Record Information
Version2.0
Creation Date2012-05-31 14:06:02 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB04131
Identification
Name:3-Phosphoglycerate
Description3-phosphoglyceric acid (3PG) is a 3-carbon molecule that is a metabolic intermediate in both glycolysis and the Calvin cycle. This chemical is often termed PGA when referring to the Calvin cycle. In the Calvin cycle, two glycerate 3-phosphate molecules are reduced to form two molecules of glyceraldehyde 3-phosphate (GALP). (wikipedia)
Structure
Thumb
Synonyms:
  • 3-(Dihydrogen phosphate)Glycerate
  • 3-(Dihydrogen phosphate)Glyceric acid
  • 3-(Dihydrogen phosphoric acid)glyceric acid
  • 3-Glycerophosphate
  • 3-Glycerophosphorate
  • 3-Glycerophosphoric acid
  • 3-P-D-Glycerate
  • 3-P-D-Glyceric acid
  • 3-P-Glycerate
  • 3-P-Glyceric acid
  • 3-Pg
  • 3-PGA
  • 3-Phospho-(R)-glycerate
  • 3-Phospho-(R)-glyceric acid
  • 3-Phospho-D-glycerate
  • 3-Phospho-D-glyceric acid
  • 3-Phospho-glycerate
  • 3-Phospho-glyceric acid
  • 3-Phosphoglycerate
  • 3-Phosphoglyceric acid
  • D-(-)-3-Phosphoglycerate
  • D-(-)-3-Phosphoglyceric acid
  • D-3-Phosphoglycerate
  • D-3-Phosphoglyceric acid
  • D-Glycerate 3-phosphate
  • D-Glycerate-3-P
  • D-Glyceric acid 3-phosphate
  • D-Glyceric acid 3-phosphoric acid
  • D-Glyceric acid-3-P
  • G3P
  • Glycerate 3-phosphate
  • Glycerate-3-P
  • Glyceric acid 3-phosphate
  • Glyceric acid 3-phosphoric acid
  • Glyceric acid-3-P
  • Phosphoglycerate
  • Phosphoglyceric acid
Chemical Formula:C3H7O7P
Weight:Average: 186.0572
Monoisotopic: 185.99293909
InChI Key:OSJPPGNTCRNQQC-UHFFFAOYSA-N
InChI:InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)
CAS number:820-11-1
IUPAC Name:2-hydroxy-3-(phosphonooxy)propanoic acid
Traditional IUPAC Name:phosphoglycerate
SMILES:OC(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
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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 Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Gluconeogenesis from L-malic acidPW000819 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: cysteine biosynthesis from serinePW000977 ThumbThumb?image type=greyscaleThumb?image type=simple
cysteine biosynthesisPW000800 ThumbThumb?image type=greyscaleThumb?image type=simple
fructose metabolismPW000913 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolismPW000914 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IIPW000915 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)PW000916 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IV (glycerophosphoglycerol)PW000917 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism V (glycerophosphoserine)PW000918 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
glycolysis and pyruvate dehydrogenasePW000785 ThumbThumb?image type=greyscaleThumb?image type=simple
serine biosynthesis and metabolismPW000809 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
1540± 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
4080± 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 glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1510± 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 acetateMid-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 (Non-derivatized)splash10-0002-0974000000-41479250991be9cc1e07View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0974000000-41479250991be9cc1e07View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-2d6f0050126bbc72d771View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fu-9081000000-487a9a33cdad68046ff3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-002k-9300000000-4fafb3c93719c5a41327View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004j-9000000000-c6bb9644e70a338c03beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-9d164579c98406ad7c88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-cea59554251398a27835View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-8a976aaa2f56f074d975View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a5c-9500000000-4bd264fcf029200c55c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9100000000-1a020681f04042ff6966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-cea59554251398a27835View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-8a976aaa2f56f074d975View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a5c-9600000000-4bd264fcf029200c55c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-1a020681f04042ff6966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0005-8900000000-bd4e0c8adef56968d87aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-9100000000-abd08e7a88ff6e65bc4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-002b-9000000000-f8afa9e495e0f6c94717View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-9200000000-30ac9f237fd5b07a8ad8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-623d31045a6d2723a66bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0005-9800000000-592cc43b2d6718b5e805View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-75f21a1b3e228e0af7f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-3900000000-9d9dc94243143123d53bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kv-8900000000-b21c05dfded763ce62a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c460ca316484eef90129View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-5900000000-653e5055531f19df4952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-15195031d70847a75881View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-59550676899d259aeab5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-9000000000-0b41dc890757740bbb51View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Glaus M, Schneider W: Iron release from transferrin induced by mixed ligand complexes of copper(II). Biol Met. 1989;2(3):185-90. Pubmed: 2490073
  • Grisolia S, Salinas M, Wallace R, Singh GK: Influence of size, protein concentration, protein synthesis inhibitors,and carbon on clearance of enzymes and proteins from blood. Physiol Chem Phys. 1976;8(1):37-52. Pubmed: 183226
  • 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
  • Mair J: Progress in myocardial damage detection: new biochemical markers for clinicians. Crit Rev Clin Lab Sci. 1997;34(1):1-66. Pubmed: 9055056
  • Mayo Medical Laboratories 2005 Test Catalog
  • Nakai A, Shigematsu Y, Liu YY, Kikawa Y, Sudo M: Urinary sugar phosphates and related organic acids in fructose-1,6-diphosphatase deficiency. J Inherit Metab Dis. 1993;16(2):408-14. Pubmed: 8412001
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  • Sayed A, Matsuyama S, Inoue K, Alsina J, Cai F, Chen J, Inouye M: ATPase and GTPase activities copurifying with GTP-binding proteins in E. coli. J Mol Microbiol Biotechnol. 2000 Jul;2(3):261-3. Pubmed: 10937433
  • 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
  • Uchida K, Kondoh K, Matuo Y: Recombinant M-, B- and MB-type isozymes of human phosphoglyceric acid mutase: their large-scale production and preparation of polyclonal antibodies specific to M- and B-type isozymes. Clin Chim Acta. 1995 Jun 15;237(1-2):43-58. Pubmed: 7664478
  • Uchida K, Mori K, Matuo Y: [Phosphoglyceric acid mutase] Nippon Rinsho. 1995 May;53(5):1247-52. Pubmed: 7602787
  • 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
  • Veech RL, Lawson JW, Cornell NW, Krebs HA: Cytosolic phosphorylation potential. J Biol Chem. 1979 Jul 25;254(14):6538-47. Pubmed: 36399
  • 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
  • Yu KT, Pendley C 2nd, Herczeg T, Pendleton RG: 2,3-Diphosphoglycerate phosphatase/synthase: a potential target for elevating the diphosphoglycerate level in human red blood cells. J Pharmacol Exp Ther. 1990 Jan;252(1):192-200. Pubmed: 2153800
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.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17050
HMDB IDHMDB00807
Pubchem Compound ID724
Kegg IDC00597
ChemSpider ID704
Wikipedia3-Phosphoglycerate
BioCyc IDG3P
EcoCyc IDG3P

Enzymes

General function:
Involved in phosphoglycerate kinase activity
Specific function:
ATP + 3-phospho-D-glycerate = ADP + 3-phospho- D-glyceroyl phosphate
Gene Name:
pgk
Uniprot ID:
P0A799
Molecular weight:
41118
Reactions
ATP + 3-phospho-D-glycerate = ADP + 3-phospho-D-glyceroyl phosphate.
General function:
Involved in catalytic activity
Specific function:
2-phospho-D-glycerate = 3-phospho-D-glycerate
Gene Name:
gpmB
Uniprot ID:
P0A7A2
Molecular weight:
24065
Reactions
2-phospho-D-glycerate = 3-phospho-D-glycerate.
General function:
Involved in amino acid binding
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
serA
Uniprot ID:
P0A9T0
Molecular weight:
44175
Reactions
3-phospho-D-glycerate + NAD(+) = 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) = 2-oxoglutarate + NADH.
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 catalytic activity
Specific function:
Catalyzes the interconversion of 2-phosphoglycerate and 3-phosphoglycerate
Gene Name:
gpmI
Uniprot ID:
P37689
Molecular weight:
56193
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:
gpmA
Uniprot ID:
P62707
Molecular weight:
28556
Reactions
2-phospho-D-glycerate = 3-phospho-D-glycerate.
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.