Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:27:37 UTC |
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Update Date | 2020-06-04 20:58:01 UTC |
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BMDB ID | BMDB0000267 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pyroglutamic acid |
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Description | Pyroglutamic acid, also known as pyroglutamate or pidolate, magnesium, 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 possibly soluble (in water) and 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 potentially toxic compound. |
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Structure | |
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Synonyms | Value | 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 |
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Chemical Formula | C5H7NO3 |
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Average Molecular Weight | 129.114 |
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Monoisotopic Molecular Weight | 129.042593095 |
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IUPAC Name | (2S)-5-oxopyrrolidine-2-carboxylic acid |
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Traditional Name | pyroglutamic acid |
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CAS Registry Number | 98-79-3 |
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SMILES | OC(=O)[C@@H]1CCC(=O)N1 |
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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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Chemical Taxonomy |
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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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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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Physical Properties |
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State | Solid |
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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 | 476.0 mg/mL at 13 °C | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0ab9-8900000000-f79dc90370ba38f587c9 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0ab9-8900000000-f79dc90370ba38f587c9 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0900000000-90fb43273551aeb9b2c4 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a6r-9000000000-130a8f31f82e83c4be07 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-05fr-9200000000-d69b52257404ab658d5b | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-9500000000-ebc64308ec5d5bdb303e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-053r-9000000000-7377cb17491942e9589c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-053u-9000000000-fcab1396867356ebd6ae | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-5b0c6536e1b3217b8544 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0900000000-c30ac0bd264c8007ef92 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-5900000000-ea3a164653e4235716ae | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0f89-9000000000-f6620738e68f990d0594 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0udi-9000000000-7937bee2e9a6d6b29cbd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-f20401903b234914b936 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0900000000-9446bb65e0edd72cfd59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0059-7900000000-74eccdeb9f0d5fd17614 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0f8a-9000000000-8786a9cd5e488192f34d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0f6t-9000000000-ebcc1ac4acd525218e80 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-01q9-2900000000-754ae9b699ec1b22cd76 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-001i-9300000000-eabb8c4dc0d1111e0431 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00lr-9100000000-1dd17702aee7e5bce618 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-067i-9000000000-c9669794d3a8746be498 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9000000000-9e103abb0a6ed890051e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-03e9-3900000000-da8cf252285c1d616586 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-01q9-9400000000-96a7fe5a81188c49d1ba | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-014i-9000000000-356215339a43217dea66 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-02vl-9000000000-ed47ec6e675eb338da19 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9000000000-f647da344adbdf7bfb1b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-001i-9200000000-0bddc68d58c6fb981d1a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-0900000000-c70c79fa828bbf137ebc | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-001i-9000000000-6c87253da642bb4800df | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 233 +/- 64 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 384.1 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 486.8 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 524.7 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 355.9 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 384 +/- 59 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 486 +/- 94 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 525 +/- 120 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 356 +/- 45 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 356 +/- 45 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 355.94 +/- 44.73 uM | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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General References | - Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]
- Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.
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