Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 19:26:31 UTC |
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Update Date | 2022-09-22 18:34:25 UTC |
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HMDB ID | HMDB0034566 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Neotame |
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Description | Potential high-intensity sweetener, sweetness variously stated to be 40 x sucrose and 7000-13000 x sucrose Neotame is an artificial sweetener made by NutraSweet that is between 7,000 and 13,000 times sweeter than sucrose (table sugar). In the European Union it is known by the E number E961. Neotame is moderately heat stable and extremely potent. Neotame is rapidly metabolized, completely eliminated, and does not accumulate in the body |
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Structure | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(O)=O)NCCC(C)(C)C InChI=1S/C20H30N2O5/c1-20(2,3)10-11-21-15(13-17(23)24)18(25)22-16(19(26)27-4)12-14-8-6-5-7-9-14/h5-9,15-16,21H,10-13H2,1-4H3,(H,22,25)(H,23,24) |
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Synonyms | Value | Source |
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3-[(3,3-Dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)-C-hydroxycarbonimidoyl]propanoate | HMDB |
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Chemical Formula | C20H30N2O5 |
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Average Molecular Weight | 378.4626 |
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Monoisotopic Molecular Weight | 378.21547208 |
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IUPAC Name | 3-[(3,3-dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid |
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Traditional Name | 3-[(3,3-dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid |
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CAS Registry Number | 165450-17-9 |
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SMILES | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(O)=O)NCCC(C)(C)C |
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InChI Identifier | InChI=1S/C20H30N2O5/c1-20(2,3)10-11-21-15(13-17(23)24)18(25)22-16(19(26)27-4)12-14-8-6-5-7-9-14/h5-9,15-16,21H,10-13H2,1-4H3,(H,22,25)(H,23,24) |
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InChI Key | HLIAVLHNDJUHFG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. |
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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 | Peptides |
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Alternative Parents | |
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Substituents | - Alpha peptide
- Phenylalanine or derivatives
- Aspartic acid or derivatives
- Alpha-amino acid ester
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- Amphetamine or derivatives
- Fatty acid ester
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Benzenoid
- Methyl ester
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Amino acid
- Carboxylic acid ester
- Carboxamide group
- Secondary amine
- Secondary aliphatic amine
- Carboxylic acid
- Amine
- Carbonyl group
- Organic nitrogen compound
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxide
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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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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Neotame,1TMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O[Si](C)(C)C)NCCC(C)(C)C | 2621.2 | Semi standard non polar | 33892256 | Neotame,1TMS,isomer #2 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O)NCCC(C)(C)C)[Si](C)(C)C | 2654.5 | Semi standard non polar | 33892256 | Neotame,1TMS,isomer #3 | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O)N(CCC(C)(C)C)[Si](C)(C)C | 2677.2 | Semi standard non polar | 33892256 | Neotame,2TMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O[Si](C)(C)C)NCCC(C)(C)C)[Si](C)(C)C | 2608.1 | Semi standard non polar | 33892256 | Neotame,2TMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O[Si](C)(C)C)NCCC(C)(C)C)[Si](C)(C)C | 2664.0 | Standard non polar | 33892256 | Neotame,2TMS,isomer #2 | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O[Si](C)(C)C)N(CCC(C)(C)C)[Si](C)(C)C | 2624.0 | Semi standard non polar | 33892256 | Neotame,2TMS,isomer #2 | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O[Si](C)(C)C)N(CCC(C)(C)C)[Si](C)(C)C | 2691.5 | Standard non polar | 33892256 | Neotame,2TMS,isomer #3 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O)N(CCC(C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2700.6 | Semi standard non polar | 33892256 | Neotame,2TMS,isomer #3 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O)N(CCC(C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2702.6 | Standard non polar | 33892256 | Neotame,3TMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O[Si](C)(C)C)N(CCC(C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2666.2 | Semi standard non polar | 33892256 | Neotame,3TMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O[Si](C)(C)C)N(CCC(C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2746.4 | Standard non polar | 33892256 | Neotame,1TBDMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O[Si](C)(C)C(C)(C)C)NCCC(C)(C)C | 2847.2 | Semi standard non polar | 33892256 | Neotame,1TBDMS,isomer #2 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O)NCCC(C)(C)C)[Si](C)(C)C(C)(C)C | 2912.4 | Semi standard non polar | 33892256 | Neotame,1TBDMS,isomer #3 | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O)N(CCC(C)(C)C)[Si](C)(C)C(C)(C)C | 2950.1 | Semi standard non polar | 33892256 | Neotame,2TBDMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O[Si](C)(C)C(C)(C)C)NCCC(C)(C)C)[Si](C)(C)C(C)(C)C | 3076.6 | Semi standard non polar | 33892256 | Neotame,2TBDMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O[Si](C)(C)C(C)(C)C)NCCC(C)(C)C)[Si](C)(C)C(C)(C)C | 3037.1 | Standard non polar | 33892256 | Neotame,2TBDMS,isomer #2 | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O[Si](C)(C)C(C)(C)C)N(CCC(C)(C)C)[Si](C)(C)C(C)(C)C | 3140.7 | Semi standard non polar | 33892256 | Neotame,2TBDMS,isomer #2 | COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O[Si](C)(C)C(C)(C)C)N(CCC(C)(C)C)[Si](C)(C)C(C)(C)C | 3044.6 | Standard non polar | 33892256 | Neotame,2TBDMS,isomer #3 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O)N(CCC(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3201.3 | Semi standard non polar | 33892256 | Neotame,2TBDMS,isomer #3 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O)N(CCC(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3049.1 | Standard non polar | 33892256 | Neotame,3TBDMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O[Si](C)(C)C(C)(C)C)N(CCC(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3389.5 | Semi standard non polar | 33892256 | Neotame,3TBDMS,isomer #1 | COC(=O)C(CC1=CC=CC=C1)N(C(=O)C(CC(=O)O[Si](C)(C)C(C)(C)C)N(CCC(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3249.9 | 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 - Neotame GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-5923000000-32b316dcb7691f6fc7a0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neotame GC-MS (1 TMS) - 70eV, Positive | splash10-0006-9082100000-44e7ca6efcad5c7c1c78 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neotame 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 - Neotame 10V, Positive-QTOF | splash10-03di-2209000000-d19a9a5790a672e592bb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 20V, Positive-QTOF | splash10-00dr-6913000000-200e92bd1750b1e260f2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 40V, Positive-QTOF | splash10-009l-9500000000-25d473f3f05cab7dedf0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 10V, Negative-QTOF | splash10-004i-0009000000-8a5a71caeab8b3ff01b3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 20V, Negative-QTOF | splash10-0fba-1629000000-62264add783f4a6a781e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 40V, Negative-QTOF | splash10-0fte-3910000000-0c94d574c878a0faf288 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 10V, Positive-QTOF | splash10-004i-0319000000-042ebfb74113212fa423 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 20V, Positive-QTOF | splash10-00di-3962000000-82a43b87b5bd061eb859 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 40V, Positive-QTOF | splash10-0udl-4900000000-5ec7634ce54d82588664 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 10V, Negative-QTOF | splash10-004i-0009000000-fcd4610bdba901fffcc2 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 20V, Negative-QTOF | splash10-0kxr-1429000000-4adbcf47f2022f24ef37 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neotame 40V, Negative-QTOF | splash10-07bf-6941000000-c72b1eb7c2947695b4d6 | 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, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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