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Record Information
Version	2.0
Creation Date	2012-05-31 14:06:02 -0600
Update Date	2015-09-13 12:56:14 -0600
Secondary Accession Numbers	ECMDB04131
Identification
Name:	3-Phosphoglycerate
Description	3-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9fac50a4> Close
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Sugar acids and derivatives
Alternative Parents	Monoalkyl phosphates Monosaccharides Alpha hydroxy acids and derivatives Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	tetronic acid derivative (CHEBI:17050 ) monophosphoglyceric acid (CHEBI:17050 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 21 g/L ALOGPS logP -2.3 ALOGPS logP -1.6 ChemAxon logS -0.95 ALOGPS pKa (Strongest Acidic) 1.3 ChemAxon pKa (Strongest Basic) -4.2 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 124.29 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 31.26 m³·mol⁻¹ ChemAxon Polarizability 13.29 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2-Phospho-D-glyceric acid <> 3-Phosphoglycerate Adenosine triphosphate + Glyceric acid > 3-Phosphoglycerate + ADP + Hydrogen ion 3-Phosphoglycerate + NAD > Phosphohydroxypyruvic acid + Hydrogen ion + NADH 3-Phosphoglycerate + Adenosine triphosphate <> Glyceric acid 1,3-biphosphate + ADP 3-Phosphoglycerate <> 2-Phospho-D-glyceric acid 3-Phosphoglycerate + NAD <> Hydrogen ion + Phosphohydroxypyruvic acid + NADH Glyceric acid 1,3-biphosphate + Adenosine diphosphate + Glyceric acid 1,3-biphosphate + ADP > Adenosine triphosphate + 3-Phosphoglyceric acid + 3-Phosphoglycerate 3-Phosphoglyceric acid + Adenosine triphosphate + 3-Phosphoglycerate > Adenosine diphosphate + Glyceric acid 1,3-biphosphate + ADP + Glyceric acid 1,3-biphosphate 3-Phosphoglyceric acid + Adenosine triphosphate + 3-Phosphoglycerate > 3-phospho-D-glyceroyl phosphate + Adenosine diphosphate + ADP 3-Phosphoglyceric acid + 3-Phosphoglycerate > 2-Phospho-D-glyceric acid 2-Phosphoglyceric acid + 2-Phosphoglyceric acid > 3-Phosphoglyceric acid + 3-Phosphoglycerate Glyceric acid + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + 3-Phosphoglyceric acid + ADP + 3-Phosphoglycerate 3-Phosphoglyceric acid + NAD + 3-Phosphoglycerate > NADH + Hydrogen ion + Phosphohydroxypyruvic acid
SMPDB Pathways:	Gluconeogenesis from L-malic acid PW000819 Secondary Metabolites: cysteine biosynthesis from serine PW000977 cysteine biosynthesis PW000800 fructose metabolism PW000913 glycerol metabolism PW000914 glycerol metabolism II PW000915 glycerol metabolism III (sn-glycero-3-phosphoethanolamine) PW000916 glycerol metabolism IV (glycerophosphoglycerol) PW000917 glycerol metabolism V (glycerophosphoserine) PW000918 glycolate and glyoxylate degradation PW000827 glycolate and glyoxylate degradation II PW002021 glycolysis and pyruvate dehydrogenase PW000785 serine biosynthesis and metabolism PW000809
KEGG Pathways:	Not Available
EcoCyc Pathways:	gluconeogenesis I GLUCONEO-PWY glycolate and glyoxylate degradation I GLYCOLATEMET-PWY glycolysis I GLYCOLYSIS homoserine biosynthesis SERSYN-PWY
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 1540± 0 uM K12 NCM3722 Gutnick 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 glucose Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 4080± 0 uM K12 NCM3722 Gutnick 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 glycerol Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 1510± 0 uM K12 NCM3722 Gutnick 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 acetate Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-0974000000-41479250991be9cc1e07 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-0974000000-41479250991be9cc1e07 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9200000000-2d6f0050126bbc72d771 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00fu-9081000000-487a9a33cdad68046ff3 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) splash10-002k-9300000000-4fafb3c93719c5a41327 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) splash10-004j-9000000000-c6bb9644e70a338c03be View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) splash10-004i-9000000000-9d164579c98406ad7c88 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-0a4i-0900000000-cea59554251398a27835 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-0udi-0900000000-8a976aaa2f56f074d975 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-0a5c-9500000000-4bd264fcf029200c55c6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-001i-9100000000-1a020681f04042ff6966 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0a4i-0900000000-cea59554251398a27835 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0udi-0900000000-8a976aaa2f56f074d975 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0a5c-9600000000-4bd264fcf029200c55c6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-001i-9100000000-1a020681f04042ff6966 View in MoNA LC-MS/MS LC-MS/MS Spectrum - , positive splash10-0005-8900000000-bd4e0c8adef56968d87a View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Negative splash10-004i-9100000000-abd08e7a88ff6e65bc4b View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-002b-9000000000-f8afa9e495e0f6c94717 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Negative splash10-004i-9200000000-30ac9f237fd5b07a8ad8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-004j-9000000000-623d31045a6d2723a66b View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Positive splash10-0005-9800000000-592cc43b2d6718b5e805 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-75f21a1b3e228e0af7f2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00kr-3900000000-9d9dc94243143123d53b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00kv-8900000000-b21c05dfded763ce62a0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-c460ca316484eef90129 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-003r-5900000000-653e5055531f19df4952 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9100000000-15195031d70847a75881 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-59550676899d259aeab5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004j-9000000000-0b41dc890757740bbb51 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View 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)
Links
External Links:	Resource Link CHEBI ID 17050 HMDB ID HMDB00807 Pubchem Compound ID 724 Kegg ID C00597 ChemSpider ID 704 Wikipedia 3-Phosphoglycerate BioCyc ID G3P EcoCyc ID G3P

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