You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameOxalic Acid
Accession NumberDB03902  (DB02737, EXPT02457)
TypeSmall Molecule
GroupsExperimental
Description

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]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number144-62-7
WeightAverage: 90.0349
Monoisotopic: 89.995308552
Chemical FormulaC2H2O4
InChI KeyInChIKey=MUBZPKHOEPUJKR-UHFFFAOYSA-N
InChI
InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)
IUPAC Name
oxalic acid
SMILES
OC(=O)C(O)=O
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
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5405
Blood Brain Barrier+0.8251
Caco-2 permeable-0.881
P-glycoprotein substrateNon-substrate0.782
P-glycoprotein inhibitor INon-inhibitor0.9872
P-glycoprotein inhibitor IINon-inhibitor0.9886
Renal organic cation transporterNon-inhibitor0.968
CYP450 2C9 substrateNon-substrate0.8612
CYP450 2D6 substrateNon-substrate0.9274
CYP450 3A4 substrateNon-substrate0.8021
CYP450 1A2 substrateNon-inhibitor0.9621
CYP450 2C9 inhibitorNon-inhibitor0.9267
CYP450 2D6 inhibitorNon-inhibitor0.9593
CYP450 2C19 inhibitorNon-inhibitor0.9828
CYP450 3A4 inhibitorNon-inhibitor0.9751
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9962
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6444
BiodegradationReady biodegradable0.8559
Rat acute toxicity1.1107 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9936
hERG inhibition (predictor II)Non-inhibitor0.9809
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point189.5 dec °CPhysProp
water solubility2.2E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logS0.38ADME Research, USCD
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
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-1z00000000-eaa92cf80964dd7d345aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0z00000000-b9206a3a54b5be6f07d9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-zl10000000-e5db327eab9e8a2f149eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-ez40000000-75af6e42d4cc12d798f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-z000000000-cb3d53cc3c40c1cbbba7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z000000000-53a009b344e3920ffca1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z000000000-2bafb6c472ab1030cd0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-z000000000-8aef9a64d926571c2de0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-z000000000-d1ff7c94a720b1eecaf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-z000000000-21d33d1d99d80526ee71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-z000000000-ac27102ff43446c313d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-z000000000-fe58eaea122c39178fbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-z000000000-3850c6a7016e2874d55bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-z000000000-32ac4118fe0eb9a5abb2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-z000000000-538465f019815d5e1b4aView in MoNA
References
Synthesis Reference

Giuseppe Messina, Giovanni M. Sechi, Loreno Lorenzoni, Giovanni Chessa, “Method of preparation of oxalic acid esters and amides.” U.S. Patent US4981963, issued July, 1971.

US4981963
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Proto-oncogene tyrosine-protein kinase Src

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Proto-oncogene tyrosine-protein kinase Src P12931 Details

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
  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
  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

Transporters

1. Solute carrier organic anion transporter family member 2B1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2B1 O94956 Details

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

2. Solute carrier family 22 member 8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Race JE, Grassl SM, Williams WJ, Holtzman EJ: Molecular cloning and characterization of two novel human renal organic anion transporters (hOAT1 and hOAT3). Biochem Biophys Res Commun. 1999 Feb 16;255(2):508-14. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23