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Identification
YMDB IDYMDB00341
Name3-Phosphoglyceric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Phosphoglyceric acid, also known as glycerate 3-phosphate or 3-PG, 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. 3-Phosphoglyceric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Phosphoglyceric acid exists in all living species, ranging from bacteria to humans.
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-pg
  • 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
  • G3P
  • Glycerate 3-phosphate
  • glycerate-3-P
  • Glyceric acid 3-phosphate
  • Phosphoglycerate
  • DL-Glycerate 3-phosphate
  • Glycerate 3-phosphates
  • 3-(Dihydrogen phosphoric acid)glyceric acid
  • DL-Glyceric acid 3-phosphoric acid
  • Glyceric acid 3-phosphoric acid
  • Glyceric acid 3-phosphates
  • 3-Phosphoglycerate, trisodium salt
  • 3-Phosphoglycerate, (R)-isomer
  • 3-Phosphoglycerate, monosodium salt
CAS number820-11-1
WeightAverage: 186.0572
Monoisotopic: 185.99293909
InChI KeyOSJPPGNTCRNQQC-UHFFFAOYSA-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)
IUPAC Name2-hydroxy-3-(phosphonooxy)propanoic acid
Traditional IUPAC Namephosphoglycerate
Chemical FormulaC3H7O7P
SMILES[H]OC(=O)C([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]
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
Polarizability13.29 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
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
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
2,3-bisphospho-D-glyceric acid + water3-Phosphoglyceric acid + phosphate
Glyceric acid 1,3-biphosphate + ADP3-Phosphoglyceric acid + Adenosine triphosphate
2,3-bisphospho-D-glyceric acid + water3-Phosphoglyceric acid + phosphate
3-Phosphoglyceric acid2-phospho-D-glyceric acid
3-Phosphoglyceric acid + NADNADH + hydron + Phosphohydroxypyruvic acid
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0974000000-41479250991be9cc1e07JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0974000000-41479250991be9cc1e07JSpectraViewer | MoNA
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, Positivesplash10-00fu-9081000000-487a9a33cdad68046ff3JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-002k-9300000000-4fafb3c93719c5a41327JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004j-9000000000-c6bb9644e70a338c03beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-9d164579c98406ad7c88JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-cea59554251398a27835JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-8a976aaa2f56f074d975JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a5c-9500000000-4bd264fcf029200c55c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9100000000-1a020681f04042ff6966JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-cea59554251398a27835JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-8a976aaa2f56f074d975JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a5c-9600000000-4bd264fcf029200c55c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-1a020681f04042ff6966JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0005-8900000000-bd4e0c8adef56968d87aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-3900000000-9d9dc94243143123d53bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kv-8900000000-b21c05dfded763ce62a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c460ca316484eef90129JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-5900000000-653e5055531f19df4952JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-15195031d70847a75881JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-59550676899d259aeab5JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
  • Takada, Y., Noguchi, T. (1985). "Characteristics of alanine: glyoxylate aminotransferase from Saccharomyces cerevisiae, a regulatory enzyme in the glyoxylate pathway of glycine and serine biosynthesis from tricarboxylic acid-cycle intermediates." Biochem J 231:157-163.3933486
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
  • 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:Jakoby, Wm. B.; Brummond, Dewey O.; Ochoa, Severo. Formation of 3-phosphoglyceric acid by carbon dioxide fixation with spinach-leaf enzymes. Journal of Biological Chemistry (1956), 218 811-22.
External Links:
ResourceLink
CHEBI ID17050
HMDB IDHMDB00807
Pubchem Compound ID724
Kegg IDC00597
ChemSpider ID704
FOODB IDFDB022255
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 intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:
Not Available
Uniprot ID:
Q03262
Molecular weight:
71068.60156
Reactions
Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-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.