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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:23 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
ValueSource
3-(Dihydrogen phosphate)glycerateChEBI
3-(Dihydrogen phosphate)glyceric acidChEBI
3-PhosphoglycerateChEBI
DL-Glycerate 3-phosphateChEBI
Glycerate 3-phosphateChEBI
Glycerate 3-phosphatesChEBI
3-(Dihydrogen phosphoric acid)glyceric acidGenerator
2-Hydroxy-3-phosphonooxypropanoateGenerator
3-Phosphoglyceric acidGenerator
DL-Glyceric acid 3-phosphoric acidGenerator
Glyceric acid 3-phosphoric acidGenerator
Glyceric acid 3-phosphatesGenerator
3-GlycerophosphorateHMDB
3-Glycerophosphoric acidHMDB
3-P-D-GlycerateHMDB
3-P-GlycerateHMDB
3-PGHMDB
3-PGAHMDB
3-phospho-(R)-GlycerateHMDB
3-phospho-D-GlycerateHMDB
3-phospho-GlycerateHMDB
3-phospho-Glyceric acidHMDB
D-(-)-3-Phosphoglyceric acidHMDB
D-Glycerate 3-phosphateHMDB
G3PHMDB
Glycerate-3-PHMDB
Glyceric acid 3-phosphateHMDB
PhosphoglycerateHMDB
Chemical FormulaC3H7O7P
Average Molecular Weight186.0572
Monoisotopic Molecular Weight185.99293909
IUPAC Name2-hydroxy-3-(phosphonooxy)propanoic acid
Traditional Namephosphoglycerate
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 KeyInChIKey=OSJPPGNTCRNQQC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Glyceric_acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 Solubility21.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.26 m3·mol-1ChemAxon
Polarizability13.29 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
3-Phosphoglycerate dehydrogenase deficiencySMP00721Not Available
D-glyceric aciduraSMP00529Not Available
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)SMP00179Not Available
Dimethylglycine Dehydrogenase DeficiencySMP00242Not Available
Dimethylglycine Dehydrogenase DeficiencySMP00484Not Available
Familial lipoprotein lipase deficiencySMP00530Not Available
Fanconi-bickel syndromeSMP00572Not Available
Fructose-1,6-diphosphatase deficiencySMP00562Not Available
GluconeogenesisSMP00128map00010
Glycerol Kinase DeficiencySMP00187Not Available
Glycerolipid MetabolismSMP00039map00561
Glycine and Serine MetabolismSMP00004map00260
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseSMP00374Not Available
Glycogen synthetase deficiencySMP00552Not Available
Glycogenosis, Type IA. Von gierke diseaseSMP00581Not Available
Glycogenosis, Type IBSMP00573Not Available
Glycogenosis, Type ICSMP00574Not Available
Glycogenosis, Type III. Cori disease, Debrancher glycogenosisSMP00553Not Available
Glycogenosis, Type IV. Amylopectinosis, Anderson diseaseSMP00554Not Available
Glycogenosis, Type VI. Hers diseaseSMP00555Not Available
Glycogenosis, Type VII. Tarui diseaseSMP00531Not Available
GlycolysisSMP00040map00010
Hyperglycinemia, non-ketoticSMP00485Not Available
Mucopolysaccharidosis VI. Sly syndromeSMP00556Not Available
Non Ketotic HyperglycinemiaSMP00223Not Available
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)SMP00560Not Available
SarcosinemiaSMP00244Not Available
Starch and Sucrose MetabolismSMP00058map00500
Sucrase-isomaltase deficiencySMP00557Not Available
Triosephosphate isomeraseSMP00563Not Available
Warburg EffectSMP00654Not Available
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
SalivaDetected and Quantified6.34 +/- 3.26 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified6.07 +/- 3.08 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified7.73 +/- 6.31 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified8.40 +/- 9.51 uMAdult (>18 years old)BothLewy body disease details
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. [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. [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. [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. [7664478 ]
  5. Uchida K, Mori K, Matuo Y: [Phosphoglyceric acid mutase] Nippon Rinsho. 1995 May;53(5):1247-52. [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. [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. [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. [183226 ]
  9. Mair J: Progress in myocardial damage detection: new biochemical markers for clinicians. Crit Rev Clin Lab Sci. 1997;34(1):1-66. [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. [2490073 ]
  11. Veech RL, Lawson JW, Cornell NW, Krebs HA: Cytosolic phosphorylation potential. J Biol Chem. 1979 Jul 25;254(14):6538-47. [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