Identification

Name
Oxalic Acid
Accession Number
DB03902  (EXPT02457, DB02737)
Type
Small Molecule
Groups
Experimental
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
Synonyms
Not Available
Categories
UNII
9E7R5L6H31
CAS number
144-62-7
Weight
Average: 90.0349
Monoisotopic: 89.995308552
Chemical Formula
C2H2O4
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProto-oncogene tyrosine-protein kinase SrcNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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 References
Not Available
External Links
Human Metabolome Database
HMDB02329
KEGG Compound
C00209
PubChem Compound
971
PubChem Substance
46507830
ChemSpider
946
BindingDB
14674
ChEBI
16995
ChEMBL
CHEMBL146755
HET
OXD
PDB Entries
1o4n / 1ytm / 4inf / 4iuw / 4r2k / 4uzi / 4wj8 / 4ywb / 4z0p / 5ie3
show 2 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)189.5 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0002-0900000000-eaa92cf80964dd7d345a
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0900000000-b9206a3a54b5be6f07d9
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00dj-9500000000-e5db327eab9e8a2f149e
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00sl-3910000000-75af6e42d4cc12d798f4
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-8aef9a64d926571c2de0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-eaa92cf80964dd7d345a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-b9206a3a54b5be6f07d9
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dj-9500000000-e5db327eab9e8a2f149e
GC-MS Spectrum - GC-MSGC-MSsplash10-00sl-3910000000-75af6e42d4cc12d798f4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-3cee49bf06349fbe625e
Mass Spectrum (Electron Ionization)MSsplash10-0002-9000000000-538465f019815d5e1b4a
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-cb3d53cc3c40c1cbbba7
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0uk9-9000000000-53a009b344e3920ffca1
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-000i-9000000000-2bafb6c472ab1030cd0f
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-0006-9000000000-8aef9a64d926571c2de0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-d1ff7c94a720b1eecaf2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-21d33d1d99d80526ee71
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-ac27102ff43446c313d3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-fe58eaea122c39178fbe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-3850c6a7016e2874d55b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-32ac4118fe0eb9a5abb2

Taxonomy

Description
This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Dicarboxylic acids and derivatives
Direct Parent
Dicarboxylic acids and derivatives
Alternative Parents
Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Dicarboxylic acid or derivatives / Carboxylic acid / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
alpha,omega-dicarboxylic acid (CHEBI:16995)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sh3/sh2 adaptor activity
Specific Function
Non-receptor protein tyrosine kinase which is activated following engagement of many different classes of cellular receptors including immune response receptors, integrins and other adhesion recept...
Gene Name
SRC
Uniprot ID
P12931
Uniprot Name
Proto-oncogene tyrosine-protein kinase Src
Molecular Weight
59834.295 Da
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

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane 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
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
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:10049739]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:34