Record Information
Version2.0
Creation Date2012-05-31 09:57:38 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00119
Identification
Name:Glyoxylic acid
Description:Glyoxylic acid or oxoacetic acid is an organic compound that is both an aldehyde and a carboxylic acid. 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. (PMID: 16396466)
Structure
Thumb
Synonyms:
  • A-Ketoacetate
  • A-Ketoacetic acid
  • Alpha-Ketoacetate
  • Alpha-Ketoacetic acid
  • Formylformate
  • Formylformic acid
  • Glyox
  • Glyoxalate
  • Glyoxalic acid
  • Glyoxylate
  • Glyoxylic acid
  • Oxalaldehydate
  • Oxalaldehydic acid
  • Oxoacetate
  • Oxoacetic acid
  • Oxoethanoate
  • Oxoethanoic acid
  • α-Ketoacetate
  • α-Ketoacetic acid
Chemical Formula:C2H2O3
Weight:Average: 74.0355
Monoisotopic: 74.00039393
InChI Key:HHLFWLYXYJOTON-UHFFFAOYSA-N
InChI:InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
CAS number:298-12-4
IUPAC Name:2-oxoacetic acid
Traditional IUPAC Name:glyoxylic acid
SMILES:OC(=O)C=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentCarboxylic acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:-1
Melting point:-93 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility224.0 mg/mLALOGPS
logP-0.59ALOGPS
logP-0.13ChemAxon
logS0.48ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP
Glycolic acid + Ubiquinone-8 > Glyoxylic acid + Ubiquinol-8
Glycolic acid + Menaquinone 8 > Glyoxylic acid + Menaquinol 8
2-Demethylmenaquinone 8 + Glycolic acid > 2-Demethylmenaquinol 8 + Glyoxylic acid
Glyoxylic acid + Hydrogen ion + NADH > Glycolic acid + NAD
Acetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acid
2 Hydrogen ion + Water + (S)-Ureidoglycolic acid > Carbon dioxide + Glyoxylic acid +2 Ammonium
2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxide
FMNH + Oxygen + Sulfoacetate > Flavin Mononucleotide + Glyoxylic acid + Hydrogen ion + Water + Sulfite
Isocitric acid <> Glyoxylic acid + Succinic acid
2 Glyoxylic acid <> Tartronate semialdehyde + Carbon dioxide
Glycolic acid + NADP <> Glyoxylic acid + NADPH + Hydrogen ion
(S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxide
4-Hydroxy-2-oxoglutaric acid <> Pyruvic acid + Glyoxylic acid
D-4-Hydroxy-2-oxoglutarate <> Pyruvic acid + Glyoxylic acid
L-Malic acid + Coenzyme A <> Acetyl-CoA + Water + Glyoxylic acid
Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide
Isocitric acid <> Succinic acid + Glyoxylic acid
Dehydroglycine + Water > Glyoxylic acid + Ammonia
4-Hydroxy-2-oxoglutaric acid Glyoxylic acid + Pyruvic acid
an oxidized electron acceptor + Glycolic acid > a reduced electron acceptor + Glyoxylic acid
Hydrogen ion + Glyoxylic acid > Carbon dioxide + Tartronate semialdehyde
Glycolic acid + NADP < Hydrogen ion + NADPH + Glyoxylic acid
Propionyl-CoA + Water + Glyoxylic acid <> 2-hydroxyglutarate + Hydrogen ion + Coenzyme A
Isocitric acid <> Glyoxylic acid + Succinic acid

SMPDB Pathways:
Secondary Metabolites: Glyoxylate cyclePW000967 Pw000967Pw000967 greyscalePw000967 simple
glycolate and glyoxylate degradationPW000827 Pw000827Pw000827 greyscalePw000827 simple
glycolate and glyoxylate degradation IIPW002021 Pw002021Pw002021 greyscalePw002021 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-03di-3900000000-16bc69e0e9d51e54854eView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0096-9000000000-042540a05be250278f8bView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-03di-3900000000-16bc69e0e9d51e54854eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00fr-9200000000-c60b627ed670285ec37fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9000000000-72c34bc34b8c3341442bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9000000000-920a0dc738957201d4baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-857c7f2d72c3d4c10dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-9b5825d5d9d8b094fefaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-de556f03ea428deff5e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00dl-9000000000-74b253632894213d473cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-9b5825d5d9d8b094fefaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-de556f03ea428deff5e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-9000000000-74b253632894213d473cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-a8cc2c89793394fdf9e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-d20183b08984d4766e8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ea9968e3933fd734506cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-cef8efc477a2500a7eadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-3817c0865df629803538View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-bb935f857fb5fd08c7e3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-a04bafbf8e0b990094a3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • 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
  • 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
  • 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
  • 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
  • Davis WL, Goodman DB: Evidence for the glyoxylate cycle in human liver. Anat Rec. 1992 Dec;234(4):461-8. Pubmed: 1456449
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • Popov, V. N., Moskalev, E. A., Shevchenko, M. I. u., Eprintsev, A. T. (2005). "[Comparative analysis of the glyoxylate cycle clue enzyme isocitrate lyases from organisms of different systemic groups]." Zh Evol Biokhim Fiziol 41:507-513. Pubmed: 16396466
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Jie, Yuanping; Song, Zhen. Method for preparing glyoxylic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16891
HMDB IDHMDB00119
Pubchem Compound ID760
Kegg IDC00048
ChemSpider ID740
WikipediaGlyoxylic acid
BioCyc IDGLYOX
EcoCyc IDGLYOX
Ligand ExpoGLV

Enzymes

General function:
Involved in catalytic activity
Specific function:
Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA
Gene Name:
aceB
Uniprot ID:
P08997
Molecular weight:
60273
Reactions
Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA.
General function:
Involved in catalytic activity
Specific function:
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate
Gene Name:
eda
Uniprot ID:
P0A955
Molecular weight:
22284
Reactions
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate.
2-dehydro-3-deoxy-D-gluconate 6-phosphate = pyruvate + D-glyceraldehyde 3-phosphate.
General function:
Involved in isocitrate lyase activity
Specific function:
Catalyzes the formation of succinate and glyoxylate from isocitrate, a key step of the glyoxylate cycle. May be involved in the assimilation of one-carbon compounds via the isocitrate lyase- positive serine pathway
Gene Name:
aceA
Uniprot ID:
P0A9G6
Molecular weight:
47521
Reactions
Isocitrate = succinate + glyoxylate.
General function:
Involved in tartronate-semialdehyde synthase activity
Specific function:
Catalyzes the condensation of two molecules of glyoxylate to give 2-hydroxy-3-oxopropanoate (also termed tartronate semialdehyde)
Gene Name:
gcl
Uniprot ID:
P0AEP7
Molecular weight:
64731
Reactions
2 glyoxylate = tartronate semialdehyde + CO(2).
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
glcD
Uniprot ID:
P0AEP9
Molecular weight:
53811
General function:
Involved in catalytic activity
Specific function:
Accounts for almost the entire malate-synthesizing activity in cells metabolizing glyoxylate
Gene Name:
glcB
Uniprot ID:
P37330
Molecular weight:
80488
Reactions
Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Can also reduce 2,5-diketo-D-gluconate (25DKG) to 5-keto-D- gluconate (5KDG), 2-keto-D-gluconate (2KDG) to D-gluconate, and 2- keto-L-gulonate (2KLG) to L-idonate (IA), but it is not its physiological function. Inactive towards 2-oxoglutarate, oxaloacetate, pyruvate, 5-keto-D-gluconate, D-fructose and L- sorbose. Activity with NAD is very low
Gene Name:
ghrB
Uniprot ID:
P37666
Molecular weight:
35395
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
D-gluconate + NADP(+) = 2-dehydro-D-gluconate + NADPH.
General function:
Involved in iron-sulfur cluster binding
Specific function:
Specific function unknown
Gene Name:
glcF
Uniprot ID:
P52074
Molecular weight:
45110
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Inactive towards 2-oxo-D-gluconate, 2-oxoglutarate, oxaloacetate and pyruvate. Only D- and L-glycerate are involved in the oxidative activity with NADP. Activity with NAD is very low
Gene Name:
ghrA
Uniprot ID:
P75913
Molecular weight:
35343
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
General function:
Involved in ureidoglycolate hydrolase activity
Specific function:
Involved in the anaerobic utilization of allantoin. Reinforces the induction of genes involved in the degradation of allantoin and glyoxylate by producing glyoxylate
Gene Name:
allA
Uniprot ID:
P77731
Molecular weight:
18169
Reactions
(S)-ureidoglycolate + H(2)O = glyoxylate + 2 NH(3) + CO(2).
General function:
Involved in alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Uniprot ID:
P80645
Molecular weight:
41736
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
glcE
Uniprot ID:
P52073
Molecular weight:
38361

Transporters

General function:
Lipid transport and metabolism
Specific function:
Responsible for the intake of short-chain fatty acids
Gene Name:
atoE
Uniprot ID:
P76460
Molecular weight:
47527