Common Name(r)-glycerate
DescriptionGlyceric acid is a colourless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria, an inborn error of metabolism, and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive, and metabolic acidosis. At sufficiently high levels, glyceric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Glyceric acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glyceric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. Elevated values may also be due to microbial sources such as yeast (Aspergillus, Penicillium, probably Candida) or due to dietary sources containing glycerol (glycerine). Glyceric acid is isolated from various plants (e.g. brassicas, pulses, and Vicia faba).
Structure
Molecular FormulaC3H6O4
Average Mass106.07730
Monoisotopic Mass106.02661
IUPAC Name(2R)-2,3-dihydroxypropanoic acid
Traditional NameGlyceric acid
CAS Registry Number473-81-4
SMILESO=C([O-])[C@H](O)CO
InChI IdentifierInChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1
InChI KeyRBNPOMFGQQGHHO-UWTATZPHSA-N
CHEBI IDCHEBI:16659
HMDB IDHMDB0000139
Pathways
NameSMPDB/PathBank
Glycine, serine and threonine metabolism
Glycerolipid Metabolism
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Glycerol Kinase Deficiency
Non Ketotic Hyperglycinemia
Dimethylglycine Dehydrogenase Deficiency
Sarcosinemia
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
D-glyceric acidura
Familial lipoprotein lipase deficiency
3-Phosphoglycerate dehydrogenase deficiency
StateNot Available
Water Solubility6.39e+02 g/l
logP-1.72
logS0.78
pKa (Strongest Acidic)3.42
pKa (Strongest Basic)-3.04
Hydrogen Acceptor Count4
Hydrogen Donor Count3
Polar Surface Area77.76 Ų
Rotatable Bond Count2
Physiological Charge-1
Formal Charge0
Refractivity20.38 m³·mol⁻¹
Polarizability8.96

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