P. aeruginosa Metabolome Database: glycolate (PAMDB110053)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110053

Identification

Name:

glycolate

Description:

A hydroxy monocarboxylic acid anion that is acetate where the methyl group has been hydroxylated.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

hydroxyacetic acid
glycolic acid
glycollate

Chemical Formula:

C₂H₃O₃

Average Molecular Weight:

75.044

Monoisotopic Molecular Weight:

76.0160439947

InChI Key:

AEMRFAOFKBGASW-UHFFFAOYSA-M

InChI:

InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)/p-1

CAS number:

79-14-1

IUPAC Name:

hydroxyacetate

Traditional IUPAC Name:

glycolic acid

SMILES:

C(C(=O)[O-])O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organic acids and derivatives

Sub Class

Hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Alpha-hydroxy acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:17497 )
2-hydroxy monocarboxylic acid (CHEBI:17497 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

75 - 80 °C

Experimental Properties:

Property	Value	Reference
Melting Point	75 - 80 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.11	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	608.0 mg/mL	ALOGPS
logP	-1	ALOGPS
logP	-1	ChemAxon
logS	0.9	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	14.35 m³·mol^-1	ChemAxon
Polarizability	6.2 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:

Not Available

Reactions:

glycolate + Oxygen → glyoxylate + Hydrogen peroxide
Acceptor + glycolate → Donor-H2 + glyoxylate

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-9000000000-e942bdae1d60e5f5d649	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-f225de2de3540c3f50a4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-7de217d97b44f53aad82	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-88af2b259f82cd1d8938	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-c968a24f0640b154325b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-d961c3c14ec415e3141e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-67f73be970ba9f885c4a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-7445713a5fe347bbc8b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-26e13242443efc1aa846	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6ba976b949118cd0a86a	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-2885890e3bb8c015742f	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. Physiological genomics 29, Pubmed: 17190852
Grostern A, Sales CM, Zhuang WQ, Erbilgin O, Alvarez-Cohen L (2012)Glyoxylate metabolism is a key feature of the metabolic degradation of 1,4-dioxane by Pseudonocardia dioxanivorans strain CB1190. Applied and environmental microbiology 78, Pubmed: 22327578
Niessen M, Krause K, Horst I, Staebler N, Klaus S, Gaertner S, Kebeish R, Araujo WL, Fernie AR, Peterhansel C (2012)Two alanine aminotranferases link mitochondrial glycolate oxidation to the major photorespiratory pathway in Arabidopsis and rice. Journal of experimental botany 63, Pubmed: 22268146
Schmitt DC, Malow EJ, Johnson JS (2012)Three-component glycolate Michael reactions of enolates, silyl glyoxylates, and a,ß-enones. The Journal of organic chemistry 77, Pubmed: 22394389
Jiang J, Johnson LC, Knight J, Callahan MF, Riedel TJ, Holmes RP, Lowther WT (2012)Metabolism of [13C5]hydroxyproline in vitro and in vivo: implications for primary hyperoxaluria. American journal of physiology. Gastrointestinal and liver physiology 302, Pubmed: 22207577
Knight J, Hinsdale M, Holmes R (2012)Glycolate and 2-phosphoglycolate content of tissues measured by ion chromatography coupled to mass spectrometry. Analytical biochemistry 421, Pubmed: 22093610
Salido E, Pey AL, Rodriguez R, Lorenzo V (2012)Primary hyperoxalurias: disorders of glyoxylate detoxification. Biochimica et biophysica acta 1822, Pubmed: 22446032

Synthesis Reference:

Witzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CAS	79-14-1
ChEBI	29805
ChemSpider	4573887
DrugBank	DB03085
HMDB	HMDB00115
IAF1260	34090
KEGG	C00160
MetaboLights	MTBLC29805
PubChem	5460308

glycolate (PAMDB110053)

Structure for glycolate (PAMDB110053)