Glyoxylic acid (YMDB00033)

Identification

YMDB ID

YMDB00033

Name

Glyoxylic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Glyoxylic acid, also known as a-ketoacetate or glyoxalate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Glyoxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyoxylic acid exists in all living species, ranging from bacteria to humans. Glyoxylic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

a-Ketoacetate
a-Ketoacetic acid
acetic acid
Acetic acid, oxo-
alpha-Ketoacetate
alpha-Ketoacetic acid
Formic acid, formyl-
Formylformate
Formylformic acid
Glyoxalate
Glyoxalic acid
Glyoxalsaeure
Glyoxylat
Glyoxylate
Glyoxylic acid
Glyoxylic acid, 14c2-labeled
Glyoxylic acid, 2-(14)C-labeled
Glyoxylic acid, calcium salt
Glyoxylic acid, sodium salt
Glyoxylic acid, sodium salt, 14C-labeled
Glyoxylic acid, sodium salt, 2-(14)C-labeled
Glyoxylsaeure
Kyselina glyoxylova
OCHCOOH
Oxalaldehydate
Oxalaldehydic acid
Oxoacetate
Oxoacetic acid
Oxoethanoate
Oxoethanoic acid
α-ketoacetate
α-ketoacetic acid

CAS number

298-12-4

Weight

Average: 74.0355
Monoisotopic: 74.00039393

InChI Key

HHLFWLYXYJOTON-UHFFFAOYSA-N

InChI

InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)

IUPAC Name

2-oxoacetic acid

Traditional IUPAC Name

glyoxylic acid

Chemical Formula

C₂H₂O₃

SMILES

[H]OC(=O)C([H])=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:16891 )
aldehydic acid (CHEBI:16891 )

Physical Properties

State

Liquid

Charge

Melting point

-93 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	224 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	-0.13	ChemAxon
logS	0.48	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	-9.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	13.5 m³·mol⁻¹	ChemAxon
Polarizability	5.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm
Extracelular
Peroxisome

Organoleptic Properties

Not Available

SMPDB Pathways

Cysteine Metabolism	PW002383
Ether lipid metabolism	PW002492
Fatty acid biosynthesis	PW002458
Glyoxylate cycle	PW002419
Methionine metabolism and salvage	PW002384

KEGG Pathways

Methane metabolism	ec00680
Purine metabolism	ec00230
Pyruvate metabolism	ec00620
Selenocompound metabolism	ec00450
Sulfur metabolism	ec00920

SMPDB Reactions

Glyoxylic acid + L-Alanine → Pyruvic acid + Glycine

Glyoxylic acid + Acetyl-CoA + water → Coenzyme A + hydron + (S)-Malic acid

D-threo-Isocitric acid → Succinic acid + Glyoxylic acid

KEGG Reactions

Glyoxylic acid + L-Alanine → Pyruvic acid + Glycine

Isocitric acid → Glyoxylic acid + Succinic acid

Glyoxylic acid + Acetyl-CoA + water → hydron + Coenzyme A + (S)-malate(2-)

water + hydron + Ureidoglycolic acid ↔ Glyoxylic acid + Carbon dioxide + Ammonium

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-03di-3900000000-16bc69e0e9d51e54854e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03di-3900000000-16bc69e0e9d51e54854e	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9000000000-042540a05be250278f8b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9200000000-c60b627ed670285ec37f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9000000000-72c34bc34b8c3341442b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-920a0dc738957201d4ba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-857c7f2d72c3d4c10dbf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-9b5825d5d9d8b094fefa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-de556f03ea428deff5e2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00dl-9000000000-74b253632894213d473c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-9b5825d5d9d8b094fefa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-de556f03ea428deff5e2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00dl-9000000000-74b253632894213d473c	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-a8cc2c89793394fdf9e4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-d20183b08984d4766e8a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-ea9968e3933fd734506c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-cef8efc477a2500a7ead	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-3817c0865df629803538	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-bb935f857fb5fd08c7e3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-8f50f0d32d4c40b5b935	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-b6216caa16afdf328489	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-aa6a654e73df38a43273	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-c6f38ec60bcf8724ecd1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-c6f38ec60bcf8724ecd1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-641421c616a0929ce01e	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-004l-9000000000-a04bafbf8e0b990094a3	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Takada, Y., Noguchi, T. (1985). "Characteristics of alanine: glyoxylate aminotransferase from Saccharomyces cerevisiae, a regulatory enzyme in the glyoxylate pathway of glycine and serine biosynthesis from tricarboxylic acid-cycle intermediates." Biochem J 231:157-163.3933486
Kunze, M., Kragler, F., Binder, M., Hartig, A., Gurvitz, A. (2002). "Targeting of malate synthase 1 to the peroxisomes of Saccharomyces cerevisiae cells depends on growth on oleic acid medium." Eur J Biochem 269:915-922.11846793
Yoo, H. S., Cooper, T. G. (1991). "The ureidoglycollate hydrolase (DAL3) gene in Saccharomyces cerevisiae." Yeast 7:693-698.1776360

Synthesis Reference:

Jie, Yuanping; Song, Zhen. Method for preparing glyoxylic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp.

External Links:

Resource	Link
CHEBI ID	16891
HMDB ID	HMDB00119
Pubchem Compound ID	760
Kegg ID	C00048
ChemSpider ID	740
FOODB ID	FDB007244
Wikipedia	Glyoxylic_acid
BioCyc ID	GLYOX

Enzymes

Protein Details

1. Alanine--glyoxylate aminotransferase 1

General function:: Involved in metabolic process
Specific function:: Has alanine:glyoxylate aminotransferase activity
Gene Name:: AGX1
Uniprot ID:: P43567
Molecular weight:: 41906.80078

Reactions

L-alanine + glyoxylate → pyruvate + glycine.

Protein Details

2. Isocitrate lyase

General function:: Involved in isocitrate lyase activity
Specific function:: Catalyzes the formation of succinate and glyoxylate from isocitrate, a key step of the glyoxylate cycle, which operates as an anaplerotic route for replenishing the tricarboxylic acid cycle. Required for growth on ethanol or acetate, but dispensable when fermentable carbon sources are available. Acts also on 2- methylisocitrate
Gene Name:: ICL1
Uniprot ID:: P28240
Molecular weight:: 62408.30078

Reactions

Isocitrate → succinate + glyoxylate.

Protein Details

3. Ureidoglycolate hydrolase

General function:: Involved in ureidoglycolate hydrolase activity
Specific function:: Utilization of purines as secondary nitrogen sources, when primary sources are limiting
Gene Name:: DAL3
Uniprot ID:: P32459
Molecular weight:: 21726.59961

Reactions

(S)-ureidoglycolate + H(2)O → glyoxylate + 2 NH(3) + CO(2).

Protein Details

4. Malate synthase 1, glyoxysomal

General function:: Involved in catalytic activity
Specific function:: This isozyme is necessary for growth on acetate as sole C-source
Gene Name:: MLS1
Uniprot ID:: P30952
Molecular weight:: 62790.60156

Reactions

Acetyl-CoA + H(2)O + glyoxylate → (S)-malate + CoA.

Protein Details

5. Malate synthase 2, glyoxysomal

General function:: Involved in catalytic activity
Specific function:: This isozyme is involved in the degradation of allantoin (purine catabolism)
Gene Name:: DAL7
Uniprot ID:: P21826
Molecular weight:: 62793.39844

Reactions

Acetyl-CoA + H(2)O + glyoxylate → (S)-malate + CoA.

Protein Details

6. Putative 2-hydroxyacid dehydrogenase YNL274C

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: P53839
Molecular weight:: 38831.19922

Reactions

glycolate + NADP+ → glyoxylate + NADPH + H+.

Structure for #<Compound:0xa61a1d04>

Enzymes

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