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Record Information
Version3.6
Creation Date2006-05-22 14:17:48 UTC
Update Date2016-02-11 01:05:34 UTC
HMDB IDHMDB02329
Secondary Accession NumbersNone
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.
Structure
Thumb
Synonyms
ValueSource
EthandisaeureChEBI
Ethane-1,2-dioic acidChEBI
Ethanedioic acidChEBI
H2OxChEBI
HOOCCOOHChEBI
OxalsaeureChEBI
OxalateGenerator
Ethane-1,2-dioateGenerator
EthanedioateGenerator
Ammonium oxalateHMDB
Ethanedioic acid dihydrateHMDB
EthanedionateHMDB
Ethanedionic acidHMDB
Kyselina stavelovaHMDB
OxaalzuurHMDB
Oxalic acid 2-hydrateHMDB
Oxalic acid anhydrousHMDB
Oxalic acid diammonium saltHMDB
Oxalic acid dihydrateHMDB
Chemical FormulaC2H2O4
Average Molecular Weight90.0349
Monoisotopic Molecular Weight89.995308552
IUPAC Nameoxalic acid
Traditional Nameoxalic acid
CAS Registry Number144-62-7
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 KeyInChIKey=MUBZPKHOEPUJKR-UHFFFAOYSA-N
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
Substituents
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Microbial
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Extracellular
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility220 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility65.7 mg/mLALOGPS
logP-0.51ALOGPS
logP-0.26ChemAxon
logS-0.14ALOGPS
pKa (Strongest Acidic)1.36ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.44 m3·mol-1ChemAxon
Polarizability6.23 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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)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
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
  • Saliva
  • Urine
Tissue Location
  • Bladder
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Pancreas
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 ...
details
BloodDetected and Quantified3.33 +/- 1.11 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified8.2 (3.9-14.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.26 +/- 9.04 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified27.00 (0.00-54.00) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.11-33.34 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified<52.55 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified18.4 +/- 6.5 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified<= 30.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified47.2 +/- 22.9 uMAdult (>18 years old)Both
Hemodialysis
details
BloodDetected and Quantified16.9 +/- 10.5 uMAdult (>18 years old)Both
Hemodialysis
details
BloodDetected and Quantified43.32 +/- 6.66 uMAdult (>18 years old)Bothuremia details
UrineDetected and Quantified220.00 (90.00-350.00) umol/mmol creatinineChildren (1-13 years old)BothPrimary hyperoxaluria I details
Associated Disorders and Diseases
Disease References
Hemodialysis
  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. [15353324 ]
Primary hyperoxaluria I
  1. MetaGene [Link]
Associated OMIM IDsNone
DrugBank IDDB03902
DrugBank Metabolite IDDBMET00552
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003357
KNApSAcK IDC00001198
Chemspider ID946
KEGG Compound IDC00209
BioCyc IDCUPRIZONE
BiGG ID34265
Wikipedia LinkOxalic acid
NuGOwiki LinkHMDB02329
Metagene LinkHMDB02329
METLIN ID113
PubChem Compound971
PDB IDOXD
ChEBI ID16995
References
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. [11562405 ]
  2. Pirulli D, Marangella M, Amoroso A: Primary hyperoxaluria: genotype-phenotype correlation. J Nephrol. 2003 Mar-Apr;16(2):297-309. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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] Nippon Jinzo Gakkai Shi. 2006;48(1):22-8. [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. [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. [16922352 ]
  17. Robertson WG: Renal stones in the tropics. Semin Nephrol. 2003 Jan;23(1):77-87. [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. [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. [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. [9604805 ]

Enzymes

General function:
Involved in protein kinase activity
Specific function:
ATP + a [protein]-L-tyrosine = ADP + a [protein]-L-tyrosine phosphate
Gene Name:
SRC
Uniprot ID:
P12931
Molecular weight:
59834.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  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. [10592235 ]

Transporters

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:
SLCO2B1
Uniprot ID:
O94956
Molecular weight:
76697.9
References
  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. [12724351 ]