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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:22 UTC
HMDB IDHMDB00807
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Phosphoglyceric acid
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
  1. 3-(Dihydrogen phosphate)Glycerate
  2. 3-(Dihydrogen phosphate)Glyceric acid
  3. 3-Glycerophosphorate
  4. 3-Glycerophosphoric acid
  5. 3-P-D-Glycerate
  6. 3-P-Glycerate
  7. 3-Pg
  8. 3-PGA
  9. 3-Phospho-(R)-glycerate
  10. 3-Phospho-D-glycerate
  11. 3-Phospho-glycerate
  12. 3-Phospho-glyceric acid
  13. 3-Phosphoglycerate
  14. 3-Phosphoglyceric acid
  15. D-(-)-3-Phosphoglyceric acid
  16. D-Glycerate 3-phosphate
  17. G3P
  18. Glycerate 3-phosphate
  19. Glycerate-3-P
  20. Glyceric acid 3-phosphate
  21. Phosphoglycerate
Chemical FormulaC3H7O7P
Average Molecular Weight186.0572
Monoisotopic Molecular Weight185.99293909
IUPAC Name2-hydroxy-3-(phosphonooxy)propanoic acid
Traditional IUPAC Name3-phosphoglyceric acid
CAS Registry Number820-11-1
SMILES
OC(COP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)
InChI KeyOSJPPGNTCRNQQC-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassSugar Acids and Derivatives
Sub ClassN/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • monophosphoglyceric acid(ChEBI)
  • tetronic acid derivative(ChEBI)
Substituents
  • Alpha Hydroxy Acid
  • Carboxylic Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct ParentSugar Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area124.29ChemAxon
rotatable bond count4ChemAxon
refractivity31.26ChemAxon
polarizability13.29ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
GluconeogenesisSMP00128map00010
Glycerolipid MetabolismSMP00039map00561
Glycine and Serine MetabolismSMP00004map00260
GlycolysisSMP00040map00010
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified58.2 +/- 14.4 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified47.2 +/- 7.4 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cellular CytoplasmDetected and Quantified45 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022255
KNApSAcK IDNot Available
Chemspider ID704
KEGG Compound IDC00597
BioCyc IDG3P
BiGG ID34230
Wikipedia Link3-Phosphoglycerate
NuGOwiki LinkHMDB00807
Metagene LinkHMDB00807
METLIN ID150
PubChem Compound724
PDB ID13PK
ChEBI ID17050
References
Synthesis ReferenceJakoby, 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)
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. Uchida K, Mori K, Matuo Y: [Phosphoglyceric acid mutase] Nippon Rinsho. 1995 May;53(5):1247-52. Pubmed: 7602787
  6. 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
  7. 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
  8. 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
  9. Mair J: Progress in myocardial damage detection: new biochemical markers for clinicians. Crit Rev Clin Lab Sci. 1997;34(1):1-66. Pubmed: 9055056
  10. 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
  11. Veech RL, Lawson JW, Cornell NW, Krebs HA: Cytosolic phosphorylation potential. J Biol Chem. 1979 Jul 25;254(14):6538-47. Pubmed: 36399
  12. Mayo Medical Laboratories 2005 Test Catalog

Enzymes

General function:
Involved in catalytic activity
Specific function:
Plays a major role in regulating hemoglobin oxygen affinity by controlling the levels of its allosteric effector 2,3-bisphosphoglycerate (2,3-BPG). Also exhibits mutase (EC 5.4.2.1) and phosphatase (EC 3.1.3.13) activities.
Gene Name:
BPGM
Uniprot ID:
P07738
Molecular weight:
30004.98
Reactions
2-Phospho-D-glyceric acid → 3-Phosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Phosphoric aciddetails
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:
PGAM2
Uniprot ID:
P15259
Molecular weight:
28765.96
Reactions
2-Phospho-D-glyceric acid → 3-Phosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Molecular weight:
28776.605
Reactions
2-Phospho-D-glyceric acid → 3-Phosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Phosphoric aciddetails
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:
PGAM1
Uniprot ID:
P18669
Molecular weight:
28803.675
Reactions
2-Phospho-D-glyceric acid → 3-Phosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Phosphoric aciddetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP2
Uniprot ID:
P14621
Molecular weight:
11139.52
Reactions
Glyceric acid 1,3-biphosphate + Water → 3-Phosphoglyceric acid + Phosphoric aciddetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP1
Uniprot ID:
P07311
Molecular weight:
11260.84
Reactions
Glyceric acid 1,3-biphosphate + Water → 3-Phosphoglyceric acid + Phosphoric aciddetails
General function:
Involved in phosphoglycerate dehydrogenase activity
Specific function:
Not Available
Gene Name:
PHGDH
Uniprot ID:
O43175
Molecular weight:
56650.03
Reactions
3-Phosphoglyceric acid + NAD → Phosphohydroxypyruvic acid + NADHdetails
3-Phosphoglyceric acid + NAD → Phosphohydroxypyruvic acid + NADH + Hydrogen Iondetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PGK2
Uniprot ID:
P07205
Molecular weight:
44795.79
Reactions
Adenosine triphosphate + 3-Phosphoglyceric acid → ADP + Glyceric acid 1,3-biphosphatedetails
General function:
Involved in phosphoglycerate kinase activity
Specific function:
In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein).
Gene Name:
PGK1
Uniprot ID:
P00558
Molecular weight:
44614.36
Reactions
Adenosine triphosphate + 3-Phosphoglyceric acid → ADP + Glyceric acid 1,3-biphosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GLYCTK
Uniprot ID:
Q8IVS8
Molecular weight:
25036.865
Reactions
Adenosine triphosphate + Glyceric acid → ADP + 3-Phosphoglyceric aciddetails
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Glucose 1,6-bisphosphate synthase using 1,3-bisphosphoglycerate as a phosphate donor and a series of 1-phosphate sugars as acceptors, including glucose 1-phosphate, mannose 1-phosphate, ribose 1-phosphate and deoxyribose 1-phosphate. 5 or 6-phosphosugars are bad substrates, with the exception of glucose 6-phosphate. Also synthesizes ribose 1,5-bisphosphate. Has only low phosphopentomutase and phosphoglucomutase activities.
Gene Name:
PGM2L1
Uniprot ID:
Q6PCE3
Molecular weight:
70441.085
Reactions
Glyceric acid 1,3-biphosphate + Glucose 1-phosphate → 3-Phosphoglyceric acid + Alpha-D-Glucose 1,6-bisphosphatedetails