Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-23 01:26:16 UTC |
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Update Date | 2021-09-14 15:44:46 UTC |
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HMDB ID | HMDB0006348 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pseudoecgonine |
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Description | Pseudoecgonine is a metabolic byproduct of cocaine. Cocaine is extensively metabolized in the liver, with only about 1% excreted unchanged in the urine. The metabolism is dominated by hydrolytic ester cleavage, so the eliminated metabolites consist mostly of benzoylecgonine, the major metabolite, and in lesser amounts ecgonine methyl ester and ecgonine. Pseudoecgonine is a steroisomer of ecgonine and may be conjugated to CoA to form Pseudoecgonyl-CoA through the action of gut microlfora (PMID: 8572717 ). |
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Structure | CN1C2CCC1[C@@H]([C@@H](O)C2)C(O)=O InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8-/m0/s1 |
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Synonyms | Value | Source |
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(+)-Pseudoecgonine | HMDB | (2S,3S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | HMDB | (2S,3S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid | HMDB | D-Pseudoecgonine | HMDB | D-Psi-ecgonine | HMDB | delta-Pseudoecgonine | HMDB | delta-Psi-ecgonine | HMDB | pseudo-Ecgonine | HMDB |
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Chemical Formula | C9H15NO3 |
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Average Molecular Weight | 185.2203 |
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Monoisotopic Molecular Weight | 185.105193351 |
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IUPAC Name | (2S,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid |
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Traditional Name | pseudoecgonine |
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CAS Registry Number | Not Available |
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SMILES | CN1C2CCC1[C@@H]([C@@H](O)C2)C(O)=O |
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InChI Identifier | InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8-/m0/s1 |
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InChI Key | PHMBVCPLDPDESM-GHNGIAPOSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Tropane alkaloids |
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Sub Class | Not Available |
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Direct Parent | Tropane alkaloids |
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Alternative Parents | |
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Substituents | - Piperidinecarboxylic acid
- Tropane alkaloid
- Beta-hydroxy acid
- Hydroxy acid
- Piperidine
- N-alkylpyrrolidine
- Cyclic alcohol
- Pyrrolidine
- Amino acid or derivatives
- Amino acid
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Amine
- Organic oxide
- Organopnictogen compound
- Alcohol
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organic oxygen compound
- 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 | 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 | 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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Pseudoecgonine,1TMS,isomer #1 | CN1C2CCC1[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)C2 | 1668.1 | Semi standard non polar | 33892256 | Pseudoecgonine,1TMS,isomer #2 | CN1C2CCC1[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)C2 | 1607.2 | Semi standard non polar | 33892256 | Pseudoecgonine,2TMS,isomer #1 | CN1C2CCC1[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2 | 1686.6 | Semi standard non polar | 33892256 | Pseudoecgonine,1TBDMS,isomer #1 | CN1C2CCC1[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C2 | 1880.3 | Semi standard non polar | 33892256 | Pseudoecgonine,1TBDMS,isomer #2 | CN1C2CCC1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C2 | 1834.7 | Semi standard non polar | 33892256 | Pseudoecgonine,2TBDMS,isomer #1 | CN1C2CCC1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2 | 2128.7 | Semi 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 - Pseudoecgonine GC-MS (Non-derivatized) - 70eV, Positive | splash10-001j-9200000000-48c3b8ee572b2dc52292 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pseudoecgonine GC-MS (2 TMS) - 70eV, Positive | splash10-006t-9132000000-9a8887ca9dce4b08af81 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pseudoecgonine 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 - Pseudoecgonine 10V, Positive-QTOF | splash10-014r-0900000000-84cf8248e17a8b226247 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 20V, Positive-QTOF | splash10-0gb9-0900000000-ada9e3b58a4a68bf34fe | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 40V, Positive-QTOF | splash10-0fk9-3900000000-4fe8aa09d75ccea8cb33 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 10V, Negative-QTOF | splash10-007o-0900000000-c8352412d369827945bc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 20V, Negative-QTOF | splash10-00dl-0900000000-143c9c6dc9126fa654dc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 40V, Negative-QTOF | splash10-00dl-1900000000-cb49be4d17eb1921ff3e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 10V, Positive-QTOF | splash10-000i-0900000000-4a6fc2f9a39f6a7a3d44 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 20V, Positive-QTOF | splash10-00kv-5900000000-a2ec3ebcb3ee1f393d9b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 40V, Positive-QTOF | splash10-00dj-9700000000-ac3cdeb9ee66f2c193db | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 10V, Negative-QTOF | splash10-0159-0900000000-dc9636670e82e30cec7c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 20V, Negative-QTOF | splash10-007o-1900000000-5cbac175885e0c570c49 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pseudoecgonine 40V, Negative-QTOF | splash10-0089-6900000000-987da97e182a8b3e0ba9 | 2021-09-23 | 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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