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Human Metabolome Database Version 3.5

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Showing metabocard for Oxalic acid (HMDB02329)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:48 -0600
Update Date 2013-02-08 17:11:45 -0700
HMDB ID HMDB02329
Secondary Accession Numbers None
Metabolite Identification
Common Name Oxalic acid
Description Oxalic acid is a strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent. -- Pubchem; Oxalic acid (IUPAC name: ethanedioic acid, formula H2C2O4) is a dicarboxylic acid with structure (HOOC)-(COOH). Because of the joining of two carboxyl groups, this is one of the strongest organic acids. It is also a reducing agent. The anions of oxalic acid as well as its salts and esters are known as oxalates. -- Wikipedia; Bodily oxalic acid may also be synthesized via the metabolism of either glyoxylic acid or unused ascorbic acid (vitamin C), which is a serious health consideration for long term megadosers of vitamin C supplements. 80% of kidney stones are formed from calcium oxalate. Some Aspergillus species produce oxalic acid, which reacts with blood or tissue calcium to precipitate calcium oxalate. There is some preliminary evidence that the administration of probiotics can affect oxalic acid excretion rates (and presumably oxalic acid levels as well.) -- Wikipedia.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Ammonium oxalate
  2. Ethane-1,2-dioate
  3. Ethane-1,2-dioic acid
  4. Ethanedioate
  5. Ethanedioic acid
  6. Ethanedioic acid dihydrate
  7. Ethanedionate
  8. Ethanedionic acid
  9. Kyselina stavelova
  10. Oxaalzuur
  11. Oxalate
  12. Oxalic acid
  13. Oxalic acid 2-Hydrate
  14. Oxalic acid anhydrous
  15. Oxalic acid diammonium salt
  16. Oxalic acid dihydrate
Chemical Formula C2H2O4
Average Molecular Weight 90.0349
Monoisotopic Molecular Weight 89.995308552
IUPAC Name oxalic acid
Traditional IUPAC Name oxalic acid
CAS Registry Number 144-62-7
SMILES OC(=O)C(O)=O
InChI Identifier InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)
InChI Key MUBZPKHOEPUJKR-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Dicarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • alpha,omega-dicarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Dicarboxylic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Extracellular
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 189.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 220 mg/mL at 25 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 65.7 g/L ALOGPS
LogP -0.51 ALOGPS
LogP -0.26 ChemAxon
LogS -0.14 ALOGPS
pKa (strongest acidic) 1.36 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 14.44 ChemAxon
Polarizability 6.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Gas-MS Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (Unknown)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Extracellular
  • Peroxisome
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Intestine
  • Pancreas
  • Testes
  • Kidney
  • Liver
  • Epidermis
  • Eye Lens
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
6.43 +/- 1.06 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
22.2 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
9.2 +/- 2.7 uM Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
8.2 (3.9-14.0) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Urine Detected and Quantified
Article_icon
3.26 +/- 9.04 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
27.00 (0.00-54.00) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
1.11-33.34 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
Article_icon
18.4 +/- 6.5 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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<= 30.0 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
47.2 +/- 22.9 uM Adult (>18 years old) Both Hemodialysis Prior to dialysis
Blood Detected and Quantified
Article_icon
16.9 +/- 10.5 uM Adult (>18 years old) Both Hemodialysis After dialysis
Urine Detected and Quantified
Article_icon
220.00 (90.00-350.00) umol/mmol creatinine Adult (>18 years old) Both Primary hyperoxaluria I Not Available
Associated Disorders and Diseases
Disease References
Hemodialysis
  • Ogawa Y, Machida N, Jahana M, Gakiya M, Chinen Y, Oda M, Morozumi M, Sugaya K: Major factors modulating the serum oxalic acid level in hemodialysis patients. Front Biosci. 2004 Sep 1;9:2901-8. Pubmed: 15353324 Link_out
    Primary hyperoxaluria I, PH1
      • http://www.metagene.de/program/d.prg?mp=PRIMARY%20HYPEROXALURIA%20I,%20PH1
      Associated OMIM IDs None
      DrugBank ID DB03902 Link_out
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB003357
      KNApSAcK ID C00001198 Link_out
      Chemspider ID 946 Link_out
      KEGG Compound ID C00209 Link_out
      BioCyc ID CUPRIZONE Link_out
      BiGG ID 34265 Link_out
      Wikipedia Link Oxalic acid Link_out
      NuGOwiki Link HMDB02329 Link_out
      Metagene Link HMDB02329 Link_out
      METLIN ID 113 Link_out
      PubChem Compound 971 Link_out
      PDB ID OXD Link_out
      ChEBI ID 16995 Link_out
      References
      Synthesis Reference Not Available
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. de O G Mendonca C, Martini LA, Baxmann AC, Nishiura JL, Cuppari L, Sigulem DM, Heilberg IP: Effects of an oxalate load on urinary oxalate excretion in calcium stone formers. J Ren Nutr. 2003 Jan;13(1):39-46. Pubmed: 12563622 Link_out
      2. Singh S, Tai C, Ganz G, Yeung CK, Magil A, Rosenberg F, Applegarth D, Levin A: Steroid-responsive pleuropericarditis and livedo reticularis in an unusual case of adult-onset primary hyperoxaluria. Am J Kidney Dis. 1999 Apr;33(4):e5. Pubmed: 10196036 Link_out
      3. Astarcioglu I, Karademir S, Gulay H, Bora S, Astarcioglu H, Kavukcu S, Turkmen M, Soylu A: Primary hyperoxaluria: simultaneous combined liver and kidney transplantation from a living related donor. Liver Transpl. 2003 Apr;9(4):433-6. Pubmed: 12682898 Link_out
      4. Selvam R, Kalaiselvi P: A novel basic protein from human kidney which inhibits calcium oxalate crystal growth. BJU Int. 2000 Jul;86(1):7-13. Pubmed: 10886075 Link_out
      5. Kwak C, Jeong BC, Kim HK, Kim EC, Chox MS, Kim HH: Molecular epidemiology of fecal Oxalobacter formigenes in healthy adults living in Seoul, Korea. J Endourol. 2003 May;17(4):239-43. Pubmed: 12816588 Link_out
      6. Vicanova J, Boelsma E, Mommaas AM, Kempenaar JA, Forslind B, Pallon J, Egelrud T, Koerten HK, Ponec M: Normalization of epidermal calcium distribution profile in reconstructed human epidermis is related to improvement of terminal differentiation and stratum corneum barrier formation. J Invest Dermatol. 1998 Jul;111(1):97-106. Pubmed: 9665394 Link_out
      7. Mydlik M, Derzsiova K, Pribylincova V, Reznicek J: [Urinary oxalic acid excretion in chronic kidney failure and after kidney transplantation] Vnitr Lek. 1996 Dec;42(12):813-7. Pubmed: 9072879 Link_out
      8. Mizusawa Y, Parnham AP, Falk MC, Burke JR, Nicol D, Yamanaka J, Lynch SV, Strong RW: Potential for bilateral nephrectomy to reduce oxalate release after combined liver and kidney transplantation for primary hyperoxaluria type 1. Clin Transplant. 1997 Oct;11(5 Pt 1):361-5. Pubmed: 9361924 Link_out
      9. Pecorella I, McCartney AC, Lucas S, Michaels L, Ciardi A, Di Tondo U, Garner A: Histological study of oxalosis in the eye and adnexa of AIDS patients. Histopathology. 1995 Nov;27(5):431-8. Pubmed: 8575733 Link_out
      10. Huang MY, Chaturvedi LS, Koul S, Koul HK: Oxalate stimulates IL-6 production in HK-2 cells, a line of human renal proximal tubular epithelial cells. Kidney Int. 2005 Aug;68(2):497-503. Pubmed: 16014026 Link_out
      11. Shapiro R, Weismann I, Mandel H, Eisenstein B, Ben-Ari Z, Bar-Nathan N, Zehavi I, Dinari G, Mor E: Primary hyperoxaluria type 1: improved outcome with timely liver transplantation: a single-center report of 36 children. Transplantation. 2001 Aug 15;72(3):428-32. Pubmed: 11502971 Link_out
      12. Motoyoshil Y, Hattori M, Chikamoto H, Nakakura H, Furue T, Miyakawa S, Kohno M, Ito K, Kai K, Nakajima I, Fuchinoue S, Teraoka S, Akiba T, Kitayama H, Wada N, Ogawa Y: [Sequential combined liver-kidney transplantation for a one-year-old boy with infantile primary hyperoxaluria type 1] Nippon Jinzo Gakkai Shi. 2006;48(1):22-8. Pubmed: 16480063 Link_out
      13. de Water R, Noordermeer C, van der Kwast TH, Nizze H, Boeve ER, Kok DJ, Schroder FH: Calcium oxalate nephrolithiasis: effect of renal crystal deposition on the cellular composition of the renal interstitium. Am J Kidney Dis. 1999 Apr;33(4):761-71. Pubmed: 10196021 Link_out
      14. van Woerden CS, Groothof JW, Wanders RJ, Waterham HR, Wijburg FR: [From gene to disease; primary hyperoxaluria type I caused by mutations in the AGXT gene] Ned Tijdschr Geneeskd. 2006 Jul 29;150(30):1669-72. Pubmed: 16922352 Link_out
      15. Pirulli D, Marangella M, Amoroso A: Primary hyperoxaluria: genotype-phenotype correlation. J Nephrol. 2003 Mar-Apr;16(2):297-309. Pubmed: 12768081 Link_out
      16. Amoroso A, Pirulli D, Florian F, Puzzer D, Boniotto M, Crovella S, Zezlina S, Spano A, Mazzola G, Savoldi S, Ferrettini C, Berutti S, Petrarulo M, Marangella M: AGXT gene mutations and their influence on clinical heterogeneity of type 1 primary hyperoxaluria. J Am Soc Nephrol. 2001 Oct;12(10):2072-9. Pubmed: 11562405 Link_out
      17. Robertson WG: Renal stones in the tropics. Semin Nephrol. 2003 Jan;23(1):77-87. Pubmed: 12563603 Link_out
      18. Nakagawa Y, Abram V, Parks JH, Lau HS, Kawooya JK, Coe FL: Urine glycoprotein crystal growth inhibitors. Evidence for a molecular abnormality in calcium oxalate nephrolithiasis. J Clin Invest. 1985 Oct;76(4):1455-62. Pubmed: 4056037 Link_out
      19. Massey LK, Palmer RG, Horner HT: Oxalate content of soybean seeds (Glycine max: Leguminosae), soyfoods, and other edible legumes. J Agric Food Chem. 2001 Sep;49(9):4262-6. Pubmed: 11559120 Link_out
      20. Petrarulo M, Vitale C, Facchini P, Marangella M: Biochemical approach to diagnosis and differentiation of primary hyperoxalurias: an update. J Nephrol. 1998 Mar-Apr;11 Suppl 1:23-8. Pubmed: 9604805 Link_out
      Enzymes
      Name: Proto-oncogene tyrosine-protein kinase Src
      Reactions:
      • ATP + a [protein]-L-tyrosine = ADP + a [protein]-L-tyrosine phosphate [RN:R02584]
      Gene Name: SRC
      Uniprot ID: P12931 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Transporters
      Name: Solute carrier organic anion transporter family member 2B1
      Reactions:
      • --- []
      Gene Name: SLCO2B1
      Uniprot ID: O94956 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA