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Identification
YMDB IDYMDB02299
NameGlyceric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlyceric acid, also known as glycerate or D-groa, 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. Glyceric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceric acid exists in all living species, ranging from bacteria to humans. Glyceric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (R)-glycerate
  • a,b-Hydroxypropionate
  • a,b-Hydroxypropionic acid
  • D-Glyceric acid
  • Glycerate
  • Glyceric acid
  • D-Glycerate
  • alpha,beta-Hydroxypropionic acid
  • D-GroA
  • R-Glyceric acid
  • Glycerate
  • (R)-Glycerate
  • a,b-Hydroxypropionate
  • a,b-Hydroxypropionic acid
  • alpha,beta-Hydroxypropionate
  • R-Glycerate
  • (R)-Glyceric acid
  • D-Glyceric acid
  • (2R)-2,3-Dihydroxypropanoic acid
  • (R)-2,3-Dihydroxypropanoic acid
  • D-2,3-Dihydroxypropanoic acid
CAS number473-81-4
WeightAverage: 106.0773
Monoisotopic: 106.02660868
InChI KeyRBNPOMFGQQGHHO-UWTATZPHSA-N
InChIInChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1
IUPAC Name(2R)-2,3-dihydroxypropanoic acid
Traditional IUPAC Nameglycerate
Chemical FormulaC3H6O4
SMILESOC[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
StateLiquid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility1000.0 mg/mL [MERCK INDEX (1996)]PhysProp
LogPNot AvailablePhysProp
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 LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerol metabolismPW002407 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
NADH + hydron + Glyceric acidGlyceraldehyde + NAD + water
3-Phosphoglyceric acid + ADPAdenosine triphosphate + Glyceric acid
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f6t-0910000000-52b917dbc684454452aeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0uei-0920000000-4d5f18f14464b7289e4eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f72-0920000000-7727c90167e5f1e15f7cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-0910000000-52b917dbc684454452aeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uei-0920000000-4d5f18f14464b7289e4eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01po-9000000000-e74d8dcadd449f32f28fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0avr-9362000000-4ae43a853db514e46cc7JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0ufr-9800000000-f68cee7fd839cc0c350aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0pb9-9300000000-c9741b095b361aa0bf2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-8900000000-2ca9bd370ef2f7afdf64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-2c68fcd2a4c9cc998e14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9400000000-a3e0c92f667ab9fdfbe5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-e2f8962c5a4a4bde459aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-052e-9000000000-08ad44e661510838b17fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0007-9000000000-b65c29cedef64ad74dfbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-1900000000-2d91902f3a95d7e66bbaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-2c68fcd2a4c9cc998e14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9400000000-a3e0c92f667ab9fdfbe5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-e2f8962c5a4a4bde459aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052e-9000000000-08ad44e661510838b17fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0007-9000000000-b65c29cedef64ad74dfbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-2d91902f3a95d7e66bbaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-9600000000-6c887f0d5bb5b5b43e47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-9100000000-4dcb939c91e313be7889JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0ddbae5fe95cd5c2cc3aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-7900000000-483a2fcbaa1f9e4282f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-c37acde4cab84c418b98JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c2110468981b90e60c2bJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
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.
External Links:
ResourceLink
CHEBI ID16659
HMDB IDHMDB00139
Pubchem Compound ID439194
Kegg IDC00258
ChemSpider ID388334
FOODB IDFDB012242
Wikipedia IDGlyceric acid
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD3
Uniprot ID:
P54114
Molecular weight:
55384.80078
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.