Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:57 UTC
HMDB IDHMDB00139
Secondary Accession NumbersNone
Metabolite Identification
Common NameGlyceric acid
DescriptionGlyceric acid is a colorless 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 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.
Structure
Thumb
Synonyms
  1. (R)-glycerate
  2. a,b-Hydroxypropionate
  3. a,b-Hydroxypropionic acid
  4. D-Glycerate
  5. D-Glyceric acid
  6. Glycerate
  7. Glyceric acid
Chemical FormulaC3H6O4
Average Molecular Weight106.0773
Monoisotopic Molecular Weight106.02660868
IUPAC Name(2R)-2,3-dihydroxypropanoic acid
Traditional IUPAC Nameglyceric acid
CAS Registry Number473-81-4
SMILES
OC[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1
InChI KeyRBNPOMFGQQGHHO-UWTATZPHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassSugar Acids and Derivatives
Sub ClassN/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Beta Hydroxy Acids and Derivatives
  • trionic acid(ChEBI)
Substituents
  • 1,2 Diol
  • Alpha Hydroxy Acid
  • Carboxylic Acid
  • Primary Alcohol
  • Secondary Alcohol
  • Triose Monosaccharide
Direct ParentSugar Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility639 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS0.78ALOGPS
pKa (strongest acidic)3.42ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area77.76ChemAxon
rotatable bond count2ChemAxon
refractivity20.38ChemAxon
polarizability8.96ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Glycerolipid MetabolismSMP00039map00561
Glycine and Serine MetabolismSMP00004map00260
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified10.0 (0.0-24.0) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified<5 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified34.0+/- 34.0 uMAdult (>18 years old)Not SpecifiedNormal
UrineDetected and Quantified14.4 (7.8-28.8) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified21.6 (0.5-91.1) umol/mmol creatinineNewborn (0-30 days old)BothNormal
UrineDetected and Quantified8.9 (2.4-60.0) umol/mmol creatinineInfant (0-1 year old)BothNormal
UrineDetected and Quantified5.3 (0.1-37.3) umol/mmol creatinineChildren (1-13 year old)BothNormal
UrineDetected and Quantified3.5 (0.1-8.0) umol/mmol creatinineChildren (1-13 year old)BothNormal
UrineDetected and Quantified4.5 (0.00-9.0) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified15.9 (7.8-31.1) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified1.7 (0.2-6.0) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified4.1 umol/mmol creatinineNewborn (0-30 days old)BothNormal
UrineDetected and Quantified20.4 umol/mmol creatinineInfant (0-1 year old)BothNormal
UrineDetected and Quantified18.9 umol/mmol creatinineInfant (0-1 year old)BothNormal
UrineDetected and Quantified3.5 (2.8 - 4.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected and Quantified300.00 (150.00-450.00) umol/mmol creatinineChildren (1-13 year old)BothPrimary hyperoxaluria II
UrineDetected and Quantified15000.0 (10000.0-20000.0) umol/mmol creatinineChildren (1-13 year old)BothD-Glyceric acidura
UrineDetected and Quantified2360.0 (1.2 - 1450.0) umol/mmol creatinineAdult (>18 years old)BothPrimary Hyperoxaluria II, PH2
Associated Disorders and Diseases
Disease References
D-Glyceric acidemia
Primary hyperoxaluria
  • Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20. Pubmed: 9267307
Primary hyperoxaluria II, PH2
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012242
KNApSAcK IDC00001185
Chemspider ID388334
KEGG Compound IDC00258
BioCyc ID2-PG
BiGG ID34424
Wikipedia LinkGlyceric acid
NuGOwiki LinkHMDB00139
Metagene LinkHMDB00139
METLIN ID280
PubChem Compound439194
PDB IDDGY
ChEBI ID32398
References
Synthesis ReferenceKyriacou, Demetrios; Tougas, Terrence P. Preparation of glyceric acid by anodic oxidation of glycerol at a silver oxide electrode. Journal of Organic Chemistry (1987), 52(11), 2318-19.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. Pubmed: 14708889
  3. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  4. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
  5. Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20. Pubmed: 9267307
  6. Topcu M, Saatci I, Haliloglu G, Kesimer M, Coskun T: D-glyceric aciduria in a six-month-old boy presenting with West syndrome and autistic behaviour. Neuropediatrics. 2002 Feb;33(1):47-50. Pubmed: 11930278
  7. Fontaine M, Porchet N, Largilliere C, Marrakchi S, Lhermitte M, Aubert JP, Degand P: Biochemical contribution to diagnosis and study of a new case of D-glyceric acidemia/aciduria. Clin Chem. 1989 Oct;35(10):2148-51. Pubmed: 2551543
  8. Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. Pubmed: 1444166
  9. Rashed MS, Aboul-Enein HY, AlAmoudi M, Jakob M, Al-Ahaideb LY, Abbad A, Shabib S, Al-Jishi E: Chiral liquid chromatography tandem mass spectrometry in the determination of the configuration of glyceric acid in urine of patients with D-glyceric and L-glyceric acidurias. Biomed Chromatogr. 2002 May;16(3):191-8. Pubmed: 11920944

Enzymes

Gene Name:
ALDH9A1
Uniprot ID:
P49189
Reactions
Glyceraldehyde + NAD + Water unknown Glyceric acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Reactions
Glyceraldehyde + NAD + Water unknown Glyceric acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH2
Uniprot ID:
P05091
Reactions
Glyceraldehyde + NAD + Water unknown Glyceric acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Reactions
Glyceraldehyde + NAD + Water unknown Glyceric acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Reactions
Glyceraldehyde + NAD + Water unknown Glyceric acid + NADH + Hydrogen Iondetails
Gene Name:
GRHPR
Uniprot ID:
Q9UBQ7
Reactions
Glyceric acid + NAD(P)(+) unknown Hydroxypyruvic acid + NAD(P)Hdetails
Glyceric acid + NAD unknown Hydroxypyruvic acid + NADH + Hydrogen Iondetails
Glyceric acid + NADP unknown Hydroxypyruvic acid + NADPH + Hydrogen Iondetails
Gene Name:
GLYCTK
Uniprot ID:
Q8IVS8
Reactions
Adenosine triphosphate + Glyceric acid unknown ADP + 3-Phosphoglyceric aciddetails