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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2023-02-21 17:16:20 UTC
HMDB IDHMDB0002329
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. Oxalic acid is a marker for yeast overgrowth from Aspergillus, Penicillum and/or Candida. Can also be elevated due to exposures from vitamin C or ethylene glycol poisoning. Oxalate is elevated in the urine of children with autism. (PMID: 21911305 ). Oxalic acid has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
Data?1676999780
Synonyms
ValueSource
EthandisaeureChEBI
Ethane-1,2-dioic acidChEBI
Ethanedioic acidChEBI
H2OxChEBI
HOOCCOOHChEBI
OxalsaeureChEBI
Ethane-1,2-dioateGenerator
EthanedioateGenerator
OxalateGenerator
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
Acid, oxalicHMDB
Aluminum oxalateHMDB
Chromium (3+) oxalate (3:2)HMDB
Dipotassium oxalateHMDB
Iron oxalateHMDB
Magnesium oxalateHMDB
Magnesium oxalate (1:1)HMDB
Oxalate, dilithiumHMDB
Oxalate, disodiumHMDB
Oxalate, monohydrogen monopotassiumHMDB
Oxalate, monopotassiumHMDB
Oxalate, potassiumHMDB
Chromium oxalateHMDB
Dilithium oxalateHMDB
Manganese (2+) oxalate (1:1)HMDB
Monosodium oxalateHMDB
Oxalate, chromiumHMDB
Oxalate, dipotassiumHMDB
Oxalate, magnesiumHMDB
Oxalate, monosodiumHMDB
Oxalate, potassium chromiumHMDB
Oxalate, sodiumHMDB
Potassium oxalateHMDB
Potassium oxalate (2:1)HMDB
Diammonium oxalateHMDB
Disodium oxalateHMDB
Oxalate, aluminumHMDB
Oxalate, diammoniumHMDB
Oxalate, ferricHMDB
Oxalate, monoammoniumHMDB
Potassium chromium oxalateHMDB
Chromium (2+) oxalateHMDB
Ferric oxalateHMDB
Iron (2+) oxalate (1:1)HMDB
Iron (3+) oxalateHMDB
Monoammonium oxalateHMDB
Monohydrogen monopotassium oxalateHMDB
Monopotassium oxalateHMDB
Oxalate, ironHMDB
Sodium oxalateHMDB
Oxalic acidKEGG
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 KeyMUBZPKHOEPUJKR-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point189.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility220 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility65.7 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.44 m³·mol⁻¹ChemAxon
Polarizability6.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+115.32131661259
DarkChem[M-H]-108.90431661259
DeepCCS[M+H]+121.76330932474
DeepCCS[M-H]-118.96530932474
DeepCCS[M-2H]-155.33330932474
DeepCCS[M+Na]+129.91930932474
AllCCS[M+H]+125.732859911
AllCCS[M+H-H2O]+121.332859911
AllCCS[M+NH4]+129.832859911
AllCCS[M+Na]+131.032859911
AllCCS[M-H]-120.532859911
AllCCS[M+Na-2H]-125.232859911
AllCCS[M+HCOO]-130.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oxalic acidOC(=O)C(O)=O1699.1Standard polar33892256
Oxalic acidOC(=O)C(O)=O1373.6Standard non polar33892256
Oxalic acidOC(=O)C(O)=O898.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxalic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)O995.1Semi standard non polar33892256
Oxalic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)O[Si](C)(C)C1139.6Semi standard non polar33892256
Oxalic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)O1244.0Semi standard non polar33892256
Oxalic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)O[Si](C)(C)C(C)(C)C1556.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0900000000-eaa92cf80964dd7d345a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-b9206a3a54b5be6f07d92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9500000000-e5db327eab9e8a2f149e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-MS (2 TMS)splash10-00sl-3910000000-75af6e42d4cc12d798f42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid EI-B (Non-derivatized)splash10-0006-9000000000-8aef9a64d926571c2de02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-eaa92cf80964dd7d345a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-b9206a3a54b5be6f07d92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-EI-TOF (Non-derivatized)splash10-00dj-9500000000-e5db327eab9e8a2f149e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-MS (Non-derivatized)splash10-00sl-3910000000-75af6e42d4cc12d798f42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxalic acid GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-3cee49bf06349fbe625e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-f5e8094c68372ab25a632017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxalic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9510000000-28b0e365a156d2091afd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-538465f019815d5e1b4a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxalic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-9000000000-cb3d53cc3c40c1cbbba72012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxalic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0uk9-9000000000-53a009b344e3920ffca12012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxalic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-9000000000-2bafb6c472ab1030cd0f2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxalic acid EI-B (Unknown) , Positive-QTOFsplash10-0006-9000000000-8aef9a64d926571c2de02012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 10V, Positive-QTOFsplash10-0006-9000000000-d1ff7c94a720b1eecaf22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 20V, Positive-QTOFsplash10-0006-9000000000-21d33d1d99d80526ee712015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 40V, Positive-QTOFsplash10-0006-9000000000-ac27102ff43446c313d32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 10V, Negative-QTOFsplash10-000i-9000000000-fe58eaea122c39178fbe2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 20V, Negative-QTOFsplash10-000i-9000000000-3850c6a7016e2874d55b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 40V, Negative-QTOFsplash10-000i-9000000000-32ac4118fe0eb9a5abb22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 10V, Negative-QTOFsplash10-000i-9000000000-43de084d66dd1bebdeac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 20V, Negative-QTOFsplash10-000i-9000000000-159ed524013577f6f8012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 40V, Negative-QTOFsplash10-0006-9000000000-d948d5d95ae14e701f572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 10V, Positive-QTOFsplash10-00di-9000000000-8e2d2f7a8acc88f001952021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 20V, Positive-QTOFsplash10-0006-9000000000-d7b47276d03e46ce72a22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxalic acid 40V, Positive-QTOFsplash10-0006-9000000000-a1e091bb1f5fa6e9cbc72021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Bladder
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Pancreas
  • Placenta
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified3.333 +/- 1.111 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal 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 Quantified1.11-33.34 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
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
Normal
    • BC Children's Hos...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
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 ...
details
UrineDetected and Quantified<= 30.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0-0.8 umol/mmol creatinineInfant (0-1 year old)Female
Normal
details
UrineDetected and Quantified0-2.8 umol/mmol creatinineInfant (0-1 year old)Male
Normal
details
UrineDetected and Quantified0-3.5 umol/mmol creatinineInfant (0-1 year old)Male
Normal
details
UrineDetected and Quantified0-6.4 umol/mmol creatinineInfant (0-1 year old)Female
Normal
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...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified37.310-243.200 uMChildren (1-13 years old)Both
Primary hyperoxaluria I
details
BloodDetected and Quantified54.444 +/- 15.556 uMAdult (>18 years old)Both
Uremia
details
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
details
UrineDetected and Quantified629.333-1636 umol/mmol creatinineChildren (1-13 years old)BothPrimary hyperoxaluria I details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified>101 umol/mmol creatinineChildren (1-13 years old)BothGlycolic aciduria
    • Primary Hyperoxal...
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. [PubMed:15353324 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. doi: 10.1371/journal.pone.0016957. [PubMed:21359215 ]
  3. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  4. Hoppe B, Kemper MJ, Hvizd MG, Sailer DE, Langman CB: Simultaneous determination of oxalate, citrate and sulfate in children's plasma with ion chromatography. Kidney Int. 1998 May;53(5):1348-52. [PubMed:9573551 ]
  5. Bouatra S, Aziat F, Mandal R, Guo AC, Wilson MR, Knox C, Bjorndahl TC, Krishnamurthy R, Saleem F, Liu P, Dame ZT, Poelzer J, Huynh J, Yallou FS, Psychogios N, Dong E, Bogumil R, Roehring C, Wishart DS: The human urine metabolome. PLoS One. 2013 Sep 4;8(9):e73076. doi: 10.1371/journal.pone.0073076. eCollection 2013. [PubMed:24023812 ]
  6. 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 ]
  7. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
  8. (). Merck Manual of Diagnosis and Therapy. . . [ISBN:978-0-911910-19-3 ]
  9. (). David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971. .
  10. (). Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.. .
  11. (). Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.. .
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 ]
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: https://www.ncbi.nlm.nih.gov/books/NBK1283/. University of Washington, Seattle.
Associated OMIM IDs
DrugBank IDDB03902
Phenol Explorer Compound IDNot Available
FooDB IDFDB031074
KNApSAcK IDC00001198
Chemspider ID946
KEGG Compound IDC00209
BioCyc IDOXALATE
BiGG ID34265
Wikipedia LinkOxalic_acid
METLIN ID113
PubChem Compound971
PDB IDNot Available
ChEBI ID16995
Food Biomarker OntologyNot Available
VMH IDOXA
MarkerDB IDMDB00000389
Good Scents IDNot Available
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. [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 ]
  21. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  22. Konstantynowicz J, Porowski T, Zoch-Zwierz W, Wasilewska J, Kadziela-Olech H, Kulak W, Owens SC, Piotrowska-Jastrzebska J, Kaczmarski M: A potential pathogenic role of oxalate in autism. Eur J Paediatr Neurol. 2012 Sep;16(5):485-91. doi: 10.1016/j.ejpn.2011.08.004. Epub 2011 Sep 10. [PubMed:21911305 ]
  23. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:12724351 ]