Record Information
Version2.0
Creation Date2012-05-31 14:04:17 -0600
Update Date2015-09-13 12:56:13 -0600
Secondary Accession Numbers
  • ECMDB04077
Identification
Name:Glyceric acid
DescriptionGlyceric acid is a colorless syrupy acid, obtained from oxidation of glycerol. It is a natural three-carbon sugar acid. Salts and esters of glyceric acid are known as glycerates. Several phosphate derivatives of glyceric acid, including 2-phosphoglyceric acid, 3-phosphoglyceric acid, 2,3-bisphosphoglyceric acid, and 1,3-bisphosphoglyceric acid, are important biochemical intermediates. (Wikipedia)
Structure
Thumb
Synonyms:
  • (R)-glycerate
  • (R)-glyceric acid
  • D-glycerate
  • A,b-Hydroxypropionate
  • A,b-Hydroxypropionic acid
  • Alpha,beta-Hydroxypropionate
  • Alpha,beta-Hydroxypropionic acid
  • D-Glycerate
  • D-Glyceric acid
  • Glycerate
  • Glyceric acid
  • α,β-Hydroxypropionate
  • α,β-Hydroxypropionic acid
Chemical Formula:C3H6O4
Weight:Average: 106.0773
Monoisotopic: 106.02660868
InChI Key:RBNPOMFGQQGHHO-UWTATZPHSA-N
InChI:InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1
CAS number:473-81-4
IUPAC Name:(2R)-2,3-dihydroxypropanoic acid
Traditional IUPAC Name:glycerate
SMILES:OC[C@@H](O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Glyceric_acid
  • Sugar acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • 1,2-diol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [MERCK INDEX (1996)]PhysProp
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 Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.38 m³·mol⁻¹ChemAxon
Polarizability8.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD
Hydrogen ion + Hydroxypyruvic acid + NADH > Glyceric acid + NAD
Hydrogen ion + Hydroxypyruvic acid + NADPH > Glyceric acid + NADP
Adenosine triphosphate + Glyceric acid > 3-Phosphoglycerate + ADP + Hydrogen ion
Water + 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate > Glyceric acid + Mannose 6-phosphate
Adenosine triphosphate + Glyceric acid > 2-Phospho-D-glyceric acid + ADP + Hydrogen ion
Glyceric acid + NAD <> Hydroxypyruvic acid + NADH + Hydrogen ion
Glyceric acid + NADP <> Hydroxypyruvic acid + NADPH + Hydrogen ion
Adenosine triphosphate + Glyceric acid <> ADP + 3-Phospho-D-glycerate
Glyceric acid + NAD <> Tartronate semialdehyde + NADH + Hydrogen ion
Glyceric acid + NADP <> Tartronate semialdehyde + NADPH + Hydrogen ion
Tartaric acid <> Glyceric acid + Carbon dioxide
NAD(P)<sup>+</sup> + Glyceric acid < NAD(P)H + Tartronate semialdehyde + Hydrogen ion
Glyceric acid + NAD(P)(+) > Tartronate semialdehyde + NAD(P)H
Glyceric acid + NAD(P)(+) > Hydroxypyruvic acid + NAD(P)H
Adenosine triphosphate + Glyceric acid > ADP + 2-Phospho-D-glyceric acid
Adenosine triphosphate + Glyceric acid > ADP + 3-Phospho-D-glycerate
2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid
Glyceric acid + NAD + NADP <> Tartronate semialdehyde + NADH + NADPH + Hydrogen ion
2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Water <> Mannose 6-phosphate + Glyceric acid
Tartronate semialdehyde + Hydrogen ion + NADPH + NADPH > NADP + Glyceric acid
Glyceric acid + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + 2-Phosphoglyceric acid + ADP + 2-Phosphoglyceric acid
Glyceric acid + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + 3-Phosphoglyceric acid + ADP + 3-Phosphoglycerate
Tartronate semialdehyde + NADH + Hydrogen ion > NAD + Glyceric acid
2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid

SMPDB Pathways:
2-O-alpha-mannosyl-D-glycerate degradationPW002096 ThumbThumb?image type=greyscaleThumb?image type=simple
glycolate and glyoxylate degradationPW000827 ThumbThumb?image type=greyscaleThumb?image type=simple
glycolate and glyoxylate degradation IIPW002021 ThumbThumb?image type=greyscaleThumb?image type=simple
superpathway of D-glucarate and D-galactarate degradationPW000795 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
1410± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f6t-0910000000-52b917dbc684454452aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0uei-0920000000-4d5f18f14464b7289e4eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f72-0920000000-7727c90167e5f1e15f7cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-0910000000-52b917dbc684454452aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uei-0920000000-4d5f18f14464b7289e4eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01po-9000000000-e74d8dcadd449f32f28fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0avr-9362000000-4ae43a853db514e46cc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0ufr-9800000000-f68cee7fd839cc0c350aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0pb9-9300000000-c9741b095b361aa0bf2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-8900000000-2ca9bd370ef2f7afdf64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-2c68fcd2a4c9cc998e14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9400000000-a3e0c92f667ab9fdfbe5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-e2f8962c5a4a4bde459aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-052e-9000000000-08ad44e661510838b17fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0007-9000000000-b65c29cedef64ad74dfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-1900000000-2d91902f3a95d7e66bbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-2c68fcd2a4c9cc998e14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9400000000-a3e0c92f667ab9fdfbe5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-e2f8962c5a4a4bde459aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052e-9000000000-08ad44e661510838b17fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0007-9000000000-b65c29cedef64ad74dfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-2d91902f3a95d7e66bbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-9600000000-6c887f0d5bb5b5b43e47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-9100000000-4dcb939c91e313be7889View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0ddbae5fe95cd5c2cc3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-7900000000-483a2fcbaa1f9e4282f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-c37acde4cab84c418b98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c2110468981b90e60c2bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • 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
  • 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
  • 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
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Kyriacou, 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)
External Links:
ResourceLink
CHEBI ID16659
HMDB IDHMDB00139
Pubchem Compound ID439194
Kegg IDC00258
ChemSpider ID388334
WikipediaGlyceric acid
BioCyc IDGLYCERATE
EcoCyc IDGLYCERATE
Ligand ExpoDGY

Enzymes

General function:
Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:
(R)-glycerate + NAD(P)(+) = 2-hydroxy-3- oxopropanoate + NAD(P)H
Gene Name:
garR
Uniprot ID:
P0ABQ2
Molecular weight:
30427
Reactions
D-glycerate + NAD(P)(+) = 2-hydroxy-3-oxopropanoate + NAD(P)H.
General function:
Involved in glycerate kinase activity
Specific function:
ATP + (R)-glycerate = ADP + 3-phospho-(R)- glycerate
Gene Name:
garK
Uniprot ID:
P23524
Molecular weight:
39104
Reactions
ATP + (R)-glycerate = ADP + 3-phospho-(R)-glycerate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Can also reduce 2,5-diketo-D-gluconate (25DKG) to 5-keto-D- gluconate (5KDG), 2-keto-D-gluconate (2KDG) to D-gluconate, and 2- keto-L-gulonate (2KLG) to L-idonate (IA), but it is not its physiological function. Inactive towards 2-oxoglutarate, oxaloacetate, pyruvate, 5-keto-D-gluconate, D-fructose and L- sorbose. Activity with NAD is very low
Gene Name:
ghrB
Uniprot ID:
P37666
Molecular weight:
35395
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
D-gluconate + NADP(+) = 2-dehydro-D-gluconate + NADPH.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Inactive towards 2-oxo-D-gluconate, 2-oxoglutarate, oxaloacetate and pyruvate. Only D- and L-glycerate are involved in the oxidative activity with NADP. Activity with NAD is very low
Gene Name:
ghrA
Uniprot ID:
P75913
Molecular weight:
35343
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the NAD(+)-dependent oxidative decarboxylation of D-malate into pyruvate. Is essential for aerobic growth on D- malate as the sole carbon source. But is not required for anaerobic D-malate utilization, although DmlA is expressed and active in those conditions. Appears to be not able to use L- tartrate as a substrate for dehydrogenation instead of D-malate
Gene Name:
dmlA
Uniprot ID:
P76251
Molecular weight:
40315
Reactions
(R)-malate + NAD(+) = pyruvate + CO(2) + NADH.
General function:
Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:
(R)-glycerate + NAD(P)(+) = 2-hydroxy-3- oxopropanoate + NAD(P)H
Gene Name:
glxR
Uniprot ID:
P77161
Molecular weight:
30800
Reactions
D-glycerate + NAD(P)(+) = 2-hydroxy-3-oxopropanoate + NAD(P)H.
General function:
Involved in glycerate kinase activity
Specific function:
ATP + (R)-glycerate = ADP + 3-phospho-(R)- glycerate
Gene Name:
glxK
Uniprot ID:
P77364
Molecular weight:
38734
Reactions
ATP + (R)-glycerate = ADP + 3-phospho-(R)-glycerate.
General function:
Involved in catalytic activity
Specific function:
May hydrolyze mannosyl-D-glycerate to mannose-6- phosphate and glycerate
Gene Name:
mngB
Uniprot ID:
P54746
Molecular weight:
100014
Reactions
2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate + H(2)O = D-mannose 6-phosphate + D-glycerate.

Transporters

General function:
Involved in transporter activity
Specific function:
Uptake of D-glucarate
Gene Name:
gudP
Uniprot ID:
Q46916
Molecular weight:
49142
General function:
Involved in transporter activity
Specific function:
Uptake of D-galactarate
Gene Name:
garP
Uniprot ID:
P0AA80
Molecular weight:
49009
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368