very strong basic compound (based on its pKa). 6-Aminopenicillanic acid exists in all living organisms, ranging from bacteria to humans. |
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Structure | CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1 |
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Synonyms | Value | Source |
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(+)-6-Aminopenicillanic acid | ChEBI | (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | ChEBI | 6-Aminopenicillamine acid | ChEBI | 6-Aminopenicillanate | ChEBI | 6-APA | ChEBI | 6-Aps | ChEBI | 6beta-Aminopenicillanic acid | ChEBI | Aminopenicillanic acid | ChEBI | Penicin | ChEBI | Penin | ChEBI | Phenacyl 6-aminopenicillinate | ChEBI | (+)-6-Aminopenicillanate | Generator | (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | 6b-Aminopenicillanate | Generator | 6b-Aminopenicillanic acid | Generator | 6beta-Aminopenicillanate | Generator | 6Β-aminopenicillanate | Generator | 6Β-aminopenicillanic acid | Generator | Aminopenicillanate | Generator | Phenacyl 6-aminopenicillinic acid | Generator | 6-APA CPD | HMDB | Aminopenicillanic acid, potassium salt | HMDB | Aminopenicillanic acid, sodium salt | HMDB |
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Chemical Formula | C8H12N2O3S |
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Average Molecular Weight | 216.257 |
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Monoisotopic Molecular Weight | 216.05686295 |
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IUPAC Name | (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
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Traditional Name | penin |
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CAS Registry Number | Not Available |
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SMILES | CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O |
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InChI Identifier | InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1 |
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InChI Key | NGHVIOIJCVXTGV-ALEPSDHESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
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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 | Dipeptides |
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Alternative Parents | |
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Substituents | - Alpha-dipeptide
- Alpha-amino acid or derivatives
- Penam
- Beta-lactam
- Tertiary carboxylic acid amide
- Thiazolidine
- Amino acid or derivatives
- Azetidine
- Amino acid
- Carboxamide group
- Lactam
- Carboxylic acid
- Azacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Dialkylthioether
- Hemithioaminal
- Thioether
- Amine
- Primary aliphatic amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Primary amine
- Organopnictogen compound
- Organic oxide
- Carbonyl group
- 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 | 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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6-Aminopenicillanic acid,1TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 1850.4 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,1TMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O | 1897.3 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 1937.4 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 1942.7 | Standard non polar | 33892256 | 6-Aminopenicillanic acid,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2490.7 | Standard polar | 33892256 | 6-Aminopenicillanic acid,2TMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O | 1944.0 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,2TMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O | 2042.0 | Standard non polar | 33892256 | 6-Aminopenicillanic acid,2TMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O | 2479.8 | Standard polar | 33892256 | 6-Aminopenicillanic acid,3TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 1997.7 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,3TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2116.9 | Standard non polar | 33892256 | 6-Aminopenicillanic acid,3TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2213.6 | Standard polar | 33892256 | 6-Aminopenicillanic acid,1TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2077.2 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,1TBDMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O | 2110.2 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2346.3 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2458.8 | Standard non polar | 33892256 | 6-Aminopenicillanic acid,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2626.3 | Standard polar | 33892256 | 6-Aminopenicillanic acid,2TBDMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O | 2400.5 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,2TBDMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O | 2525.3 | Standard non polar | 33892256 | 6-Aminopenicillanic acid,2TBDMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O | 2615.6 | Standard polar | 33892256 | 6-Aminopenicillanic acid,3TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2626.8 | Semi standard non polar | 33892256 | 6-Aminopenicillanic acid,3TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2799.0 | Standard non polar | 33892256 | 6-Aminopenicillanic acid,3TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2532.1 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 6-Aminopenicillanic acid GC-EI-TOF (Non-derivatized) | splash10-0uxr-1930000000-8b3dad9f5db3d8512110 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 6-Aminopenicillanic acid GC-EI-TOF (Non-derivatized) | splash10-0uxr-1930000000-14be07ea22813265cdf3 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 6-Aminopenicillanic acid GC-EI-TOF (Non-derivatized) | splash10-0uxr-1930000000-8b3dad9f5db3d8512110 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 6-Aminopenicillanic acid GC-EI-TOF (Non-derivatized) | splash10-0uxr-1930000000-14be07ea22813265cdf3 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Aminopenicillanic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9200000000-e33fe5dc6f7515fb41d5 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Aminopenicillanic acid GC-MS (1 TMS) - 70eV, Positive | splash10-05fr-9220000000-0d97e3938474120b9e87 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Aminopenicillanic 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Aminopenicillanic acid Linear Ion Trap , negative-QTOF | splash10-00di-9300000000-e9bd620d9e681c167ae5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Aminopenicillanic acid Linear Ion Trap , negative-QTOF | splash10-00di-9300000000-d0d73fa955283a4de8e1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Aminopenicillanic acid Linear Ion Trap , positive-QTOF | splash10-00dr-0900000000-c0222f314effc3d7ad8a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Aminopenicillanic acid Linear Ion Trap , positive-QTOF | splash10-00dr-0900000000-f17a9cc1b1e04e3b7e71 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 10V, Positive-QTOF | splash10-0a4i-9330000000-0853f16f9d9fb3a3f86e | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 20V, Positive-QTOF | splash10-03di-1910000000-fbdab9a3772fcfd7c0c8 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 40V, Positive-QTOF | splash10-0a4i-9200000000-6b276429012b5ee9844f | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 10V, Negative-QTOF | splash10-00di-9200000000-9ffda48df6b90d12f303 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 20V, Negative-QTOF | splash10-0ab9-9200000000-f630fdfcda8c288572e2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 40V, Negative-QTOF | splash10-00di-9200000000-e7d207177892f580f3c9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 10V, Positive-QTOF | splash10-00kr-0950000000-bbef363560f5d2d25c16 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 20V, Positive-QTOF | splash10-03di-1910000000-8a0d3e001608783c72a0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 40V, Positive-QTOF | splash10-014i-9800000000-64b11c9f70ce0cb2d2b0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 10V, Negative-QTOF | splash10-00di-9100000000-25f442a83faa3f7da843 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 20V, Negative-QTOF | splash10-00di-9200000000-7d7718220a18a63d2655 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Aminopenicillanic acid 40V, Negative-QTOF | splash10-00di-9000000000-766302f54e49d015548c | 2021-10-12 | 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) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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General References | - Shimizu T, Souma S, Nagakura N, Masuzawa T, Iwamoto Y, Yanagihara Y: Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity. Int Arch Allergy Immunol. 1992;98(4):392-7. [PubMed:1384868 ]
- Zhao Y, Qiao H: Detection of specific IgE antibodies to major and minor antigenic determinants in sera of penicillin allergic patients. Chin Med J (Engl). 2003 Dec;116(12):1904-10. [PubMed:14687482 ]
- Harle DG, Baldo BA: Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy. Mol Immunol. 1990 Nov;27(11):1063-71. [PubMed:1701026 ]
- Ariza A, Barrionuevo E, Mayorga C, Montanez MI, Perez-Inestrosa E, Ruiz-Sanchez A, Rodriguez-Gueant RM, Fernandez TD, Gueant JL, Torres MJ, Blanca M: IgE to penicillins with different specificities can be identified by a multiepitope macromolecule: Bihaptenic penicillin structures and IgE specificities. J Immunol Methods. 2014 Apr;406:43-50. doi: 10.1016/j.jim.2014.03.001. Epub 2014 Mar 13. [PubMed:24631718 ]
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