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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-10-29 17:03:27 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 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
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Glycerolipid MetabolismSMP00039map00561
Glycine and Serine MetabolismSMP00004map00260
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.0 (0.0-24.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<5 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified34.0+/- 34.0 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified8.20 +/- 3.95 uMAdult (>18 years old)BothNormal
    • Dame, ZT. et al. ...
details
UrineDetected and Quantified14.4 (7.8-28.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified21.6 (0.5-91.1) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified8.9 (2.4-60.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified5.3 (0.1-37.3) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified3.5 (0.1-8.0) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified4.5 (0.00-9.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified15.9 (7.8-31.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.7 (0.2-6.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.1 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified20.4 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified18.9 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified3.5 (2.8 - 4.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified300.00 (150.00-450.00) umol/mmol creatinineChildren (1-13 years old)BothPrimary hyperoxaluria II details
UrineDetected and Quantified15000.0 (10000.0-20000.0) umol/mmol creatinineChildren (1-13 years old)BothD-Glyceric acidura details
UrineDetected and Quantified2360.0 (1.2 - 1450.0) umol/mmol creatinineAdult (>18 years old)BothPrimary Hyperoxaluria II, PH2 details
Associated Disorders and Diseases
Disease References
D-Glyceric acidemia
  1. MetaGene
Primary hyperoxaluria
  1. 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
  1. MetaGene
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)Download (PDF)
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

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
Glyceraldehyde + NAD + Water → Glyceric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Glyceraldehyde + NAD + Water → Glyceric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Glyceraldehyde + NAD + Water → Glyceric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Glyceraldehyde + NAD + Water → Glyceric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Glyceraldehyde + NAD + Water → Glyceric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:
GRHPR
Uniprot ID:
Q9UBQ7
Molecular weight:
35667.875
Reactions
Glyceric acid + NAD(P)(+) → Hydroxypyruvic acid + NAD(P)Hdetails
Glyceric acid + NAD → Hydroxypyruvic acid + NADH + Hydrogen Iondetails
Glyceric acid + NADP → Hydroxypyruvic acid + NADPH + Hydrogen Iondetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GLYCTK
Uniprot ID:
Q8IVS8
Molecular weight:
25036.865
Reactions
Adenosine triphosphate + Glyceric acid → ADP + 3-Phosphoglyceric aciddetails