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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2018-03-01 03:14:19 UTC
Secondary Accession Numbers
  • HMDB02329
Metabolite Identification
Common NameOxalic acid
DescriptionOxalic 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). Oxalic acid is found to be associated with fumarase deficiency and primary hyperoxaluria I, which are inborn errors of metabolism.
Ethane-1,2-dioic acidChEBI
Ethanedioic acidChEBI
Ammonium oxalateHMDB
Ethanedioic acid dihydrateHMDB
Ethanedionic acidHMDB
Kyselina stavelovaHMDB
Oxalic acid 2-hydrateHMDB
Oxalic acid anhydrousHMDB
Oxalic acid diammonium saltHMDB
Oxalic acid dihydrateHMDB
Acid, oxalicMeSH
Aluminum oxalateMeSH
Chromium (3+) oxalate (3:2)MeSH
Dipotassium oxalateMeSH
Iron oxalateMeSH
Magnesium oxalateMeSH
Magnesium oxalate (1:1)MeSH
Oxalate, dilithiumMeSH
Oxalate, disodiumMeSH
Oxalate, monohydrogen monopotassiumMeSH
Oxalate, monopotassiumMeSH
Oxalate, potassiumMeSH
Chromium oxalateMeSH
Dilithium oxalateMeSH
Manganese (2+) oxalate (1:1)MeSH
Monosodium oxalateMeSH
Oxalate, chromiumMeSH
Oxalate, dipotassiumMeSH
Oxalate, magnesiumMeSH
Oxalate, monosodiumMeSH
Oxalate, potassium chromiumMeSH
Oxalate, sodiumMeSH
Potassium oxalateMeSH
Potassium oxalate (2:1)MeSH
Diammonium oxalateMeSH
Disodium oxalateMeSH
Oxalate, aluminumMeSH
Oxalate, diammoniumMeSH
Oxalate, ferricMeSH
Oxalate, monoammoniumMeSH
Potassium chromium oxalateMeSH
Chromium (2+) oxalateMeSH
Ferric oxalateMeSH
Iron (2+) oxalate (1:1)MeSH
Iron (3+) oxalateMeSH
Monoammonium oxalateMeSH
Monohydrogen monopotassium oxalateMeSH
Monopotassium oxalateMeSH
Oxalate, ironMeSH
Sodium oxalateMeSH
Chemical FormulaC2H2O4
Average Molecular Weight90.0349
Monoisotopic Molecular Weight89.995308552
IUPAC Nameoxalic acid
Traditional Nameoxalic acid
CAS Registry Number144-62-7
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    Musculoskeletal and connective tissue disorders:

    General disorders and administration site conditions:

    Metabolism and nutrition disorders:

    Renal and urinary disorders:


Biological location:

  Cell and elements:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:



Route of exposure:





Naturally occurring process:

  Biological process:

    Biochemical pathway:


Biological role:

Industrial application:

  Pharmaceutical industry:

Physical Properties
Experimental Properties
Melting Point189.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility220 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility65.7 g/LALOGPS
pKa (Strongest Acidic)1.36ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.44 m³·mol⁻¹ChemAxon
Polarizability6.23 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0900000000-eaa92cf80964dd7d345aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-b9206a3a54b5be6f07d9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9500000000-e5db327eab9e8a2f149eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00sl-3910000000-75af6e42d4cc12d798f4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-8aef9a64d926571c2de0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-eaa92cf80964dd7d345aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-b9206a3a54b5be6f07d9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9500000000-e5db327eab9e8a2f149eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00sl-3910000000-75af6e42d4cc12d798f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-3cee49bf06349fbe625eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-f5e8094c68372ab25a63View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9510000000-28b0e365a156d2091afdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-cb3d53cc3c40c1cbbba7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-9000000000-53a009b344e3920ffca1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-2bafb6c472ab1030cd0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9000000000-8aef9a64d926571c2de0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d1ff7c94a720b1eecaf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-21d33d1d99d80526ee71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ac27102ff43446c313d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-fe58eaea122c39178fbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-3850c6a7016e2874d55bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-32ac4118fe0eb9a5abb2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-538465f019815d5e1b4aView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Peroxisome
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Location
  • Bladder
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Pancreas
  • Testes
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified6.43 +/- 1.06 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified22.2 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified9.2 +/- 2.7 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
BloodDetected and Quantified3.33 +/- 1.11 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SalivaDetected but not Quantified Adult (>18 years old)Male
SweatDetected but not Quantified Adult BothNormal details
UrineDetected and Quantified8.2 (3.9-14.0) umol/mmol creatinineAdult (>18 years old)Both
UrineDetected and Quantified3.26 +/- 9.04 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified1.11-33.34 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
UrineDetected and Quantified6.2-13 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified<52.55 umol/mmol creatinineChildren (1 - 18 years old)Both
    • BC Children's Hos...
UrineDetected but not Quantified Adult (>18 years old)Both
UrineDetected and Quantified<50.229 umol/mmol creatinineInfant (0-1 year old)MaleNormal details
UrineDetected and Quantified18.4 +/- 6.5 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
UrineDetected and Quantified<= 30.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified7.7-10 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0-101 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Primary Hyperoxal...
Abnormal Concentrations
BloodDetected and Quantified47.2 +/- 22.9 uMAdult (>18 years old)Both
BloodDetected and Quantified16.9 +/- 10.5 uMAdult (>18 years old)Both
BloodDetected and Quantified43.32 +/- 6.66 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified37.310-243.200 uMChildren (1-13 years old)Both
Primary hyperoxaluria I
UrineDetected and Quantified84.134 umol/mmol creatinineInfant (0-1 year old)MaleFumarase deficiency details
UrineDetected and Quantified651.333 umol/mmol creatinineAdult (>18 years old)Male
Primary hyperoxaluria I
UrineDetected and Quantified629.333-1636 umol/mmol creatinineChildren (1-13 years old)BothPrimary hyperoxaluria I details
UrineDetected and Quantified>101 umol/mmol creatinineChildren (1-13 years old)BothGlycolic aciduria
    • Primary Hyperoxal...
Associated Disorders and Diseases
Disease References
Fumarase deficiency
  1. Bastug O, Kardas F, Ozturk MA, Halis H, Memur S, Korkmaz L, Tag Z, Gunes T: A rare cause of opistotonus; fumaric aciduria: The first case presentation in Turkey. Turk Pediatri Ars. 2014 Mar 1;49(1):74-6. doi: 10.5152/tpa.2014.442. eCollection 2014 Mar. [PubMed:26078636 ]
Glycolic aciduria
  1. Coulter-Mackie MB, White CT, Lange D, et al. (2002). Primary Hyperoxaluria Type 1. 2002 Jun 19 [Updated 2014 Jul 17]. In: Adam MP, Ardinger HH, Pagon RA, et al., editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2017. Available from: University of Washington, Seattle.
  1. 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 ]
Primary hyperoxaluria I
  1. Holmgren G, Hornstrom T, Johansson S, Samuelson G: Primary hyperoxaluria (glycolic acid variant): a clinical and genetical investigation of eight cases. Ups J Med Sci. 1978;83(1):65-70. [PubMed:705974 ]
Associated OMIM IDs
DrugBank IDDB03902
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003357
KNApSAcK IDC00001198
Chemspider ID946
KEGG Compound IDC00209
BiGG ID34265
Wikipedia LinkOxalic_acid
PubChem Compound971
ChEBI ID16995
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Pirulli D, Marangella M, Amoroso A: Primary hyperoxaluria: genotype-phenotype correlation. J Nephrol. 2003 Mar-Apr;16(2):297-309. [PubMed:12768081 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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]. Nihon Jinzo Gakkai Shi. 2006;48(1):22-8. [PubMed:16480063 ]
  15. 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 ]
  16. 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 ]
  17. Robertson WG: Renal stones in the tropics. Semin Nephrol. 2003 Jan;23(1):77-87. [PubMed:12563603 ]
  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 ]
  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 ]
  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 ]


General function:
Involved in protein kinase activity
Specific function:
ATP + a [protein]-L-tyrosine = ADP + a [protein]-L-tyrosine phosphate
Gene Name:
Uniprot ID:
Molecular weight:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
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  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]


General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:
Uniprot ID:
Molecular weight:
  1. Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane. J Pharmacol Exp Ther. 2003 Aug;306(2):703-8. Epub 2003 Apr 30. [PubMed:12724351 ]