| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2006-05-22 14:17:37 UTC |
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| Update Date | 2023-02-21 17:16:10 UTC |
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| HMDB ID | HMDB0002113 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 3-Hydroxy-L-proline |
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| Description | 3-Hydroxy-L-proline 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. 3-Hydroxy-L-proline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxy-L-proline a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Hydroxy-L-proline. |
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| Structure | InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1 |
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| Synonyms | | Value | Source |
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| cis-3-Hydroxy-D-proline | ChEBI | | Procollagen trans-3-hydroxy-L-proline | HMDB |
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| Chemical Formula | C5H9NO3 |
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| Average Molecular Weight | 131.1299 |
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| Monoisotopic Molecular Weight | 131.058243159 |
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| IUPAC Name | (2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid |
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| Traditional Name | 3-hydroxy-L-proline |
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| CAS Registry Number | 4298-08-2 |
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| SMILES | O[C@H]1CCN[C@H]1C(O)=O |
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| InChI Identifier | InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1 |
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| InChI Key | BJBUEDPLEOHJGE-IUYQGCFVSA-N |
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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
- D-alpha-amino acid
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Beta-hydroxy acid
- Hydroxy acid
- Pyrrolidine
- Amino acid
- Secondary alcohol
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Organic oxide
- Organonitrogen compound
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Amine
- Organic nitrogen compound
- Organopnictogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic 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 | 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 | 235 °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 Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 1.16 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 8.8792 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 7.29 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 387.2 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 429.7 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 317.3 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 41.6 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 201.3 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 74.3 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 286.5 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 223.5 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 834.5 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 563.9 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 39.2 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 658.1 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 207.1 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 297.3 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 770.1 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 492.6 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 352.6 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| 3-Hydroxy-L-proline,1TMS,isomer #1 | C[Si](C)(C)O[C@H]1CCN[C@H]1C(=O)O | 1408.6 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,1TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O | 1346.0 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,1TMS,isomer #3 | C[Si](C)(C)N1CC[C@H](O)[C@@H]1C(=O)O | 1414.9 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,2TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O[Si](C)(C)C | 1444.3 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,2TMS,isomer #2 | C[Si](C)(C)O[C@H]1CCN([Si](C)(C)C)[C@H]1C(=O)O | 1466.8 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,2TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@H]1[C@@H](O)CCN1[Si](C)(C)C | 1421.3 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,3TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C | 1503.2 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,3TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C | 1566.1 | Standard non polar | 33892256 | | 3-Hydroxy-L-proline,3TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C | 1653.9 | Standard polar | 33892256 | | 3-Hydroxy-L-proline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1CCN[C@H]1C(=O)O | 1671.2 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O | 1588.8 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1CC[C@H](O)[C@@H]1C(=O)O | 1691.3 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O[Si](C)(C)C(C)(C)C | 1898.5 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H]1CCN([Si](C)(C)C(C)(C)C)[C@H]1C(=O)O | 1939.3 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O)CCN1[Si](C)(C)C(C)(C)C | 1912.2 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C | 2181.5 | Semi standard non polar | 33892256 | | 3-Hydroxy-L-proline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C | 2192.3 | Standard non polar | 33892256 | | 3-Hydroxy-L-proline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C | 2076.7 | Standard polar | 33892256 |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, Positive | splash10-054o-9000000000-b543b8f19baf933e2510 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (2 TMS) - 70eV, Positive | splash10-0a4i-8920000000-a1f57d10065421ae5629 | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Positive-QTOF | splash10-03e9-2900000000-128ccf9715c5890c5404 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Positive-QTOF | splash10-03xr-9600000000-8c3c68532a2b86bfd028 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Positive-QTOF | splash10-0fr6-9000000000-d018e434f138775d4120 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Negative-QTOF | splash10-001r-7900000000-3230ec745853fb03ffc2 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Negative-QTOF | splash10-02u9-9300000000-8240d8b2c6fddad07085 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Negative-QTOF | splash10-0673-9000000000-a3fea27c28e95706d0ec | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Positive-QTOF | splash10-000i-9400000000-f8803de3984022a6de11 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Positive-QTOF | splash10-00kr-9000000000-7199742da3eaa66ad564 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Positive-QTOF | splash10-00kf-9000000000-f8bbde6aa62a6d9afa3b | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Negative-QTOF | splash10-001i-1900000000-df968a68e6f2ab76adc2 | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Negative-QTOF | splash10-0006-9200000000-c73aa9b436f74ef75e9c | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Negative-QTOF | splash10-052f-9000000000-08bc65f1f17e8bcb3d04 | 2021-09-23 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
IR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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