Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:19 UTC |
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Update date | 2019-11-26 03:10:13 UTC |
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Primary ID | FDB014506 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | L-5-Oxo-2-pyrrolidinecarboxylic acid |
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Description | Pyroglutamic acid, also known as pyroglutamate or pidolate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Pyroglutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Pyroglutamic acid exists in all living species, ranging from bacteria to humans. Pyroglutamic acid is a mild, sweet, and ethereal tasting compound. Pyroglutamic acid is found, on average, in the highest concentration within soy beans and beers. Pyroglutamic acid has also been detected, but not quantified in, several different foods, such as common buckwheats, allspices, butternut squash, pulses, and hazelnuts. This could make pyroglutamic acid a potential biomarker for the consumption of these foods. Pyroglutamic acid is a potentially toxic compound. |
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CAS Number | 98-79-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-2-Pyrrolidone-5-carboxylic acid | ChEBI | (S)-(-)-2-Pyrrolidone-5-carboxylic acid | ChEBI | (S)-Pyroglutamic acid | ChEBI | 5-Pyrrolidone-2-carboxylic acid | ChEBI | L-5-Pyrrolidone-2-carboxylic acid | ChEBI | L-Pyroglutamic acid | ChEBI | Pidolic acid | ChEBI | Pyroglutamate | ChEBI | 5-oxo-L-Proline | Kegg | (-)-2-Pyrrolidone-5-carboxylate | Generator | (S)-(-)-2-Pyrrolidone-5-carboxylate | Generator | (S)-Pyroglutamate | Generator | 5-Pyrrolidone-2-carboxylate | Generator | L-5-Pyrrolidone-2-carboxylate | Generator | L-Pyroglutamate | Generator | Pidolate | Generator | (-)-Pyroglutamate | HMDB | (-)-Pyroglutamic acid | HMDB | (5S)-2-Oxopyrrolidine-5-carboxylate | HMDB | (5S)-2-Oxopyrrolidine-5-carboxylic acid | HMDB | (S)-(-)-g-Butyrolactam-g-carboxylate | HMDB | (S)-(-)-g-Butyrolactam-g-carboxylic acid | HMDB | (S)-(-)-gamma-Butyrolactam-gamma-carboxylate | HMDB | (S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid | HMDB | (S)-2-Pyrrolidone-5-carboxylate | HMDB | (S)-2-Pyrrolidone-5-carboxylic acid | HMDB | (S)-5-oxo-2-Pyrrolidinecarboxylate | HMDB | (S)-5-oxo-2-Pyrrolidinecarboxylic acid | HMDB | 2-L-Pyrrolidone-5-carboxylate | HMDB | 2-L-Pyrrolidone-5-carboxylic acid | HMDB | 2-Oxopyrrolidine-5(S)-carboxylate | HMDB | 2-Oxopyrrolidine-5(S)-carboxylic acid | HMDB | 2-Pyrrolidinone-5-carboxylate | HMDB | 2-Pyrrolidinone-5-carboxylic acid | HMDB | 5-Carboxy-2-pyrrolidinone | HMDB | 5-L-Oxoproline | HMDB | 5-Oxoproline | HMDB | 5-Pyrrolidinone-2-carboxylate | HMDB | 5-Pyrrolidinone-2-carboxylic acid | HMDB | Ajidew a 100 | HMDB | Glutimate | HMDB | Glutimic acid | HMDB | Glutiminate | HMDB | Glutiminic acid | HMDB | L-2-Pyrrolidone-5-carboxylate | HMDB | L-2-Pyrrolidone-5-carboxylic acid | HMDB | L-5-Carboxy-2-pyrrolidinone | HMDB | L-5-oxo-2-Pyrrolidinecarboxylate | HMDB | L-5-oxo-2-Pyrrolidinecarboxylic acid | HMDB | L-5-Oxoproline | HMDB | L-Glutamic acid g-lactam | HMDB | L-Glutimate | HMDB | L-Glutimic acid | HMDB | L-Glutiminate | HMDB | L-Glutiminic acid | HMDB | L-Pyrrolidinonecarboxylate | HMDB | L-Pyrrolidinonecarboxylic acid | HMDB | L-Pyrrolidonecarboxylate | HMDB | L-Pyrrolidonecarboxylic acid | HMDB | Oxoproline | HMDB | Oxopyrrolidinecarboxylate | HMDB | Oxopyrrolidinecarboxylic acid | HMDB | Pidolidone | HMDB | Pyrrolidinonecarboxylate | HMDB | Pyrrolidinonecarboxylic acid | HMDB | Pyrrolidone-5-carboxylate | HMDB | Pyrrolidone-5-carboxylic acid | HMDB | Pyrrolidonecarboxylic acid | HMDB | 5-Ketoproline | HMDB | Pidolate, magnesium | HMDB | 5-Oxopyrrolidine-2-carboxylic acid | HMDB | Magnesium pidolate | HMDB | 2-Pyrrolidone-5-carboxylic acid | HMDB | 5-Oxoprolinate | HMDB | PCA | HMDB | (2S)-5-oxopyrrolidine-2-carboxylic acid | biospider | (s)-(-)-g-butyrolactam-g-carboxylate | biospider | (s)-(-)-g-butyrolactam-g-carboxylic acid | biospider | (s)-(-)-gamma-butyrolactam-gamma-carboxylate | biospider | (s)-(-)-gamma-butyrolactam-gamma-carboxylic acid | biospider | (S)-5-Oxo-2-pyrrolidinecarboxylate | biospider | (S)-5-Oxo-2-pyrrolidinecarboxylic acid | biospider | (s)-pyroglutamate | biospider | (s)-pyroglutamic acid | biospider | 5-L-oxoproline | biospider | 5-Oxo-2-pyrrolidinecarboxylic acid; L-form | db_source | 5-Oxo-L-proline | biospider | L-5-Oxo-2-pyrrolidinecarboxylate | biospider | L-5-Oxo-2-pyrrolidinecarboxylic acid | biospider | l-5-Pyrrolidone-2-carboxylic acid | biospider | L-glutamic acid g-lactam | biospider | L-glutamic acid gamma-lactam | biospider | L-glutimate | biospider | L-glutimic acid | biospider | L-glutiminate | biospider | L-glutiminic acid | biospider | L-pyroglutamate | biospider | L-pyroglutamic acid | biospider | L-pyrrolidinonecarboxylate | biospider | L-pyrrolidinonecarboxylic acid | biospider | L-pyrrolidonecarboxylate | biospider | L-pyrrolidonecarboxylic acid | biospider | Pyroglutamic acid | ChEBI |
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Predicted Properties | |
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Chemical Formula | C5H7NO3 |
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IUPAC name | (2S)-5-oxopyrrolidine-2-carboxylic acid |
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InChI Identifier | InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 |
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InChI Key | ODHCTXKNWHHXJC-VKHMYHEASA-N |
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Isomeric SMILES | OC(=O)[C@@H]1CCC(=O)N1 |
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Average Molecular Weight | 129.114 |
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Monoisotopic Molecular Weight | 129.042593095 |
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Classification |
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Description | Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
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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 | Alpha amino acids and derivatives |
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Alternative Parents | |
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Substituents | - Alpha-amino acid or derivatives
- Pyrroline carboxylic acid
- Pyrroline carboxylic acid or derivatives
- Pyrroline
- Cyclic carboximidic acid
- Lactim
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Azacycle
- Organoheterocyclic compound
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organic nitrogen compound
- Organonitrogen compound
- 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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Ontology | No ontology term |
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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 46.51%; H 5.46%; N 10.85%; O 37.17% | DFC |
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Melting Point | Mp 156-157° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 476 mg/mL at 13 oC | BEILSTEIN |
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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]20D -11.45 (c, 4.44 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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-001i-9000000000-6c87253da642bb4800df | 2019-05-16 | View Spectrum | GC-MS | Psidiolic acid, 2 TMS, GC-MS Spectrum | splash10-0ab9-8900000000-f79dc90370ba38f587c9 | Spectrum | GC-MS | Psidiolic acid, non-derivatized, GC-MS Spectrum | splash10-0ab9-8900000000-f79dc90370ba38f587c9 | Spectrum | GC-MS | Psidiolic acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-0900000000-90fb43273551aeb9b2c4 | Spectrum | Predicted GC-MS | Psidiolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a6r-9000000000-130a8f31f82e83c4be07 | Spectrum | Predicted GC-MS | Psidiolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05fr-9200000000-d69b52257404ab658d5b | Spectrum | Predicted GC-MS | Psidiolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Psidiolic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Psidiolic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Psidiolic acid, TBDMS_1_2, 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 - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-9500000000-ebc64308ec5d5bdb303e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-053r-9000000000-7377cb17491942e9589c | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-053u-9000000000-fcab1396867356ebd6ae | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-5b0c6536e1b3217b8544 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0900000000-c30ac0bd264c8007ef92 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-5900000000-ea3a164653e4235716ae | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0f89-9000000000-f6620738e68f990d0594 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0udi-9000000000-7937bee2e9a6d6b29cbd | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-f20401903b234914b936 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0900000000-9446bb65e0edd72cfd59 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0059-7900000000-74eccdeb9f0d5fd17614 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0f8a-9000000000-8786a9cd5e488192f34d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0f6t-9000000000-ebcc1ac4acd525218e80 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-01q9-2900000000-754ae9b699ec1b22cd76 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-001i-9300000000-eabb8c4dc0d1111e0431 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00lr-9100000000-1dd17702aee7e5bce618 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-067i-9000000000-c9669794d3a8746be498 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9000000000-9e103abb0a6ed890051e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-03e9-3900000000-da8cf252285c1d616586 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-01q9-9400000000-96a7fe5a81188c49d1ba | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-014i-9000000000-356215339a43217dea66 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-02vl-9000000000-ed47ec6e675eb338da19 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9000000000-f647da344adbdf7bfb1b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-001i-9200000000-0bddc68d58c6fb981d1a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-0900000000-c70c79fa828bbf137ebc | 2012-08-31 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 7127 |
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ChEMBL ID | CHEMBL397976 |
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KEGG Compound ID | C01879 |
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Pubchem Compound ID | 7405 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18183 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB03088 |
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HMDB ID | HMDB00267 |
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CRC / DFC (Dictionary of Food Compounds) ID | HQL64-D:JRM15-X |
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EAFUS ID | Not Available |
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Dr. Duke ID | PYROGLUTAMIC-ACID |
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BIGG ID | 1800372 |
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KNApSAcK ID | C00007403 |
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HET ID | PCA |
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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 | rw1142131 |
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SuperScent ID | Not Available |
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Wikipedia ID | Pyroglutamic acid |
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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 | |
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Enzymes | Name | Gene Name | UniProt ID |
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Gamma-glutamylcyclotransferase | GGCT | O75223 | 5-oxoprolinase | OPLAH | O14841 | Angiogenin | ANG | P03950 | Vascular endothelial growth factor A | VEGFA | P15692 | Orexin | HCRT | O43612 | Ig lambda-1 chain C regions | IGLC1 | P0CG04 |
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Pathways | |
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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 | Flavor | Citations |
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mild |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| ethereal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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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).
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