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Identification
YMDB IDYMDB00756
Name3-phospho-D-glyceric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Glycerate 3-phosphate, also known as 3-phosphoglyceric acid or 3-phospho-(R)-glycerate, 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. D-Glycerate 3-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 3-(dihydrogen phosphate)Glycerate
  • 3-(dihydrogen phosphate)Glyceric acid
  • 3-Glycerophosphorate
  • 3-Glycerophosphoric acid
  • 3-P-D-glycerate
  • 3-P-glycerate
  • 3-PGA
  • 3-phospho-(R)-glycerate
  • 3-phospho-D-glycerate
  • 3-phospho-glycerate
  • 3-phospho-glyceric acid
  • 3-phosphoglycerate
  • 3-phosphoglyceric acid
  • D-(-)-3-Phosphoglyceric acid
  • d-glycerate 3-phosphate
  • D-glycerate-3-P
  • Glycerate 3-phosphate
  • glycerate-3-P
  • Glyceric acid 3-phosphate
  • Phosphoglycerate
  • 3-Phospho-(R)-glyceric acid
  • 3-Phospho-D-glyceric acid
  • D-Glyceric acid 3-phosphoric acid
  • (2R)-2-Hydroxy-3-(phosphonatooxy)propanoic acid
  • (2R)-2-Hydroxy-3-(phosphonooxy)propanoic acid
  • 2-Hydroxy-3-(phosphonatooxy)propanoate
  • D-3-Phosphoglyceric acid
  • D-Glyceric acid 3-phosphate
  • 3-Phosphoglycerate, trisodium salt
  • 3-Phosphoglycerate, monosodium salt
  • 3-Phosphoglycerate, (R)-isomer
CAS number820-11-1
WeightAverage: 186.0572
Monoisotopic: 185.99293909
InChI KeyOSJPPGNTCRNQQC-UWTATZPHSA-N
InChIInChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1
IUPAC Name(2R)-2-hydroxy-3-(phosphonooxy)propanoic acid
Traditional IUPAC NameD-glycerate 3-phosphate
Chemical FormulaC3H7O7P
SMILESO[C@H](COP(O)(O)=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
  • Glyceric_acid
  • Monoalkyl phosphate
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility21 g/LALOGPS
logP-2.3ALOGPS
logP-1.6ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)1.3ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.26 m³·mol⁻¹ChemAxon
Polarizability13.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerol metabolismPW002407 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
glycine metabolismPW002398 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
Glycine, serine and threonine metabolismec00260 Map00260
Glycolysis / Gluconeogenesisec00010 Map00010
Glyoxylate and dicarboxylate metabolismec00630 Map00630
Methane metabolismec00680 Map00680
SMPDB ReactionsNot Available
KEGG Reactions
NAD + 3-phospho-D-glyceric acidNADH + Phosphohydroxypyruvic acid + hydron
Adenosine triphosphate + 3-phospho-D-glyceric acid3-phospho-D-glyceroyl dihydrogen phosphate + ADP
2-phospho-D-glyceric acid3-phospho-D-glyceric acid
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
120 ± 10 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
630 ± 100 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-2d6f0050126bbc72d771JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-9150000000-ebe296689ddfcee96d61JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00kb-9500000000-3a504199c8820dbd44a1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2900000000-97a3da464b710b2684a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kv-8900000000-f897e638356fb29020cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-655876160dc523273c42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-5900000000-b5d234c9dd7df3920489JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-6b06c4977ed320e922a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-69afa1a98654e3a171eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e64736ac1f9d1f7dd9efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-b24e251f42140de98cedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-7c1557a43a172be0e63dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-9000000000-0b41dc890757740bbb51JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Faller, L. D., Johnson, A. M. (1974). "Calorimetric studies of the role of magnesium ions in yeast enolase catalysis." Proc Natl Acad Sci U S A 71:1083-1087.4598292
  • Melcher, K., Entian, K. D. (1992). "Genetic analysis of serine biosynthesis and glucose repression in yeast." Curr Genet 21:295-300.1326413
  • Albers, E., Laize, V., Blomberg, A., Hohmann, S., Gustafsson, L. (2003). "Ser3p (Yer081wp) and Ser33p (Yil074cp) are phosphoglycerate dehydrogenases in Saccharomyces cerevisiae." J Biol Chem 278:10264-10272.12525494
  • Rodicio, R., Heinisch, J. (1987). "Isolation of the yeast phosphoglyceromutase gene and construction of deletion mutants." Mol Gen Genet 206:133-140.3033435
  • Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17794
HMDB IDHMDB00807
Pubchem Compound ID25245548
Kegg IDC00197
ChemSpider ID388326
FOODB IDFDB030460
Wikipedia3-Phosphoglyceric_acid
BioCyc IDG3P

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
SER33
Uniprot ID:
P40510
Molecular weight:
51187.80078
Reactions
3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.
General function:
Involved in phosphoglycerate kinase activity
Specific function:
ATP + 3-phospho-D-glycerate = ADP + 3-phospho- D-glyceroyl phosphate
Gene Name:
PGK1
Uniprot ID:
P00560
Molecular weight:
44738.0
Reactions
ATP + 3-phospho-D-glycerate → ADP + 3-phospho-D-glyceroyl phosphate.
General function:
Involved in catalytic activity
Specific function:
Interconversion of 3- and 2-phosphoglycerate with 2,3- bisphosphoglycerate as the primer of the reaction. Can also Catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity
Gene Name:
GPM1
Uniprot ID:
P00950
Molecular weight:
27608.30078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Involved, either directly or indirectly, in the bidirectional transport of sterols between the endoplasmic reticulum and the plasma membrane
Gene Name:
DET1
Uniprot ID:
Q99288
Molecular weight:
39171.80078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the interconversion of 2-phosphoglycerate and 3-phosphoglycerate
Gene Name:
Not Available
Uniprot ID:
Q12040
Molecular weight:
26176.5
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Could be non-functional
Gene Name:
GPM3
Uniprot ID:
Q12326
Molecular weight:
34863.19922
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Could be non-functional
Gene Name:
GPM2
Uniprot ID:
Q12008
Molecular weight:
36072.80078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
SER3
Uniprot ID:
P40054
Molecular weight:
51192.80078
Reactions
3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.