Human Metabolome Database Version 3.5

Showing metabocard for Glyoxylic acid (HMDB00119)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:24:46 -0600
HMDB ID HMDB00119
Secondary Accession Numbers None
Metabolite Identification
Common Name Glyoxylic acid
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 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 Link_out].
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C2H2O3
Average Molecular Weight 74.0355
Monoisotopic Molecular Weight 74.00039393
IUPAC Name 2-oxoacetic acid
Traditional IUPAC Name glyoxalate, glyoxylate
CAS Registry Number 298-12-4
SMILES OC(=O)C=O
InChI Identifier InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
InChI Key HHLFWLYXYJOTON-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Carboxylic Acid Derivatives
Other Descriptors
  • 2-oxo monocarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • semialdehyde(ChEBI)
Substituents
  • Aldehyde
Direct Parent Carboxylic Acids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Mitochondria
  • Peroxisome
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -93 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 224 g/L ALOGPS
LogP -0.59 ALOGPS
LogP -0.13 ChemAxon
LogS 0.48 ALOGPS
pKa (strongest acidic) 2.61 ChemAxon
pKa (strongest basic) -9.2 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 13.5 ChemAxon
Polarizability 5.35 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Alanine Metabolism SMP00055 map00250 Link_out
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
3.05 (0.25–12.78) uM Adult (>18 years old) Male Normal
Urine Detected and Quantified
5.5 (0.00-11.00) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
3.28 (2.0-5.32) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
1.27 (0.46-3.26) umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
1.88 (0.63-3.22) umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 76 uM Adult (>18 years old) Not Specified Transurethral Prostatic Resection
Urine Detected and Quantified 20.00 (10.00-30.00) umol/mmol creatinine Children (1-13 year old) Both Primary hyperoxaluria I
Associated Disorders and Diseases
Disease References
Transurethral resection of the prostate
  • 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 Link_out
      Primary hyperoxaluria I, PH1
          Associated OMIM IDs None
          DrugBank ID DB04343 Link_out
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB001478
          KNApSAcK ID C00001186 Link_out
          Chemspider ID 740 Link_out
          KEGG Compound ID C00048 Link_out
          BioCyc ID GLYOX Link_out
          BiGG ID 33659 Link_out
          Wikipedia Link Glyoxylic acid Link_out
          NuGOwiki Link HMDB00119 Link_out
          Metagene Link HMDB00119 Link_out
          METLIN ID 3213 Link_out
          PubChem Compound 760 Link_out
          PDB ID GLV Link_out
          ChEBI ID 16891 Link_out
          References
          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)
          General References
          1. 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 Link_out
          2. 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 Link_out
          3. 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 Link_out
          4. 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 Link_out
          5. 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 Link_out
          6. 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 Link_out
          7. 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 Link_out
          8. 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 Link_out
          9. 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 Link_out
          10. 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 Link_out
          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 Link_out
          12. Davis WL, Goodman DB: Evidence for the glyoxylate cycle in human liver. Anat Rec. 1992 Dec;234(4):461-8. Pubmed: 1456449 Link_out
          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 Link_out
          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 Link_out

          Enzymes
          Name: D-amino-acid oxidase
          Reactions:
          Glycine + Water + Oxygen unknown Glyoxylic acid + Ammonia + Hydrogen peroxide details
          Gene Name: DAO
          Uniprot ID: P14920 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Peptidyl-glycine alpha-amidating monooxygenase
          Reactions:
          Peptidylamidoglycolate unknown peptidyl amide + Glyoxylic acid details
          Gene Name: PAM
          Uniprot ID: P19021 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Glyoxylate reductase/hydroxypyruvate reductase
          Reactions:
          Glycolic acid + NADP unknown Glyoxylic acid + NADPH details
          Glycolic acid + NADP unknown Glyoxylic acid + NADPH + Hydrogen Ion details
          Gene Name: GRHPR
          Uniprot ID: Q9UBQ7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Alanine--glyoxylate aminotransferase 2, mitochondrial
          Reactions:
          L-Alanine + Glyoxylic acid unknown Pyruvic acid + Glycine details
          Glycine + Oxoglutaric acid unknown Glyoxylic acid + L-Glutamic acid details
          Gene Name: AGXT2
          Uniprot ID: Q9BYV1 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Hydroxyacid oxidase 1
          Reactions:
          Glycolic acid + Oxygen unknown Glyoxylic acid + Hydrogen peroxide details
          Gene Name: HAO1
          Uniprot ID: Q9UJM8 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Hydroxyacid oxidase 2
          Reactions:
          Glycolic acid + Oxygen unknown Glyoxylic acid + Hydrogen peroxide details
          Gene Name: HAO2
          Uniprot ID: Q9NYQ3 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Serine--pyruvate aminotransferase
          Reactions:
          L-Alanine + Glyoxylic acid unknown Pyruvic acid + Glycine details
          Glycine + Oxoglutaric acid unknown Glyoxylic acid + L-Glutamic acid details
          L-Serine + Glyoxylic acid unknown Hydroxypyruvic acid + Glycine details
          Gene Name: AGXT
          Uniprot ID: P21549 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Kynurenine--oxoglutarate transaminase 3
          Reactions:
          L-Kynurenine + Glyoxylic acid unknown 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glycine details
          Gene Name: CCBL2
          Uniprot ID: Q6YP21 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Probable 4-hydroxy-2-oxoglutarate aldolase, mitochondrial
          Reactions:
          4-Hydroxy-2-oxoglutaric acid unknown Pyruvic acid + Glyoxylic acid details
          Gene Name: HOGA1
          Uniprot ID: Q86XE5 Link_out
          Protein Sequence: FASTA
          Transporters
          Name: Monocarboxylate transporter 4
          Reactions: Not Available
          Gene Name: SLC16A3
          Uniprot ID: O15427 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA