Livestock Metabolome Database: Showing metabocard for Oxalic acid (LMDB00391)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:47 UTC

Update Date

2016-07-20 21:00:31 UTC

Lmdb

LMDB00391

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oxalic acid

Description

Oxalic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ethandisaeure	ChEBI
Ethane-1,2-dioic acid	ChEBI
Ethanedioic acid	ChEBI
H2Ox	ChEBI
HOOCCOOH	ChEBI
Oxalsaeure	ChEBI
Ethane-1,2-dioate	Generator
Ethanedioate	Generator
Oxalate	Generator
Ammonium oxalate	HMDB
Ethanedioic acid dihydrate	HMDB
Ethanedionate	HMDB
Ethanedionic acid	HMDB
Kyselina stavelova	HMDB
Oxaalzuur	HMDB
Oxalic acid 2-hydrate	HMDB
Oxalic acid anhydrous	HMDB
Oxalic acid diammonium salt	HMDB
Oxalic acid dihydrate	HMDB
Acid, oxalic	HMDB
Aluminum oxalate	HMDB
Chromium (3+) oxalate (3:2)	HMDB
Dipotassium oxalate	HMDB
Iron oxalate	HMDB
Magnesium oxalate	HMDB
Magnesium oxalate (1:1)	HMDB
Oxalate, dilithium	HMDB
Oxalate, disodium	HMDB
Oxalate, monohydrogen monopotassium	HMDB
Oxalate, monopotassium	HMDB
Oxalate, potassium	HMDB
Chromium oxalate	HMDB
Dilithium oxalate	HMDB
Manganese (2+) oxalate (1:1)	HMDB
Monosodium oxalate	HMDB
Oxalate, chromium	HMDB
Oxalate, dipotassium	HMDB
Oxalate, magnesium	HMDB
Oxalate, monosodium	HMDB
Oxalate, potassium chromium	HMDB
Oxalate, sodium	HMDB
Potassium oxalate	HMDB
Potassium oxalate (2:1)	HMDB
Diammonium oxalate	HMDB
Disodium oxalate	HMDB
Oxalate, aluminum	HMDB
Oxalate, diammonium	HMDB
Oxalate, ferric	HMDB
Oxalate, monoammonium	HMDB
Potassium chromium oxalate	HMDB
Chromium (2+) oxalate	HMDB
Ferric oxalate	HMDB
Iron (2+) oxalate (1:1)	HMDB
Iron (3+) oxalate	HMDB
Monoammonium oxalate	HMDB
Monohydrogen monopotassium oxalate	HMDB
Monopotassium oxalate	HMDB
Oxalate, iron	HMDB
Sodium oxalate	HMDB
Oxalic acid	KEGG

Chemical Formula

C₂H₂O₄

Average Molecular Weight

90.0349

Monoisotopic Molecular Weight

89.995308552

IUPAC Name

oxalic acid

Traditional Name

oxalic acid

CAS Registry Number

144-62-7

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 Key

MUBZPKHOEPUJKR-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.

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

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.51	ALOGPS
logP	-0.26	ChemAxon
logS	-0.14	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	14.44 m³·mol⁻¹	ChemAxon
Polarizability	6.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-0900000000-eaa92cf80964dd7d345a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-b9206a3a54b5be6f07d9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-9500000000-e5db327eab9e8a2f149e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00sl-3910000000-75af6e42d4cc12d798f4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-8aef9a64d926571c2de0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-eaa92cf80964dd7d345a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-b9206a3a54b5be6f07d9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-9500000000-e5db327eab9e8a2f149e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00sl-3910000000-75af6e42d4cc12d798f4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-3cee49bf06349fbe625e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9000000000-f5e8094c68372ab25a63	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-9510000000-28b0e365a156d2091afd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9000000000-cb3d53cc3c40c1cbbba7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0uk9-9000000000-53a009b344e3920ffca1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-2bafb6c472ab1030cd0f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0006-9000000000-8aef9a64d926571c2de0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-d1ff7c94a720b1eecaf2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-21d33d1d99d80526ee71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ac27102ff43446c313d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-fe58eaea122c39178fbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-3850c6a7016e2874d55b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-32ac4118fe0eb9a5abb2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-43de084d66dd1bebdeac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-159ed524013577f6f801	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-8e2d2f7a8acc88f00195	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-d7b47276d03e46ce72a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a1e091bb1f5fa6e9cbc7	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-538465f019815d5e1b4a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Plasma
Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details