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Identification
YMDB IDYMDB00807
Nameglycolic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlycolic acid, also known as 2-hydroxyacetate or glycolate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. Glycolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycolic acid exists in all living species, ranging from bacteria to humans. Glycolic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-Hydroxyacetate
  • 2-Hydroxyacetic acid
  • a-Hydroxyacetate
  • a-Hydroxyacetic acid
  • Acetic acid, hydroxy-
  • alpha-Hydroxyacetate
  • alpha-Hydroxyacetic acid
  • Glycocide
  • Glycolate
  • Glycolic acid
  • Glycollate
  • Glycollic acid
  • Hydroxyacetate
  • hydroxyacetic acid
  • Hydroxyethanoate
  • Hydroxyethanoic acid
  • Kyselina glykolova
  • Kyselina hydroxyoctova
  • Polyglycolic acid
  • Sodium glycolate
  • 2-Hydroxyethanoic acid
  • HOCH2COOH
  • 2-Hydroxyethanoate
  • Α-hydroxyacetate
  • Α-hydroxyacetic acid
  • GlyPure
  • GlyPure 70
  • Glycolic acid, 2-(14)C-labeled
  • Glycolic acid, 1-(14)C-labeled
  • Glycolic acid, potassium salt
  • Glycolic acid, monopotassium salt
  • Glycolic acid, calcium salt
  • Glycolic acid, monoammonium salt
  • Glycolic acid, monolithium salt
  • Glycolic acid, monosodium salt
  • Potassium glycolate
CAS number79-14-1
WeightAverage: 76.0514
Monoisotopic: 76.016043994
InChI KeyAEMRFAOFKBGASW-UHFFFAOYSA-N
InChIInChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
IUPAC Name2-hydroxyacetic acid
Traditional IUPAC Nameglycolic acid
Chemical FormulaC2H4O3
SMILESOCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point75-80 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-1.11 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility608 g/LALOGPS
logP-1ALOGPS
logP-1ChemAxon
logS0.9ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.35 m³·mol⁻¹ChemAxon
Polarizability6.2 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Glyoxylate and dicarboxylate metabolismec00630 Map00630
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • 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
Synthesis Reference:Witzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12.
External Links:
ResourceLink
CHEBI ID17497
HMDB IDHMDB00115
Pubchem Compound ID757
Kegg IDC00160
ChemSpider ID737
FOODB IDFDB003298
WikipediaGlycolic_acid
BioCyc IDGLYCOLLATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes the enolization of 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P) into the intermediate 2-hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (HK-MTPenyl-1-P), which is then dephosphorylated to form the acireductone 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene)
Gene Name:
UTR4
Uniprot ID:
P32626
Molecular weight:
25187.19922
Reactions
5-(methylthio)-2,3-dioxopentyl phosphate + H(2)O → 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + phosphate.
2-Phosphoglycolate + H2O → glycolate + phosphate
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+.
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q12486
Molecular weight:
24839.80078
Reactions
2-Phosphoglycolate + H2O → glycolate + phosphate
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q04223
Molecular weight:
35278.10156
Reactions
2-Phosphoglycolate + H2O → glycolate + phosphate