Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:34 UTC |
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Update date | 2019-11-26 02:54:51 UTC |
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Primary ID | FDB000463 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Stachydrine |
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Description | Proline betaine, also known as stachydrine, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Proline betaine exists in all living organisms, ranging from bacteria to humans. Proline betaine is found, on average, in the highest concentration within capers (Capparis spinosa). Proline betaine has also been detected, but not quantified in, several different foods, such as flour, fruit juice, chickens (Gallus gallus), quinoas (Chenopodium quinoa), and common wheats (Triticum aestivum). This could make proline betaine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Proline betaine. |
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CAS Number | 471-87-4 |
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Structure | |
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Synonyms | Synonym | Source |
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(S)-2-Carboxylato-1,1-dimethylpyrrolidinium | ChEBI | N,N-Dimethyl-L-proline | ChEBI | Stachydrine | ChEBI | L-Proline betaine | Kegg | (2S)-2-Carboxy-1,1-dimethylpyrrolidinium | HMDB | (S)-2-Carboxy-1,1-dimethylpyrrolidinium | HMDB | Homostachydrine | HMDB | Prestwick-08g03 | HMDB | Dimethylproline | MeSH, HMDB | Stachydrine chloride | MeSH, HMDB | Stachydrine chloride, (S)-isomer | MeSH, HMDB | Stachydrine, (+-)-isomer | MeSH, HMDB | Proline betaine | ChEBI | (2S)-1,1-Dimethylpyrrolidinium-2-carboxylate | biospider | L-Stachydrine | manual | Pyrrolidinium, 2-carboxy-1,1-dimethyl-, inner salt, (2S)- | biospider | S-Stachydrine | manual | Stachydrine; L-form | db_source |
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Predicted Properties | |
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Chemical Formula | C7H13NO2 |
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IUPAC name | (2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate |
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InChI Identifier | InChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1 |
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InChI Key | CMUNUTVVOOHQPW-LURJTMIESA-N |
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Isomeric SMILES | C[N+]1(C)CCC[C@H]1C([O-])=O |
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Average Molecular Weight | 143.1836 |
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Monoisotopic Molecular Weight | 143.094628665 |
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Classification |
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Description | Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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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 | Proline and derivatives |
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Alternative Parents | |
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Substituents | - Proline or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- N-alkylpyrrolidine
- Tetraalkylammonium salt
- Pyrrolidine
- Quaternary ammonium salt
- Carboxylic acid salt
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Amine
- Carbonyl group
- Organic salt
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: Biological role: |
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Foods | Fruits and vegetables: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 58.72%; H 9.15%; N 9.78%; O 22.35% | DFC |
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Melting Point | Mp 235 dec. (anhyd.) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D -40.25 (c, 4 in H2O) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | L-Stachydrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002e-9000000000-36bbb91342358293711a | Spectrum | Predicted GC-MS | L-Stachydrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0bt9-9200000000-395432f0cf8795dd4cf7 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0900000000-ea4782d2282bc28329c0 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0007-4900000000-75a3b0df6adc0100b9fe | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aou-9000000000-5df24b6079668b584f79 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-34921bec4b2fad07f505 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-3900000000-da3a14fcb5a4909b775e | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000f-9000000000-7b04a861eee46ac86b66 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9500000000-135bbe696520934e172e | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9100000000-6d9ce7552b62c3e5d66c | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-059w-9100000000-1648e60acdd97fc80a9d | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-bf6e206b443f53ef90b5 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0900000000-bf6e206b443f53ef90b5 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-94164ee813c486cb0b96 | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 103115 |
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ChEMBL ID | CHEMBL1456892 |
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KEGG Compound ID | C10172 |
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Pubchem Compound ID | 115244 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 35280 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB04827 |
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CRC / DFC (Dictionary of Food Compounds) ID | BCP48-N:BCP49-O |
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EAFUS ID | Not Available |
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Dr. Duke ID | STACHYDRINE|L-STACHYDRINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002074 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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cardiotonic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | emmenagogue | | | DUKE | insectifuge | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | lactagogue | | | DUKE | oxytocic | 36063 | A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients). | DUKE | systolic depressant | | | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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