Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-12 23:34:27 UTC |
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Update Date | 2023-02-21 17:16:44 UTC |
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HMDB ID | HMDB0003551 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Carbamic acid |
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Description | Carbamic acid is occasionally found as carbamate in workers exposed to pesticides. Carbamates, particularly carbofuran, seem to be more associated with exuberant and diversified symptomatology of pesticide exposure than organophosphates. Neurological symptoms occur among farmers occupationally exposed to acetylcholinesterase-inhibiting insecticides such as carbamates. Carbamic acid products of several amines, such as beta-N-methylamino-L-alanine (BMAA), ethylenediamine, and L-cysteine have been implicated in toxicity. Studies suggested that a significant portion of amino-compounds in biological samples (that naturally contain CO2/bicarbonate) can be present as a carbamic acid. The formation of carbamate glucuronide metabolites has been described for numerous pharmaceuticals and they have been identified in all of the species commonly used in drug metabolism studies (rat, dog, mouse, rabbit, guinea pig, and human). There has been no obvious species specificity for their formation and no preference for 1 or 2 degree amines. Many biological reactions have also been described in the literature that involve the reaction of CO2 with amino groups of biomolecules. For example, CO2 generated from cellular respiration is expired in part through the reversible formation of a carbamate between CO2 and the -amino groups of the alpha and beta-chains of hemoglobin. Glucuronidation is an important mechanism used by mammalian systems to clear and eliminate both endogenous and foreign chemicals. Many functional groups are susceptible to conjugation with glucuronic acid, including hydroxyls, phenols, carboxyls, activated carbons, thiols, amines, and selenium. Primary and secondary amines can also react with carbon dioxide (CO2) via a reversible reaction to form a carbamic acid. The carbamic acid is also a substrate for glucuronidation and results in a stable carbamate glucuronide metabolite. The detection and characterization of these products has been facilitated greatly by the advent of soft ionization mass spectrometry techniques and high field NMR instrumentation. (PMID: 16268118 , 17168688 , 12929145 ). |
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Structure | InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4) |
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Synonyms | Value | Source |
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Aminoameisensaeure | ChEBI | Aminoformic acid | ChEBI | Carbamate | ChEBI | Carbamidsaeure | ChEBI | Aminoformate | Generator | Carbamate ion | HMDB | Chlorphenesin carbamate | HMDB | Maolate | HMDB | Calcium carbamate | MeSH, HMDB | Carbamic acid, potassium salt | MeSH, HMDB | Carbamic acid, sodium salt | MeSH, HMDB | Sodium carbamate | MeSH, HMDB | Ammonium carbamate | MeSH, HMDB | Carbamic acid, ammonia salt | MeSH, HMDB | Carbamic acid, calcium salt | MeSH, HMDB | Potassium carbamate | MeSH, HMDB |
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Chemical Formula | CH3NO2 |
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Average Molecular Weight | 61.04 |
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Monoisotopic Molecular Weight | 61.016378345 |
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IUPAC Name | carbamic acid |
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Traditional Name | carbamic acid |
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CAS Registry Number | 463-77-4 |
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SMILES | NC(O)=O |
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InChI Identifier | InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4) |
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InChI Key | KXDHJXZQYSOELW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as organic carbonic acids and derivatives. Organic carbonic acids and derivatives are compounds comprising the organic carbonic acid or a derivative thereof. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic carbonic acids and derivatives |
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Sub Class | Not Available |
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Direct Parent | Organic carbonic acids and derivatives |
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Alternative Parents | |
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Substituents | - Carbonic acid derivative
- Carbamic acid derivative
- Carbamic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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 | |
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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 | 1000000 mg/L @ 25 °C (est) | The Good Scents Company Information System | 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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Carbamic acid,1TMS,isomer #1 | C[Si](C)(C)OC(N)=O | 960.8 | Semi standard non polar | 33892256 | Carbamic acid,1TMS,isomer #2 | C[Si](C)(C)NC(=O)O | 1074.6 | Semi standard non polar | 33892256 | Carbamic acid,2TMS,isomer #1 | C[Si](C)(C)NC(=O)O[Si](C)(C)C | 1067.5 | Semi standard non polar | 33892256 | Carbamic acid,2TMS,isomer #1 | C[Si](C)(C)NC(=O)O[Si](C)(C)C | 1073.8 | Standard non polar | 33892256 | Carbamic acid,2TMS,isomer #1 | C[Si](C)(C)NC(=O)O[Si](C)(C)C | 1245.9 | Standard polar | 33892256 | Carbamic acid,2TMS,isomer #2 | C[Si](C)(C)N(C(=O)O)[Si](C)(C)C | 1201.3 | Semi standard non polar | 33892256 | Carbamic acid,2TMS,isomer #2 | C[Si](C)(C)N(C(=O)O)[Si](C)(C)C | 1052.1 | Standard non polar | 33892256 | Carbamic acid,2TMS,isomer #2 | C[Si](C)(C)N(C(=O)O)[Si](C)(C)C | 1242.1 | Standard polar | 33892256 | Carbamic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C | 1176.8 | Semi standard non polar | 33892256 | Carbamic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C | 1148.2 | Standard non polar | 33892256 | Carbamic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C | 1125.1 | Standard polar | 33892256 | Carbamic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(N)=O | 1165.2 | Semi standard non polar | 33892256 | Carbamic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)O | 1264.0 | Semi standard non polar | 33892256 | Carbamic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)O[Si](C)(C)C(C)(C)C | 1502.7 | Semi standard non polar | 33892256 | Carbamic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)O[Si](C)(C)C(C)(C)C | 1436.3 | Standard non polar | 33892256 | Carbamic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)O[Si](C)(C)C(C)(C)C | 1471.4 | Standard polar | 33892256 | Carbamic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C(=O)O)[Si](C)(C)C(C)(C)C | 1569.5 | Semi standard non polar | 33892256 | Carbamic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C(=O)O)[Si](C)(C)C(C)(C)C | 1447.5 | Standard non polar | 33892256 | Carbamic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C(=O)O)[Si](C)(C)C(C)(C)C | 1482.9 | Standard polar | 33892256 | Carbamic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1834.6 | Semi standard non polar | 33892256 | Carbamic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1788.6 | Standard non polar | 33892256 | Carbamic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1557.8 | 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 - Carbamic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-9000000000-d4ec45366294deee461d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Carbamic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9200000000-39800d42e236043754c2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Carbamic 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 - Carbamic acid 10V, Positive-QTOF | splash10-03di-9000000000-33c2cd9e9f87e70aeee7 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 20V, Positive-QTOF | splash10-03dl-9000000000-80dc946b5f814bf962fc | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 40V, Positive-QTOF | splash10-0006-9000000000-db68c8dff28932d0bd97 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 10V, Negative-QTOF | splash10-03dl-9000000000-54e827d7f4201ae683bf | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 20V, Negative-QTOF | splash10-03dl-9000000000-3158c8b265d264989bd7 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 40V, Negative-QTOF | splash10-0006-9000000000-24350f23db0893ec042c | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 10V, Positive-QTOF | splash10-0006-9000000000-fd9f25340762315b4515 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 20V, Positive-QTOF | splash10-0006-9000000000-fd9f25340762315b4515 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 40V, Positive-QTOF | splash10-0006-9000000000-fd9f25340762315b4515 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 10V, Negative-QTOF | splash10-03di-9000000000-7b9a18058ceeb7cfe64a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 20V, Negative-QTOF | splash10-0006-9000000000-c8501e98acf811129533 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Carbamic acid 40V, Negative-QTOF | splash10-0006-9000000000-90726b17dc36e29c5299 | 2021-09-25 | 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, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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