Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 05:24:33 UTC |
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Updated at | 2022-09-09 05:24:34 UTC |
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NP-MRD ID | NP0279866 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 4 hydroxyproline |
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Description | Cis-4-Hydroxyproline, also known as L-allo-hydroxyproline or H-cis-hyp-OH, 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. Cis-4-Hydroxyproline is a very strong basic compound (based on its pKa). Outside of the human body, cis-4-Hydroxyproline is found, on average, in the highest concentration within a few different foods, such as oats, ryes, and wheats and in a lower concentration in saskatoon berries, nanking cherries, and yellow bell peppers. Cis-4-Hydroxyproline has also been detected, but not quantified in, green bell peppers. 4 hydroxyproline is found in Daucus carota, Festuca rubra and Santalum album. It was first documented in 2012 (PMID: 22770225). This could make cis-4-hydroxyproline a potential biomarker for the consumption of these foods. |
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Structure | [H][C@@]1(O)CN[C@@]([H])(C1)C(O)=O InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1 |
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Synonyms | Value | Source |
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(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylic acid | ChEBI | 4-cis-L-Hydroxyproline | ChEBI | Allo-4-hydroxy-L-proline | ChEBI | L-Allo-hydroxyproline | ChEBI | L-cis-4-Hydroxyproline | ChEBI | L-Allohydroxyproline | Kegg | (2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylate | Generator | Hydroxyproline | HMDB | 4 Hydroxyproline | HMDB | 4-Hydroxyproline | HMDB | Oxyproline | HMDB | cis 4 Hydroxyproline | HMDB | cis-4-Hydroxy-L-proline | HMDB | cis-Hydroxyproline | HMDB | (4S)-4-Hydroxy-L-proline | HMDB | (2S,4S)-4-Hydroxyproline | HMDB | (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid | HMDB | (S)-Allo-hydroxyproline | HMDB | 4(S)-Hydroxy-2(S)-pyrrolidinecarboxylic acid | HMDB | 4-cis-Hydroxy-L-proline | HMDB | 4-Allo-hydroxyproline | HMDB | L-Allo-4-hydroxyproline | HMDB | Allo-4-hydroxyproline | HMDB | Allo-hydroxy-L-proline | HMDB | Allo-L-hydroxyproline | HMDB | H-cis-Hyp-OH | HMDB | NSC 206274 | HMDB | cis-4-Hydroxyproline | HMDB, MeSH |
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Chemical Formula | C5H9NO3 |
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Average Mass | 131.1299 Da |
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Monoisotopic Mass | 131.05824 Da |
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IUPAC Name | (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid |
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Traditional Name | L-hydroxyproline |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]1(O)CN[C@@]([H])(C1)C(O)=O |
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InChI Identifier | InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1 |
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InChI Key | PMMYEEVYMWASQN-IMJSIDKUSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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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
- Pyrrolidine
- 1,2-aminoalcohol
- Amino acid
- Secondary alcohol
- Carboxylic acid
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Azacycle
- Secondary amine
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Amine
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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