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| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-10-09 20:57:44 UTC |
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| HMDB ID | HMDB0000119 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Glyoxylic acid |
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| Description | Glyoxylic acid or oxoacetic acid is an organic compound that is both an aldehyde and a carboxylic acid. Glyoxylic acid is a liquid with a melting point of -93°C and a boiling point of 111°C. It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates. The conjugate base of glyoxylic acid is known as glyoxylate (PMID: 16396466 ). In humans, glyoxylate is produced via two pathways: (1) through the oxidation of glycolate in peroxisomes and (2) through the catabolism of hydroxyproline in mitochondria. In the peroxisomes, glyoxylate is converted into glycine by glyoxylate aminotransferase (AGT1) or into oxalate by glycolate oxidase. In the mitochondria, glyoxylate is converted into glycine by mitochondrial glyoxylate aminotransferase AGT2 or into glycolate by glycolate reductase. A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase. Glyoxylic acid is found to be associated with primary hyperoxaluria I, which is an inborn error of metabolism. Under certain circumstances, glyoxylate can be a nephrotoxin and a metabotoxin. A nephrotoxin is a compound that causes damage to the kidney and kidney tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. High levels of glyoxylate are involved in the development of hyperoxaluria, a key cause of nephrolithiasis (commonly known as kidney stones). Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (SAT-1), a gene responsible for oxalate transportation, allowing it to increase SAT-1 mRNA expression, and as a result oxalate efflux from the cell. The increased oxalate release allows the buildup of calcium oxalate in the urine, and thus the eventual formation of kidney stones. As an aldehyde, glyoxylate is also highly reactive and will modify proteins to form advanced glycation products (AGEs). |
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| Structure | |
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| Synonyms | | Value | Source |
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| alpha-Ketoacetic acid | ChEBI | | Formylformic acid | ChEBI | | Glyoxalate | ChEBI | | Glyoxalsaeure | ChEBI | | Glyoxylate | ChEBI | | Glyoxylsaeure | ChEBI | | Oxalaldehydic acid | ChEBI | | Oxoethanoic acid | ChEBI | | a-Ketoacetate | Generator | | a-Ketoacetic acid | Generator | | alpha-Ketoacetate | Generator | | Α-ketoacetate | Generator | | Α-ketoacetic acid | Generator | | Formylformate | Generator | | Glyoxalic acid | Generator | | Oxalaldehydate | Generator | | Oxoethanoate | Generator | | Oxoacetate | HMDB | | Oxoacetic acid | HMDB | | Glyoxylic acid, 2-(14)C-labeled | HMDB | | Glyoxylic acid, sodium salt | HMDB | | Glyoxylic acid, sodium salt, 2-(14)C-labeled | HMDB | | Glyoxylic acid, 14c2-labeled | HMDB | | Glyoxylic acid, calcium salt | HMDB | | Glyoxylic acid, sodium salt, 14C-labeled | HMDB |
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| Chemical Formula | C2H2O3 |
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| Average Molecular Weight | 74.0355 |
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| Monoisotopic Molecular Weight | 74.00039393 |
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| IUPAC Name | 2-oxoacetic acid |
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| Traditional Name | glyoxylic acid |
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| CAS Registry Number | 298-12-4 |
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| SMILES | OC(=O)C=O |
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| InChI Identifier | InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) |
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| InChI Key | HHLFWLYXYJOTON-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. |
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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 | Carboxylic acids |
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| Direct Parent | Carboxylic acids |
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| Alternative Parents | |
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| Substituents | - Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Short-chain aldehyde
- Organooxygen compound
- Carbonyl group
- Aldehyde
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Indirect biological role: Industrial application: |
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -93 °C | 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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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-03di-3900000000-16bc69e0e9d51e54854e | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-03di-3900000000-16bc69e0e9d51e54854e | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0096-9000000000-042540a05be250278f8b | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00fr-9200000000-c60b627ed670285ec37f | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-00di-9000000000-72c34bc34b8c3341442b | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00di-9000000000-920a0dc738957201d4ba | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00di-9000000000-857c7f2d72c3d4c10dbf | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00di-9000000000-9b5825d5d9d8b094fefa | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00di-9000000000-de556f03ea428deff5e2 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00dl-9000000000-74b253632894213d473c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-9b5825d5d9d8b094fefa | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-de556f03ea428deff5e2 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00dl-9000000000-74b253632894213d473c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-a8cc2c89793394fdf9e4 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-9000000000-d20183b08984d4766e8a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-ea9968e3933fd734506c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-cef8efc477a2500a7ead | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-3817c0865df629803538 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-bb935f857fb5fd08c7e3 | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-004l-9000000000-a04bafbf8e0b990094a3 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Urine
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 3.05 (0.25–12.78) uM | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 3.28 (2.0-5.32) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 1.467 (0.467-3.933) umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 1.27 (0.46-3.26) umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 1.88 (0.63-3.22) umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details |
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| Abnormal Concentrations |
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| Cerebrospinal Fluid (CSF) | Detected and Quantified | 76 uM | Adult (>18 years old) | Not Specified | Transurethral prostatectomy syndrome | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Interstitial cystitis | | details | | Urine | Detected and Quantified | 74 umol/mmol creatinine | Adult (>18 years old) | Male | Primary hyperoxaluria I | | details | | Urine | Detected and Quantified | 36-270 umol/mmol creatinine | Children (1-13 years old) | Both | Primary hyperoxaluria I | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Transurethral resection of the prostate |
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- Perier C, Mahul P, Molliex S, Auboyer C, Frey J: Progressive changes in glycine and glycine derivatives in plasma and cerebrospinal fluid after transurethral prostatic resection. Clin Chem. 1990 Dec;36(12):2152-3. [PubMed:2253377 ]
| | Bladder infections |
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- Braundmeier-Fleming A, Russell NT, Yang W, Nas MY, Yaggie RE, Berry M, Bachrach L, Flury SC, Marko DS, Bushell CB, Welge ME, White BA, Schaeffer AJ, Klumpp DJ: Stool-based biomarkers of interstitial cystitis/bladder pain syndrome. Sci Rep. 2016 May 18;6:26083. doi: 10.1038/srep26083. [PubMed:27188581 ]
| | Primary hyperoxaluria I |
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- Holmgren G, Hornstrom T, Johansson S, Samuelson G: Primary hyperoxaluria (glycolic acid variant): a clinical and genetical investigation of eight cases. Ups J Med Sci. 1978;83(1):65-70. [PubMed:705974 ]
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| Associated OMIM IDs | None |
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| External Links |
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| DrugBank ID | DB04343 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB007244 |
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| KNApSAcK ID | C00001186 |
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| Chemspider ID | 740 |
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| KEGG Compound ID | C00048 |
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| BioCyc ID | GLYOX |
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| BiGG ID | 33659 |
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| Wikipedia Link | Glyoxylic_acid |
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| METLIN ID | 3213 |
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| PubChem Compound | 760 |
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| PDB ID | Not Available |
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| ChEBI ID | 16891 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | GLX |
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| MarkerDB ID | MDB00000055 |
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| References |
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| Synthesis Reference | Jie, Yuanping; Song, Zhen. Method for preparing glyoxylic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Naghizadeh F, Barlow D, King J: The reduction of oxo-acids by human tissue extracts. Clin Biochem. 1976 Apr;9(2):65-6. [PubMed:1261003 ]
- Borondy PE, Michniewicz BM: Metabolic disposition of isoxicam in man, monkey, dog, and rat. Drug Metab Dispos. 1984 Jul-Aug;12(4):444-51. [PubMed:6148211 ]
- Arvesen A, Maehlen J, Rosen L, Aas P: Myointimal hyperplasia and sympathetic reinnervation following local cold injury and rapid rewarming in the rabbit central ear artery. Vasa. 2001 Jul;30(3):176-83. [PubMed:11582947 ]
- Motomiya Y, Oyama N, Iwamoto H, Uchimura T, Maruyama I: N epsilon-(carboxymethyl)lysine in blood from maintenance hemodialysis patients may contribute to dialysis-related amyloidosis. Kidney Int. 1998 Oct;54(4):1357-66. [PubMed:9767556 ]
- Holmes E, Foxall PJ, Spraul M, Farrant RD, Nicholson JK, Lindon JC: 750 MHz 1H NMR spectroscopy characterisation of the complex metabolic pattern of urine from patients with inborn errors of metabolism: 2-hydroxyglutaric aciduria and maple syrup urine disease. J Pharm Biomed Anal. 1997 Jul;15(11):1647-59. [PubMed:9260660 ]
- Mentasti E, Savigliano M, Marangella M, Petrarulo M, Linari F: High-performance liquid chromatographic determination of glyoxylic acid and other carbonyl compounds in urine. J Chromatogr. 1987 Jul 3;417(2):253-60. [PubMed:3654878 ]
- Bruzzese FJ, Dix JA, Rava RP, Cerny LC: Resonance Raman spectroscopy of chemically modified hemoglobins. Biomater Artif Cells Artif Organs. 1990;18(2):143-56. [PubMed:2369642 ]
- Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
- Schmitt A, Gasic-Milenkovic J, Schmitt J: Characterization of advanced glycation end products: mass changes in correlation to side chain modifications. Anal Biochem. 2005 Nov 1;346(1):101-6. Epub 2005 Aug 15. [PubMed:16168380 ]
- Booth ED, Dofferhoff O, Boogaard PJ, Watson WP: Comparison of the metabolism of ethylene glycol and glycolic acid in vitro by precision-cut tissue slices from female rat, rabbit and human liver. Xenobiotica. 2004 Jan;34(1):31-48. [PubMed:14742135 ]
- Tainio H, Vaalasti A, Rechardt L: The distribution of sympathetic adrenergic, tyrosine hydroxylase- and neuropeptide Y-immunoreactive nerves in human axillary sweat glands. Histochemistry. 1986;85(2):117-20. [PubMed:2875046 ]
- Davis WL, Goodman DB: Evidence for the glyoxylate cycle in human liver. Anat Rec. 1992 Dec;234(4):461-8. [PubMed:1456449 ]
- Arvesen A, Maehlen J, Rosen L, Aas P: Early and late functional and histopathological perturbations in the rabbit ear-artery following local cold injury. Vasa. 1999 May;28(2):85-94. [PubMed:10409918 ]
- Popov VN, Moskalev EA, Shevchenko MIu, Eprintsev AT: [Comparative analysis of the glyoxylate cycle clue enzyme isocitrate lyases from organisms of different systemic groups]. Zh Evol Biokhim Fiziol. 2005 Nov-Dec;41(6):507-13. [PubMed:16396466 ]
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