Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 23:12:39 UTC |
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Update Date | 2022-03-07 02:55:34 UTC |
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HMDB ID | HMDB0037942 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid |
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Description | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid is found in alcoholic beverages. (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid is widespread in many foodstuffs especially fruit juices, jams and fermented foods or beverages including beer and soy sauce. Also present in the toxic fly agaric mushroom (Amanita muscaria). (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid is formed by Pictet-Spengler condensation between acetaldehyde and L-tryptophan in nature or during food processing. |
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Structure | CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O InChI=1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17) |
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Synonyms | Value | Source |
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(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-b-carboline-3-carboxylate | Generator | (1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-b-carboline-3-carboxylic acid | Generator | (1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-beta-carboline-3-carboxylate | Generator | (1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylate | Generator | (1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylic acid | Generator | MTCA | HMDB | 1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid | HMDB | 1-Methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate | HMDB |
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Chemical Formula | C13H14N2O2 |
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Average Molecular Weight | 230.2625 |
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Monoisotopic Molecular Weight | 230.105527702 |
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IUPAC Name | 1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid |
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Traditional Name | 1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O |
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InChI Identifier | InChI=1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17) |
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InChI Key | ZUPHXNBLQCSEIA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Harmala alkaloids |
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Sub Class | Not Available |
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Direct Parent | Harmala alkaloids |
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Alternative Parents | |
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Substituents | - Harman
- Beta-carboline
- Pyridoindole
- Alpha-amino acid
- Alpha-amino acid or derivatives
- 3-alkylindole
- Indole
- Indole or derivatives
- Aralkylamine
- Benzenoid
- Heteroaromatic compound
- Pyrrole
- Amino acid or derivatives
- Amino acid
- Carboxylic acid derivative
- Carboxylic acid
- Secondary aliphatic amine
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Secondary amine
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxide
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | Property | Value | Reference |
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Melting Point | 290 °C | 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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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(1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid | CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O | 3776.5 | Standard polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid | CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O | 2176.8 | Standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid | CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O | 2411.1 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,1TMS,isomer #1 | CC1NC(C(=O)O[Si](C)(C)C)CC2=C1[NH]C1=CC=CC=C21 | 2359.6 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,1TMS,isomer #2 | CC1C2=C(CC(C(=O)O)N1[Si](C)(C)C)C1=CC=CC=C1[NH]2 | 2438.7 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,1TMS,isomer #3 | CC1NC(C(=O)O)CC2=C1N([Si](C)(C)C)C1=CC=CC=C21 | 2417.2 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TMS,isomer #1 | CC1C2=C(CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C1=CC=CC=C1[NH]2 | 2426.3 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TMS,isomer #1 | CC1C2=C(CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C1=CC=CC=C1[NH]2 | 2257.3 | Standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TMS,isomer #2 | CC1NC(C(=O)O[Si](C)(C)C)CC2=C1N([Si](C)(C)C)C1=CC=CC=C21 | 2365.3 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TMS,isomer #2 | CC1NC(C(=O)O[Si](C)(C)C)CC2=C1N([Si](C)(C)C)C1=CC=CC=C21 | 2164.1 | Standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TMS,isomer #3 | CC1C2=C(CC(C(=O)O)N1[Si](C)(C)C)C1=CC=CC=C1N2[Si](C)(C)C | 2377.7 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TMS,isomer #3 | CC1C2=C(CC(C(=O)O)N1[Si](C)(C)C)C1=CC=CC=C1N2[Si](C)(C)C | 2263.8 | Standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,3TMS,isomer #1 | CC1C2=C(CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C1=CC=CC=C1N2[Si](C)(C)C | 2395.9 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,3TMS,isomer #1 | CC1C2=C(CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C1=CC=CC=C1N2[Si](C)(C)C | 2316.9 | Standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,1TBDMS,isomer #1 | CC1NC(C(=O)O[Si](C)(C)C(C)(C)C)CC2=C1[NH]C1=CC=CC=C21 | 2622.5 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,1TBDMS,isomer #2 | CC1C2=C(CC(C(=O)O)N1[Si](C)(C)C(C)(C)C)C1=CC=CC=C1[NH]2 | 2739.7 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,1TBDMS,isomer #3 | CC1NC(C(=O)O)CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21 | 2662.9 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TBDMS,isomer #1 | CC1C2=C(CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)C1=CC=CC=C1[NH]2 | 2906.1 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TBDMS,isomer #1 | CC1C2=C(CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)C1=CC=CC=C1[NH]2 | 2725.9 | Standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TBDMS,isomer #2 | CC1NC(C(=O)O[Si](C)(C)C(C)(C)C)CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21 | 2775.9 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TBDMS,isomer #2 | CC1NC(C(=O)O[Si](C)(C)C(C)(C)C)CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21 | 2600.2 | Standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TBDMS,isomer #3 | CC1C2=C(CC(C(=O)O)N1[Si](C)(C)C(C)(C)C)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2827.6 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,2TBDMS,isomer #3 | CC1C2=C(CC(C(=O)O)N1[Si](C)(C)C(C)(C)C)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2712.7 | Standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,3TBDMS,isomer #1 | CC1C2=C(CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2977.4 | Semi standard non polar | 33892256 | (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid,3TBDMS,isomer #1 | CC1C2=C(CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2952.0 | 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 - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0aou-1930000000-7a78c37d340d68524ffa | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid GC-MS (1 TMS) - 70eV, Positive | splash10-000i-7940000000-9ec7bb65f7ecad46c397 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic 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 - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 10V, Positive-QTOF | splash10-001i-0490000000-6920716b3a40419c8884 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 20V, Positive-QTOF | splash10-053i-0910000000-09a8091ac6df02ac47f6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 40V, Positive-QTOF | splash10-001i-0900000000-661d888d0936cb5ce873 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 10V, Negative-QTOF | splash10-004i-0290000000-9c8452fa2dde716857dc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 20V, Negative-QTOF | splash10-004r-0970000000-d588c12af965ad276cbc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 40V, Negative-QTOF | splash10-02uc-1910000000-5fff8901fdedaae39a15 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 10V, Positive-QTOF | splash10-01q9-0090000000-63e90ed2e8db2c9f00a3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 20V, Positive-QTOF | splash10-01q0-0970000000-a8456924d6d5b96e5c5f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 40V, Positive-QTOF | splash10-0006-0900000000-717e5e29f748bc675154 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 10V, Negative-QTOF | splash10-004i-0390000000-b42178cf9913e5b6d90e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 20V, Negative-QTOF | splash10-004r-0790000000-f1ce5d76e222df217ddb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid 40V, Negative-QTOF | splash10-0006-1900000000-cd7884b0a308795112a2 | 2021-09-24 | 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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