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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-06-13 19:53:45 UTC
HMDB IDHMDB00119
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 ].
Structure
Thumb
Synonyms
  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 IUPAC Nameglyoxalate, glyoxylate
CAS Registry Number298-12-4
SMILES
OC(=O)C=O
InChI Identifier
InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
InChI KeyHHLFWLYXYJOTON-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
Sub ClassCarboxylic Acid Derivatives
Other Descriptors
  • 2-oxo monocarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • semialdehyde(ChEBI)
Substituents
  • Aldehyde
Direct ParentCarboxylic Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Peroxisome
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-93 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility224 g/LALOGPS
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 area54.37ChemAxon
rotatable bond count1ChemAxon
refractivity13.5ChemAxon
polarizability5.35ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Alanine MetabolismSMP00055map00250
Glycine and Serine MetabolismSMP00004map00260
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.05 (0.25–12.78) uMAdult (>18 years old)MaleNormal details
UrineDetected and Quantified5.5 (0.00-11.00) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.28 (2.0-5.32) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
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
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified76 uMAdult (>18 years old)Not SpecifiedTransurethral prostatectomy syndrome 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. Pubmed: 2253377
Primary hyperoxaluria I
  1. MetaGene
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
BioCyc IDGLYOX
BiGG ID33659
Wikipedia LinkGlyoxylic acid
NuGOwiki LinkHMDB00119
Metagene LinkHMDB00119
METLIN ID3213
PubChem Compound760
PDB IDGLV
ChEBI ID16891
References
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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 2875046
  12. Davis WL, Goodman DB: Evidence for the glyoxylate cycle in human liver. Anat Rec. 1992 Dec;234(4):461-8. Pubmed: 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. Pubmed: 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. Pubmed: 16396466

Enzymes

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:
DAO
Uniprot ID:
P14920
Molecular weight:
39473.75
Reactions
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:
PAM
Uniprot ID:
P19021
Molecular weight:
108402.425
Reactions
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:
GRHPR
Uniprot ID:
Q9UBQ7
Molecular weight:
35667.875
Reactions
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:
AGXT2
Uniprot ID:
Q9BYV1
Molecular weight:
57155.905
Reactions
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:
HAO1
Uniprot ID:
Q9UJM8
Molecular weight:
40923.945
Reactions
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:
HAO2
Uniprot ID:
Q9NYQ3
Molecular weight:
38838.35
Reactions
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
General function:
Involved in metabolic process
Specific function:
Not Available
Gene Name:
AGXT
Uniprot ID:
P21549
Molecular weight:
43009.535
Reactions
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:
CCBL2
Uniprot ID:
Q6YP21
Molecular weight:
51399.855
Reactions
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:
HOGA1
Uniprot ID:
Q86XE5
Molecular weight:
17953.475
Reactions
4-Hydroxy-2-oxoglutaric acid → Pyruvic acid + Glyoxylic aciddetails

Transporters

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:
SLC16A3
Uniprot ID:
O15427
Molecular weight:
49468.9
References
  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. Pubmed: 11101640