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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:31:02 UTC
HMDB IDHMDB01270
Secondary Accession NumbersNone
Metabolite Identification
Common NameGlyceric acid 1,3-biphosphate
Description1,3-Bisphosphogylcerate (1,3BPG), also known as PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration. 1,3BPG have been recognized as regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. 1,3BPG concentration in erythrocytes changes in a number of pathological conditions, such as Inherited Phosphoglycerate kinase deficiency in erythrocytes (involved in the synthesis and breakdown of 1,3 BPG). (PMID 3555887 ). 1,3-bisphosphoglycerate is the anion form of bisphosphoglyceric acid. It is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP.(wikipedia).
Structure
Thumb
Synonyms
  1. 1,3-Biphosphoglycerate
  2. 1,3-Biphosphoglyceric acid
  3. 1,3-Bis-phosphoglycerate
  4. 1,3-Bisphosphoglycerate
  5. 1,3-Diphosphateglycerate
  6. 1,3-Diphosphoglycerate
  7. 13-DPG
  8. 2-Hydroxy-3-(phosphonooxy)-Propanoate
  9. 2-Hydroxy-3-(phosphonooxy)-Propanoic acid
  10. 2-Hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphorate
  11. 2-Hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphoric acid
  12. 3-P-Glyceroyl-P
  13. 3-Phospho-D-glyceroyl phosphate
  14. 3-Phospho-D-glyceroyl-phosphate
  15. 3-Phosphoglyceroyl phosphate
  16. 3-Phosphoglyceroyl-P
  17. 3-Phosphoglyceroyl-phosphate
  18. DPG
  19. Glycerate 1,3-Biphosphate
  20. Glycerate 1,3-bisphosphate
  21. Glycerate 1,3-diphosphate
  22. Glyceric acid 1,3-biphosphate
  23. P-Glyceroyl-P
  24. Phosphoglyceroyl-P
Chemical FormulaC3H8O10P2
Average Molecular Weight266.0371
Monoisotopic Molecular Weight265.9592695
IUPAC Name[2-hydroxy-3-oxo-3-(phosphonooxy)propoxy]phosphonic acid
Traditional IUPAC Name2-hydroxy-3-oxo-3-(phosphonooxy)propoxyphosphonic acid
CAS Registry Number1981-49-3
SMILES
OC(COP(O)(O)=O)C(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)
InChI KeyLJQLQCAXBUHEAZ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganophosphorus Compounds
ClassOrganic Phosphoric Acids and Derivatives
Sub ClassOrganophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organophosphate Esters
Substituents
  • Alpha Hydroxy Acid
  • Glyceric Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Secondary Alcohol
Direct ParentAcyl Phosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility9.64 g/LALOGPS
logP-1.1ALOGPS
logP-2.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.42ChemAxon
Polarizability18.04ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Cellular Cytoplasm
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
GluconeogenesisSMP00128map00010
Glycerol Phosphate ShuttleSMP00124Not Available
GlycolysisSMP00040map00010
Mitochondrial Electron Transport ChainSMP00355map00190
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified0.4 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 IDFDB022524
KNApSAcK IDNot Available
Chemspider ID663
KEGG Compound IDC00236
BioCyc IDDPG
BiGG ID34342
Wikipedia Link1,3-Biphosphoglycerate
NuGOwiki LinkHMDB01270
Metagene LinkHMDB01270
METLIN IDNot Available
PubChem Compound683
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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
  2. Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8. Pubmed: 8753225
  3. 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
  4. Inoue H, Moriyasu M, Hamasaki N: Metabolism of 3-phosphoglyceroyl phosphate in phosphoenolpyruvate-enriched human erythrocytes. J Biol Chem. 1987 Jun 5;262(16):7635-8. Pubmed: 3584133
  5. Fabry ME, Nagel RL: Heterogeneity of red cells in the sickler: a characteristic with practical clinical and pathophysiological implications. Blood Cells. 1982;8(1):9-15. Pubmed: 7115982
  6. Flachner B, Varga A, Szabo J, Barna L, Hajdu I, Gyimesi G, Zavodszky P, Vas M: Substrate-assisted movement of the catalytic Lys 215 during domain closure: site-directed mutagenesis studies of human 3-phosphoglycerate kinase. Biochemistry. 2005 Dec 27;44(51):16853-65. Pubmed: 16363799
  7. Carreras J, Bartrons R, Climent F, Cusso R: Bisphosphorylated metabolites of glycerate, glucose, and fructose: functions, metabolism and molecular pathology. Clin Biochem. 1986 Dec;19(6):348-58. Pubmed: 3555887
  8. Fokina KV, Dainyak MB, Nagradova NK, Muronetz VI: A study on the complexes between human erythrocyte enzymes participating in the conversions of 1,3-diphosphoglycerate. Arch Biochem Biophys. 1997 Sep 15;345(2):185-92. Pubmed: 9308888
  9. Jovanovic S, Du Q, Crawford RM, Budas GR, Stagljar I, Jovanovic A: Glyceraldehyde 3-phosphate dehydrogenase serves as an accessory protein of the cardiac sarcolemmal K(ATP) channel. EMBO Rep. 2005 Sep;6(9):848-52. Pubmed: 16082386
  10. Oimomi M, Yoshimura Y, Kubota S, Tanke G, Takagi K, Baba S: Effect of hydrocortisone on the synthesis of 2,3-diphosphoglycerate in human erythrocytes. Transfusion. 1982 Jul-Aug;22(4):266-8. Pubmed: 7101418
  11. Joao HC, Williams RJ: The anatomy of a kinase and the control of phosphate transfer. Eur J Biochem. 1993 Aug 15;216(1):1-18. Pubmed: 8365395

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
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric 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
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Molecular weight:
28776.605
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric 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
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric 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 glyceraldehyde-3-phosphate dehydrogenase activity
Specific function:
May play an important role in regulating the switch between different pathways for energy production during spermiogenesis and in the spermatozoon. Required for sperm motility and male fertility (By similarity).
Gene Name:
GAPDHS
Uniprot ID:
O14556
Molecular weight:
44500.835
Reactions
D-Glyceraldehyde 3-phosphate + Phosphoric acid + NAD → Glyceric acid 1,3-biphosphate + NADHdetails
D-Glyceraldehyde 3-phosphate + Phosphoric acid + NAD → Glyceric acid 1,3-biphosphate + NADH + Hydrogen Iondetails
General function:
Involved in glyceraldehyde-3-phosphate dehydrogenase activity
Specific function:
Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including transcription, RNA transport, DNA replication and apoptosis. Nuclear functions are probably due to the nitrosylase activity that mediates cysteine S-nitrosylation of nuclear target proteins such as SIRT1, HDAC2 and PRKDC. Modulates the organization and assembly of the cytoskeleton. Facilitates the CHP1-dependent microtubule and membrane associations through its ability to stimulate the binding of CHP1 to microtubules (By similarity). Glyceraldehyde-3-phosphate dehydrogenase is a key enzyme in glycolysis that catalyzes the first step of the pathway by converting D-glyceraldehyde 3-phosphate (G3P) into 3-phospho-D-glyceroyl phosphate. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma treatment assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
Gene Name:
GAPDH
Uniprot ID:
P04406
Molecular weight:
31547.76
Reactions
D-Glyceraldehyde 3-phosphate + Phosphoric acid + NAD → Glyceric acid 1,3-biphosphate + NADHdetails
D-Glyceraldehyde 3-phosphate + Phosphoric acid + NAD → Glyceric acid 1,3-biphosphate + 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:
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