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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2015-03-09 23:54:15 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameGlyoxylic acid
DescriptionGlyoxylic 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 degree centigrade and a boiling Point of 111 degree centigrade. It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates. The conjugate base of gloxylic acid is known as glyoxylate. This compound is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, fungi and plants to convert fatty acids into carbohydrates. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides. The glyoxylate cycle is a metabolic pathway occurring in plants, and several microorganisms, such as E. coli and yeast. Recent research shows that it is present in vertebrates (including humans) and insects. The glyoxylate cycle allows these organisms to use fats for the synthesis of carbohydrates. [PMID: 16396466 ].
  1. a-Ketoacetate
  2. a-Ketoacetic acid
  3. alpha-Ketoacetate
  4. alpha-Ketoacetic acid
  5. Formylformate
  6. Formylformic acid
  7. Glyoxalate
  8. Glyoxalic acid
  9. Glyoxylate
  10. Glyoxylic acid
  11. Oxalaldehydate
  12. Oxalaldehydic acid
  13. Oxoacetate
  14. Oxoacetic acid
  15. Oxoethanoate
  16. Oxoethanoic acid
Chemical FormulaC2H2O3
Average Molecular Weight74.0355
Monoisotopic Molecular Weight74.00039393
IUPAC Name2-oxoacetic acid
Traditional Nameglyoxylic acid
CAS Registry Number298-12-4
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Peroxisome
Physical Properties
Experimental Properties
Melting Point-93 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility224.0 mg/mLALOGPS
pKa (Strongest Acidic)2.61ChemAxon
pKa (Strongest Basic)-9.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity13.5 m3·mol-1ChemAxon
Polarizability5.35 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-ez00000000-16bc69e0e9d51e54854eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-z000000000-72c34bc34b8c3341442bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-z000000000-920a0dc738957201d4baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-z000000000-857c7f2d72c3d4c10dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-z000000000-9b5825d5d9d8b094fefaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-z000000000-de556f03ea428deff5e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-z000000000-74b253632894213d473cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-z000000000-a8cc2c89793394fdf9e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-z000000000-d20183b08984d4766e8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-z000000000-ea9968e3933fd734506cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-z000000000-cef8efc477a2500a7eadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-z000000000-3817c0865df629803538View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-z000000000-bb935f857fb5fd08c7e3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-z000000000-a04bafbf8e0b990094a3View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
Alanine MetabolismSMP00055map00250
Glycine and Serine MetabolismSMP00004map00260
Normal Concentrations
BloodDetected and Quantified3.05 (0.25–12.78) uMAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
UrineDetected and Quantified3.28 (2.0-5.32) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
UrineDetected and Quantified1.27 (0.46-3.26) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified1.88 (0.63-3.22) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Cerebrospinal Fluid (CSF)Detected and Quantified76 uMAdult (>18 years old)Not SpecifiedTransurethral prostatectomy syndrome details
UrineDetected and Quantified5.5 (0.00-11.00) umol/mmol creatinineAdult (>18 years old)BothPrimary hyperoxaluria I details
UrineDetected and Quantified20.00 (10.00-30.00) umol/mmol creatinineChildren (1-13 years old)BothPrimary hyperoxaluria I details
Associated Disorders and Diseases
Disease References
Transurethral resection of the prostate
  1. 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. [2253377 ]
Primary hyperoxaluria I
  1. MetaGene [Link]
Associated OMIM IDsNone
DrugBank IDDB04343
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001478
KNApSAcK IDC00001186
Chemspider ID740
KEGG Compound IDC00048
BiGG ID33659
Wikipedia LinkGlyoxylic acid
NuGOwiki LinkHMDB00119
Metagene LinkHMDB00119
PubChem Compound760
ChEBI ID16891
Synthesis ReferenceJie, Yuanping; Song, Zhen. Method for preparing glyoxylic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [9869358 ]
  2. 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. [14742135 ]
  3. Naghizadeh F, Barlow D, King J: The reduction of oxo-acids by human tissue extracts. Clin Biochem. 1976 Apr;9(2):65-6. [1261003 ]
  4. Borondy PE, Michniewicz BM: Metabolic disposition of isoxicam in man, monkey, dog, and rat. Drug Metab Dispos. 1984 Jul-Aug;12(4):444-51. [6148211 ]
  5. 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. [11582947 ]
  6. 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. [9767556 ]
  7. 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. [9260660 ]
  8. 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. [3654878 ]
  9. 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. [2369642 ]
  10. 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. [16168380 ]
  11. 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. [2875046 ]
  12. Davis WL, Goodman DB: Evidence for the glyoxylate cycle in human liver. Anat Rec. 1992 Dec;234(4):461-8. [1456449 ]
  13. 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. [10409918 ]
  14. 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. [16396466 ]


General function:
Involved in D-amino-acid oxidase activity
Specific function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
Uniprot ID:
Molecular weight:
Glycine + Water + Oxygen → Glyoxylic acid + Ammonia + Hydrogen peroxidedetails
General function:
Involved in monooxygenase activity
Specific function:
Bifunctional enzyme that catalyzes 2 sequential steps in C-terminal alpha-amidation of peptides. The monooxygenase part produces an unstable peptidyl(2-hydroxyglycine) intermediate that is dismutated to glyoxylate and the corresponding desglycine peptide amide by the lyase part. C-terminal amidation of peptides such as neuropeptides is essential for full biological activity.
Gene Name:
Uniprot ID:
Molecular weight:
Peptidylamidoglycolate → peptidyl amide + Glyoxylic aciddetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:
Uniprot ID:
Molecular weight:
Glycolic acid + NADP → Glyoxylic acid + NADPHdetails
Glycolic acid + NADP → Glyoxylic acid + NADPH + Hydrogen Iondetails
General function:
Involved in transaminase activity
Specific function:
Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:
Uniprot ID:
Molecular weight:
L-Alanine + Glyoxylic acid → Pyruvic acid + Glycinedetails
Glycine + Oxoglutaric acid → Glyoxylic acid + L-Glutamic aciddetails
General function:
Involved in FMN binding
Specific function:
Has 2-hydroxyacid oxidase activity. Most active on the 2-carbon substrate glycolate, but is also active on 2-hydroxy fatty acids, with high activity towards 2-hydroxy palmitate and 2-hydroxy octanoate.
Gene Name:
Uniprot ID:
Molecular weight:
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
General function:
Involved in FMN binding
Specific function:
Catalyzes the oxidation of L-alpha-hydroxy acids as well as, more slowly, that of L-alpha-amino acids.
Gene Name:
Uniprot ID:
Molecular weight:
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
General function:
Involved in metabolic process
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
L-Alanine + Glyoxylic acid → Pyruvic acid + Glycinedetails
Glycine + Oxoglutaric acid → Glyoxylic acid + L-Glutamic aciddetails
L-Serine + Glyoxylic acid → Hydroxypyruvic acid + Glycinedetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
L-Kynurenine + Glyoxylic acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glycinedetails
General function:
Not Available
Specific function:
Catalyzes the final step in the metabolic pathway of hydroxyproline (Probable).
Gene Name:
Uniprot ID:
Molecular weight:
4-Hydroxy-2-oxoglutaric acid → Pyruvic acid + Glyoxylic aciddetails


General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
Uniprot ID:
Molecular weight:
  1. Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [11101640 ]